Taking the Leap into Freelance

May 17th, 2024 · 5 min read

After nine years of working in-house at tech companies, I’ve decided to pivot and re-enter the world of freelance—and I couldn’t be more excited! There were a lot of things I enjoyed about my in-house journey (especially the friends I’ve made along the way), but there are a few reasons why I think this is the perfect decision for me right now…

I have experience to offer

I say “re-entering the world of freelance” because it’s actually how I began my career back in 2012. I worked as a part-time junior designer throughout college, and continued contracting for another year after graduation. While I got to work with some amazing people, and enjoyed the variety of projects, it also felt like I was starting my career on hard mode.

Not only was it tough to find clients without an established network, but I was also still learning the ropes as a designer. I found it difficult to hone my craft, while also trying to meet client deadlines and ship great work. These conflicting goals gave me a lot of imposter syndrome, and without a dedicated mentor, I didn’t know if I was making any progress. Eventually, I decided to go in-house to better develop my skills, and I’m really glad that I did.

But now, almost a decade later — it’s a much different story. I’ve designed and shipped all kinds of products. I’ve grown and led healthy, effective teams. I can advise companies on design strategy, and deliver designs with speed and quality. With years of experience under my belt, I’m able to help companies achieve their vision with more confidence and clarity.

A builder, helping builders

For many years, I saw myself on the traditional design leadership path, with the next ~20 years playing out something like this: Director, to Senior Director, to VP, SVP, CDO, etc. If you’re a designer trying to move up the career ladder, working in-house will be your clearest route (and you can make good money doing it!). If I hadn’t worked in-house, I don’t think I would have had the opportunity to develop as a leader, so I’m grateful for that. But now I’m not sure that the in-house leadership path is still for me.

I was in player-coach roles for several years, eventually becoming a full-time people manager and director. Building and leading a team of talented folks was a hugely rewarding experience, but as time went on, I started to feel more and more removed from the craft (an issue Cap Watkins wrote about recently). I knew I was making an impact, but it was harder to feel it. By the end of each week, I’d be mentally tapped out from all the meetings and initiatives, and lost all my energy for side projects. I worried about the long-term effects of not practicing design, and losing my edge.

Maybe more alarmingly, the entire design industry is hella weird right now, and I’ve grown skeptical about design leadership as a viable, long-term career path. In an already tough tech job market, UX roles have been disproportionately affected, and many design leadership openings (manager+) now expect the “hands-on player-coach”. Most design orgs still report into a Head of Product. After a decade vying to get that seat at the table, the future of design leadership seems to be more uncertain than ever.

I sat on these thoughts for quite a while, and over time, my perspective has shifted. I’m no longer interested in titles or moving up the ladder. I’m more interested in being closer to the work and having a more direct impact on a company’s success. I also crave the flexibility and brain space to be able to pursue my own projects (and maybe launch my own company someday). Thinking about my new path, I’ve landed on something more simple:

I’m a builder helping other builders

The move to freelance is a perfect way for me to pursue this. I’m close to the work again. I’m partnering with founders to help achieve their vision, and I have a more direct impact on their success. I can also see what it takes to launch and build a company in a way that I haven’t before. I finally have the flexibility and energy to pursue my own projects. And it feels great.

My amazing support system

I’m fortunate to be in a position to take the leap into freelance now. I have an incredible network of friends and former colleagues who have been so supportive — whether it was just listening, making connections, or offering advice. I’m so lucky to have y’all.

Of course, none of this would be possible without the support from my wife, Emily. After several years as an in-house designer, she decided to pursue freelancing at the beginning of last year. And no surprise, she is thriving! She’s enjoying everything about the work and the flexibility she gets from it, and her success was hugely influential in my decision. Hun, your support means everything. Love you ❤️

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