Should You Stay in a Bad Job to Avoid Job Hopping?

Good Morning. According to a new study, the sales floor is aging faster than your LinkedIn profile photo. The average new hire in 2025 is 42 years old, and hiring of workers 25 and under has dropped 45% since 2019. Meanwhile, workers 65 and older are flooding into sales roles specifically, overrepresented by more than 10 percentage points compared to other age groups. Gen Z might be redefining workplace culture everywhere else, but in sales… It's millennials, Gen X, and boomers holding down the fort. Now, let's get into today's Follow Up.

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At some point in your sales career, you hit a crossroads.

You’re meeting expectations. Forecast calls are routine. From the outside, it all looks fine.

But the job doesn’t feel like it’s moving you forward.

A lack of deals. And the same conversations. Months go by, and your skillset feels… unchanged.

That’s where the dilemma starts.

Leaving feels risky. Another short stint on your resume. And another story to explain in interviews.

But staying also means wasting more time on a role that might be a dead end.

You’ll probably run into this eventually. Stuck between playing it safe and wanting more.

Before you think about job hopping, you need to answer one thing honestly.

Are you thinking about leaving because the role is a dead end… or because you’ve hit a rough stretch and it’s uncomfortable right now?

Working hard is normal in sales. Feeling stagnant for months isn’t.

Early in a role, especially in the first few months, there’s usually a stretch where you’re still finding your footing. That’s normal. This looks like:

That kind of pressure can make you question your job.

It can also be a sign you’re actually learning. Many reps feel this right before something clicks and their skill set levels up.

A dead-end sales job looks different:

Ask yourself this: “If I stayed one more year, would I leave with experience another company would actually want… even if my pay didn’t change?”

If the answer is yes, leaving now may be premature. You might just be in the hard part of growth.

If the answer is no, staying longer won’t fix that. At that point, you’re just delaying a move you already know is necessary.

Where you are in your career changes how risky or smart leaving is.

Still early in your career (0-3 years)? You have more flexibility, but patterns still matter.

If you can tell within the first couple of months that a role is the wrong fit, leaving early is usually cleaner than dragging it out to 6-12 months.

Short stints on their own aren’t automatic red flags anymore. Recruiters understand that roles don’t always work out.

What does raise concern is repetition. A LinkedIn survey found that 37% of hiring managers still view frequent job hopping as a red flag.

The story behind each move matters more than the move itself. But a history of job hopping on your resume can make recruiters skip over you before you have a chance to explain.

The money conversation changes based on where you are in your career.

Early on, chasing the biggest paycheck is usually a mistake.

In your first few years, optimize for experience, skills, and network. Get around people who know what they're doing. Learn how to sell.

Name brand companies matter more than you think. Some hiring managers will bring you in just because you worked at Oracle, HubSpot, or Google. That's real currency on your resume that compounds over time.

If you're choosing between a $70K base at a well-known company with strong training and a $90K base at a company no one's heard of, the first option is probably smarter long-term.

But as you get deeper into your career, earning potential becomes harder to ignore.

Here's the reality. You can take two reps with the exact same skills and the exact same network. Put one at a company selling a $1M product that everyone needs. Put the other at a company selling a $100K product no one needs.

The first rep will always make more money. And they'll probably be happier because of it.

The product you sell and the market you're selling into matter just as much as your ability to sell. Maybe more.

Here's the final test… Look at the last few months of your work.

The results you drove. The deals you owned. The rooms you were pulled into. The problems that made you stop and think.

Did the work force you to think harder? Did it expose gaps you need to work on? Did you feel yourself getting sharper?

If yes, your gut probably already knows the answer. The role is still giving you something worth staying for.

And if you're later in your career, ask yourself one more question: "Am I actually earning what I should be earning given my skills and experience?"

If the answer is no and the path to getting there doesn't exist where you are, that's information worth listening to.

Let's be honest. Job hopping isn't a great look. But wasting time in a role because it feels comfortable isn't much better.

Today’s newsletter was written by Nic Conley