Winding Over Grinding: How I Started to Love Design Again

Earlier this year I wrote about how I quit my job and was trying to think about the work I did as less of a career with list of accomplishments, and more like a practice.

While it might have seemed like it was an easy thing for me, I’m sorry to say this time was some of the hardest I’ve gone through in my career. As it often goes, doing the thing is much harder than saying the thing.

After the initial rush of quitting my job faded away, I was starting to get a bit panicked. My runway for being unemployed was fairly small and I had a family to support. Unfortunately this meant that I jumped right into portfolio building and talking with recruiters, even though I probably should have given myself more time to breathe.

As I started those conversations though, I tried to remain true to my idea: find a place that believes in me and is aligned with my practice, not just something that will pay my bills.

The more people I talked to the harder and harder it got to believe that was possible and I started doubting that such a place could exist.

Yet the more conversations I had, the more it started to clarify beliefs and traits about what my practice is. Things like:

• Creating an environment of trust and support leads to better and more creative outcomes than an environment of fear, control, and hustle
• I work better when I build through making, learning, and iterating than trying to have all the answers first
• However, if we’re just building and never making time for learning and thinking, we’ll never make anything truly exceptional
• I sweat the details because I care about people and believe they deserve the best possible experience
• I get most energized when I’m working towards an honest mission and the others around me are doing the same

This made me be more cognizant of what to look for and mindful of how companies or roles may or may not fit these areas.

Ultimately after many conversations across nearly 2 months of searching I had an epiphany: why should I keep looking for something when I instead could just start something myself? So I decided to try and go independent — or at least try it for a while.

I was very lucky to chat some inspiring folks like Kevin Twohy about how to approach it and started to build confidence it was possible. Since then I’ve had the luck to work with some amazing startups doing design/consulting work and something amazing happened — I was extremely energized.

I finally started to recognize how much I really love making things. While I love a lot of things about management, I really found my stride in making and building software again rather than building teams.

This journey helped me realize a lot of my career stress in the past was likely that I was optimizing for what types of things would get me the most respect than what would make me more creatively fulfilled.

I’ve had a lot of luck in my career and I usually took that luck and tried to continuously double down on it — to continue to climb the ladder until I could justify to myself that I was “good enough.”

What I realized instead is that I didn’t need external validation in order to feel that way. I could instead choose to respect and believe in myself and make that be enough.

Nearly immediately this mindset shift started to have massive effects on my creativity. I found myself starting to fall back in love with design again and at the risk of sounding smug, I felt I wasn’t too shabby at it.

All of this led to working with the wonderful folks at Anthropic for a two month contract. What I didn’t expect is how it felt like I had finally found a place that supported my practice well and had some truly really wonderful people that I really enjoyed working with.

And sure enough as of today I’ve started with them as a their first full-time product designer! It’s not fully what I expected or planned for when I started this independent designer experiment (I've been referring to myself as an Anthropic foster-fail) but I think that’s the point.

We put so much effort into things that we sometimes forget why we were doing them in the first place. We forget all of the magical places the winding road can take us just because we’re too busy and focused on our own goals — or worse, goals we put onto ourselves because we feel we have to.

Goals and ambition are definitely important, but we also have to step back regularly to check in and be honest with ourselves on what it is we actually desire for our life.

The beauty (and pain sometimes) is that we often don’t know what that is unless we just keep trying things.

Some things will work great, some things will be meh, and some things will be better than you could have hoped.

Learning to embrace that uncertainty and fall in love with the process of trying, more than the results of the effort, that’s what I think a true practice is. Where every day is just that — a practice for the next one.

I don’t know what the future holds. I don’t know if I’ll continue to be a designer, be a people manager again, or something else entirely.

But I look around and I see many folks who are struggling with this burden of feeling like they need to build an exceptional career and that has become their primary identity.

There’s so many expectations the world puts upon us and it’s so so easy to get caught up in it.

All I can tell you if you’re feeling that way is that you are more wonderful and amazing than you think you are and I truly believe the best has yet to come for you.

You just might have to open yourself to new possibilities you may not have really considered before and maybe let go of some things you're used to holding onto a bit too tightly.

Real generosity towards the future lies in giving all to the present.

– Albert Camus

The path is winding. All we can do is be unafraid to take the long way sometimes — to stop and smell the roses from time to time, enjoy the journey, and let the universe remind us who we are and where we actually should be going.