Open letter to a good friend on work, play, and being an adult

Hey there.

So, I see that you’re trying to take your career seriously.

Gosh, that sounded condescending. What I mean is, you’ve been slaving away as a professional for years, and you’re trying to jumpstart yourself to another level in one concentrated effort.

I have to say, I really admire your tenacity and energy. You are smart, and you really do know a lot about what you’re doing. You put in incredible hours, and I absolutely think you deserve an opportunity to level up.

But if you want the rest of the world to take you seriously — i.e., invest in your startup/apply for your incubator/fund your investment firm — you’ve got to stop with the juvenile antics.

You can’t go out and get drunk every night. You can’t constantly post about getting drunk and partying. You can’t constantly post pictures of yourself half-naked or inebriated or pictures of yourself with scantily clad hotties you don’t even know. Every time you land in a new city, you can’t pepper Facebook and Twitter with “Where’s the party at?” and “Who’s down to get wasted?”

I know you embrace the whole work hard/play hard ethos, but get serious. Do you think Steve Jobs shared stuff like that? More to the point, do you think he partied like that? Do you think Bill Gates or Ginny Rometty or Mark Zuckerberg did?

A handful of people in Silicon Valley actually do live that way, but they’re few and far between, and they’re as powerful as they are secretly despised. A certain Facebook investor, now too important to be blocked by any mortal but plagued by a grotesque sex-and-drugs habit. An investor legendary for his drinking problem as well as his stellar financials. You’re not rich or powerful enough to be in that category, and the posts about partying don’t make you look cool. They make you look lazy and possibly addicted.

And when you’re not broadcasting updates about your time-wasting, brain cell-killing, relationship-squandering social life, you’re trying to convince us all that you’re a power player who is inspired, destined for greatness, and totally crushing it.

Telling everyone how you’re hustling and crushing it all the time does not mean you’re actually succeeding.


RELATED: “You’re Not an Entrepreneur”

Let’s talk for a moment about hustling. Our generation has adopted this word and plastered it onto class pennant without really considering what it means. Sometimes, I think some of us are all hustle, no work.

The real definition of a hustle is a con. A scam. Getting out of a situation a lot more than you put into it. Sometimes, I think that’s exactly what you’re doing. You’re smart, but I question your perseverance. Do you have the courage to weather the boredom of a real job, one that last for years and is sometimes the least fun thing in the world? One that pays your bills and lets you save, slowly, for a retirement that’s a couple decades down the road? Or are you so sold on the get-rich-quick schemes of the startup world that hustling is the only kind of work you know?

My last beef: Your language. Call me “grandma,” but the only one who gets to say the F word in professional contexts with any credibility is Dave McClure, and even he’s outgrowing that habit. Stop swearing. You’re alienating some of your most valuable allies every time you do. You’re disappointing your colleagues, and you’re turning off potential partners.

I like you, I really do. And on most levels, I still consider you a friend. But I wouldn’t do business with you, and I wouldn’t recommend you.

I used to be a partier and a hustler, too, and I wouldn’t have recommended myself back then, either. One of the things I love most about my life now is that I can ask people to take me seriously with a shred of credibility. I’ve had my job for a couple years. I go to work every day and do my job, even when it’s boring and slow and I don’t feel like it. I rarely post overly personal stuff on the Internet, but when I do, I try to uplift others. I’ve realized it takes more than a burst of energy to succeed, and it takes more than Twitter followers to be respected.

In the end, it all comes down to self-awareness. I don’t think you realize how your actions and words (and pictures) reflect on your work; I wouldn’t be writing this incredibly difficult letter otherwise.

The fact of the matter is, this isn’t really an open letter to one friend. It’s an open letter to dozens of people in the startup scene, young and not-so-young, all incredibly bright and talented and all wasting their time on parties, “hustling,” and social media.

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Photo by Ken Yeung/thelettertwo.com