Breaking the pattern in choosing my next design role

How I found an unexpected career opportunity

Six months ago I started looking for a new design role, and it was the first time I’d actively had to look for a new job in nearly 6 years. Going through the job search process this time around I noticed a pattern in my career choices that lines up with many fellow designers’: when we’re looking for our next career move, we’re drawn to the extremes. It’s either the companies where design is already well established, offering design-first cultures and polished product execution. Or, it’s the early stage startups offering the opportunity to be the first designer on a stealth team with the chance to create something from scratch.

Those aren’t the only options, of course, but they represent the ends of a spectrum of tantalizing design roles that often overshadow some incredibly compelling, but admittedly less glamorous design opportunities. I’ve seen so many friends and colleagues bounce back and forth, going from big shiny unicorns to nascent startups and back as they look to grow in their careers. And up until recently, I’d always worked on the extreme ends of this spectrum. Most recently, I co-founded a startup focused on building collaboration tools, and immediately before that I spent 4 years leading consumer design teams on YouTube’s browse and discovery experiences. But then something changed.

Let’s back up for a moment. Six months ago when I was searching for a new design role, it was the first time in 15 years where I didn’t see an obvious next step for my career. In past job searches I’d always had a clear next step — work at an agency, dive into social media, focus on interaction design, try my hand at management, and finally build my own startup.

This time around I looked at a broader swath of companies than I ever had before, and I was also evaluating potential roles with a wider range of criteria than any of my previous searches — finding a product I believed in (that was actually making the world a better place), a product that had a great business growth trajectory, leadership opportunities, potential for high individual impact, and the list goes on…

Each company and role I was looking at was attractive, for very different reasons. Some skewed more toward leadership, others were more hands-on, and others were just sexy companies with great teams and projects that looked like a ton of fun. The frustrating part of my search wasn’t a lack of exciting opportunities, it was that none of them emerged as a clear winner.

As a designer, the most gratifying feeling is finding elegant solutions to complex problems and innovating within constraints. Yet, I had never truly done that, in the sense that I’d never worked in a place where the impact of my work could fundamentally scale and transform an entire business and industry. Sure, I’ve done work that I’m proud of that I believe contributed to the success of a product, but I hadn’t yet done transformative work. And this is where I had the most obvious realization. I had grown and optimized established products and built small focused products from scratch, but I’d never designed a product at a pivotal moment of scaling and potentially become a household name. Suddenly my search narrowed and my next step became crystal clear.

So where did I end up landing? I chose an opportunity that I almost overlooked at the start of my search, because I wasn’t seeing it for the true opportunity it was. I joined Thumbtack, a 7-year old product that is at a transformative moment but isn’t (yet) known for its design. I chose opportunity in its truest sense.

All of the companies I encountered during my job search were in need of design talent, but only Thumbtack showed me an opportunity where design could be the company’s most powerful competitive advantage. It’s not a product that needs to be envisioned from scratch, but it’s not so well established that it’s at the point of refinement and optimization just yet. It’s somewhere in the middle — a growing business full of potential that’s on the verge of scaling. And with that scaling, there’s a unique design challenge that I’m excited to dive into as the next major step in my career.

Perhaps all this is obvious to you, but it wasn’t for me — and many of the best designers I know have been in the same boat. For anyone out there going through similar questioning of where to land next, I hope you take a moment to think about where you can make the biggest impact, where you can find the most interesting challenge to grow from, and where you can be a part of a 3x story. Whatever you do, look beyond what’s shiny and looks great on your resume in the short term, and search for a role where you get to help define the product story in parallel with your career story.

P.S. if you find yourself looking for an incredible and rewarding challenge, we’re building an awesome team at Thumbtack. Come join us!