I spent money for courses that led nowhere, wondering what I was doing wrong. Then I found ’s book and the perfect name she’s given to this: the entrepreneurial casino.

Reading the book was a huge relief. Not because she makes it sound easy. If anything Jessica does the opposite by telling you clearly how much work is actually involved in building something resilient, how long it really takes, and why most of what you’ve been sold is nonsense.

It’s not a particularly sexy message.

The opposite of the casino is, well, work. Honest (and sometimes really hard) work over many years. And that’s exactly why it’s so important to know what you’re really in for so that you can navigate that path successfully without burning out.

I was lucky enough to get to chat with Jessica, and I’ve written up a few of my favourite highlights below. You can listen to the full conversation on YouTube, Spotify, Apple, or wherever you get your podcasts.

Highlights from our chat

1. Social media stopped being social when TikTok arrived

Before 2020, social media worked as a genuine discovery tool. It showed you content from friends of friends and helped you find your people. After TikTok, platforms shifted to passive and shorter, faster forms of content consumption. Posting every day hoping people will find you is now a poor networking strategy, and it’s exhausting. The people who built businesses solely from social media attention mostly did it in an era that no longer exists.

2. Use “Puppy dog internet theory”

Instead of posting into the void and putting all your energy competing for attention, find people you genuinely admire and… follow them around the internet. Like a puppy, not a stalker. What communities are the people you admire in? Who do they know? Go there, support those people, build genuine relationships. It sounds slow. It is. But it compounds in marvellous ways.

3. You might be building two businesses at once

There’s the short-term stuff you do to pay the bills and then the long term business — the thing you actually want to build and spend your time doing — that grows slowly in the background.

The short-term business is often about solving immediate problems for people. A job-job. It pays the bills while you build your network, sharpen your thinking, and let the longer-term thing compound in the background, without also demanding it immediately pay you.

4. Ask “what are you optimising for?”

If you need to replace a corporate salary within one year, the level of effort required is completely different from someone exploring a creative direction while their steady day job covers the bills. Neither is wrong, but being dishonest about which situation you’re in and what you want will only lead to misaligned decisions and burnout.

Regularly asking yourself what you are actually optimising for and answering that as honestly as you can is a very powerful practise.

5. Know your ceiling and if you actually want to break through it

Growing past a certain point changes a business fundamentally. More revenue means more infrastructure, more staff, more complexity. If you want to run a solo creative business providing a bespoke service on a one to one level, you have limiting factors built in. At some point that business model breaks if you try to scale it without changing anything.

It’s good to be aware of that and ask: if I grow this thing, how will it change? Do I actually want that or am I just pushing for growth because it’s the “logical next step”?

It’s okay to stop and live under the ceiling that makes you happy.

6. Do the stuff that sucks in order to do the stuff that sings

There’s the discomfort of “this is wrong” and the discomfort of “this is hard.” Succeeding means learning to tell them apart and accepting you’re going to have to do uncomfortable things to grow. Your first newsletters will be rough. Your first outreach emails will feel awkward. That’s the price of entry. Do it anyway. You’ll get better and used to it at the same time. Again, everything leads back to long-term compounding.

7. The opposite of scarcity isn’t abundance, it’s sufficiency

Ignoring metrics and “going with the vibes” whilst having zero clue what you’re aiming for is its own failure mode and often swings too hard in the opposite direction to the hustle bros.

There’s a minimum level of activity required to build momentum. In content, in networking, in outreach. Figure out the minimum you need to put in to make the kind of progress you actually want to make, shoot for that, and adjust as you go. Put another way, target your zone of enoughness and actually measure for it.

8. Seeds → Roots → Sprouts → Fruits

Plant seeds (relationships, content), build roots (infrastructure, systems, long-form thinking), track sprouts (early signals — something lands, someone shares it), then harvest fruits (clients, revenue, real results). Most people only look for the fruits and get discouraged before the rest has had time to grow.

9. Signal and momentum are not the same thing

A post going viral, an article spreading, a concept resonating - that’s all signal. It tells you you’re onto something. In todays attention economy, one positive signal does not mean you have momentum.

Momentum takes time and requires seeding the idea across different networks. It also depends on enough people encountering you enough times to actually notice. (Case in point: I only bought Jessica’s book the third or fourth time I saw it in my socials!) Don’t expect an early hit to be an instant flywheel.

10. Niche down, but let the pattern emerge

You can’t pick a niche before you know what the pattern is. Pick a direction, a type of problem, an area where conventional advice seems to be failing, and pay attention to what people reflect back. The niche emerges from the exploration. You also probably won’t have the language of your brand when you start. That develops with time too.

11. Don’t force your art to pay the bills

One of Jessica’s colleagues ran a podcast studio for five years while developing a show on a completely different topic on the side. The studio paid the bills. The show became the business with time. But she never forced the creative work to carry the weight it wasn’t ready to carry. Putting immediate financial pressure on the creative thing you’re passionate about is a good way to ruin it.

Resources

• Leaving the Casino by Jessica Lackey

• ’s podcast:

• Book recommendations from Jessica:

  • Tiny Experiments by Anne-Laure Le Cunff

  • The Business of Expertise by David C. Baker (and the 2Bobs podcast with David C. Baker and Blair Enns)

• Full transcript available here.

Then I dropped the entire thing. A month later I’d moved on to juggling with clubs, which I obviously had to focus on! The month after that I was getting up early every day to work on a novel (for the third time).

I’m a serial project starter. Some things I see through, most I don’t. I’ll get hyper-obsessed with a topic, pour my heart into it, and then never touch that thing again.

For a long time, I saw that as failure. I lacked discipline. I was building a life made of half-finished things. I was gathering a few experiences on the way, but never really achieving anything.

Talking with on the podcast helped me confirm a growing feeling I’d been having over the last few years that this is completely untrue.

I now think of creativity a bit like Stephen King’s The Long Walk (which is, ironically, a book I put down halfway through). The premise: stop walking, and you’re dead. We’re all on that walk with our creativity. There’s no finish line or time limit other than the one nature eventually hands us.

That means the goal is to simply keep walking. I’ve landed on three things that help me do that.

Novelty

I need newness! I need to intentionally find ways to have new, exciting experiences. As Dave put it: “the joy is in the discovery.” Picking up something new is genuinely fun. I can’t not do it. I don’t want to not do it. Novelty literally triggers dopamine release.

I’ve stopped feeling guilty about the projects I drop after six weeks, because the spark they gave me often carries over into something else. Novelty creates energy. It’s the rocket fuel at the start of every project.

The easiest way to get a hit of novelty is adjust one variable. A new bit of photography gear, a new style of writing, a new place, a new hobby. If it keeps you moving, it’s worth it.

The trick is dosage. Novelty follows an inverted U-shape. Too little and you stagnate. Too much and you fragment. Moderate novelty-seeking seems to be the sweet spot. Enough to feel alive, not so much that nothing compounds.

Play

As Stuart Brown puts it, “the opposite of play is not work, it’s depression”.

Play means not worrying about failure, staying in the experiment, and letting curiosity lead. This is often powered by novelty, but not always. It’s an essential part of having fun.

Karin Majoka described this beautifully: you may know the finished picture, but you don’t yet know where the pieces go. Or you deliberately rearrange the pieces to see what emerges. That process is one of play.

Whatever you do, it’ll go better if there’s a feeling of aliveness and joy. And without play, everything starts to feel like homework.

Kill the joy, kill the project.

A reason to finish

This one runs completely contrary to the other two, because I believe everything actually does involve a bit of homework, but having some form of commitment to “hit publish” on your work is what can get you through it.

Finishing is rarely glamorous. It’s the final 20% of the Pareto principle. The sticky, fiddly, mildly boring stretch that kills a lot of projects.

That’s why if I don’t have somewhere I’m publishing my work, I will abandon it. I write way more because I publish this newsletter. I edit my photography more because I share it. Plus, putting work out there gives you feedback, which helps you steer, which keeps you going.

Don’t try to finish everything, but at least some things.

Having a rough deadline may even help. You want enough time to let ideas percolate without so much time that you never finish.

The research on this says creativity survives under deadlines when three things align: you understand why the deadline matters, you believe the work is meaningful, and you're protected from constant interruptions. That's what Teresa Amabile calls being “On a Mission.” Purposeful pressure, rather than pressure for it’s own sake.

The mistake I kept making was assuming every creative project needs all three things.

Sometimes a new hobby brings a burst of novelty that spills over and energises something else entirely. Sometimes I’ll abandon a project halfway through, and the lessons from it pull into a different one — or the clarity of dropping it gives me the resolve to finish something I actually care more about. The projects don’t even have to be connected to keep me on the walk.

The main thread, I think, is play. The day that genuinely goes dark is the day to worry. Without novelty, there’s less joy in starting. Without a reason to finish, nothing compounds. But without play, the whole thing grinds to a halt.

When I keep that one alive, the rest tends to find its footing.

On the podcast

joined me to talk about living like an octopus and embracing your multiple interests without apology. As always, we chat about all sorts:

• Why the popular Ikigai diagram is actually a lie

• Finding your “tentacle configuration”

• Why quitting isn’t failure

• How cultural obsessions with optimization are often artificially self-imposed and don’t help at all

• Why not everything needs to be monetized, and the danger of turning every passion into income

You can read the full summary here or listen to the full episode on YouTube, Spotify, Apple, or wherever you get your podcasts.

Worth your time

I’ve been battling a pretty tough dental issue and not been in much of a “deep reading” state this week, but here are a few things I’ve really enjoyed:

• An AI Agent Published a Hit Piece On Me - This is absolutely horrifying. In short: An AI agent of unknown ownership autonomously wrote and published a personalized hit piece against the person who rejected its code. This is… not great.

• When “nothing” is working and why is Linkedin like that? from are both fantastic. I had completely forgotten about “the button”.

• New Ferality from . The once-wild indie internet has been tamed into a “grinder” creator economy. This makes me quite sad, as I worry I’m part of the problem but I’m also not sure how to make things better.

• This Scattered Brain - is always a fun read, and it makes me want to include more images and fun headings into these articles.

• Someone is using AI to exploit lonely writers on Substack from - Dead internet theory strikes again. I hope Substack will do something to combat this. I have seen more and more ghost likes on my own articles from quite clearly AI driven accounts in the last few weeks.

• Becoming an artist to outrun the machines from - the skills that still matter as AI progresses, and how to develop them.

Dave Kang spent years trying to figure out his “one thing.” You know the drill: find your purpose, your passion, your Ikigai. That one perfect intersection of what you love, what you’re good at, what the world needs, and what you can get paid for.

It was frustrating. And it didn’t work. And it’s not even the original meaning of Ikigai!

So instead, he’s embraced life as a CEO. No, not that kind. A Chief Exploratory Octopus.

Living as a generalist with multiple interests (aka tentacles) reaching in different directions, without forcing it all to converge into one neat identity.

Now he writes about this on his Substack, helping other multi-talented, multi-interested people break free from the pressure to pick just one thing. As another identity-struggled creative generalist, that’s exactly how I found his work, and it was a huge relief to realise there were others like me and a mental model for thinking about it.

Chatting with Dave was an absolute joy, and I left feeling inspired and reassured about being someone with “too many” interests. Here’s a few highlights from our conversation.

Highlights from my chat with

1. The Ikigai diagram you know isn’t actually Japanese

That famous Venn diagram with four overlapping circles is not part of the original Japanese concept of Ikigai. The diagram was created by a Spanish astrologer in 2011, then a British blogger relabeled it “Ikigai” in 2014 after watching a TED Talk.

The original Japanese concept, researched by psychiatrist Mieko Kamiya in 1966, had nothing to do with finding "your one thing." It was about everyday joys and small life-affirming moments. Dave wrote about this and it went viral because it hit a nerve: people are tired of forcing themselves into frameworks that force them to find their “one true purpose”. Which leads us onto…

2. You don’t have to do just “one thing”

For multi-interested people, the pressure to find one calling is exhausting and often counterproductive. Dave realized he didn’t have one thing, couldn’t figure out what it was, and finally gave up trying. That’s when things got interesting. If you’re a “jack of all trades” or an “octopus” person who likes doing lots of different things, you don’t have to fight this part of yourself. You can invent your own framework instead of squeezing yourself into someone else’s box.

3. Embarrassment is often the price of entry for an interesting life

Most good things are on the other side of embarrassment. Starting a podcast. Sharing your work. Being passionate about eight things instead of one. Quitting your job to try something new. People worry about what others will think. In reality, nobody cares as much as you think they do. You care a hundred million times more than anyone else. And even if they do judge you, so what? The alternative is living your entire life based on imagined criticism from people who aren’t even paying attention.

If anything, you probably need to lean into the cringe if you want to do something interesting.

4. Play like an octopus

Octopuses have eight tentacles, three hearts, and brain cells in their arms. They’re constantly exploring with their tentacles, picking things up, examining them, and dropping them if they’re not interesting. They don’t always deploy all eight tentacles at once. They don’t have a rigid schedule. They’re organic, fluid creatures who have survived for millions of years with this approach. It’s a fun metaphor, and it works. Be like an octopus.

5. Your tentacles don’t have to be equal

You don’t need eight equally-weighted interests. Maybe you’re a three-tentacle octopus. Maybe one tentacle is way stronger than the others. Maybe you deploy two tentacles intensely for a while and let the rest dangle. The point isn’t balance in the traditional sense, but instead giving yourself permission to engage with multiple things in whatever proportion feels right at the time.

6. You don’t have to win Wimbledon

Roger Federer dedicated 40 years to tennis and became the best in the world. Leonardo da Vinci had a dozen interests and was fantastic at most of them. Both had meaningful lives. You don’t need to aim at being either of them. You don’t need a Wikipedia article. You don’t need to win Wimbledon. You just need to be true to yourself, deploy your gifts, and live in a way that feels authentic. That’s enough.

7. Stop optimizing your calendar like a factory worker

Calendars, clocks, time blocking, Pomodoro timers - these are all artifacts of industrial work culture. They evolved because factories needed to track when workers punched in and out. Not all cultures are obsessive about time. Many treat it far more fluidly. Dave doesn’t use rigid schedules anymore. He follows his energy and intuition.

8. Leave room for serendipity

If you pre-optimize your entire week, you’ve already decided what you’ll do before you’ve felt what you actually want to do. You’ve blocked out all the white space where accidents, inspiration, and discovery happen. Scheduling everything “perfectly” means you’ll have zero room for serendipity, play, and chance encounters, and that is exactly where the interesting stuff usually happens.

9. It’s okay to quit. In fact, it’s good for you.

We stigmatize quitting, but life is full of it. Kids quit activities all the time, and good parents let them. Quitting helps you figure out what you don’t like, which is just as valuable as knowing what you do like. Dave quit football after a week and a half in high school. Quitting gives you data. It helps you discover yourself. Go ahead and quit things. It’s good for you.

10. “Why not?” is more useful than “Why?”

Simon Sinek says “start with why.” Dave says start with “why not?” Finding your why is hard. It requires sitting around thinking about your life’s purpose. Why not just try things instead? Experiment. See what sticks. You might discover your why by accumulating a lot of “why nots.” Action beats contemplation. You’ll learn by doing and experimenting, not by challenging yourself with a big “why” before you even start. Rarely is something so serious that you can’t give it a go. So why not?

11. Overthinking is an illusion of control

Overthinking can feel productive and safe. If you just think through every scenario, maybe you can prevent bad outcomes. That’s an illusion. No amount of thinking prepares you for reality. And while you’re overthinking, you’re not doing anything. That’s why the cure for overthinking is just doing things. Action gives you information and feedback that thinking never will.

12. Not everything needs to make money

It’s easy to let every hobby become “how do I turn this into a side hustle?” But most things are worth doing just for the joy of it. Dave played pickleball recently. He’s not making money from it. It’s just fun. If you try to monetize everything you love, you risk killing what made it enjoyable in the first place. Protect some tentacles from commerce.

Resources Mentioned

• Dave’s Substack:

• Dave’s book recommendations:

  • The Pathless Path by

  • The Great Work of Your Life by Stephen Cope

  • Range by David Epstein

  • Four Thousand Weeks: Time Management for Mortals by

Full transcript available here.

This is also a new format I’m trying, a monthly roundup of interesting articles and topics I’m thinking about. Let me know if you find it useful, or if there’s anything you’d like to see more (or less) of.

Are you Claude-pilled? I think I might be.

I’ve worked in tech and built websites and other nerdy side projects for 15+ years (yikes). So I don’t know why I’ve been slow to adopt tools like Claude Code in my personal life when I use it every day at work. Maybe it’s the AI-skeptic in me or the knowledge of just how much data these tools actually extract from us and where that may head. A lot of my friends in tech are also the least heavy personal users.

I don’t quite know where I land yet, and in this round-up I am intentionally trying to show both sides, from “the data grab is real” to “it’s damn fun to build with Claude”.

And that’s what I finally started doing this month: building personal projects with Claude. And I think I get it.

As shared recently, once you start spotting “software-shaped problems” and realising the cost of building them is basically zero now, well, it becomes addictive. In one week, I’ve built:

• A tool to backup all my Substack posts into Notion and local markdown files that runs every month (and can be fed back into Claude for playing around with content creation).

• A small collection of utilities for my podcast to one-shot tasks like cleaning up messy transcripts.

• A silly multiplayer web game I then played with my family online

• A small journal prompts app that gives you a prompt in a certain category and a timer.

Each was done in a matter of hours. I can’t help but wonder how this changes the SaaS industry. Why pay for 20 euros a month for software that does “most” of what you want when you can create your own customised tool in about an hour with prompting?

A few more great articles I’ve been reading that convinced me to finally give it a go:

• Claude Code and What Comes Next and Management as AI superpower from are fantastic.

• claude code psychosis - paywalled, but worth it, from . “Claudecrastination” is absolutely going to be part of my vocabulary going forward.

• And for a hilarious but still accurate take (albeit also partially paywalled), Generative AI is an expensive edging machine - “It is not a revolution in computing, but a revolution in accepting lower standards.”

Worth reading

On careers & trade-offs

The Opportunity Cost of Your Dream Job from resurfaced and reminded me of the great Thomas Sowell quote: “there are no solutions, only trade-offs”. Every decision opens some doors and closes others. Every yes is a no to something else. The tricky bit is that you often can’t see what you’re giving up in advance. I forget this lesson when it comes to my own work. Right now it feels like there are limitless opportunities, and it’s hard to resist trying to do all of the things all at once.

On audience growth & creative practice

How to grow a following without compromising everything good in your life - on sustainable audience building. She breaks down how to build something that doesn’t require you to sacrifice your sanity or turn into a content machine, which is very much on my mind right now.

Do what the platform wants - on growing a Substack audience and that if you’re trying to build an audience on a platform, you need to play to that platform’s strengths. It reminded me that I’m not very good at being disagreeable. The opposite is my biggest strength in my day job (building cohesion). But clear, persuasive opinions may matter more than hedging everything all the time.

The relentless pursuit of purpose can hold us back - on moral perfectionism, and the trap of needing every creative thing to be world‑changing. Felt this one a lot as a recovering try-hard. I used to think every project had to prove something about me or connect to my ‘purpose’, but most things can just be joyful experiments that don’t carry the weight of my whole identity.

A cheat sheet to do great work - A straightforward, pretty little graphic based on a Paul Graham essay about doing things that are important to you.

On AI & creativity

Ben Affleck on why AI won’t replace writers - explains how AI companies are incentivised to scare us, but the reality is that AI is still very much in “the vortex of mid” in creative work. I feel this every time I try to brainstorm anything genuinely creative with AI and the result is “meh”.

James Popsy’s latest video on art and authenticity - Can you tell what you’re looking at is made by a human? Is that important? Personally I’m with James: it is. As he says, “there is nothing more interesting in the world than another person’s perspective.” I want art to be imperfect, flawed, and well... human. I also love the idea of “participatory discrepancies”. Human error in art is how art becomes relatable and palatable. With generative art looming over us, it’s nice to be reminded that good art is inherently flawed and human.

The Ladder to Nowhere: How OpenAI Plans to Learn Everything About You - ’s harrowing deep-dive shows just exactly how AI companies are laddering themselves to more and more of your data.

Books

Art Work: On the Creative Life by Sally Mann - Really, really good. A few things that stuck with me:

• Every creative should write or log their journey over time.

• Everyone doubts or goes through periods where nothing works. Keep creating anyway. Let something emerge, happy accidents happen.

• You can’t just wait to have time. A lot of good work happens in the cracks of life. Sometimes you have to just squeeze it in where you can.

• It’s really damn hard to make a living doing creative work that matters to you. You absolutely should do it anyway.

• Yes luck matters. Making connections matters. Talking to real people and making new connections has to be a regular part of your life.

• Your relationship to your work is going to change over time. The important thing is you keep making it. You’ll discard bangers and publish flops. But keep honing your gut and putting stuff out.

• Sometimes the hardest part is keeping things simple and avoiding gimmicks and trends.

• Sally keeps a notepad that she fills with quotes by hand and it kind of makes me want to make one.

• Passion doesn’t ensure success and it’s not an excuse to drop everything in your life (including civic duty). It’s something to be harnessed.

There Is No Antimemetics Division by qntm - One of the most inventive, crazy, brain-bending original stories I’ve ever read. Hard to describe. Essentially it’s a fight against “antimemes,” ideas that attack memory. Recommended if you like bizarre and creative sci-fi.

Unhinged Habits - Pre-ordered the hardback. Really excited to read this after hearing lots of good things, and I’ve loved following ’s journey on Substack with his .

In the Imperfect World

New podcast episodes:

→ Karin Majoka on why experimentation beats perfection, creative balance, and the pressure to pick just one thing
I got to chat with one of my photography heroes who juggles a career in psychology with photography and YouTube. Her first answer when I asked how she balances it all? “Probably don’t do it like me. It’s not healthy.”

→ Rick Foerster - Why Getting Lost Might Be Exactly What You Need
Rick walked away from a lucrative corporate career and almost barrelled straight into the next thing. And then he stopped and let himself get lost. He emerged on the other side writing apocalyptic fiction. This conversation felt very pivotal for me and I’m still thinking about how I can embrace “the wilderness phase” of figuring out what to do in life.

I’m posting all new episodes to YouTube! I’m enjoying the challenge of doing video and slowly growing on a new platform much more than I expected. 31 subscribers is a start!

Regarding creative experiments and having fun, I’ve switched my default camera app on my phone to Leica Lux. I have started shooting way more when I’m out and about, it’s made my day a little bit more creative and reduced the friction to shoot. I’m frequently surprised by the quality (like the two shots above) that I can now get with just my phone

In summary, it seems January's been about building things, getting lost, and lowering the barriers to creating. Whether that's coding tools with Claude or just having a better camera app ready in my pocket. If you liked this round-up format please let me know and I’ll do it again in February.

— Mike.

Balancing a full-time job with creative work and side projects is a constant struggle for me, and I suspect for many others too. So talking with Karin Majoka, one of my photography heroes who juggles a career in psychology and psychotherapy with photography and YouTube, was an absolute pleasure.

Her first answer when I asked how she does it? “Probably don’t do it like me. It’s not healthy.”

That feels like a good summary of our chat, as Karin is very open and honest about what it’s like juggling a mix of creative passions with a “traditional” career, as well as how she handles overthinking, creative balance, and her struggles with identity and labels like “artist”. Below are a few highlights from our chat.

Highlights from my chat with Karin Majoka

1. Kill your dreams to live an interesting life

“When you die, it’s better to go with experiences than dreams”. Dreams stay perfect because they never face reality. They’re beautiful, idealised versions of what could be. But if you never actually do the thing you’re dreaming about, you’ll never know what it’s really like. Real experiences might not be as flawless as your fantasies, but at least you experienced them. Better to have messy reality than pristine fantasy.

2. Build a habit of solving the puzzle

External metrics won’t motivate you long term, but the discipline of completing projects and putting them out into the world has a special something to it. Having a publishing habit (whether that’s posting photos, releasing videos, or shipping any creative work) keeps you in tune with your craft. It flexes the muscle of actually solving the puzzle. Of finishing things rather than endlessly perfecting them. The act of shipping is what you can control, and it’s what keeps you going regardless of how the work performs externally.

3. Leave room to surprise yourself

Karin doesn’t script her videos from start to finish, and she doesn’t plan every photography shoot down to the last detail. She works with a rough sketch, knowing the key points or themes, but leaves enough room for the project to surprise her. Having everything planned out can be boring and kill the creative energy. Having nothing planned can feel overwhelming. The sweet spot is a rough lane with space to follow your curiosity as you go.

4. “That’s not for you to decide. You have to do it, then reevaluate.”

Karin’s received this advice from an abstract painting teacher: You can’t imagine how adding yellow to your canvas will look. You can’t think your way to the answer. You have to actually do it, see what happens, and then decide if it works. Stop overthinking it or trying to imagine it. Go with your gut, try it, and adjust based on what you actually see. The same applies to photography, writing, video editing, or any creative work.

5. Style can’t be forced. It has to grow organically.

When you see creatives with a clear, recognisable style, it’s tempting to try to manufacture your own. But you can’t force it. If you try to decide “this will be my style” or “this is the format I’ll follow forever,” it won’t work. Style develops naturally over time. And honestly, it would be boring if you’d already figured everything out. Give yourself permission to still be searching and to develop new directions over time. You wouldn’t want your favourite musician to pump out the same songs for the next twenty years. Don’t expect the same from yourself.

6. Your different identities make each other better

Multiple interests can be seen as complementary rather than competing. Psychology makes Karin a better photographer. Photography makes her a better psychologist. She can connect with patients struggling with creative blocks or identity issues because she’s living through those same questions. Having something outside your main work doesn’t dilute your focus. It deepens your understanding of both. We contain multitudes. Embrace it.

7. Your creative medium is just one language

Karin started with painting, tried sculpture and improv theatre, and eventually landed on photography. But she’s not married to it. For her, the medium matters less than the goal: understanding the world and herself. If another “language” fits better someday, she’ll switch. Don’t lock yourself into one form of expression just because it’s working now. Let yourself move between mediums as your curiosity shifts.

8. Overthinking is the illusion of control, and doing is the cure

Overthinking comes from wanting to be prepared and avoid bad outcomes. If you just think through every scenario, maybe you can prevent things from going wrong. But Karin points out that that’s an illusion. No amount of thinking prepares you for every possibility, and while you’re overthinking, you’re not actually doing anything. Writing helps. Talking to people who are doing the things you’re dreaming about helps. But ultimately, the best medicine for overthinking is just doing things anyway. Action gives you information that thinking never will.

9. Be honest: external feedback does matter

Nobody wants to admit they care about clicks and comments. But we’re human. Other people’s reactions do affect us. The key is distinguishing between chasing superficial attention and being genuinely open to feedback, including feedback that challenges you. Putting work out there shouldn’t be about proving you’re good. It should be about learning and growing from the responses you get. Don’t pretend you’re above external validation. Just be intentional about how you use it.

10. Social media can keep you accountable (even if it isn’t always fulfilling)

Instagram is instant, disposable, full of fire emojis and generic “nice shot” comments. YouTube gives more meaningful engagement. But Instagram still serves a purpose: accountability. Knowing you’ll post motivates you to actually edit your photos, develop your film, and keep working. The grid becomes a visual reminder of projects you’ve done. It’s about staying in motion and training yourself to finish and publish your work on a regular basis.

11. Low expectations grant you creative freedom

Karin started her YouTube channel during lockdown when street photography wasn’t accessible. She had no audience and no pressure. That freedom let her experiment without worrying about performance or whether people would like it. She even uses an artist name (Karin Majoka isn’t her real name) to keep her creative and professional psychology identities separate. Not having an audience is actually liberating.

12. Creativity lives in experimentation

If you stick to one thing forever, you limit novelty. Cross-pollination between disciplines (drawing inspiration from music, poetry, film, anything outside your main medium) is where interesting work emerges. Don’t marry yourself to one creative path. Stay curious. Try things. See what sticks. The best work comes from following weird pulls and giving yourself permission to experiment without needing it to be permanent.

Resources Mentioned

• Karin’s YouTube Channel: Karin Majoka

• Karin’s Instagram: @karinmajoka

• Book recommendations:

  • You Are What You Do by Daniel Arnold

  • Twilight by Gregory Crewdson

  • Art Work: On the Creative Life - Sally Mann

Full transcript available here.

.

Every morning, he'd look in the mirror and be shocked at how old he was, his mind frozen at 27, his face aging to 82. Or at least that’s how the story goes.

After doing some digging, I learned that his primary researcher said this never actually happened. Through repeated daily exposure, Henry gradually updated his implicit sense of what he looked like, even though he couldn't form explicit memories. Still, the question the story raises is real. What would it be like to live 55 years and have almost no memory of it?

We don't have Henry's condition, but we do have a gap between our memory and reality. We have thousands of thoughts every day, but can you remember many specific ones from yesterday? How about from last week on Tuesday? I can’t either. And yet in the moment, every thought is incredibly real and important.

When I’m stuck overthinking or worrying about something, I now try to ask myself: Will I remember this thought next week? Have I worried about this exact thing before? What happened then?

The other thing this story encouraged me to do is write and journal more. This does three things:

1. It forces you to notice and process. I’ve experienced this with photography too, the act of framing up shots changes how I experience and remember moments. With writing, it’s the same. You have to actually notice what you’re thinking and feeling to put it into words, rather than letting it pass by unprocessed. The science backs this (Dr. K has a great breakdown) - when you write about something difficult, you’re processing those emotions in a safe, controlled environment. You’re not avoiding them, but you’re also not being overwhelmed by them. You’re actually dealing with it.

2. Regular practice reduces avoidance and builds agency. When I write regularly, I’m less stuck in my head and more likely to actually do things. This happens because safe processing builds tolerance to discomfort over time. The more you practice noticing and processing through writing, the less you avoid the things that make you anxious or stressed. Reduced avoidance means increased ability to face things, which means more action.

3. Long-term documentation reveals patterns. I just finished reading Sally Mann’s “Art Work”. She kept journals for decades, and going back through them she could see how her ideas evolved, which arguments mattered at the time and which didn’t. Combined with her photography archive, she could see the whole shape of her creative work over years.

When I look back at my own writing, I see the same thoughts and fears surfacing again and again. Patterns I’d never notice otherwise.

We all experience a bit of Henry’s mirror. We forget we forget. The difference is we can choose to notice - both in the moment and over time.

On the podcast

Last week’s episode was with . We talked about Rick’s journey from executive to writer, why he is only loosely coupled to that new identity, why the best creative work is often work you’d pay to do, and why you may want to avoid grasping for “the next thing” if you’re navigating a career transition. Watch on YouTube or read the highlights here.

Next week: Karin Majoka, one of my favourite photographers and YouTubers, on juggling YouTube, photography, plus her day job as a psychologist and psychotherapist in training. We get into how those worlds actually connect and what it’s like managing multiple creative practices alongside serious work. Subscribe so you don’t miss it: Spotify, Apple, YouTube.

Good stuff this week

• The full history behind Henry’s case is fascinating and apparently it changed how we understand memory formation.

• Shout-out to who is doing a very public version of creative journaling over on her Substack. I love reading these notes!

• Sally Mann’s Art Work: On the Creative Life is soooo good. An honest, touching, and practical look on what it’s like to be a professional creative and all that involves. I have so many notes that it may become a separate post.

• Speaking of the power of writing, writing is building now by knocks it out of the park.

• If you’d like a daily reminder that life’s too short, The Life Calendar wallpaper for your phone does a pretty good job!

• The Tale of the Phantom Book Group - . Fascinating. Scams are only getting more creative with time (and with AI).

• And finally, on the gap between feeling and doing:

I’ve published 17 podcast episodes so far. At a guess, each one takes me at least 3 hours to edit. That’s 51 hours doing the part of podcasting I strongly dislike.

Over fifty hours I could have spent having more conversations (the bit I truly love), writing, promoting the show, or literally anything else that brings me joy.

But hiring an editor costs money. So instead of investing anything to reclaim those hours, I’ve chosen to suffer through every single one of them myself. The “best” part is that I’m already paying for editing software. So I’m spending money on tools AND spending hours using those tools myself, when I could just... pay someone to do it and get my time back.

When I write it out like that, it sounds completely absurd. And yet that’s exactly what I’ve been doing for the past year.

And that is what a limiting belief looks like in practice. A real decision to waste dozens of hours because “I’m not making money with the podcast, so spending more money on it feels unreasonable.”

Today is for quitters

Which brings me to the fact that today is Quitters Day. The second Friday of January, when most people abandon their New Year’s resolutions. I’ve been planning to write this post since July 2025 after reading Tiny Experiments by Anne-Laure Le Cunff and learning about that special date. Back then, I even put this in my calendar:

In the book, she writes about running "tiny experiments" through pacts: you make commitments to try something for a set period, then reflect on the results. My version was: "Publish one podcast episode every two weeks for six months." January 9th became my Quit Day, a guilt-free checkpoint to ask: keep going, stop, or adjust?

I’m not quitting the podcast. I absolutely love having deep conversations with people about their work. But the editing is where I go to suffer. I’ve been stuck in a loop all year:

Love having the conversations and feel totally energised → Dread editing → Put it off → Deadline approaches → Panic & edit late → Tell myself I’m wasting money if I outsource → Suffer → Repeat

So my new experiment: I’m quitting editing and instead paying an editor for a few episodes. Hypothesis: My enjoyment goes up, my output increases, and the money isn’t a loss since it buys back time and sanity. We’ll see how the data looks in a few months. If you know a good editor, please let me know.

I hope you quit

It’s easy to treat quitting like failure when it’s actually just data. But search for “Quitters Day” online and you’ll see the same stuff everywhere: “How to stick to your resolutions,” or “don’t be a quitter.”

I disagree. I hope you quit. Quit the stupid, obvious thing that you know is making you miserable but you’re holding onto for reasons that don’t make sense when you say them out loud.

Or at least set Quit Dates in your calendar for whatever experiments you’re running. Give yourself permission to check in and ask: is this still working?

And if you’ve already abandoned something and feel guilty about it, don’t. Run the experiment properly: ask what you learned, why you want to quit, and what you might want to try instead.

You may as well get some good data out of it. That’s just good experimental design.

On the podcast

Season two kicked off with a wonderful chat with . It was a true pleasure to talk to Rick, and he did a better summary than me, so I’m stealing his words. We talk about:

• Why the best work is work you’d pay to do

• The unsexy reality of how creative work actually gets funded (spoiler: by something else)

• Why grasping for “the next thing” leaves you worse off

• Why he’s not latching onto his new identity of “writer”

Read more highlights here or watch on YouTube, Spotify, Apple, or wherever you get your podcasts.

Good stuff this week

A few great things I read this week:

• 6 months later: A sabbatical reflection - . A really awesome, honest and detailed look into the reality of a sabbatical that shows what an experimental mindset looks like in real life.

• How To Manufacture Luck - Rules for engineering serendipity by .

• 10 things I’d tell you about Substack if I wasn’t afraid to hurt your feelings - - Not new, but great advice I found myself nodding along to for anyone looking to post regularly here on Substack.

• The Best of World Builders ('25 Edition) - . Worldbuilders is awesome and I believe storytelling is an essential skill. So much good stuff in here!

• And finally, I can’t stop thinking about the idea of “unclenching” (yes, seriously):

writes one of my favourite newsletters on Substack, , so I was thrilled to chat with him about work, meaning, and creativity to kick off Season Two of the podcast.

Rick spent 12 years at a healthcare startup, from early employee to public company exec managing hundreds of people. He left, armed with a war chest and soon after 100+ company ideas of his own ready to go. He was at the starting line of what he thought was his entrepreneurial dream.

Then he stopped.

What was supposed to be a three-month sabbatical turned into two years of what Rick calls "the wilderness phase". No building or “output”. Rick wanted to figure out who he was and what he wanted to do when he wasn't on the hook to actually do anything.

He’s now emerged from the other side of that wilderness writing post-apocalyptic fiction.

We talk about why his executive coach told him to disappear, what led him to writing about his experiences on Substack, the trap of suppressing existential questions with productivity, the "first mountain vs. second mountain", and why following weird creative interests matters more than having a plan.

Highlights from my chat with Rick

1. “You need to sit down in the middle of the road”

When Rick told his coach something felt off, she told him to go dark for six months. Stop networking, stop building, stop producing. Just read, write, disappear, but nothing public. Most people treat transitions like crossing a road: get to the other side as fast as possible and avoid the discomfort. But Rick found his way through by sitting in the middle of traffic and letting himself be fully, uncomfortably lost.

2. Doing can be a form of avoidance

Rick spent three months building 100+ startup ideas after leaving his exec role. He was busy as hell. He was also running away from the real question: why am I doing any of this? Sometimes hustle is just existential angst dressed up as ambition. Staying busy feels productive, but it can be the most effective way to avoid sitting with what’s actually wrong.

3. Don’t grasp for the next permanent identity.

The temptation after leaving something is to grab the next label fast. Founder. Coach. Writer. Whatever stops the discomfort of not knowing who you are or what you want to do. Rick learned to stop searching for “the one thing” that would define him forever. Instead he asked: What interests me today? What am I curious about right now? He’s writing fiction, but he’s not tied to the “writer” identity. If he stops enjoying it in a year, he’ll move on.

4. The best signal might be work you’d pay to do

Everyone wants to “get paid to do what you love.” Rick flips it: the best work is what you’d be willing to lose money doing. If you’re only doing it because it pays well, you’re probably avoiding finding out what you truly want. Money warps your sense of value, even when you have enough. Ask yourself: what would I pay for the privilege to do?

5. Avoid “either/or” thinking

You don’t have to choose between “quit everything and pursue your creative dreams” or “stay in corporate hell forever.” There’s a whole menu of options: side project experiments, sabbaticals, moving somewhere cheaper, working 3 days a week, stair-stepping your way there. Even successful creative people fund their work through something else, often for a long time (or forever).

6. Not having an audience is liberating

There can be a lot of pressure online to “build an audience” before you do anything else. Rick found that having no audience for his fiction work freed him from expectations entirely. He could write his book without worrying about what his followers would think, whether it fit his “brand,” or if it would disappoint people. He could quit the experiment if he wanted to.

7. Avoid the pressure to monetize everything

These days, every hobby gets the same question: “how do you monetize it?” Start a YouTube channel. Launch a course. Build an audience. We’ve been conditioned to ask “what’s the monetary value?” of literally everything. When you reduce creative work to its dollar value, you destroy the intrinsic joy that made it worth doing in the first place.

8. Follow your weird creative inklings

Don’t overthink it. Don’t ask if it’ll make money. If you’re curious about something, be it writing fiction, playing an instrument, or painting, just try it. Don’t worry if it’s permanent. Don’t put a deadline on it. Just see where it takes you. Enjoy it. Most of the good stuff in life comes from following those weird pulls. Get weird with it.

Resources Mentioned

• Rick’s Substack: .

• Brandon Sanderson’s writing lectures

• Transitions by William Bridges

• Rick’s Book recommendations:

  • Working Identity by Herminia Ibarra

  • The Second Mountain by David Brooks

Full transcript available here.

He wasn’t being mean. His baby was due! But it worked.

I didn’t have a plan or know anything about making a podcast, but Phil knew a studio we could rent and was willing to give his time and energy to show me the ropes and record an episode in the process. And the deadline was absolutely not negotiable. So we did it!

I try to think of this whenever I’m overthinking something. The best way forward is almost always to tell myself “you have two weeks”.

Three escape routes from overthinking

New Year’s carries a weird energy. It’s the weight of possibility. I both love and hate it. The good news is that if you’re feeling a pull to “finally do something”, you’re already halfway there.

I’m currently in Potsdam, Germany. My girlfriend and I come here every New Year to hike, journal, and think without Berlin’s chaos. And every January 5th, the imperfect.club domain renews (it took me 3 months from recording that episode to picking a name - yes, I was overthinking it again).

The name, and the renewal, is a permanent reminder that nothing I do has to be perfect, including the names I give things. I just have to start.

Looking at my journals from previous trips to Potsdam, I noticed a few prompts that help me go from “thinking about it way too much” to “actually doing it”:

1. What could go right?

Most of my overthinking is just fear. Fear of failing, of looking stupid, of wasting time. Buried under that fear is genuine excitement about what could happen. What I did right before buying the domain and publishing that first episode was to grab a piece of paper, write “what could go right?” at the top, and then write a long list of things I was excited about that could only happen if I started.

Fear and excitement tend to show up together when there’s potential for growth. I’ve learnt that starting is easiest when you tilt the scales in favour of the excitement.

2. What makes this time different?

If you keep setting the same goal year after year, something’s in the way.

I’ve said I want to “get fitter” for the last five years. I’d been “thinking about starting a podcast” for even longer. It’s easy to blame discipline or motivation. In reality I hadn’t figured out what was actually stopping me or what I really wanted.

With fitness, vagueness has been the problem all along. I can’t tell if I’m making progress because I’ve never defined what “fit” means. Squat my body weight? Run 5k? Without that clarity, even real progress has felt like failure.

With the podcast, I didn’t know how to start, and I was scared. So I just kept thinking about it. Phil removed both barriers by showing me how it worked and giving me a deadline.

One technique I’ve found useful is the “future-retro.” Pretend it’s six months from now. You didn’t do the thing. Why? Write it down, address it now, and then start.

If the answer is “because I don’t actually want to prioritise this,” then great, don’t do it. Remove it from your list and stop feeling guilty.

3. Can you start it today?

There’s a few things I’ve done within hours of returning from Potsdam. One was buying the domain. Another was setting up an ETF savings plan I’d been “meaning to look into” for months.

I gave myself one hour and it took twenty minutes. Most things you’re overthinking can be started literally today. Even if starting means the smallest possible step.

Let the excitement get you started. Don’t worry yet about whether this will work long-term or what systems you’ll need.

The summary of all of this is if you’re feeling that New Year’s motivation to change or start something, do that thing right now as imperfectly as you can.

When you start doing the stuff you’ve always wanted to do, you realise there’s no secret. You just have to do it and see what happens.

Overthinking is the enemy of good work actually getting done.

Pretend you just got Phil’s message: You’ve got two weeks.

On the podcast

Season Two of the Imperfect Creatives podcast kicks off on January 7th! The first episode is with the wonderful and I am sooo excited to share it. Being able to chat with people like Rick was absolutely on my “what could go right” list.

We talk about Rick's journey from working at startups and being a high-level executive to quitting and writing a post-apocalyptic fiction novel, his fantastic writing here on Substack, finding meaning in our work, and more.

If you don’t want to miss it, you can subscribe on Spotify, Apple, YouTube (this will be the first video episode!) or wherever you get your podcasts.

Good stuff this week

• A huge shout out to for being a great friend and mentor over the years and giving me more than the odd push or two when needed. Go hire him for his leadership skills here and read his genuinely fantastic book “Punk Leadership” here.

• The roads not taken - on leaving her investment banking job to work for a YouTuber, and taking hard lefts when something pulls at you, “illogical” or not. I look forward to Becky’s newsletter every week, and this one feels particularly relevant this week concerning the topic of finally doing things (fun fact: this newsletter used to be called “Roads Untaken” for similar reasons).

• For Christmas I got Art Work: On the Creative Life by Sally Mann. I’m a third of the way in and loving it. She makes the case that writing is essential for thinking, unblocking, and recording your life, regardless of your creative medium. Since starting to write every week for the past year, I’ve realised how true this is. It’s a weekly practice that helps me find clarity, and having something to look back at shows me how my thinking has changed over time.

• How My Career Break Failed & Why That Failure IS the Point - another great post by about what career breaks are actually like and what they really give you.

• life is a crying baby. A container for ideas created during a specific time, sent to you as they were thought up. I love this project by . Creative, fun, and different. Feels like a great example of “just go do the thing and put it out into the world without overthinking it to death”.

• Unrelated to everything else here, Four Tet does a set for TheLotRadio every year in December and I always look forward to it. This year’s is amazing as always.

• And finally, a good note:

Hello! I’ve been too sick this week to write anything new, but I’ve still been absorbing a bunch of stuff from others, so this week is a round-up of my recent favourites as this year winds down.

Worth reading

On careers & winding paths

• All three parts of On Wise Agency by is the best series I’ve read all year. I’ve already fallen into the “identity trap” of wanting to grab a new work identity before even fully leaving another behind (or knowing if I actually want to). It’s something I constantly struggle with (who do I want to be, a tech lead who podcasts? a “creator”? something else?). It’s a reminder that I need to be comfortable being lost for a while, which I also struggle with a lot.

• Dare to abandon the 5-year plan - I loved this post by on her journey as an artist. Consider it a wholehearted nudge to ditch the plan and bet on momentum. Sometimes cluelessness is a feature, not a bug.

• Mentorship, sending scary emails, and making cool connections from and landed in my inbox at the perfect time, as I’ve been thinking a lot about mentorship outside traditional structures (and finding one myself). If you have any experiences with mentorship, good or bad, please send me a message, as I’d love to do a deep dive into this very topic!

• Stick or Twist: Should You Quit Your Job? - A great, practical way of thinking about what I suspect is the perennial question for many who read this newsletter, from .

• Positioning for portfolio careers from is a straightforward guide on how to position yourself as someone who does multiple things. The biggest takeaway for me is not to feel forced to treat every platform the same. Definitely will be attempting to apply this advice to my own profiles.

• The year I published my novel - An honest look behind the scenes from on launching her first book and going from full time tech to author. I feel like life as an author always seems a bit vague and mystical so it’s nice to see a glimpse of what that really looks like, especially from someone who has pivoted from the 9-5.

On meaning

• Aliveness and where to find it - I’m a sucker for a good graph, and the “meaning matrix” here is excellent. breaks meaning into four quadrants, and it made me realise how much I default to just one or two of them. Quadrant 4 (“creating together”) is the one I neglect most. The big takeaway: meaning is created, not discovered. You have to actively build it across multiple areas, or you can end up hollow even when you’re “productive.”

• I thought about that a lot is a wonderful collection of 24 essays by 24 contributors. This year I particularly enjoyed the things I want to say to my boss (a good reminder of what it takes to lead people & maybe even yourself) as well as finding the space to belong (“I used to think belonging meant being surrounded by people who spoke your language. Now I think it’s about being understood without apologising for who you are.”)

On AI & creativity

• I’m an AI-assisted author. You’ll get over it - writes from the heart about his author journey and using AI. AI-use often feels like a weird witch hunt these days, and I partly get it. There’s so much slop around that it’s Merriam-Webster’s word of the year. It’s absolutely something to be cautious of, and yet I absolutely hate gatekeepers telling you what counts as “real” creativity and who counts as a “real” writer.

  Two things have proven consistently true for me: (1) AI can become a crutch that stops you from learning your craft - whether that’s writing, coding, or anything else. Be very cautious of this. (2) The result is ultimately what matters. Obvious and lazy AI usage is obvious, but for those using it really well, you probably don’t even notice. Spending your energy trying to figure out if something is AI-assisted already feels pointless.

Books I’m loving

• Consider This: Moments in My Writing Life After Which Everything Was Different - Chuck Palahniuk. Recently finished and absolutely loved this. I’ve been writing more and more fiction lately so this was a well timed pick-up. A lot of actionable writing advice wrapped in memorable stories, making the book itself feel like a “show don’t tell” lesson on how to write well.

• Leaving the Casino from - I’m about halfway through and it’s been a good reality check. The ‘casino’ is treating your work like a slot machine and hoping for a jackpot instead of building something sustainable, backed by your values. As I’m trying to build something of my own, it’s helping me to ask: am I actually building with intention or gambling?

Worth doing

Reflect: There’s a lot of “end-of-year reflection” stuff online right now, and way too many apps brute-forcing a “wrapped” campaign (no LinkedIn, I absolutely don’t need you to summarise my year on your platform). That said, I’ve done written reflections for the past few years, and I do find them a great way to stop and remember all the stuff I’ve actually done in the last 12 months.

If you’re feeling that urge to take stock, here’s how to do it:

• Year Compass - My favourite. Print off a copy and do it on paper. All you have to do is follow the booklet. It’s free and available in a bunch of languages.

• Reflect on your year in 90 minutes - A great method outlined by which is actually pretty similar to the Year Compass in method, but even more straight forward and easy to get started with.

• Reflecting Forwards by - Uses archetypes and comes in two modes: first-timer (light) or deep dive. Also includes a collection of other yearly review templates if you want more inspiration to roll your own.

And a random tip: At the end of the year I try to clean all my email subs. I recently learnt that if you’re a gmail user this is incredibly easy, as going to this URL gives you a clean list of all your subscriptions with a one-click unsubscribe button for each. It’s even sorted by frequency: https://mail.google.com/mail/u/0/#sub

This is the last newsletter until the new year. I’m going to rest, recover, and do my own reflecting. Thanks for being here! Whether you’ve been reading for months or this is your first one.

If you’ve sent me a message this year, opted in for a paid subscription, or even just opened these emails every now and then, it means a lot to me. It’s crazy to think I’ve only been sending these regularly again since May, but I’ve made so many awesome connections that I’m very grateful for.

See you in January!

— Mike

I’m writing this on the train back from Paris to Berlin after a very hectic week, watching the countryside blur past, and thinking about my experiment to treat the last few months of the year completely differently than I normally do.

For me, December is usually like hitting “pause” in a video game. I stop doing, start planning, and wait to hit “play” again in January. There’s nothing wrong with that, but this year I tried a little hack my girlfriend uses for running her own business.

She calls it the bonus year.

Instead of hitting pause, it lets you switch to sandbox mode.

The bonus year (aka sandbox mode)

In November, she reviews the year, decides the main story arc is complete and tells herself: you’ve done enough.

From that moment, everything until January becomes a bonus level. Low-stakes time to try things without pressure. She picks one or two things from her “next year” list and does the smallest, scrappiest versions of them until the end of the year.

Because it’s sandbox mode, nothing’s at stake. It’s all extra XP and a chance to play around. Hence the name. It’s like having a little bonus year tacked on at the end.

This year I tried it myself.

My bonus year side-quests

Side Quest 1: Video podcast - I’ve been wanting to add video for months and kept planning to start “properly” next year. A few weeks back, I treated it as a bonus year experiment instead. I shipped a tiny solo video in a day just to figure out the mechanics. It wasn’t perfect, but it let me play around with the setup and gave me confidence to record several video episodes ahead of next year that I’m genuinely excited to release.

Side Quest 2: Paid subscriptions - Another “maybe next year” item that I decided to try now and see how it felt, rather than letting it sit on a list for later (or never doing it). The result was a handful of very lovely readers and friends upgrading to paid subscriptions!

Both experiments felt frictionless because I’d removed all the pressure. I was just playing around in bonus time.

Your own bonus year can start right now

Today is December 12th, which means there are roughly two and a half weeks left of 2025. More than enough time for a little bonus year.

If you have something on your “next year” list, consider this your friendly nudge to switch to sandbox mode and play around with the simplest, scrappiest version of it right now.

Subscribe now

Good stuff this week

On account of all the gallivanting around Paris this week, I haven’t had much reading time, so this will be short:

• Advice for a friend who wants to start a blog, from , one of my favourite newsletters from the wonderful .

• made me want to go find a retro calendar for 2026:

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There’s a scene in the Fellowship of the Ring where Gandalf and the gang (which is coincidentally a great band name) stand in front of a huge wall with a glowing door on it. The Walls of Moria.

Gandalf utters the magic words. Nothing happens. He tries again. Still nothing. He threatens to bash Peregrin Took’s head against it. He can see the problem. He can even see the damn solution, it’s literally glowing. But the door will. not. open.

I’m sure we’ve all felt like Gandalf at some point (minus the ancient wizard part). That’s actually the way I’ve felt a lot in the past five years, asking myself big imposing questions for which I had absolutely no answer for and no idea how to “open the door”: What do I really want to do with my life? What’s really meaningful to me? Why can’t I just figure it out?

Sometimes I could see the door glowing in front of me. Sometimes it was just a wall.

Worse, I solve problems for a living. I’m an engineering manager by day. I’m (usually) good at taking vague problems and turning them into concrete next steps. So why was I spiralling?

Why abstraction keeps us stuck

Then I learnt about rumination, and that there’s actual psychology behind why these kinds of problems keep us stuck. Psychiatrist Dr. K has a great video on it. He explains that when we think about problems in abstract, generalised terms, it interferes with our ability to solve them. The more abstract we get (”what’s meaning anyway,” “why does nothing ever work out”), the more our brains struggle to identify concrete actions we can actually take.

When your brain is in “what’s the point of anything?” mode, it literally can’t generate a next step.

The abstraction is too great. It makes us pessimistic, strips away the specific details we need to move forward, and leaves us with conclusions that feel profound but are completely inactionable. We might even think we’re problem-solving, but we’re actually just magnifying the problem and making it harder to find a way forward.

Like Gandalf, you might just be overthinking it.

Enter the Five Whys

This is where my LOTR metaphor falls apart, but stick with me.

Gandalf didn’t have the luxury of learning about ✨ corporate engineering processes ✨, but I decided to start using my own knowledge of them to my advantage. In engineering, we have a tool called the Five Whys.

Like a lot of modern tech processes, it was developed by Toyota in the 1970s (because of course it was). The idea is simple: keep asking “why” so that you can drill down from vague symptoms and big problems (“why wouldn’t the door open when we needed it to”) to specific root causes (“because Gandalf didn’t realise the riddle was literal”).

Often, doing this five times is all it takes. We use it at work all the time but I never thought to use it on my own problems.

So I decided to try it.

The Five Whys in practice

Taking a recent example from my own life, for the past year I’ve been spiralling on a problem: What should I actually do with my photography? I want to share it, but why, and where? Why do I even want to do that?

I’d find myself scrolling Instagram at 10pm on a Tuesday night, admiring all the work of other photographers, knowing all the photos from my last trip were sitting there untouched, feeling a deep urge to share my work, but simultaneously hating Instagram and the Zuck-ness of it.

I was stuck in front of the shiny door without a way through.

Starting with the problem statement, I asked myself why:

“I’m frustrated that I don’t know what to do with my photography.”

1. Why am I frustrated? Because posting on Instagram isn’t satisfying, but I still want to share somewhere.

2. Why do I want to share it if Instagram doesn’t work? Because there’s genuine joy for me in sharing my work and connecting with other photographers. Sharing motivates me to edit, collate, and “finish” my work.

3. Why don’t I like Instagram? Too many ads, no meaningful interaction, no space for context, and I don’t want to fuel Zuck’s empire.

4. Why not try other platforms? Because I don’t want to use even more social media. Actually I want to use less.

5. Why not just use the social media platforms I’m already using? Because I… haven’t?

And just like that, I opened the door.

Without really trying I came up with two ways forward. I already use Substack for this newsletter, so I could start there by: (1) Sharing photography in my newsletter posts, and (2) Sharing photos in Substack Notes.

I like the platform, it removes the Instagram sticking point, and gives me a way to try sharing again. And that’s what I’ve been doing! I don’t know if either will work long-term, but door one feels good so far. At least they haven’t lead me into Khazad-dûm.

Speak friend and enter

Jokes aside, the key thing I’ve been learning is that you have to try a few doors. And the nice thing is that in real life, there are almost always more doors to try out.

The best part is that they actually lead somewhere.

You walk through, see what’s on the other side, and recalibrate. It might not be the perfect door (and hopefully there are no orcs on the other side), but at least you learned something by trying instead of thinking. So you try another door. And repeat.

I’m sure this won’t work on everything, but if you’re stuck on something that feels unsolvable, and if you’re staring at a door you can’t open, give it a try.

You might be surprised how many doors just needed the right word to open.

I was.

Good stuff this week

• Internet companies don’t owe anyone free traffic - ’s hot take on why platforms don’t love you back, and why no one “owes” you traffic for existing. I’m very thankful I chose email as my place to write, but every day I grow more skeptical of the platform I’ve chosen to do it (Substack).

• The Big Book Launch Post - An incredible resource from on planning a book launch. I know I’m going to be coming back to this a lot in the next few months.

• An audience doesn’t solve your problems - breaks down the data on how many sign-ups he gets from a list of ~46k people.

• Can ChatGPT Land an Airplane? - A great watch if you want to be simultaneously infuriated and entertained by the limits of AI.

• And completely different to everything, watch an octopus learn how to play the piano.

You made it all the way down here! If you want to support the newsletter & podcast and get a few extras, you can do that here:

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This week a single idea changed how I’m thinking about 2026: leverage.

I heard it on Jonathan Courtney’s podcast The Unscheduled CEO. He mentioned that speaking at big conferences with solid pay creates less business value for him than working on his podcast with a few hundred listeners per episode. So he charges absurd amounts for conferences, because otherwise the opportunity cost isn’t worth it.

What he’s talking about there is leverage: building things that create enough value that you get to be selective about everything else. Leverage gives you freedom to focus on work you actually want to do.

This doesn’t necessarily mean working harder or being more efficient, but being aware of where you are and the things that could multiply your impact disproportionately vs work that goes nowhere.

Two ways you can immediately start creating leverage

1) Find your weirdos

My newsletter and podcast combined reach ~500 people who actually engage. This is embarrassing by typical creator standards. But I’m very appreciative for anyone who shows up and connects with any of this. My public projects help me find all you other wonderful weirdos who care and think about the same kinds of things I do. Those connections and opportunities make this completely worthwhile.

This is also why I genuinely think every creative should have some kind of public outlet on one “channel”, be it a newsletter or whatever you prefer. You don’t need a huge audience. You need a small but engaged one. The easiest way to build leverage is to share what you make.

Small, genuinely engaged audiences generate disproportionate returns.

2) Actually ask for what you want

Jonathan mentioned another key point: he doesn’t just wait for leverage to magically appear. Early in his career as a junior designer, his first corporate job wanted him commuting to another city five days a week. He hated it. So he just asked if he could work from the city he lived in instead. They said no. He found the right person to ask, asked again, and made it clear he’d leave if it couldn’t work out.

Within a week, they’d changed their policy.

I admire this because I still struggle with it. Asking can be scary. But so many things can open up when you’re direct and honest about what you need. If you’re struggling to make time for your creative work, have you explored your options? Asked for a 4-day week? Flexibility to work from home?

Of course, to do this you need to be good at what you do and be really comfortable walking away from stuff if it’s not working out. Not as a negotiation tactic, but because you genuinely know what you want and what’s worth it to you.

What matters most?

Jonathan shared the classic Tim Ferriss thought experiment: If you could only work 4 hours per week, what would you do?

It immediately exposes what you actually care about. For me, if absolutely forced, it would be writing this newsletter and working on the podcast.

And leverage can be anything you want more of. Enjoyment, money, influence, experience. But it’s worth asking: “what creates the most impact for what’s important to me right now?”

For me, heading into 2026, leverage means amplifying what brings me the most joy, connection, and opportunities.

And I can already see low-lift things I can do. The simplest being growing the visibility of Imperfect Creatives, which means getting more eyeballs on it, and some obvious changes like adding video to the podcast (which I’m already recording but not using, for no reason) and sharing it more widely.

For you, leverage might mean something completely different. Whatever it is, ask yourself: What could give me the biggest return - creatively, financially, emotionally - for the smallest input?

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Other good stuff this week

• Year Compass - The best tool I’ve ever used to reflect and start planning my new year. I do this every year and can’t recommend it enough. The 2026 booklet is ready and completely free, just print your own.

• A blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox - A very relevant read (and amazing title) from .

• 5 Years: 1 Word Per Day - A simple yet beautiful creative project. I can’t imagine being this consistent with anything honestly.

• The Sunk Cost Fallacy of Your Career - explains how reframing your career as a bouncy castle may be exactly what you need.

I’ve been using an app this week called How We Feel. It asks you to check in once or twice a day and name what you’re feeling. Specifically what you’re feeling. Not “good,” but “calm” (low energy). Not “bad,” but “frustrated” (high energy).

As someone with a lifetime subscription to low-grade anxiety, it’s been helpful. I quickly realised my mornings carried a background hum of pressure. Not quite stress or tiredness, but feeling behind before I’d even started the day.

Going through the process of stopping and really feeling and naming it made it obvious what changes I could make. I was grabbing my phone as soon as I got up, drinking coffee right away, rushing to make progress on whatever project was on my mind before work started. So now I’m on team slow autumn mornings. No phone. No coffee (gasp).

This came from listening to Chris Williamson chat with Dr. Marc Brackett, who studies emotional intelligence.

In the episode he points out that when you mislabel an emotion, you often reach for the wrong “solution”. Not that emotions need fixing, but that you end up responding to something you’re not actually experiencing. If what you’re calling “anxiety” is actually “stress” from being overloaded, no amount of calm breathing will help. You probably need to take something off your plate.

And then there’s the sneaky second-order emotions: feeling bad about feeling bad. You procrastinate, then feel guilty. You get angry, then feel ashamed.

Building emotional intelligence seems to be a lot about building the language and the curiosity to feel deeper, combined with the acceptance that all emotions are helpful information. The more precisely you can describe what you feel, the easier it is to regulate it. Is it stress, or envy? Depression, or exhaustion?

A great coaching teacher once told me: when you mess up, get feedback that stings, or feel something uncomfortable, respond with “How interesting.” This works with emotions as well. It shifts you from judgment to curiosity. “How interesting I feel defensive right now” or “how interesting I made that mistake.”

It opens you up to actually feeling whatever you’re feeling, rather than numbing it. Because you can’t numb selectively, and you can’t feel selectively.

When you stop numbing the uncomfortable stuff, you don’t just get better at handling frustration or anxiety. You also open yourself back up to things you might have accidentally blocked out: wonder, curiosity, genuine excitement.

This week has been a great reminder of that mindset.

On the pod

It’s a wrap for season one of the podcast! I hadn’t intended to do “seasons” but after a few scheduling hick-ups I broke my streak (an episode every two weeks for six months). Not a bad effort, I reckon!

I figured it’s a good time to pause rather than scramble and go into panic mode to fill the gaps. Which was absolutely my first instinct before I remembered I’ve spent the entire year interviewing people about not doing exactly that.

So I’m taking a little pause, but the pod will be back in January. I’ve got some things already lined up for 2026 that I’m genuinely super excited about.

If you’ve been listening and have thoughts, what worked, what didn’t, what you’d like more of, please drop them here or hit reply. If you DIDN’T listen, I’d love to know why as well.

This newsletter will continue every Friday as always.

Other good stuff this week

• 🍕 One of my favourite podcasts hosted one of my favourite creatives - Brennan Lee Mulligan Eats His Last Meal. A wonderful, open, honest, and hopeful discussion and a masterclass in interviewing. Podcast goals!

• 🧪 A practical guide to career experiments - Loved this article from , which urges you to bridge the gap between career clarity and real action by running small experiments, skill stacking, and connecting with the right people.

• 🗞️ Death by a thousand Substacks. An interesting take on the very platform I use to ship this newsletter, that claims it is “the consensual hallucination of independence and ownership”. Is Substack the Amazon of publishing?

I made massive progress on my non-fiction book project this week. Like, 200% more than the last months. I was absolutely locked in. And then I looked up and realised I have no podcast episodes prepped, I did no guest outreach, I’m writing this newsletter at the last moment, and I haven’t done those other 20 things on my list. Whoops!

And it stings even though I know it’s true: you can’t max out everything at once.

This week I chose the book. Partly because daylight savings is here and I now wake up every day at 6am whether I like it or not (and feel like a zombie by 9pm). And partly because I probably need a few intense bursts to actually get the thing done anyway. My default morning-person mode is in overdrive so I figure I may as well use the early writing sessions to my advantage.

In the past, that kind of accidental hyperfocus would trigger a guilt spiral and I’d hate that I let so many things fall by the wayside. I’d start comparing (“that person juggles five things amazingly and you can’t handle three!”) or doubting everything (“why are you bothering anyway, who will even want it? And you’ll never be as good as <insert unfair comparison> anyway”). And these both get worse when I’m focused on a project I really, really care about.

I’m trying to remember a few things that help me when this spiral starts:

1. You get to choose again tomorrow. This week was the book, next week is whatever I want. The only way to lose is to stop choosing altogether. To get so caught up in what you’re not doing that you stop doing anything. I get to define what progress looks like, because my own creative projects don’t have a boss (other than me) or a deadline. So keep choosing to turn up and play.

2. Doubt is just a sign you care. ’s perfectly timed post (and absolutely remarkable new hardcover) reminded me that doubt is a great sign you care. It’s a normal side-effect of caring a lot about your work, and it would be weird (and not a great sign) to not doubt yourself at all.

3. Learn or leave. Comparison usually sneaks in when I’m reading something on my phone under the pretence of “learning” or “research”, so I try to ask myself: am I actually learning something from this? If yes, great, capture that and move on! If not, the solution is almost always to put the phone down and go take an actual break.

4. Abundance mindset is the most joyful way to live. I love the expression: only look at someone else’s bowl to check they have enough, not if you have as much as them. You can be totally impressed by someone else’s work and happy for them without turning it into a self-critique.

On the pod

Last week I published an episode with where we chat about his wonderful writing and photography. We talked about everything from borders & cultural identity to shooting Leica and building a meaningful archive of the present: “The present will have its own 2025-ness and people will be nostalgic for it one day.” (Spotify, Apple, episode details)

Other good stuff this week

• 📚 Currently burning through the On the Calculation of Volume book series. Think groundhog-day-time-loop-but-it’s-literary-fiction. Sadly only the first two books are available in English so far.

• 🎵 Re-discovered Brian Eno’s Music for Airports and Secret Life as writing music after this podcast episode. It’s been absolute brain fuel for the early morning book sessions.

• ✍️ Found Help This Book whilst looking for ways to get feedback on my book. It comes with a copy of Write Useful Books which so far seems like an incredibly helpful resource.

A few days after our chat, my mum handed me an old external hard drive that I thought was long gone, lost in the chaos of moving to Germany a decade ago. After talking to Ari, I couldn’t not plug it in and go hunting for my old photos. And I was hunting for something very specific.

Back in 2007, sixteen-year-old me went on a two week trip with my mum around China, armed with both a camcorder and a tiny point-and-shoot. That trip, and the time I got to spend with my mum, is incredibly special to me. It also meant the start of a new hobby, photography, something that’s stayed in my life ever since, and it sparked a lifelong love of travel. And yet I had not looked at those photos for at least 15 years.

To my surprise, the drive worked, and buried in its folders I found literally thousands of photos of the trip. It’s fair to say I was documenting absolutely everything, mundane or not.

Looking at those photos now, I can’t say they’re masterpieces, but they carry so much meaning. It’s like peering through a little window at a previous version of myself, one that was curious, shy, and completely in love with a new hobby.

Seeing those images made me think about all the other things I’m creating now without knowing exactly why or where they’re going. That’s something I catch myself asking a lot, whether it’s with a specific project like this newsletter, or life in general.

Even though you always hear “journey, not destination”, that’s never been me. I always want to know the destination. But Ari’s way of working, and rediscovering those old images have given me something concrete: the idea of building up an archive of work to look back on with a different lens. I like the idea that future-me might stumble across these words or photos and appreciate them in ways I can’t imagine now.

We trust ourselves in the moment to do the work that feels intuitively right, and trust our future selves to figure out where it’s going.

Savouring the mundane feels like a small superpower and a way to enjoy the present. That’s been another nice byproduct of this. I’ve been picking up the camera more and capturing the small moments in daily life. Trying to embrace the idea of not knowing where it’s all headed, but trusting that it’s worth doing anyway. Building something worth revisiting, even when we don’t know what it’s for yet.

Perhaps this post will be a little reminder to future-me if he forgets that again.

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If you want to listen to the full episode with Ari, you can listen on Spotify, Apple, or wherever you get your podcasts. (Full show notes here.)

Last week I was in a section of my favourite bookshop I don’t usually visit and stumbled into what’s now my book of the year: Poor Artists. I wasn’t searching for anything specific, it just caught my eye (how can a book with “The White Pube” on the cover not?) and then I couldn’t put it down.

Accidental discoveries like that are what I love most about actual bookshops. You get to browse the aisles and find something you didn’t know you needed, algorithms be damned.

Weirdly, a lot of the last few weeks has been about getting outside my usual bubble, visiting a few random galleries, having conversations with strangers at train stations (the most unlike me thing ever, but I promise it happened), exploring areas I’m not usually in. It’s been rather lovely, even if half of it happened accidentally.

I think I’ve been opening up more. Being more open to random things happening, letting some things unfold without needing to plan every detail, going with the energy of what feels good or exciting.

Partly it may be the impact of Poor Artists. There’s a bit in the book where a character talks about stopping the constant evaluation of whether a thing is GOOD or BAD. Instead, feel the ENERGY behind it. Is it pulling you forward? Does it feel alive? That’s the signal. The judgment, good, bad, worthy, embarrassing, that all comes later, and usually from a defensive place.

I tend to slip into defensive mode by default. Tracking metrics, feeling behind, planning every step. I read somewhere that it’s almost impossible to grow from a place of defence. Growth needs curiosity and openness, not armour. Control feels safe, but it also blocks the surprises I crave most.

These last few weeks reminded me that the best things often happen by accident, but only because I showed up on purpose. There’s something worth protecting in that.

Community Spotlight

I’m trying something new. This space is to celebrate and share stories from within the Imperfect community. If you want to be featured, just hit reply and tell me what you’re working on. I’d love to do more of these!

When you first subscribe to this newsletter, I ask a simple question: What brings you here? Most people skip it. Diana didn’t. She wrote back to tell me she’d finally taken the leap to write full-time after 30+ years of being “sensible.”

After decades with a “real job” while her writing dream sat in the background, stopped waiting for permission and launched her first novel last year. Now she’s writing full-time, working on book two, and figuring out how to stay financially afloat while finally doing the work she’s been dreaming of all along.

I’m really excited to share her story, and a short Q&A about her journey:

What pushed you to take the leap after 30+ years? What changed, internally or externally, that made you say “now”?

I did a lot of creative writing all through my education. But after school, I got caught up in others’ expectations of what “success” looked like. I became successful through everything except writing. After several decades, moving to another country, and finally freeing myself from needing others’ approval, I asked myself, “Will I be happy if I die having never written a novel?” When the answer came back “no,” I committed myself to writing.

What’s one thing you wish someone had told you before you made the leap?

I wish someone had told me that the most important thing is just to keep doing what you love, even if it’s not a career. I wrote nonfiction, blogs, articles, etc. but mostly stayed away from fiction. I think if I had continued writing creative stories even while doing other things, I would have honed my craft so much more. And, I would have enjoyed being creative all the while.

You mentioned you might need other outlets to stay financially afloat. How are you navigating that balance - between protecting your writing time and keeping the lights on?

The one advantage of having had professional success for so many years is that I have a good amount of savings. I also have continued one professional pursuit I truly enjoy--being a certified hypnotherapist and coach. I work with many people, including creatives feeling insecure, stuck, or anxious. The tools and skills I have mastered are transformational, and I love to share them with others.

Where can people find and support your work?

Check out my books on Amazon, my new Substack newsletter, and my hypnotherapy website. I’m also on Instagram, X, Facebook, & LinkedIn.

Huge thanks to Diana for sharing her story so openly!

Elsewhere in the Imperfect world

It’s been a busy week! Together with we published this write-up based on our podcast episode on how to let more art into your life. Check it out for some lovely pictures of moon jars!

And if you missed it, last week on the podcast I spoke with Jacob O’Bryant about his journey into becoming a startup founder, and why he doesn’t regret quitting and getting a job again.

Whenever I saw one of those shots where the creator walks away from the camera and down the street, all I used to think was that it looked cool. Now I see someone walking twenty meters, stopping, jogging back, checking the footage, realizing they were out of focus, and doing it again three more times.

I learned this the hard way when I tried filming my own video walking around Berlin. That’s what happens when you actually do the thing you’ve been daydreaming about.

You kill the dream.

This has happened to me over and over since I started creating online. Podcasting was a dream for a long time. Deep conversations, meaningful connections. And it is! But it’s also hours spent editing, fixing audio issues, juggling schedules, doing guest outreach… the list goes on.

It’s the same with this newsletter, or the book I’m writing, or any other “dream project” I’ve started. I’ve written about it before and still keep relearning it.

The dream version is easy and wonderful. The real version is full of unexpected, unsexy details you never thought about until you started.

And that’s beautiful!

Once you know how the sausage is made, you can’t un-know it. You spot the hidden details behind everything. It’s the feeling of growth in real time.

I watch stuff differently now. I see the cuts, I notice when someone nailed a transition, I appreciate the lighting. I’m definitely not an expert, but I’m a tiny bit more literate after trying it once myself.

You can watch endless videos about starting a business or read a hundred articles about writing a novel, but none of it teaches you what you learn in the first day of trying it.

The only way to graduate from fantasy into knowledge is to ruin the fantasy.

I try to remind myself of that every single time I start something, and weirdly, the more I do it, the more I’m starting to enjoy the process and find it kind of addictive.

So I hope you kill your dreams, make a few sausages, and see what happens.

On the pod

This week’s episode is a perfect companion to this newsletter. I spoke with Jacob O’Bryant, who describes himself as a “recovering entrepreneur”, and his story is about exactly this: killing the dream by actually doing the thing.

Jacob quit his job in his early twenties to build his own products full-time. He spent four and a half years working on projects like The Sample (now Yakread, which is how I found him). And after all that, he realized that entrepreneurship wasn’t actually what he wanted. The dream didn’t match the reality.

What I loved about this conversation is how honest Jacob is about his journey. He’s not bitter and he doesn’t regret it. He just learned what the work actually required, and discovered it wasn’t for him. Going back to a day job wasn’t defeat, it was clarity. He’s now exploring “invention” as a career path and building meaningful things without the pressure of turning everything into a business.

Listen to the full conversation with Jacob O’Bryant →

Worth your time

• “Are you Serious?” - on seriousness, the difference between people who talk about doing things and the people who actually do them, and how to be committed without losing your sense of humour.

• This cold message got me $100k of work — Another banger from . Honest, practical advice on outreach that doesn’t feel slimy. The 100 Connections challenge is also great!

• Last weekend whilst browsing in my favourite bookshop I picked up a copy of “Poor Artists”. The book is “fictionalised non-fiction”, following the struggles of an artist trying to make a living off their work and navigate the art world. It’s honest, funny, and sometimes surreal. I’m already almost done reading it. It may be my book of the year. Highly recommended!

It’s also a return to the 9-5, to structure and routine. It had me thinking about which habits I have to keep my side projects moving. Also, a lot of the feedback I get from readers of this newsletter is that the biggest struggle is keeping energy and time aside for projects outside the day job. So I want to share what’s actually working for me right now.

First, the mindset: I try to accept that my todo lists will never be done. The calendar won’t ever empty. There will always be more emails, more chores, more ideas. That’s fine. That’s life. Knowing that helps. The goal isn’t doing everything, it’s doing the things that matter most at the right time, and keep showing up where/when you can. On that note, I’m a huge fan of Oliver Burkeman’s book Four Thousand Weeks: Time Management for Mortals.

What I’m actually doing:

• One goal per day: This is stolen from my day job where we follow lean processes. Every single person sets one goal daily. I now do this for my side-projects as well. Just one thing to do fully, no matter what else gets done. It’s amazing how much you can progress when you commit to this. This is by far the most important thing I do for my own work. Some days I don’t make it, or I need a break, but I try to stick to this as consistently as I can.

• Separate planning from doing: Ali Abdaal calls this the the pilot vs. the plane vs. the engineer. Spend a little time setting the course, most of your time flying it, and a tiny bit improving the system. I review my calendar weekly and briefly each day (pilot), then I commit to what’s there and execute (plane). My source of truth is my Google calendar. When I’m overwhelmed with chores or it feels like too much is popping up ad-hoc, I dump everything into a temporary list, do as many as I can in one go, and schedule whatever’s left.

• Capture ideas frictionlessly: For simplicity’s sake I use Apple Notes on my phone. Any idea that gives me even a tiny spark goes in there. Newsletter topics, podcast guests, book or product ideas, whatever. I don’t even filter or organise it other than putting “(newsletter)” or “(pod)” at the beginning of some notes. Sometimes I use Voicepal to walk and talk instead of sitting to write. The point is the same. Capturing thoughts should be easy. It’s the top of the funnel for everything else.

• Never ignore a creative spark: Sometimes I should be doing one thing, but I get a random burst of excitement around another, so I go all in and ignore everything else. Yes it’s impulsive and chaotic, but I’ve found this works better than forcing my brain to do what it “should” do. As long as I come back to the important stuff when it needs to happen. Knowing the difference between urgent and important (one of my first posts!) is really helpful here.

• Reflect regularly: Writing helps me sift and sort. I’m trying short monthly reviews right now. How I’m feeling, what I want to start or stop, finances. I do this on actual pen and paper because it forces me to slow down. I am doing it monthly because that helps me spot patterns and see how much time I actually spent working on the stuff I thought I wanted to that month and “piloting” ahead of the next one.

• Commit to a cadence: I’m sure it’s not the same for everyone, but I make more progress when I commit to some kind of timeline. Having bi-/weekly schedules for my newsletter & podcast forces me to actually hit publish rather than endlessly tweaking my work or procrastiworking forever.

• Use AI as a tireless assistant: I know AI is a divisive topic, but a lot of my side-project work I do solo, and having an assistant makes my life so much easier. I export all my content into a Claude project and use it to check typos, keep track of my guest list, do data analysis, and to brainstorm. I don’t write with it as the whole point of the newsletter is to have an excuse to write, and I don’t want to put out slop. But for grammar checks, quick summaries, and idea refinement it’s actually helping a lot.

The reality is that this not perfect and I still struggle making time and energy for everything I want to do. I’ve accepted I’m chaotically organised. I love lists and planning, but I can also be reactive and quick to act. I tend to write plans, do half of it (plus a bunch of stuff that wasn’t even on the plan), then come back and adjust.

It’s not perfect, but it keeps me moving. I’d love to know what works for you, so please do hit reply and let me know what your approach is!

On the pod

Last week: CouchPolyglot Laura on building a successful YouTube channel, language learning, and why she’s chosen to keep her day job at 80% instead of going full-time as a creator. Listen here!

I also wrote about what her approach taught me about sustainable creativity: “What if you don’t go all in?”

Worth your time

• I really enjoyed this piece from on the mental exercises he uses to confidently pivot into a new space, blending community, real-world learning, and playful building (in public) to find his groove.

• I just found out one of my favourite podcasts (Eat, Sleep, Work, Repeat) is also on Substack through this piece about how we need to adapt to the new rhythms of work.

• That led me to find this wonderful interview with Brian Eno on his book about art (“children learn through play and adults play through art”). A strongly recommended listen!

So whenever I meet someone running a great channel sustainably and actually enjoying it, I need to understand how they’re doing it. This week, that person was Laura from CouchPolyglot.

Laura has learnt 7+ languages and shares her learning process on YouTube to 44k subscribers. She’s acquired brand deals and built up a Patreon community that support her financially. Crucially, she’s still deliberately kept her day job at 80% to maintain balance. She could probably go full-time with content creation but she’s chosen not to.

Her approach completely contradicts the “go big or go home” mentality you see online. Laura has built something sustainable that serves people without burning out or risking financial stability.

So here are a few questions you may want to ask for your own work based on my chat with Laura. If you’d rather jump straight into the full episode, check it out here.

What can I actually control right now?

When the pandemic hit, Laura felt powerless. Her job changed overnight, she couldn’t see friends or family, everything felt uncertain. So she focused on the one thing she could control: creating something she was passionate about.

“I felt like I needed a project that I was passionate about and that would keep me sane,” she told me. “So I woke up one day and I said, I’m going to start a YouTube channel.”

She didn’t wait for perfect conditions. She just started with what she could control.

Your version of this might not be a YouTube channel. But there’s probably something you keep saying you’ll do “when things settle down” or “when I have more time.” What if you didn’t wait? What’s the smallest version you could start with today?

Am I creating for ten thousand, or for ten?

Laura’s original thinking was simple: as a one-to-one Italki tutor, her teachings disappeared after each session. But if she made a YouTube video, ten times as many people might benefit from that lesson forever.

She wasn’t dreaming about thousands of followers. She just wanted to help a couple more people with the same amount of effort. The bar was low, the goal still felt meaningful, and she had a really clear picture about the people she was able to help.

When you think about your creative work, are you obsessing over scale and reach? Or are you focused on genuinely impacting specific people? One approach leads to stress, the other to sustainability.

What would “good enough” look like?

Laura’s early videos had terrible video and audio quality. She didn’t have fancy equipment or editing skills. People still found them helpful and left encouraging comments. Looking back, she’s grateful she didn’t wait for perfect conditions.

This hits close to home: I’m constantly battling perfectionism with my work (hence the name). Laura’s reminder that “something imperfectly done is better than not doing it” is exactly what I need to hear on repeat.

What’s your version of ‘good enough’? Not your ideal. Not what an algorithm wants. What would be genuinely useful to someone, even if it’s messy?

What boundaries am I willing to protect?

Laura is intentionally NOT trying to maximise her YouTube “success”. She could probably go full-time, create courses, build a bigger business, make more money, but she’s chosen not to.

“I’ve met throughout the years, a couple of very stressed out creators who did this full time. And I always knew that I didn’t want to be that person.”

She has found her sweet spot: 4 days a week at the day job, content creation and language learning on the side. When she’s overwhelmed, she publishes less. Wellbeing always comes first.

She’s also still supporting her creative habit through brand deals and Patreon supporters, which is proof you don’t have to go all-in to make something financially viable. It’s about finding your right lever-combination.

What would this look like if I don’t go all-in?

Laura built exactly what she wanted: a sustainable creative project that helps people, brings in some income, and doesn’t dominate her life. She’s proven you don’t have to choose between meaningful creative work and personal stability.

The goal doesn’t have to be to build the biggest thing possible. It can be to build the thing that’s right for you, for your life, and for the people you want to help. I think it’s worth asking: What would your work look like if you weren’t trying to maximize it?

I’d love to hear what you thought of this week’s format. I’m also planning to add a community spotlight section to future posts, so if you’re working on a creative project, making art, or building something on the side, hit reply and get featured here! - Mike

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