Tom’s Meandering Mind

Poignant articles on webdev & start-ups, pointless bytes, and pure lunacy. 
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Starting Up, One Year Later: Recovery

[This entry is part of a series. Read previous entries here.]

I didn't find a hotel on the morning of June 2nd, 2008. I stuck to driving up and down the same road, too afraid of losing my bearings among the haphazardly-placed Boston streets. After an hour of slowly-increasing radii, I gave up and pulled into an eerily desolate parking garage. The mechanical clunking of the ticket machine was the only sound to break the morning silence.

My car wasn't the best of beds, but I wasn't complaining. After all, I was on the cusp of a new adventure! I'd just driven 14 hours straight, from Cincinnati to Somerville; this was my first official morning as an honest-to-god startup founder and Bostonian! Okay, so maybe we weren't totally in agreement on the whole Bruins vs. Red Wings thing.

* * *

More than a year after that fateful day, I'd learned first hand the life of a bootstrapped startup founder is an adventurous one, but also a tiring one. I'd become tired of staying in every night. I'd been worn down, working on a site that after a year was making enough money to warrant continued toil, but not enough to buy me a supreme pizza. I was tired of feeling guilty for seemingly never giving enough while simultaneously dealing with the realization there may not be an "enough". All of these issues attributed to the malaise of my previous entry.

Then, a couple weeks ago I finally got the joke: In my fervor to escape the slavery of corporate America, I'd made myself a slave to my supposed salvation. They say in Zen that when one is finally enlightened, there's nothing left to do but have a good laugh. Mine was no satori, but I laughed just the same.

And I gave up. Not on the business, but on the notion that I could be satisfied merely by clawing my way up this topless mountain each day. I now go out occasionally, even though I can't afford it. I do my best to be productive on a daily basis so that I may enjoy the free time I make (because unlike a normal job, nobody is going to give it to me). And I definitely get more done in less time as a result (thanks in part to a more disciplined schedule). I've sweat and bled and drank the Koolaid -- and it has been a blast. Yet, with balance comes perspective, and I'd been lacking both.

The most important life advice I can give after my short time as a startup founder (and comparatively short time on this earth) is this: keep yourself grounded. To many, a year isn't even an especially long time to toil at something one is passionate about, yet it took an awful toll on me -- one that I am just now beginning to fully recover from. Dedication and sacrifice can be valuable assets, but they can also be a nefarious enemy. One which slowly robs you of your ability to see the forest for the trees, until all perspective is lost.

Sacrifice is generally necessary when starting a new company, but in my case I found it to have diminishing returns. Eventually it caused me to become far less productive than I was to begin with. Even now, money is a constant stressor, one which instead of motivating me, simply gives me one more thing to needlessly worry about.

A few months back, I finally went to a mechanic to have maintenance done on my car. It wasn't until the next morning that I noticed what an enormous weight had been lifted from me. I had allowed the warning lights on my dashboard to dictate my stress level while driving for nearly six months. That's just plain stupid! And my car nearly sustained expensive damage as a result (there was no oil left, for one). Deal with warning signs when you first see them, before they send you into a downward spiral.

(This will likely be the final post on this topic for a while. The initial purpose of this blog was to educate others; to share what I've learned not only over the past year as a startup founder, but over a decade+ of web development. Up next, I have a great tutorial for architecting a Comet setup, if that's your thing!)

Comments (4)

Jul 30, 2009
boris said...
well as a geek you should know how to check oil level in the engine - there is nothing easier than that
Jul 30, 2009
James Bressi said...
Well unlike our first commenter, I would like to use this space to tell you that this post was well done. You see a lot of startup posts out there, but this entire post really hit it on the head. From slavery to warning signs. Impressive.
Jul 30, 2009
Tom Davis said...
Hahah! Thanks a lot, James! I intentionally chose not to reply concerning my ability to check the oil level of my car. It seems a less than pertinent subject in this context ;)
Aug 02, 2009
Dan McGrady said...
Well written article, this story started off on a darker note and hopefully it will end well. But regardless you will come out of it with enough experience that by the time you start your next company you will be well ahead of most.

Btw. why even own a car? Seems like the biggest expense a startuper can have these days.

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