Resources for Creatives & the Career-Confused

A curated list for the successfully confused & permanent career-questioners.

Hello! Today is a special edition of this newsletter.

If you’re like me, you sometimes think about what it actually means to be fulfilled by your work, and question what you should be best spending your time on. Maybe you've dreamed of a sabbatical, a portfolio career, or finally taking your side project seriously. Or maybe you're tired of optimising your life around other people's definitions of success.

If you’ve ever asked “is this it?” then these are some (hopefully) helpful resources for you. These are things which are personally helping me on this very journey.

Keep in mind: No amount of research will set you free. These resources are just starting points for your own experiments. The only way forward is to try things, fail at some of them, and course-correct as you go.

I’ll try to keep this list updated and I’d love to get your suggestions as well!

Books

Identity, Work, & Meaning

• The Pathless Path - Paul Millerd: Essential reading if you're considering any path other than the traditional one. Paul's honest about both the freedom and uncertainty that comes with stepping off the conventional track. This book started everything for me and this newsletter wouldn’t exist without it. Good Work is also fantastic.

• Think Big - Grace Lordan - A very practical book based on behavioural science to help you figure out and achieve mid to long term goals. A great book if you’ve hit a plateau and you’re not sure what you want next or how to get there. Gives you plenty of hands on exercises you can do.

• The Earned Life - Marshall Goldsmith - A book to make you think about what fulfilment really means, and how you might get there. I wrote about “The Triple A’s” (Action, Ambition, Aspiration) based on this book as I think it’s a really helpful framework for thinking about what your work means to you.

• Emma Gannon - The Success Myth: This book came at a really pivotal moment for me. I’ve always chased the next achievement and prioritised “traditional success” over “everything else”. But I also wanted “everything else”. It was helpful to hear how Emma navigated this, and each chapter leaves you with some nice questions to reflect on your own life and where you want to go.

• Punk Leadership - Phil Bennett: Work in tech, but not sure how to make a positive difference in the world? This is the book for you. Applicable to everyone, not just those in management roles. (I also spoke to Phil on the podcast about this book.)

• Tiny Experiments - Anne-Laure Le Cunff: Perfect for over-thinkers and perfectionists. Instead of grand life overhauls that paralyse you into inaction, this book teaches you to run small tests with your life. Lots of really good stuff in here, like “social flow”, the value of liminal spaces, growth loops. Fully recommended!

• Four Thousand Weeks - Time Management for Mortals: Trying to do meaningful work, especially if that means balancing side-projects and full-time jobs, can be exhausting. The temptation can be to think, “if I just manage my time better, I can do it all”. This book gives you an honest reality check.

Business building / Solopreneurship

Essential reading if you’ve considered making money from your creative work, on the side or full-time:

• Million dollar weekend - Noah Kagan: The simplest, no-nonsense take on ‘how do I actually build a business online and make something people want to pay for’.

• The E-myth Revisited - Michael E. Gerber: It’s a classic, and I’d take it with a pinch of salt (it’s mostly about franchising), but it definitely gave me some new mental models and changed how I think about starting my own business as well as what scaling it would look like.

• $100M Leads and $100M Offers by Alex Hormozi. I know Hormozi lands in the “hustle culture” genre, but these are still useful to read if you want to learn how to make money from your projects.

Podcasts

• The Tim Ferris podcast is still golden because the backlog is huge, if you have a guest in mind or a topic in mind, you can search the archive (or ask AI to do that for you!) and you’ll almost always find a few deep dives on your topic.

• Creator Science - Creating content is getting easier, breaking through the noise is getting harder. I really like the ‘experimentation’ approach from Jay Clouse and how openly he shares his own journey as a creator.

• How I built this with Guy Raz - Interviews with entrepreneurs on how they built their businesses (also recommended by Evelyn on my podcast!)

• My own podcast, Imperfect Creatives. Yes, I had to sneak a little self promotion in here. But literally the point of the podcast is talking with creatives and founders who have navigated this journey!

Newsletters & Blogs

• The Way of Work - Rick Foerster: The newsletter I wish I was skilled enough to write. Rick says it best: “It’s about exploring the paradoxes of work: the promises it makes, the disappointments it delivers, and ultimately, how we make it work for us.”

• Hype Yourself - Lucy Werner: If you’re doing creative work and want to make money with it, you will need to figure out how to market yourself. Lucy has fantastic resources on this.

• The Pathless Newsletter from Paul Millerd is great if you’re looking for more thoughts from Paul on modern work.

• The Next Chapter from Vinamrata Singal is great, start with On Sabbatical for an honest look at what it’s like stepping away from a successful tech career to realign with what you really want (and you can also checkout her interview on the podcast here).

• Becky Isjwara writes fantastic essays about living a creative life and being a multi-hyphenate.

• Joan Westenberg writes great essays on modern work, tech, strategy, philosophy, and everything in between.

• The AuthorStack - Russel Noherty - If you want to make money with your writing or become an author in any way, Russel has a huge backlog of resources, books, and posts all about this.

Community (Find the others)

Find your people. I strongly believe you should join a community where you can belong and meet others on a similar journey. Do this in person if possible! The internet can't replace real conversations over coffee about what you're actually going through. Every single “post-recording coffee-chat” of my podcast has been the best part about doing the show.

• Paul Millerd’s Pathless community is a good place to start (and this is now the third mention of Paul in this newsletter).

• Go to Meetup.com, have a browse for local communities, go try some! A few cities also have Substack meetups these days, which is a great way to meet interesting people. If you don’t find anything, consider starting one and see if you enjoy it. Running meetups has allowed me to meet some really cool people in my city.

• If you’d like to learn how to build and sustain your own community, checkout Rosie.land for a huge catalog of knowledge. I’m a huge fan of Rosie’s work.

Tools for Thinking

• Journal regularly. Yes, it does work. Yes, you should do it. Any method, but I suggest trying it with an actual physical notebook and a pen. It forces you to slow down. If you really want to go digital, try Day One.

  • If you speak German, this is a great journaling blog & newsletter, it’s from my partner, and I may be biased, but it's genuinely excellent and her approach to reflection and writing is what got me started with journaling in the first place.

• VoicePal (iOS, Android) is great if you’re a talk to think person like me. Turn your voice notes into text, and get interesting questions back.

• Consider coaching. Talking to someone can help a lot, even if it’s just to vent or get some feedback. Doing this with someone who’s trained on how to guide the conversation can be very effective. I offer a few limited, totally free coaching spots for this very reason. Otherwise, the least effort way to try out coaching is a platform like BetterUp (that’s exactly how I got into coaching in the first place).

That’s it for now! I’m sure this list will grow and change with time, and I’d love your suggestions, so please let me know what’s helpful or what awesome resource I’ve missed.

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