What’s The Biggest Career Mistake You’ve Ever Made?

Business blunders are always bad, right? Or are they? Our readers speak.

What’s The Biggest Career Mistake You’ve Ever Made?
[Image: Flickr user Jonathan Kos-Read]

You know the saying: Hindsight is 20/20.


We’ve all made mistakes over the years. Conventional wisdom says that mistakes in business are bad. Or are they? Some would say that if you fear failure, you’ve already failed–heck, billionaire inventor James Dyson swears by mistakes.

We’re taught to do things the right way. But if you want to discover something that other people haven’t, you need to do things the wrong way. Initiate a failure by doing something that’s very silly, unthinkable, naughty, dangerous. Watching why that fails can take you on a completely different path. It’s exciting, actually.

Hopefully, though, we can learn from our mistakes regardless of what they mean. In the spirit of sharing and learning, we posed a simple question on Facebook:

What’s The Biggest Mistake You’ve Made In Your Career So Far?

Your responses came streaming in:

Yes, Sarah. Thank you for getting us started on a positive note. Instead of looking at all of our “mistakes” as “failures,” let’s look at them as lessons. Each bump in the road leads to a learning opportunity and more informed decisions.

As our buddy James Dyson has already told us, you’re not the only one to have the same attitude. And that’s a good thing.

That said, you can’t be reckless about it. You do need to reinvest in your future and . . .


. . . make sure you’re never blinded by passion. Success can be addicting, but it can also make you delusional–which can hurt those around you.

During a recent live Q&A with Fast Company, Reddit cofounder Alexis Ohanian touched on this very subject. Ohanian’s advice? Embrace competition, but don’t pay attention to it.

First, realize no one has a really ‘new’ idea–everything is a remix, people.

A week after we launched Reddit, I discovered Digg (seriously, I found the email and quoted it in the book). I emailed Steve and PG (Paul Graham), saying “Meet the enemy:,” and PG gave some great advice: competitors will never beat you; ignore them. And he was absolutely right–look at Digg and all the Digg clones who just clumsily aped what they did. They’re all gone.

So don’t let incumbents stop you. Ignore them and out-execute them!

If your coworkers are hooked on procrastination and drama, that’s a bad situation. In fact, it sounds like you worked with the “classic” rude coworker.

So, let’s try to take this one step at a time.

Sometimes, you actually need to embrace procrastination to combat it effectively.

Procrastination can also be a serendipitous way of stalling a project that needs some further percolation before completion. Often holding off on a client proposal means I will run into someone with new information that shifts my approach and enables me to seal the deal.

Office drama’s hard, and, to be honest, it just stinks. If you’ve got a problem, just say something. Nobody wants their dirty laundry aired out to the world, (or maybe some do).


Andrea, we agree. If you need something, or have a question, just ask. It’s always faster to go directly to the source than wait around.

Uh, yeah. That’s a problem.

A startling lack of women in the workplace is not that uncommon, despite the fact that female brainpower is the secret to succeeding in today’s economy.

Working in a male-dominated workplace can work for some, but we commend you for getting out of there. Employers shouldn’t be rewarded for discrimination. They’re the ones who are missing out anyway.

If you’re ever looking for some inspiration, check out our League Of Extraordinary Women.

About the author

Former Editorial Assistant Miles Kohrman helped run Fast Company's homepage and completed miscellaneous tasks around the newsroom. He is a 2013 graduate of The New School.