How to Leave Something, Even If You Still Sorta Like It

Ask yourself: Are you holding on to a dead-end benefit?

Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that's me) shares one way to level up — and build a career or company you love.

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Today’s one thing: Feeling attached.

That one thing, better: Feeling emboldened.

Made with DALL-E

You’re ready for a change, but there’s something you can’t let go of.

Maybe you’re unhappy in your job, but there’s some perk or status you stick around for.

Maybe you’re unhappy in a relationship, but there’s some comfort or convenience you love — and it’s why you stay.

Maybe there’s a project you want to quit. Or an industry you’re sick of. Whatever it is, you’re ready to go — but you struggle to leave some small part behind, which is pleasurable and meaningful.

You keep asking yourself, “Is this worth staying for?”

Today, I’ll help you answer that question. And I’ll start with my own version of this problem. Are you ready to meet Drunk Party Jason?

A Long, Long Time Ago...

I moved to New York at the age of 28, to take a junior editing job at Men’s Health. I didn’t know many people in the city. My evening plans were often empty.

Then the invitations rolled in.

Here’s the thing: When you’re an editor at a big consumer magazine, you get invited to stuff. Movie premieres! Concerts! Swanky brand events! Here, for example, is me photobombing Bradley Cooper at... y’know, I can’t even remember.

At these events, colleagues turned into close friends. My girlfriend (now wife) and I had great adventures. They formed the foundation of my social life, and they made me feel cool and important.

But there was a problem: After a while, I was kinda sick of Men’s Health. The work got boring, and there was little room for growth. But every time I thought of leaving, I got scared… because I didn’t want the party invites to stop.

Now, as I look back on that time in my life, I realize what those parties had become. They started as a Forward Benefit, but they eventually became a Dead-End Benefit.

And if you’re ever in this situation, you better know the difference.

The many benefits of benefits.

OK, let’s step back for a moment and consider benefits.

Everything we do has some benefit. A job could have many benefits — like the pay, experience, professional relationships, lifestyle, status, access, or whatever. The same is true for every relationship you’ve been in, every project you’ve taken on, and every commitment you’ve ever made.

There’s nothing wrong with benefits. There’s nothing wrong with enjoying benefits! 

But every benefit comes with a sacrifice. The benefit is your reward for choosing one thing over another.

For example...

  • If someone has “golden handcuffs,” then they’re choosing the benefit of a high salary in sacrifice of other pursuits.

  • If someone enters a monogamous relationship, they’re sacrificing experiences with other people.

  • If someone works in the arts, they might be choosing the benefits of passion over financial security.

Hopefully, for the people choosing these benefits, the sacrifice doesn’t feel like much of a sacrifice. They have goals, they’re clear-eyed about those goals, and they see how the benefit helps them reach their goals.

If that describes you, then I’d say you have a Forward Benefit — a benefit drives you towards your goals.

But these calculations are not static. Benefits, sacrifices, and goals will change. So if you’re considering any kind of change, it’s worth asking yourself: 

Is the benefit still worth the sacrifice — or is the sacrifice now larger than the benefit?

The downside of benefits.

Here’s the moment this all collided for me: I got a job offer at Fast Company. I was now in my early 30s, bored at Men’s Health, and this new job would allow me to grow as a writer and editor. It paid better too.

But I hesitated. Fast Company doesn’t write much about booze or movies, which means I’d lose my invites to those parties. And silly as it sounds, that hurt.

I remember weighing my options. Then I made an important realization: 

When I needed to build a social life, the parties helped me do that. Again, they were a Forward Benefit — a benefit that advances your goals.

But a few years later, I had a social life! I had great friends, professional connections, and plenty to do. So I’d developed new goals: It was time to focus more on my career. 

That meant the parties were just parties. They didn’t move me forward. They were a Dead-End Benefit — a benefit that might be enjoyable, but that leads you nowhere new.

The choice was clear. I took the job.

And you know what? My old friends still got me in to a bunch of those parties… until we all got bored of them, and life moved on. Because that’s another thing about benefits: Even if you never lose them, you can outgrow them.

So if you’re considering a change, and there’s something you just can’t let go of, also consider this:

Change isn’t just about loss.

We often experience change as loss. We think about the things we have — those comfortable, familiar, warm things — and how change will cause us to lose them.

But change creates gain too, even if it’s harder to see at first. (This is a central theme of my book.) When you quit something — even if it’s something you’ve loved — you free up your time for other pursuits.

A benefit should help you reach your goals.

A benefit shouldn’t hold you back from goals.

The benefits you enjoy today are not the only benefits you’ll ever have. There are more of them, wherever you go. They will take different forms. They will serve different purposes. And if you’re intentional about your choices, those new benefits will provide what you need now and tomorrow — and not just what you needed yesterday. 

That’s how to do one thing better.

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Here’s how it’ll go:

One of our members has built a new digital product, and is figuring out her go-to-market strategy. I’m bringing in an expert who specializes in this, and we’ll talk her through it — and invite anyone else to offer advice or ask questions too. Together, we’ll learn how to jumpstart your sales.

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P.S. Did you miss last week’s newsletter? It was about how to make people do what you want. Read!

P.P.S. Did the haters come for you? I loved this advice from a writer who's been a target many times. Read!

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