They say hindsight is 20/20. They. They're right, the bastards. I always try to make decisions in the interest of never having to summons that awful cliché. I strive for foresight being 20/20, or at least as close as it can be. I even wear some pretty enormous glasses to help achieve that.
I've said before that I like to think of my attention split between the past and the future as the difference between the rear-view mirror and the windshield. Face forward, buckle up, glance behind you and go.
Unfortunately, this isn't completely a success story for that way of thinking because I, sometimes, can be a moron. This is the story of why I chose to work at SimpleGeo, and how I lost track of my foresight along the way (spoiler alert: I found it).
In August of 2009, after nearly 7 years of being at Threadless, my work life and my personal life had a very unclear divide. When I left that same month, suddenly the division between my work life and my personal life was very, very clear. Leaving Threadless kind of felt like losing a limb. As a guy who has actually lost body parts before, I won't lie, it was difficult.
I wasn't quite sure how to handle it, but I was pretty certain that the right thing to do was take a whole bunch of time off and move to SF to end the long-distance part of Kelly and my relationship. Friends, family and advisers all seemed to agree with this course of action.
Did I end up taking that time off? Of course not! Remember how I said I can sometimes be a moron? I did move to SF though. That was a step in the right direction. My free time was put on hold with the offer of joining Digg as their Director of Design & UX. I accepted and started just shy of 7 weeks after I left Threadless; the time in-between was eaten up by packing and moving.
Now, I know what you're thinking. "This is the part where he blames being laid off at Digg on it being a poor choice to be there in the first place". Not at all. I don't regret joining and helping to continue building a great team. Plus, I believed in the product and the problem we were all trying to solve together.
Digg was a comfortable place for me. I was given the freedom to come in guns-blazing on both design and some product, and they were in a place where it was advantageous for them to be evaluating all new ideas.
However after a couple months, something felt off. I did what I tend to do when I'm not 100% happy with where things are going: work until I'm happy. In the ~8 months I spent at Digg, I consistently worked 60+ hour weeks.
It was only after leaving Digg that it occurred to me what the problem was: I walked directly into a very similar situation to what I left at Threadless, only this time, I had absolutely nothing to do with how that company came to be or what it was. I was just an employee.
Fred Wilson recently wrote a really insightful blog post that, frankly, I wish he'd have written about 18 months ago. I found it to be particularly insightful because it was more or less about me (on the receiving end, in a general sense), save a few details: (1) I was not a founding member of Threadless, and (2) leaving was a mutual decision.
However, what Fred was able to articulate in 7 paragraphs gave me a lot of insight into what was likely happening at Threadless on the opposite side of my departure. It also helped me to understand why I felt more and more like the square peg in the round hole as the company grew.
Fred writes, "What works when you are five or ten people often does not work when you are fifty or more". When I started at Threadless, it was a handful of people. When I left, it was nearly 100. When I started at Digg, the team was roughly 75 (don't quote me on that, I'm just estimating).
I believe what Fred wrote about the type of people who are very effective in smaller groups but have a hard time scaling their effectiveness to very large groups. At this point in my career, I think that describes me pretty well (though I'm always working on it). Had I read Fred's post prior to interviewing at Digg, I wonder how my choices would have differed.
I think this is an important aside: Getting laid off was a blessing in disguise. I'd likely still be at Digg had I not gotten laid off. It wasn't until I had a decent chunk of time to clear my head and look at the rear-view and the windshield simultaneously and figure out what I wanted.
I think this is how people end up getting stuck doing something they don't like/want to do. It's very easy to focus on the tasks at hand, lose sight of the big picture, and leave very little time for self-reflection. The longer you remain that way, the more inconceivable it may seem to make the changes necessary to be truly happy with what you do. Believe me. I had entirely too much work to do to spend time thinking about what else I'd rather be doing.
After taking 3 months off from work, I realized what I wanted to do through a little side project work, a decent amount of interviewing with companies (big and small), and a whole lot of sitting on my ass contemplating the universe (read: playing video games).
This is what I came up with: I want to build companies, products and cultures from the ground up, and surround myself with amazing people who have amazing ideas. I want to be an integral part in the birth of innovative things. I don't need to be a founder, but I want to be early. Most importantly, I want to work with friends.
My time at Threadless has proven that culture is the core of the company. Culture creates friendships amongst you and your co-workers. By working with friends, you'll find teams will be more collaborative, feedback will be more honest, and the overall level of care and support across the company will be enormous.
For the above reasons... this is why I chose to work at SimpleGeo. Simply put, it feels like home.
Some call me a tattooed metal head with an eye for design and a nose for tomfoolery. I call myself a tireless design enthusiast, a champion of users, a designer of products and experiences, an advisor to startups, an avid consumer of food, movies,and tee shirts. A husband, and a maker of things.
You can just call me Jeffrey.