How to Fail Successfully Without Even Trying

By Derek Reimherr

I think my life has been a continuous series of “successful fails” for the past 3 years.

Wait, hold up. You’re probably wondering what that means.

I recently read an article on Buffer’s blog called “I Failed Buffer’s Bootcamp...Successfully” from a guy named Jeffrey Kranz. You see, Buffer is an amazing social media company, one whose product I use every day and engage with every week during their #bufferchat on Twitter. But if you want to work with them, you’ve got to go through a 45 day bootcamp. At the end of it, there’s no guarantee you get the job. I think you can gather how this particular story ended based on the title of the the above linked article.

You see, failing successfully is what happens when you fall flat on your face, but find a $20 bill while you’re down there. It’s when your path diverges in the woods like that over- and misquoted Robert Frost poem, and you realize you’re on the wrong path. But all of the sudden, you find a tricked-out Jeep so you off-road out of those stupid woods onto a better adventure.

Don’t believe me? Just look at my end of undergrad and post-grad series of events:

I failed successfully when I told Maggie I wasn’t interested in her after our first date, but then basically professed my love 48 hours later. She still dated me.

I failed successfully changing my major in college. I was on track to be a clinical psychologist, but the research wore me out. I upgraded my Communications minor into a major, took an extra semester, and graduated with two degrees. I landed an internship that lasted just outside of my graduation semester and took a great paying sales/marketing job with a Fortune Global company in LA.

I failed successfully at a long distance relationship with Maggie. (This one is a stretch, we were both pretty bad at it.) Our communication was so terrible, we were forced to seriously examine how much we cared about each other. Now that we’re married, I can’t thank our 2-years-ago boneheaded selves enough.

I failed successfully in my first job at the aforementioned corporation. I worked a rotation that demanded 50+ hours every. single. week, granting me very little work-life balance. Thanks to California wage practices, I got overtime pay for those hours. This overtime helped me pay in cash for Maggie’s engagement and wedding ring and our honeymoon.
 

Failing successfully landed me living in California with this view a mile from my house. Not too shabby.

Failing successfully landed me living in California with this view a mile from my house. Not too shabby.


I miserably failed successfully at corporate life. I had always dreamed of climbing that ladder because I liked the idea of being loyal to one company, but the culture was a really bad fit. I lasted for about a year and half and quit. I managed to get a social media job at an agency in Boston, after relocating with aforementioned corporation, with no prior agency work. I took a paycut, but I'm so much happier.

So yeah, my major life events have sort of been the result of major fails. Successful fails, thank you very much.

If you’re looking for some kind of lesson, it’s this: don’t be afraid to fail. Fail so hard that you have nowhere to go but into a different class altogether. You never know what you’ll find.
 

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