You Deserve to Fail

You deserve to fail.

I’m sure your mother disagrees. And while I’m sure she’s a fine woman, your mother is wrong.

Because seriously, IF you hit the snooze bar three times, skipped the gym again, stopped at Dunkin Donuts for breakfast, cranked out eight half-assed hours at work, then went home and caught up on Netflix because you were “too tired” to do anything else, then I mean it – you deserve to fail.

That said, I include myself in this group of people who deserve to fail, and I have. And I have some insights on how to get over it. In the meantime, let me count the ways I’ve failed in my unofficial list…

  • Fail #276: Couldn’t hack it in a hybrid sales/brand management role in first job post-MBA. Given 60 days to find new job. Had a chance to start my own business. Instead, took $10K pay cut at next job. #FAIL
  • Fail #304: Major anxiety attack. 15 pound weight loss. Destruction of great relationship. Quit job. Put earthly goods in storage. Drive 1,200 miles back home to live in a spare bedroom in parents’ house. On the floor. #FAIL
  • Fail #788: Mild success at running own business while personal training. Tell self to never work for anyone else again. Great opportunity at top ad agency. Take it. Make more money, totally miserable. #FAIL
  • Fail #820: Said I’d finish my book in six months and shop it around to a literary agent who could find an established publisher for it. Finished the book in four years, still haven’t reached out to a single agent. #FAIL
  • Fail #847: Another new opportunity, more money again. Do well at job. Get opportunity elsewhere year later. Inadvertently use it to get significant raise and stay at job. Get fired 10 months later. #FAIL

And yet, here I am, confident that while I’m not 100 percent where I want to be, I’m closer than ever. Thanks in large part to every failure I just listed above. Because you only face real obstacles when you’re trying to do real shit.

The guy or girl who lives out the bland routine scenario I laid out above, day in and day out, has no real obstacles. Yes, we all suffer loss and heartache. No one escapes those. But invariably, most people end up bitching about the Kardashians, the weather, or some dick bag in the comments section of a blog site.


My favorite famous failure story is that of J.K. Rowling. Her pre-Harry Potter failures are well-documented, though clearly not as much as her successes. As the keynote speaker at Harvard University in 2008, she had this to say about it:

“I think it fair to say that by any conventional measure, a mere seven years after my graduation day, I had failed on an epic scale. An exceptionally short-lived marriage had imploded, and I was jobless, a lone parent, and as poor as it is possible to be in modern Britain, without being homeless. The fears that my parents had had for me, and that I had had for myself, had both come to pass, and by every usual standard, I was the biggest failure I knew.”

At age 30 – nine years later – she finished the manuscript of her first book. A literary agent wound up representing her manuscript after the enthusiastic recommendation of a reader who’d seen the first three chapters. After shopping the book around to publishers, it was soundly rejected – 12 times. A full year later, an editor from Bloomsbury, a publishing house in London offered her a £1,500 advance for the book, which was finally published on a small run of 1,000 copies in 1997.

That book was Harry Potter. The rest is history.

So what’s your history going to be? Here are the five most common reasons that people don’t take a chance on their passions:

  1. “Ayyyy, I don’t have timeeeee.” If you know what’s happening to Jon Snow on Game of Thrones, if you slept in again or take Facebook quizzes, you have time.
  2. “The thing is, that’s like, super hard.” I wanted to update this very website a couple of weeks ago and instead of relying on someone else to eventually help me, guess what I did? Googled it. Figured it out. Did it. Turns out the internet is for more than fake news.
  3. “That sounds like a lot of work, though.” Yeah, no shit. I’m trying to revive a blog that gets two or three likes on a post when I upload it to Facebook. It’s going to require some patience, inventiveness and adjustments to get there. That’s how it goes.
  4. “Yeah, but I’m making decent money and that could take years.” I call myself and my peers the microwave generation. But only Hot Pockets are ready in 90 seconds. It took me a year and a half to finish my Master’s. Four years to finish my first book. Five years of lifting weights to bench press 300 pounds (no chance in hell I can do it now). But you get the point? Look where you’re going, not where you are.
  5. “There are other people who’ve already done that, and they’re better than me.” Yeah, and guess what? There are a lot of people who haven’t already done that, and aren’t better than you. And also, comparison to others is the ultimate dream and joy killer. Seriously, so what if someone else did it? There are hundreds of brands that sell bottled water. BOTTLED WATER. IT’S LITERALLY JUST WATER INSIDE BOTTLES. None of them stopped and said, “ya know what, maybe we shouldn’t do this.” No, fucker. They bottled their water and kept moving.

Don’t bitch out on yourself. At a minimum, give it a year. For whatever your passion is, commit a year to pursuing it. Take weekends off, even. If you dedicated 30 minutes a day, only on weekdays for a year, you’d have invested nearly a month’s worth of work days on this project.

What could you do with that kind of time?


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