#StartupLife is Like Dating a Bad Boy
I clicked on ‘Reply’ and then paused, unable to think of how exactly to word my rejection. In my quest to find a new job, after a painful parting of ways from another startup just a couple of months before, I’d applied at a small data startup in San Francisco. When they expressed mutual interest, I suddenly found myself with cold feet. Like a recently spurned suitor, I found it difficult to get excited about our upcoming meeting — too weighed down by the regret and dejection from previous experiences and uncertain about how much I really wanted to throw myself back into the fray.
In the end, my note sounded remarkably like a “Dear John” letter. Leaning on the standard messaging that “it’s not you, it’s me,” I basically told the hiring manager that a string of bad experiences at startups had left me unsure about whether this opportunity was the right next step for me. The hiring manager was very kind in his response and we later had coffee to discuss how I should be managing my job search for success.
I’ve since found and started a job, so in the metaphor that I have established at the start of this piece, I’m “taken.” But my recent bout of unemployment as well as my reading of “Disrupted: My Misadventure in the Start-Up Bubble” by Dan Lyons has led to some deep introspection of what it really means to live the #startuplife. And the best that I have come up with is that working at a startup is like dating a bad boy.
[My] recent bout of unemployment… has led to some deep introspection of what it really means to live the #startuplife. And the best that I have come up with is that working at a startup is like dating a bad boy.
For those of you who are unfamiliar with the scenario, I am happy to explain. At some point in most people’s lives, usually when they are young and don’t know any better, they date a bad boy (or bad girl, if that’s what floats your boat, though I will continue to use the phrase “bad boy” for convenience, clarity and consistency throughout this piece). The bad boy will initially catch your eye because he presents an experience that does not match in any way what you were expecting. “This is so exciting and different and new, “ you think to yourself as you jettison preconceived beliefs of what a relationship should entail.
At the start of your courtship, you feel nothing short of euphoria. The highs are so much higher, the fights are so much more passionate. You feel like you are overcoming the odds, proving the naysayers wrong and building something beautiful and wonderful and so damn sexy together. And oh, don’t even get me started on the free, on-tap kombucha. You’re having so much free kombucha that you find yourself in a perpetual state of ecstasy, telling all your friends, “Ohmagawd, girl — I just can’t get enough” and constantly taking lovey-dovey selfies and putting them on Instagram to prove that life is just so good.
But the exhilaration is short-lived when the expectations that you had previously held — you know, the ones you initially jettisoned — creep back from time to time. Maybe it’s because your friends and family — the people who will never lie to you because, even when the truth hurts, they love and care about you — never stopped telling you that you really deserve better. At the beginning, you wholly reject their pleas, screaming, “You don’t understand! You’ve never been through something as intense as this before! You’ve never felt the way that I feel! You’ve never had unlimited access to fresh kombucha and now you’re just jealous!”
But then their words start to penetrate your kombucha-addled mind and you find yourself thinking, “Wait, maybe I do deserve better.” Where your startup refuses to look ahead and commit to the state of things even months in the future, you realize that other companies provide the stability that you’ve been craving. Instead of constantly being told, “We’ll see where things end up,” and the threat of someone younger (and more naive) stepping in as your replacement, you start to yearn for the dependability that comes from being with someone wiser and more responsible, someone who’s been through this a couple of times and knows how to navigate the bumps that will inevitably come.
It will be a difficult internal push-pull until one day, you just snap. You will look over at your startup, resplendent in its dark hardwood floors and mid-century furniture, and realize, “Ohmagawd — I’ve been bamboozled!” You’ll realize that though your bad boy / startup has promised for months that he’ll get a job / paying customers, he hasn’t come through! He has no solid means of income / recurring revenue and has contributed nothing towards your future together. And when you really get worked up, you start questioning everything. Does my bad boy / startup even have what it takes? Does he even have the means to secure employment / a viable and sustainable business model? Has any of what he’s promised me ever really been true? And when you confront your bad boy / startup, inevitably he’ll respond, “But baby, what about my love / pre-IPO stock options? Isn’t that enough?” And in a blind fury, you’ll scream back, “Your love / pre-IPO stock options don’t pay the bills! They mean nothing to me right now!!!”
And when you really get worked up, you start questioning everything. Does my bad boy / startup even have what it takes? Does he even have the means to secure employment / a viable and sustainable business model? Has any of what he’s promised me ever really been true?
For some, once is enough. They quickly part ways with their startup and go in search of something, though less exciting, that is solid and predictable (and preferably comes with a 401K match — #dreamy). For others, they have to go through a few startups before they learn their lesson. And then, when they are forced to recount the decisions made in their job history, they must sheepishly admit, “Oh, that string of short term flings…? That was my startup phase.” And the interviewer will nod knowingly, empathetically adding, “Don’t worry about it. I went through that phase too. Everyone does when they’re just starting out.”
Some will vehemently disagree with the tale that I tell and that is okay. Because you’re right: some bad boys do metamorphose into responsible entities. And when they do, together you can look back at the tumultuous start to what is now a long and blissful relationship and chuckle at the chaos and excitement that once was. The key to dating the bad boy / living the #startuplife is seeing things as they really are (and not how you hope them to be), being truthful to yourself about your limits and expectations, and speaking up (or getting out) when the situation becomes disagreeable. If you feel strongly about the potential of your bad boy / startup, then by all means — disregard this story. Sit back, post a couple more selfies, and pour yourself another fresh pint of kombucha.
We’ll see where things end up.
