Overcoming indecision

A story about pursuing an entrepreneurial career in design

Overcoming indecision

For the last five years, I've grappled with a crippling obsession with making the right decision. This is despite knowing, intuitively, that life doesn't have right choices. The onset of this condition was likely an overconsumption of content about what is now known as “hustle culture.” Following a severe dissatisfaction with my undergraduate education, I embarked on a journey to find a career in the gap left by academia. What I discovered were the blogs of technologists and entrepreneurs who flaunted their highly optimized workflows and mental models. Each shilled their own tools or routines that got them to where they were (in positions that seemed desirable given how pleased these writers were with themselves). I obsessively took notes and downloaded the different apps in search of a way to optimize my own decision making, as I was lost and looking for an efficient way to find answers.

I went about building my career by testing different approaches and integrating the lessons I learned from these magical blogs. I tried freelancing, but the experience was far too lonely for me. Add a note in a new to-do app about freelancing. I got well-paid positions in organizations of various sizes, ranging from well established to months-old startup teams. Eventually, the need to forge my own path came crashing back into my mind. Journal about employment using the three-question method. I tried creating content on social media, but monetizing this pursuit with ads and sponsorships required a type of work I simply wasn't interested in at the time. Put up sticky notes, clustered by theme on a vision board in my home office. Back to freelancing… Rinse and repeat.

After testing thousands of approaches intended to help me come to a clear conclusion about my career, I realized I was only confusing myself more. I can list upward of 200 tools and routines I’ve tried, and all I can say with confidence is that none of them truly work for anyone but their creator.

Over time, I realized I had yet to scratch the itch of building my own company. Ideally, I would build a product that could help the world in some meaningful way, but I still don't have any concrete product ideas. An old dream of mine to build a design studio cropped up a few times, but I always talked myself out of it. Using the research techniques I teach every week in my design lectures, I interviewed people to glean insights about the solution of "starting a design studio." I asked mentors and people I respected to give their thoughts about me launching one. I read online forum posts written by agency founders and chatted with a few of them directly.

What I discovered is that design agencies and studios are broadly considered to be some of the hardest businesses to run.

  • Time management can be a problem, resulting in burnout for the team.
  • Antagonistic relationships with clients generate a lot of stress for account managers.
  • Business models in the industry are stale, and profit margins tend to be quite low.

None of these issues were new to me. I worked briefly for an ad agency early in my career, and I saw firsthand the culture these kinds of companies can have. In fact, that experience, plus grumblings I'd heard from others years ago, kept making me shy away from starting my own studio. My interviews only further confirmed, with plenty of anecdotal evidence, that my reluctance was well-placed. And yet I kept going back to freelancing because I love helping passionate people develop their ideas. I don't have my own idea — and I might never — but I love building things and helping people. I just don't want to do it alone. This might make it seem obvious that I should have started a studio years ago. It’s an environment with the potential to give me the rush of freelancing with the collaborative nature of a team.

So why wasn't it obvious? For starters, I psyched myself out by applying the tools and mental models of people whose lived experiences were nothing like my own. On top of it, the very processes I use daily at work — consulting users and experts to discover problem-based solutions — betrayed me in my search for a fulfilling career. Ironically, the way I applied these techniques would have merited a below-average grade if I was one of my students. While I did interview agency founders, who are technically "users" in this scenario, the only user who matters in my life is me. Yet my opinion was the one I ignored the most. It might be difficult to run your average agency, but I wasn't interested in starting something average.

This is why about a month ago, I decided to recruit a friend and trusted collaborator to co-found a design studio with me. For each complaint I’d come across, though they made sense at face value, we felt unconvinced that these issues were a certain fate.

  • On time management: We put processes in place to ensure we work in a way that makes sense for us, even if it may result in less revenue early on.
  • On client relationships: We will be highly selective of who we choose to work with, and once we've picked them, we'll be radically transparent.
  • On business models: We will approach this as an ongoing experiment to create value for clients, and find ways to make income both from services and passively, allowing us to earn enough to live comfortably (note, I didn't say filthy rich).

It took me becoming completely disenchanted by the idea of finding a frictionless answer to finally listen to my gut. Our new studio is meant to be a place where we can express our love of helping people. We believe there’s room for much more empathy in business dealings. We want to use our passion for mixing disciplines to tackle pressing problems in the world. We want to work together with others who believe fun and rest are essential ingredients for high-quality output.

At the risk of sounding like the entrepreneurs whose blogs I used to try to live by, if you've ever struggled with indecision, I invite you to try approaching decision making in a less structured way. Sometimes our best decisions are born out of a feeling or a vision, rather than the culmination of data and expert opinions.

In my case, I reached a breaking point. The only rational thing for me to do was ignore all the external noise and just listen to the nagging desire to create my own team. That team is now called Pragmatics Studio, and I can't wait to see where we go with it.

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