Year 1 as an indie consultant

Exactly 365 days ago, I started my first day of work as an indie consultant. It felt like the first day of school, except it was only my first day of school, so there was no sense of collective excitement, no gaggle of other kids also looking to make friends, and no teacher to welcome me into the classroom. It was just me and my butterflies and my laptop.

I felt curious, nervous, motivated, and self-conscious, but I definitely didn’t feel alone. A big reason for that is the writing of other indie consultants and creators. These folks — Tom Critchlow, Venkatesh Rao, Behzod Sirjani, Paul Millerd, and others — were the closest I had to teachers, and their reflections allowed me to learn some of the hard lessons the easy way.

So in that tradition, here’s a look back at my Year 1.

Year in review

I certainly haven’t figured it all out, but being out on my own has forced me to ask hard questions about what I wanted from my work and, more broadly, what I wanted from my life. I’ve loved that.

Year 1 confirmed that I can make a solid living out on my own. It has given me an even deeper appreciation for my independence. It has allowed me to spend more quality time with my spouse and my friends. And it has made me comfortable with the fact that the answers to the deeper questions — who I am, what I want, how I live, what I’m making — are not settled and probably never will be.

I decided go indie because I wanted to travel the business world, in a way. I’d spent the majority of my career at a single company, and after a little over a year at an early stage startup, wanderlust kicked in. (Some of this was literal wanderlust: I’d left Squarespace in February 2020 to travel for a year with my wife, only to never board our first flight because of Covid.)

There was so much I didn’t know because I’d seen so few companies up close. I knew I liked founder-led, product-driven tech businesses. And I knew I was very good at technical data analysis, understanding founders, and clarifying complex problems. Indie consulting felt like the best way to gather as much context as I could and develop a clearer picture of who I was and how I wanted to be.

I also had a hunch I’d be well-suited to the role. I’m very low ego, so the low status of indie consulting felt comfortable to me even though it would feel uncomfortable to most. I like tinkering, so constantly re-arranging my business felt like a fun puzzle for me even though it would feel like a chore to most. I’m exceedingly curious, so highly varied work felt energizing to me even though it would feel exhausting to most.

I half-jokingly told people that Year 1 was all about “finding Andrew-market fit.” The psychological safety created by this Year 1 mission allowed me to play without worrying about what it all added up to. I was willing to take on a wide variety of work and wasn’t going to be precious about engagement structures, pricing, or positioning as long as I felt I was learning. Now that I’m at the end of Year 1, the bill’s come due: Time to add everything up.

Truth is, I’m still not sure what it adds up to. But I’ve learned over the course of the year that that’s okay. I feel a bit like a bowerbird, wandering the forest gathering the scraps that interest me. The bowerbird doesn’t lose sleep wondering what it all means, and neither should I. (Though like most animals, the bowerbird’s motivations are perhaps easier to understand: He gathers objects to attract a mate.)

For me, the process of wandering and gathering is the meaning of the work. My purpose is very simple: To observe, deeply, the world around me. To understand and, hopefully, to be understood.

The overwhelming majority of my work has been with just three clients, which surprised me. I found my clients through former colleagues who had joined new companies. In each case, I charge a day rate and embed deeply for 1-3 days each week over the course of at least several months. Each week I join the companies’ weekly leadership meetings and meet one on one with the founder CEO. I also spend time with the data and go to market teams, build data infrastructure, do one-off analysis, prep board decks, or do whatever else needs doing.

Though all three CEOs hired me with a few immediate problems to solve, the truth is that I was brought in with a vague mandate: “Help us understand the business better so we’re working on the right things in the right way.” Now that I have a complete picture of what’s going on, I’ve shifted from individual projects to broader team development questions. Despite my attempts to avoid the title of “coach,” I find myself doing more coaching than I expected, and enjoying it. It’s all the good parts of management without the bad.

Lessons I’ve learned

Indie consulting feels way less risky than I expected

I expected to feel a constant, low hum of anxiety. Instead, having a basket of stable clients has dramatically reduced my angst. I spend more time thinking about upside questions than downside questions. I find myself asking “What could make this go right?” much more often than “What happens if this goes wrong?” This is true both for my work with clients and for questions about my non-work life.

It’s totally fine to charge based on time

Most indie consultants I talk to give similar advice: Figure out how to charge for value rather than time. This will maximize income, but it can be bad advice.

My goal is not to maximize income but to do interesting work. Often simply charging for my time is the best way for a client to give me access to the good stuff. Charging for value can be a trap that forces you to commodify what you sell, to package it and make it predictable. I’m actively avoided commodification. (Tom Critchlow nailed this, so just read what he wrote on the subject.)

Find fellow travelers, then resist jealousy

I’ve benefited so much from the guidance of other indies. Some of this has been explicit advice, but just as often it has been by getting the chance to observe how they work. The diversity of their business models is thrilling. Between advising, angel investing, bootstrap founding, collective building, book writing, podcast hosting, and more, there are just so many ways to assemble a strong indie business.

It’s easy to look at the great things other people are building and get a little down. It’s easy to wonder why you haven’t figured out what they’ve figured out, or even more poisonously, to settle on answers for why you can’t figure out what they’ve figured out.

Instead, just recognize that everyone’s on their own journey. Take theirs as inspiration.

Have a story, but don’t take it too seriously

I cannot overstate the value of my “Year 1 Andrew-market fit” narrative. Without it, I would have leaned too heavily on familiar stories. Some of these familiar stories are those I’ve told about myself — what I’m good at and bad at, what I like and don’t like, what I want and don’t want — that deserved to be questioned and might not have helped in the new context of indie life. Many of these familiar stories are just part of the unspoken foundation of modern life, conventional stories about work and employer-employee relationships and how to use your time and make meaning.

Developing a story that could allow my work to just be, without overburdening it, has made the past year much more fruitful. The right story has allowed me to look at things with clear eyes.

Hard truths I’ve resisted

Neither of the below is new news. But doing each well requires a kind of work that’s uncomfortable for me. I’ve avoided them, and am sharing them here to create a bit of accountability.

Top of funnel marketing matters

Finding interesting work means helping interesting people find me. I haven’t done enough to build any sort of “brand.” Partly this is because I only want to do it well, and most personal brand building is cringe. But mostly this is because I worry about boxing myself in, and becoming known for a particular set of opinions or skills scares me. I know this fear is unfounded, but there it is. Every business comes down to marketing and sales; it’s time to embrace that.

Breadth of network matters

Clients ask for introductions all the time. “Do you know a great growth marketer we could hire for a few months?” “Do you know anyone who we could talk to about scaling customer support?” Most of my network is people who’ve done the same work as me, but most of the value comes from the folks who’ve done things that are quite different. I need to build more weak ties.

Questions I still can’t answer

The voice in my head that used to be devoted to the minutiae of my full time operator responsibilities has moved on to a new set of questions that are often more existential. This has been one of the joys of indie work, but also one of its perils.

Here are a bunch of these questions that I still can’t answer clearly:

  • Am I building new social capital faster than my existing social capital decomposes?

  • Am I thinking too small? Should I be starting a company of my own? Am I building a “shadow career”?

  • If I lost all my clients tomorrow and had to start from scratch, would I still build the same practice the same way?

  • To what degree do I create unseen political waves in an organization, given that I’m allied with the founder CEO?

Looking ahead

If Year 1’s theme was “Find Andrew-market fit,” Year 2’s will be “Build leverage.” This means the search for new ways to share my ideas more broadly, to meet more interesting people, and to make a lasting impression on the people I work with. I don’t know what form this leverage takes. It’s a puzzle to solve, and one I’ll enjoy solving.

A few great links

Please say hi

If you’re a fellow indie, or a founder, or an employee at a business that could use my help, please say hi: