My "Going Solo" Reading List

Back when I first started down the indie career path, I distinctly remember the feeling of finding other, smarter people who had navigated the path before me. Such relief. There are so many things to figure out, so part of the benefit is not having to build things from scratch—but part of it is just reducing the sense of isolation.

So, if you’re considering "going solo"—indie consulting, contracting, freelancing, solopreneurship... whatever you call it!—here are the resources that were the most helpful to me:

Tom Critchlow

Tom is a long-time indie... and I think the first place I even heard the term "independent consultant." Start with:

• A map for indie living - If you read one thing on this list, read this. It outlines the progression of pursuing this kind of work, including "above the surface" (what to do), "below the surface" (what to think about), and potential failure modes... for each phase! It also introduced me to his concept of "narrative aircover" and the fact that indie life is about energy management, more than time management—both have been super important for me.
• The Strategic Independent - This is Tom's magnum opus. It's a series of essays that will eventually be a book, but for now is free to read online! Just browse around and read what seems interesting, but I loved Workshops as Portals and Rejecting Specialization.

Elena Verna

Elena is my hero and role model when it comes to career stuff. She calls this type of thing 'solopreneurship' and has mastered the art of career independence. Her model of interim roles, advising, and content creation has been my aspirational template for years. Some concepts to check out:

• Grow Your Career Like You Grow a Product - The article is great, but the mental model itself was the major unlock for me—as someone coming from a growth/marketing background, it showed me that you can use you professional skillset... to grow yourself. If you come from a different background, you can still apply the same framework: How can you treat your own work as a kind of client? How can you create value for the business you're building for yourself?
• The path to your first advising contract - "Advising" is at the top of the indie job role totem pole, but how do you get started? Read this.
• Unpacking what it means to be an interim leader - "Interim" is also very trendy, but not super well understood. This is a great 101 guide to how it works. (Shameless plug: Elena let me write a guest post about how to get started, if you don't have her credibility and clout: How to land an interim leadership role… if you’re not Elena. I think the "Interim vs. Fractional vs. Advising vs. Contracting vs. Consulting vs. Freelancing" section may be helpful, if you're new to all of this!)
• A solopreneur's guide to pricing yourself - Very practical tips on how to evolve what you charge—from free gigs to $4,000/hour advising 😳

Paul Millerd

Paul is one of the defining voices of this approach. As a former McKinsey guy, he brings a unique take on both leaving a glamorous career path, as well as the differences between indie consulting vs. big four consulting. I wouldn't say there's one specific article or piece from him that captures everything, but check out his newsletter.
And if you're open to something more long-form, Paul is best known for his book, The Pathless Path. He published it on his own, so he's also got a lot of great insights on indie publishing. You can read his post from the first week of launching it... and then his reflections (and transparent stats and numbers!) on his unexpected, but progressively expanding success: I (accidentally) launched my book a year ago and then it magically sold 10,000 copies and then I sold 50k books (and I didn't predict this either)
Paul is also a great curator and connector—this list of '50+ links worth reading' from 2022 put me onto a ton of resources that helped me figure things out.

Kevin Kelly

Author, futurist, Wired magazine founder... Kevin is known for a lot of things, but he's the OG in a lot of ways. Start with:

• 1,000 true fans - The concept from this essay kickstarted the creator economy with a simple point: if have 1000 people willing to pay you $100/year for your work, that's $100k, which is enough for most people to live.
• Flounder Mode - An interview with Kevin by another one of my heroes, Brie Wolfson.

More

I want to keep adding to this list, so consider these additional bullets as bonus items.

• Behzod Sirjani's Me-as-a-Service. I find Behzod's perspective particularly valuable because, in addition to being super thoughtful about how to approach solo life, in general, he also focuses on a different mix of services, including courses and trainings.
• Shlomo Genchin’s How I get clients as a freelance creative. Arguably the biggest question for anyone starting down this path is... how do I find clients? It's a big topic, but this is a great, concise framework: Trust / Pain / Taste. Plus: memes!

What am I missing? If you're exploring this path, what's the best thing you've read on the topic?