Whenever people ask how I ended up as a freelance consultant, I always find myself using the same language: I accidentally “fell into” it.
And it’s true - this wasn’t the plan.
3 years ago, I made the incredibly difficult decision to leave a dream job running product and sales at Electricity Maps. At the time, it felt like the culmination of a “startup education” - I’d been through highs and lows, learned a ton, and felt ready to take my place in the “founder” seat. I was leaving to start something; I just didn’t know what it would be. While I figured that out, I decided to look for consulting work as a means to make some money, explore, and stay sharp.
Then I started feeling stuck. The startup ideas didn’t magically start flowing, and it was easier find flaws than exciting aspects in the many great opportinities I had in front of me. This first year was filled with uncertainty about what path I was really on - I had few reference points to turn to, and was constantly weighing different potential next steps in my head.
Meanwhile, the consulting work was actually going well - it felt good to be genuinely helpful. For me, the term “consulting” had previously evoked the idea of a money-sucking barnacle on the “hull” of an organization - extracting value, but providing little in return. But over time, I started to let myself accept the idea that my help had value - and feel pride in being a “consultant”.
At the time, I agonized a lot about framing what I do (product vs. design, studio vs. solo freelancer, etc.). My skillset and interests are span several disciplines, and I struggled to find a way to fit that into a “box” that I could market to the world.
I think it’s no coincidence that I became more comfortable with the ambiguity of my work, where it was going, and what path I was on the more I developed as a “consultant”. In Year 2, I took on more ambitious, larger, longer-term projects. Not only did I become a stronger designer and product person, but I started to develop better instincts in how to be most helpful to clients.
My confidence also grew significantly during this period, and I started to worry less about framing myself and my work. I now had a track record to look back on; the narrative of “Trevor as a service” became less theoretical, more grounded in actual consulting projects. In short, I could start to see my weird, ambiguous path compound.
Now, at the end of Year 3, I feel as though I’m hitting my stride. This year represented another step up in terms of ambition, variety, and challenge in client work.
I also feel like I’m shedding the last of my anxiety about where this is all going, perhaps because I can look back and see how far it’s come. At this point, I remain open to any exciting possibilities ahead - from scaling up my practice to starting a startup to getting another “real job” - but I no longer feel the pressure to craft a narrative in my head about precisely what path I’m on.
In this last year, I dove deep into the discourse around these uncertain paths - “pathless paths”, as Paul Millerd calls them. Reading many books and blog posts about other folks’ experiences gave me the words to describe the challenges I’ve faced, and also a sense of reassured calmness about my circumstances. It’s an incredible privilege to be in the position I’m in, despite the uncertainty that can come with it.
During these three years, one of the unexpected pleasures has been my professional growth. The previous years working at a startup felt like a “crash course” that couldn’t be topped - I was worried that my growth curve would start to flatten.
Instead, I’ve grown tremendously as a designer and product manager - largely because I’ve been able to get closer to the work than I had in years, as well as the compounding nature of having many varied experiences in a short amount of time.
In the last 3 years, I worked on 16 different digital products at various stages. I’ve worked with teams at startups, large enterprises, small and large non-profits, VC funds, and everything in between, on every continent except Antarctica. I’ve not only gotten a lot of “reps” in building products, but I’ve also seen how many different organisations work (or don’t work).
But at the same time, this journey hasn’t always been easy. Even after the pandemic passed, it was easy to feel isolated. I work with most of my clients remotely, and while I’m often quite integrated into their teams, I don’t get the same “in the trenches” camaraderie that one can find in a full time role, especially in early-stage startups.