10 Tough-but-Valuable Career Lessons to Learn by 30


a woman standing in an art gallerySome of the most important lessons you learn during your first decade working in “the real world” come from one source: The school of hard knocks.

There are professional failures you can’t predict, opportunities that end up being too good to be true, and moments when you don’t live up to your potential.

Although they may seem career-ending in the moment, these workplace setbacks can prove their value over time.

In part, it’s because they are mistakes you’ll never forget or repeat.

We rounded up 10 tough career scenarios that often happen as you’re building your career in your 20s—along with expert advice on how to find the “silver lining” lessons within these career clouds.

#1: Your dream job is a dud.

It’s a common predicament: You nailed what you thought was the perfect gig—but your day-to-day hasn’t lived up to the hype or your lofty expectations.

That’s the situation Golda Manuel found herself in when, at 28, she scored a pharmacist position at a health care company in San Francisco.

“My attraction to the job was the breadth of impact I thought I could have, but there was no time to focus on one customer—it was very impersonal,” recalls Manuel. “I expected it to make me happy and earn me respect. Boy, was I wrong.”

The Silver Lining Lesson: This kind of career reality check can inspire soul-searching—and ultimately lead you in an unexpected, more satisfying direction.

Take Manuel, who cofounded Social Scout, an app that helps small business sellers succeed on Amazon—a complete 180 from her pharmacist gig.

“I’m now able to speak to fellow small business owners to understand their growing pains, and work in a community with a common goal and purpose,” she says.

A dream job’s letdown is also a reminder not to assume any one thing will make you happy—be it a job or a purchase.

Cheryl Palmer, founder of Washington, D.C., coaching firm Call to Career, emphasizes setting realistic expectations from the get-go for any job—even those purported “dream gigs.”

So instead of being bummed that your job isn’t as fast-paced as you’d hoped it would be, for example, look at it from the viewpoint that you can channel that energy toward networking and getting more involved with industry events.

“I encourage clients to find as much job satisfaction as they can while still being realistic,” Palmer says. To keep the pros and cons in perspective, she recommends regularly taking the pulse on your job satisfaction. If it’s at 80%, you’re doing pretty well—but if it dips to 40%, it may be time to move on.

#2: You didn’t adequately prep for an interview.

You’re burned out from months of job hunting. You’re overconfident. You’re just not that into the position—but you need a job.

Whatever the reason, not knowing enough about a company, a role or the person interviewing you leaves an equally poor impression.

That’s what happened to Karen Robertson. At 21 she felt overqualified for a telemarketing job but needed the income. “I was about to get my [teaching] degree, and I was arrogant,” she says. “I felt like any fool could do the job—and it came off that way in the interview.”

Needless to say, she didn’t get the gig.

The Silver Lining Lesson: An interview requires your valuable time—and someone else’s. Flubbing it takes you down a few notches.

So how do you save face?

“Send a thank-you note, anyway,” suggests Rosalinda Randall, a career etiquette expert and author of “Don’t Burp in the Boardroom.” “I believe there’s value in acknowledging that you were unprepared, and that with the research you’ve done now, you would be grateful for another opportunity.”

Doing your homework is just as important when networking.

Toronto-based career and leadership coach Kamara Toffolo once confidently approached an exec at a financial services conference to introduce herself. It went well—until she introduced herself again later in the day.

His response? “You’re in a business where you need to remember names.” Ouch.

“I am now an expert at remembering faces and names,” she says. “It’s a skill that has served me very well.” In fact, Toffolo graciously apologized for her error and, years later, that same man gave her a job.

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