The question that made me quit the best job I ever had

"Great Wall" by akasped via Flickr

I was grinding my teeth, I was wasting my youth
And using up my teeth

Now, I’m done chewing my nails
Hanging my head, chasing my tail
It got so bad I quit my job
Then I got a new job climbing the walls

-They Might Be Giants, “Climbing the Walls”

I was haunted by that song. From time to time, I’d realize it described my exact situation at a job, and the song would get stuck in my head. I would “vaguetweet” the lyrics, hoping to express the faintest shadow of the existential malaise I actually felt, while hoping my bosses didn’t realize I was scouting for the next job.

Yet this was a massive improvement over my prior situation.

I’m going somewhere with this, but I’ll have to start at the bottom.

Bottoming out

Four years ago, I was on the marketing team for a company that we all knew was (very slowly) circling the drain. Nearly every time a meeting was called, my heart would race, and the halls filled with chatter about whether people would be laid off. This had gone on for years, but I felt unemployable enough that I didn’t see an option but to endure and agonize.

On this particular day (December 30, 2009, but who’s keeping track), they brought the designer and me in, the last of the marketing team, and let us go. I put on a brave face, but I was crushed. I’d poured years of my life into the company, and they’d rejected me.

I cleaned out my desk, said a few goodbyes, and went home to an empty house with my wife at work and my 1-year-old in daycare. I heard a strange noise, as if someone was running the shower, and came downstairs to find that a hot water pipe had burst, caving in part of the ceiling and flooding my basement with five or six inches of water.

Gravity seemed to instantly quadruple. I collapsed into a chair, surrounded by water, unsure of how I would deal with everything that was happening, and sobbed.

But as one does, I quickly shifted into management mode, shutting water off, calling a cleanup company, contacting insurance, arranging a place to stay with family. Within a few weeks, the house was livable and I was in a new job.

Waking up

Being laid off was miraculous. First, I learned that losing my job didn’t kill me. My spouse didn’t leave me. We didn’t get our house repossessed. My kid was as happy as ever. The flooding thing was probably not a direct result of losing my job, so we’ll chalk that up to coincidence.

Just as importantly, I learned that I could interview for, land, and perform a job to the satisfaction of the people that hired me. That may sound obvious, but it was a revelation after being beaten down by a job culture that essentially said, “where else are ya gonna go?”

Most of the fear that had paralyzed me into staying in a terrible job for years was just gone. I was employable.

The seven-month itch

I’d been working toward becoming a professional programmer, a goal that seemed out of reach to me at the time, so I took a job that I thought would get me closer to my goal.

(The “breaking into the software development game” post will have to wait for later, but I was very lucky to have friends who guided me through this process, including Dave Brady, who is so good at this he’s writing a book.)

In short, after becoming disillusioned with the broken promises at one job, I’d move on to another. And then another.

All in all, over the course of 3 1/2 years, I took (and quit) five jobs, ranging from 3 to 14 months. But a pattern did start to emerge: at each job, I’d start with excitement and optimism. After a few months, I began to notice an organization’s problems, which would then fade into a general sense of anxiety and frustration, rooted in the fact that the company was a mess and there wasn’t much I could do about it.

I’d sit in the parking lot, staring at the building each morning, working to summon the will to go inside.

I always saw myself as a responsible, dependable person, so it was very difficult to look at this and wonder if the problem was me. But each time, typically after a six-month honeymoon, I’d start looking around and seeing my workplace’s dysfunction and a deepening sense that I was just in the wrong place. I’d work to improve things, then try to fake it for a while, and ultimately, I’d leave.

The dreamiest dream job ever

Then, after leaving yet another dysfunctional company, a good friend helped me find my dream job. It ticked off everything I could possibly want. Working from home on a 100% remote team. Great compensation. The opportunity to learn from some of the kindest and most intelligent people I’ve worked with.

I spent a lot of time pairing with amazing developers who also happen to be good friends, leveled up my skills as a programmer, and felt valued for bringing my own unique flavor to the team.

And my boss! He is, to this day, the best boss I’ve ever known. No one is perfect, but I could (and definitely should) spend an entire article examining what sets him apart. But in short, he is kind, empathetic, and sees his role as a protector of a team’s autonomy from organizational pressures. His reputation precedes him in this regard, so he attracts some amazing people to work with him, creating a virtuous cycle.

In every area, professionally, I’d finally hit the jackpot. To this day, I thank my lucky stars (and that good friend) for the opportunity to work on a team like that.

There’s simply no way the four-years-ago version of me, sitting in a chair, sobbing, could have even dreamed that I’d find myself in that work situation.

Things were going great. And then I quit.

What is wrong with me?

Believe me, I resisted. Strongly. I didn’t want to quit this time, honest.

I’d interacted with an open source developer several times over the last few years, online, and then in person after moving to Austin. He stuck out to me as someone uniquely worth listening to, and I was struck by how kind, empathetic, and whip-smart he was in our interactions.

Ultimately, the opportunity came up to partner with him to take a small consultancy, focus on Rails and Ember.js, two technologies I love, and grow a business and team together.

Everything about it was less attractive on the surface: It wasn’t remote, less flexible, more work and stress, and a huge (over 50%) cut in pay. Initially, I was firmly against the idea.

But these conversations started gnawing at my subconscious, and a sense began to grow in me that I was heading down a path that wasn’t mine: a path of comfort at the expense of seeking my own destiny.

The deciding question

For me, it came down to one question:

“Will I regret not having tried?”

I was actually angry to have to admit that the answer was an unequivocal “Yes.” I couldn’t run from that fact.

There are a lot of reasons backing that up that I won’t delve into here, only that my heart knew with crystal clarity something that took me weeks to begrudgingly admit to myself. That I prefer adventure to comfort. That I can’t be happy only exercising a small portion of my capabilities, no matter how great the other circumstances are.

What I’m up to now

So I quit my dream job to help run a software consultancy. My boss, in typical fashion, was amazing and magnanimous about the whole thing, even though I was very embarrassed to leave so soon after starting.

So now, I’m working with The Frontside, an Austin-based software studio focusing on Ember.js and Ruby on Rails applications. We think we’re on the leading edge of the next wave of web applications, and it’s been a thrilling ride so far. I think the two of us can’t help but build something special, and I’m excited to start showing it off to the world.

My partner, Charles Lowell, is a mensch. I’ve learned so much from him over the past few months, not least of which that running a business is hard. From sales to hiring to the technologies I work in, the learning curve has actually been incredibly painful. But those lessons will have to wait for another day.

So what’s the point?

So am I telling you to quit your job? Obviously, that isn’t the point… you could quit any number of jobs without growing as a person or advancing in your career. Here’s what I want you to get from this article: It’s time, right now, to think hard about the next step in your career.

The next real, meaningful step is not a title, salary, or lifestyle upgrade. Those are side effects, and rarely (if ever) wind up justifying quitting one’s job.

The meaningful steps include things like:

  • a greater understanding about what you want and what you don’t.
  • new relationships and friends for life.
  • lessons that deepen your character.

I used to feel permanently glued to my job, so when I lost it, I felt like I’d lost everything. Since then, I’ve learned when to stick with a job and when to quit, and they’re counter-intuitive. It was time to stick it out when I was at my most frustrated. The lesson I kept having to learn was how to shape my environment, and more importantly, myself, to find happiness amidst the chaos.

Once it felt like I’d learned the most challenging lessons and things started to click into “autopilot” mode, my heart told me it was time to move on. And each subsequent move has brought with it even more perspective and relationships.

I don’t know what’s next for me. I am excited to see if I can put my money where my mouth is and build the business I always dreamed of working for. I do know that whatever happens, having tried is one less regret I’ll have, and I haven’t for one second felt like I was “climbing the walls” anymore. That’s gotta be worth something.

LivingSocial, knowing your business, and gloating

Yes, LivingSocial is imploding. Yes, we saw it coming. Yes, we knew that the multi-billion-dollar valuation was silly and to be short-lived.

It’s easy to be snarky. And fun! I get a laugh from my friends, I get to show how smart I am for having “seen it a mile away”, all from the comfort of my armchair, having taken no risk.

But when I participate in such snark, I also feel a bit hollow inside. Because I know people, human beings, work there. Hell, I know people who work there. And sarcasm and snark only pile on insult for these (typically) innocent people.

And an additional danger: flippant, snarky responses are rooted in an “I was right” mindset, preventing us from learning anything more. But there is always more to learn.

My daily deal near-miss

A few years ago, I helped create a startup with some pretty audacious (and ultimately insane) goals. Things weren’t panning out with the original, mathematically-impossible business model, and we discussed “pivoting” into the daily deals space.

It was around then that my pre-arranged 3-month contract came up, and although I received some pressure to stay, I made the decision to leave, while my friends stayed behind. And their daily deal business started to catch fire.

I watched their office jump from 3 to 5 to 10 to 50-plus employees. I still held a significant stake in the company and wanted to see them succeed, but something about this rate of expansion concerned me. In fact, a friend of mine worked there for exactly one day before the environment creeped him out to the core and he quit.

My friends told me that the company had to expand quickly, that everyone in the daily deals space was growing more quickly than was sustainable, because only the largest survive, while the smaller firms would wither and die. (Interestingly, the opposite seems to have happened.)

Their work environment disintegrated as the pressure ratcheted up, paychecks started bouncing, and the entire thing became a news-worthy fiasco. I was comfortably off in another position elsewhere, but it still broke my heart to see my friends suffer (and to toss yet another worthless stock grant into the shredder).

Don’t let bad business models catch you by surprise

One lesson in this is simple: Take the time to analyze the business model of the companies you choose to work with. Do they make money? From whom? Who benefits? Look at the founders. Are there happy customers in their wake, or a string of disappointed people?

Do a gut check. Does it feel right, or does it feel like you’re selling out a little? You know, that feeling when you put that thing you want, but don’t need, on a credit card? The trading of the long-term consequences for an immediate thrill?

If you get that second feeling, stop. Weigh it more carefully. You may not change the decision, but your reasons need to be much more clear, or you’re creating a recipe for regret.

Being right is not a license to gloat

The other lesson is for us spectators: Maybe let’s stow the sarcasm on this one. For a lot of people, LivingSocial’s (likely) collapse is going to be very personal and very painful, so please take a moment to remember that before dancing on its grave at the expense of human beings who are hurting.