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Advice / Succeeding at Work / Getting Ahead

3 Career Mistakes You Should Make (But Only Once)

I know what you’re thinking: Isn’t the point of reading advice-based articles online to avoid major mistakes?

But sometimes, lessons don’t really stick unless you experience that mistake—and all the consequences that result from it—first hand.

At least, that’s what I’ve experienced so far in my career. I’ve made some pretty big mistakes—but each one has taught me something extremely valuable that I probably wouldn’t have truly internalized if I’d just read about it from someone else’s perspective. And each was enough of a reality check for me to make sure I never made the same blunder again.

So, if you’re going to make mistakes in your career, make these three—but only once.


Mistake #1: Overpromising and Underdelivering

If you’re new to the professional world (and really, even if you’re not), it’s pretty likely that you want to impress your boss, clients, and co-workers—and you’ll do almost anything to prove your worth.

I was in that place a few years ago, as a manager at a cleaning and concierge service startup that was launching into the commercial cleaning space. We were thrilled when we were contacted by a large law firm interested in our janitorial services—but when I visited the offices to give an estimate, I knew that our small and minimally experienced team couldn’t realistically handle the job. (Seriously, the office was enormous.)

But, I was eager to please. Eager to please my boss with a huge new contract, and eager to please this potential client, who promised to recommend us to all of its large-office friends. So, to make sure we landed the deal, I raved to the client about how meticulous, detail-oriented, and reliable our employees were. I oversold the startup’s experience in commercial cleaning—by a long shot.

It only took a couple weeks for the law office to figure out we couldn’t deliver what we’d promised. Our teams spent far too long at the office each night (which meant we were losing money), and even still, complaints about the things we’d overlooked—from still-dusty shelves to toilet paper that hadn’t been restocked—skyrocketed.

Needless to say, we lost the contract.

If you, like me, make the mistake of overpromising (and not coming through) once, you’ll never make it again. I learned that it’s far better to be completely realistic about what you can offer, whether it’s to a client, your boss, or your team. Then, the only risk you run is doing even better than you promised and completely thrilling your customers, manager, or colleagues—which is a whole lot better than than disappointing them.


Mistake #2: Going Into an Interview Unprepared

About a year ago, I was in the running for an internal move at my company into a different department. I made it through two rounds of interviews before they told me there would be one final meeting with the senior VP of the department. The recruiter I was working with was super casual about the whole thing, so I assumed it was more of a meet-and-greet than a true, formal interview.

So it caught me a little off guard when the SVP launched into full-force questioning mode the minute I sat down in her office. “What makes you think you’re qualified for this position?” she fired. “What’s the biggest opportunity this department isn’t taking advantage of? What’s a critique you would give to a recent project that we’ve done?”

I looked at her in silence (and utter embarrassment) as I searched for a semi-coherent answer. Since I hadn’t done any research or asked good questions in my prior interviews, I had no idea how to respond.

Take it from me: Nothing will get you in interview-ready shape as quickly as showing up unprepared just once. My experience was terribly embarrassing (and I definitely didn’t get the job), but it knocked some serious sense into me about how to prepare for interviews. Since then, I’d never approach an interview—no matter how casual it may seem—as just a “meet and greet.”


Mistake #3: Turning Down an Opportunity Because You’re Scared

There are plenty of times you may be tempted to turn down an extra project or opportunity because you’re swamped with work already and can’t possibly take on something else. I get it.

But there are also times when, if you dig a bit deeper into your intentions, that you find that you’re actually turning it down because you’re not sure if you can do it and you’re afraid to fail.

Several months ago, I was given the opportunity to take on a new team as part of a special project initiated by my company’s executive team. I was pinpointed as a possible leader and was asked if I was interested in taking on the challenge.

Honestly, it terrified me. I felt comfortable in my current role, wasn’t sure if I’d be successful in the new role, and, overall, felt like it was a safer bet to just stay where I was. It was only after I turned it down that it really hit me how much of an opportunity I’d missed. Here was my opportunity to advance—quickly—and prove to the entire C-suite that I could be a leader. And I missed it because I was scared.

Do that once, and I promise you’ll never do it again. Sure, you may evaluate a role, project, or opportunity and decide it’s truly not right for you or your career goals (and that’s fine)—but you’ll certainly never turn anything down for the sole reason that you’re scared of failing. Because often, you’ll find the risk is worth the reward.



Are career blunders embarrassing? Yes. But are they valuable tools to help you improve as a professional, build confidence, and advance your career? Absolutely. So don’t just take it from me—experience some mistakes (with a bit of caution, of course) and learn for yourself.


Photo of crumpled paper courtesy of Shutterstock.