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.

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.

.

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.