Ask These 3 Questions to Learn from Career Mistakes Made

Career Mistakes MadeWithin 2 years of graduating college I had managed to have 3 different jobs that had nothing to do with each other (to be precise: marketing, nannying, and law).

Worse yet: in changing jobs, I did everything you’re definitely not supposed to do. Because I was so miserable, I quit my first job without having a second one lined up. Instead of finding a job within my desired salary range, I then dipped deeply in to my savings while being a nanny. Finally, when I was about to run out of money, I desperately scrambled and ended up as an admin in a law office.

Now? I’m a life and career coach for Millennials. After all my blunders and missteps and mistakes, I help people pinpoint the intersection between their career and passion so that they can feel alive and fulfilled.

And here’s what I often tell my clients: if you pause and pay attention long enough to learn, so many career mistakes (and life mistakes, too!) are completely avoidable. And I ask them these three questions, all designed to help them get the most out of their career mistakes:

1. What’s Your Definition of “Mistake,” Anyway?

Not every blunder is a mistake. Maybe you said the “wrong” thing in an interview, and didn’t get the job. Or maybe you rushed a report, missed something crucial, and got reprimanded.

Messing up is part of human existence, and there’s nothing wrong with it. Often times we need the contrast of “bad” experiences to help us get clear on what kind of experience we do desire.

Maybe saying that “wrong” thing in the interview will help you get really clear on what you actually want to say next time. Maybe rushing the report and getting told off made you realize, “I rushed because I don’t care enough about this job, anyway, and it’s time to move on.”

I’m going to be a little bold and suggest that something doesn’t really qualify as a mistake unless you make it over and over again. One time? That’s a valuable learning experience. Five times? There’s probably something deeper going on that’s keeping you stuck in the same cycle. Which leads me to…

2. What Are You Refusing to Learn?

If you’re stuck in a pattern where you keep taking missteps, like “I’ve quit 4 jobs and every new job is just like the last” or “Every boss I have is terrible, I have really bad luck” or “Every time I make more money I feel like I lose it again” … that’s a glaring sign that you’re refusing to pay attention to something deeper.

Mistakes and missteps don’t happen “to” you; if you’re in a bad pattern, you’re the common denominator of that pattern. The unfulfilling jobs, the bad bosses, and the crappy salary will keep showing up until you choose to learn why they’ve been put in front of you in the first place.

For me, history kept repeating itself because I refused to be proactive. Instead of sitting down and getting clear on why I kept job-hopping into the wrong jobs for me, I’d just let the misery build until I desperately quit and moved on to the next one. It was totally reactive and born from a place of fear.

You might have “mistakenly” chosen to work with terrible bosses because you haven’t learned how to stand up for yourself and advocate for your needs. You might have “mistakenly” landed a string of unfulfilling jobs because you haven’t wanted to admit that you’re actually attracted to entrepreneurship.

So, that means the next question becomes …

3. How Willing You Are to do Something Differently?

No “mistake” needs to happen more than once, if you’re willing to question what the “lesson” of it was and take responsibility for your part in it.

And once you’ve owned up to the lesson, it’s time to pivot. Every mistake you make is an opportunity to clarify what you really want.

OK, maybe quitting your job didn’t work. Great. What would you rather have happened, then? Maybe that conversation didn’t go the way you wanted. Alright. How could it be better next time?

Make your mistakes useful by putting them to work as a foundation for what you desire in the future. 

Life doesn’t have to be chaotic. You don’t have to careen from one blunder to the next. You don’t have to grope in the dark until you figure things out. You can be thoughtful, proactive, and enlightened about your career path.

So, how will you re-define and learn from your career mistakes? I’d love to know.


For this post, YouTern thanks our friends at Levo League!


Levo League



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