Intentionally Experience Failure – It's Not the End of the World

In this series, professionals reflect on their inevitable career mistakes. Follow the stories here and write your own (please include #BestMistake in your post).

Most career mistakes don’t happen on purpose. You screw up, you have regrets, you learn from them.

But there’s a mistake everyone should make intentionally: setting yourself up to experience failure and rejection. There are lots of ways to “achieve” this, like starting a company (plenty of opportunities to be rejected here – from fundraising to customers not responding to your product to hiring that doesn’t go as you’d hoped). Or trying something really out there that doesn’t pan out. At HotelTonight we even have a “Vest of Shame” to celebrate people who boldly and admirably take a chance on something that could go great – but doesn’t. One story that's infamous around HT HQ: when our Vegas Market Manager at the time (also named Sam) was experimenting with adding some killer HighRoller suites to the app – and accidentally took down the entire Vegas market in the process. He got it back up on the app within minutes, but had (or got!) to rock the Vest at our iPad launch party later that week. We want to encourage people to take these kind of chances, and the Vest of Shame is considered a badge of honor at HT.

One thing everyone can do: apply for a job that’s out of your league.

Choose a position that’s a total long shot. Maybe it’s an industry that you’ve never worked in or don’t know a lot about. Maybe it’s only tangentially related to what you know how to do. Maybe it’s just way over your head.

If you get the interview, go in knowing there is a very good chance you’ll be rejected. Best-case scenario: you get the job and can decide whether you really want it (maybe it turns out you actually do). But the other best case is that you will, indeed, be rejected. And it won’t kill you. Sure, even when you’re prepared for rejection, it stings. But you’ll get over it. You’ll learn a lot by how you react to failure, and how you move past it. It will help you build a thicker skin and a tolerance to whatever comes your way.

I’ve experienced plenty of failure in my career (see: starting a company, above), and I don’t regret it. Learning how to deal with it has made me stronger and much more apt to take chances – chances that often pay off.

I believe that experiencing — and getting comfortable with — failure is one of the best things you can do for your career. Rejection is not the end of the world. In fact, it can often be an impetus to something great.