Comfort is Overrated

When I finished school in 2009, I made a promise to myself to never become complacent with work or life.

I never want to be the person going through the motions in life. I want to care about whatever it is that I’m doing. I should feel excited about my the things I spend my time on. If I’m feeling anxious, it’s a good sign. It means that I’m doing something new, and probably worthwhile. I want to constantly be teetering on the edge of my expertise and diving into something completely new.

That time came in 2012. I quit my job as Principal Designer at Blue State Digital and started my own design studio, Cottleston Pie. My main reason for quitting my job and venturing off on my own was that I had become too comfortable at work. I could sense that my job had started to become routine and I wasn’t pushing myself as much as I should have been. While there’s something to be said for feeling comfortable in your job, it can become static, quickly.

So what does that mean? How did quitting my job push me to continue learning? Over the past two years, I have:

  • Started two companies, Cottleston Pie and Stash
  • Set up a billing system and a way to organize my finances as an LLC (and got an accountant to help with that)
  • Took on clients & projects where I serve not just as a designer, but as a project manager or a UX designer, or a front-end developer, or sometimes all of those
  • Managed an email list of bikes for sale.
  • Said “yes” to every coffee meeting or conversations over drinks
  • Learned how to program in Ruby on Rails, so I could make my own web apps
  • Made three web apps (What’s in Season, Stash and Songfight)
  • Figured out how to print sets of giant calendars and ran a Kickstarter campaign to get them printed (it wasn’t successful)
  • Interviewed random strangers every week

While all those things have been pushing me for the past few years, I’m comfortable doing them now. It’s an endless cycle and it looks like I’m going to be pushing myself forward again.

So what am I doing now to stay awkward?

  • I just signed a lease on a new studio space. It’s called The Works and we’re having a few people work out of the space with us
  • Creating a community within that space, getting like-minded folks to communicate and collaborate with each other
  • Working on putting together plans for teaching some classes next year. I’d like to teach middle school aged kids how to code. This is a whole new area for me and I’m really nervous about it
  • Hosting a monthly critique session for small business owners
  • Working on a retreat for small business owners
  • Pursuing the calendar product into next year and expanding it into a few different products

Hopefully those things will keep me excited for a few years. The more work I do, the less time I want to spend time on a computer. The ideas that get me the most excited right now are focused on interacting with people instead of software. So we’ll see where that takes me.

What are you doing to stay uncomfortable?

Originally published at on November 24, 2014.




Creative Director and founder of Cottleston Pie, a digital design studio for progressive causes, organizations, and companies.

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Dave Dawson

Dave Dawson

Creative Director and founder of Cottleston Pie, a digital design studio for progressive causes, organizations, and companies.

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