Why No Employee Should Be “Loyal” to Their Boss

If you quit a job and regretted it, would you ask for that job back?

Now flip the table: If you were the boss, would you take an employee back after they quit?

A lot of people are asking themselves these questions lately — because according to research from the payroll firm UKG, nearly 1 in 5 people who quit their job in the past few years have already gone back to it.

There’s even a term for these workers: They are “boomerang employees” — people who left and came back. The Great Resignation, it seems, has led to a lot of great regret.

But here, I think, is the most regrettable part about all this:

According to CNBC Make It, some bosses don’t want to take these employees back. “They think it sends a harmful signal to other employees about loyalty,” a management and HR professor told the CNBC site.

Loyalty. Ha! Loyalty is for the mafia.

In the real world, nobody should talk about loyalty.

They should talk about mutual opportunity — and sometimes, that can be strengthened by someone who leaves.

For example, here’s a quick story:

Early in my career, I quit one magazine to take a job at another. This was standard stuff — I was a junior editor looking to stretch my wings, and excited by a new opportunity.

The day I put in my resignation, the magazine’s editor in chief called me into his office. I arrived, thinking he’d congratulate me. But instead, he was waiting with his second-in-command lackey. Then the two tried to badger me into staying.

“What are you doing!?” one of them said. “You’re making a huge mistake.”

They made it clear: If I left, I was dead to them.

After that, I was very happy to be dead to them. I didn’t want to work for people like that. But more importantly, I thought: When I’m in their position, I will act very differently.

I’m proud to say, I have held up that pledge. No matter where I’ve worked, whenever someone on my team has left, I congratulated them. Yes, I’m bummed for me — but I’m happy for them. “I knew this day would come,” I often say, because they’re so damn talented that I’m obviously not the only one to notice.

Also, I know that, as a boss, I cannot provide everything they want from work. Nobody can! I mean, someone out there can offer more money than me, and different experiences, and a bigger title. A few years ago, Entrepreneur’s deputy editor left to become editor in chief at another magazine. How could I possibly begrudge that!? I cannot.

Then I say to them: I hope we get to work together again.

Because I’ve had that pleasure too! Many of my team members at Entrepreneur, for example, have also been former colleagues from other magazines. And here’s the crazy thing: They were talented the first time but they’re even more talented the second time — the result of having absorbed even more ideas and experiences at other places.

We should want this. We should value this.

If I asked my team to be “loyal,” I’d be asking them to stunt their growth. To limit their abilities. To hinder the contribution they could make to our team, or to anyone else. I’d be saying, “I expect you to value me over yourself.” What kind of boss asks that? Not one I’d want to work for.

That’s why I wrote above: Forget loyalty. Think about mutual opportunity. When people leave and reunite, they are building mutual opportunity. They are better together, because they were apart.

Now, back to the questions I asked at the top:

If you quit a job and regretted it, would you ask for that job back?

Yes, if it is truly the right move for you.

But before you do that, ask yourself: “Did I learn everything I needed to learn at that job?” Because if the answer to that question is yes, then going back may be comfortable, but it will not advance your career. You will only remain qualified to do the thing you already did.

Now flip the table: If you were the boss, would you take an employee back after they quit?

Was this person valuable to your team before? If the answer is yes, then they will be just as valuable now — if not more so.

I don’t care if that person left last month or three years ago. By leaving, they will have learned something — about themselves, about their job, about your industry. They will come back with fresh eyes. Renewed energy. Excitement for a fresh start.

Life is not a series of divergent lines. It is a jumble of squiggles that bounce off in every direction and intersect, sometimes repeatedly, in strange and wonderful ways. Let’s make room for that.

We’re not done with each other yet.

This Shark Has No Bite!

Being silly is a good business strategy.

That's what Shark Tank's Barbara Corcoran just told me — here's why.

I was just a guest on Barbara's fantastic podcast, Business Unusual, which you can hear here. Afterward, we did a bunch of goofy stuff in her office — filmed some TikToks (see here and here), took a bunch of funny photos (see above). It was a blast.

"You can't take yourself too seriously," she said.

I asked why she feels that's important.

"Because people instinctively know what genuine is," she said. "And when you're not genuine, people see right through it and you lose credibility. The most important thing in all business is trust."

I love that.

People do business with people, not with machines. They want to know you're real. That requires letting your guard down, and sometimes, making a funny face for the camera.

Oh, and finally today: Thanks to Margot Boyer-Dry for sending me the link about "boomerang employees" and inspiring today's newsletter. See something I'd like? Email me! You can just reply to this email, or go here.

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Cover credit: Getty Images / Macbrian Mun