How to Know When It's Time to Leave the Golden Handcuffs Behind

Some people leave too soon and regret it. Others stay too long and burn out. So how do you know when it’s time to pull the ripcord and move on?

This isn’t just about quitting your job. It’s about knowing when staying is costing you more than it’s gaining. Here’s how to spot the signs and start thinking about your exit the smart way.

1. The Paycheck No Longer Feels Worth It

Let’s be honest: money matters. The salary, the equity, the bonuses…they’re what made you stay in the first place. But what happens when all that starts to feel empty?

You know the feeling:

• You start dreading Mondays by Saturday night.

• You feel drained even after a long weekend.

• The thought of one more performance review makes your stomach turn.

• You're sitting in another meeting that doesn't apply to you

That paycheck might still be great on paper, but if it’s not buying you peace of mind, time with your family, or energy to enjoy life outside of work it could be time to question the tradeoff.

When you stop calling them golden, they might start to feel like just…handcuffs.

2. Your Career Has Stalled (and You’re Okay With That)

There comes a point when the chase for the next title, the bigger bonus, the corner office... just doesn’t excite you anymore. That doesn’t mean you’re lazy. It might mean you’re done climbing this ladder.

Maybe you’ve realized:

• You have zero interest in managing more people.

• The politics feel heavier than the pay.

• You’re already doing your job with your eyes closed.

I remember very specifically a role where the path ahead was very clear and I knew for sure I didn't want it.

Here’s the thing: when your career hits cruise control and you’re fine with it, it’s usually time to consider what’s next. Feeling stalled happens to everyone at some point but when it starts to erode your energy and ambition it can be a cue for more planning.

3. You’re Curious About What Else Is Out There

This is the quiet one. The one that sneaks up on you in podcasts, newsletters, and Twitter threads.

You start noticing other people doing interesting things: consulting, starting a business, freelancing. You think, "I could do that... if I had a plan."

That curiosity? That’s not nothing. That’s your brain trying to tell you you’re ready to explore. And once that voice gets loud enough, it’s hard to ignore.

If you’ve opened Google and typed in "how to start consulting," you’re already halfway out the door mentally. It’s time to get a real plan on paper.

4. You Might Have Enough (But You Haven't Done the Math)

This one hits home for a lot of people. You’ve got equity, a strong salary history, maybe even a good chunk saved. But you haven’t actually figured out how far it could take you.

So you stay. Just in case. Because giving it up for the unknown is too expensive and risky.

Meanwhile, the clock keeps ticking and your energy keeps fading.

A detailed cash flow plan could reveal:

• You have more flexibility than you thought

• You could cover a runway to launch a consulting practice

• Your income needs aren’t as high as your W2 paycheck suggests

Don't let fear of the unknown keep you stuck. Do the math and make your next move with confidence.

5. A Trigger Event Forces the Question

Sometimes you don’t get to decide when to ask the big question. Life does it for you.

Maybe your company is acquired. Your role changes. A new boss comes in with a very different vibe. Or someone in your family needs more of your time.

On the personal side of things exits can be triggered by health events or caregiving responsibilities too.

We’ve worked with many clients who didn’t leave because of some big master plan. They left because a moment came that forced the decision.

The difference between panic and confidence? Preparation.

You Don't Need to Leave Tomorrow. But You Do Need a Plan.

Leaving a high-paying job with equity, benefits, and prestige shouldn't be done on a whim.

But once you start seeing the signs, you can’t unsee them and the sooner you start thinking about your exit, the smoother it will be when the time comes.

That’s why we created our Golden Handcuffs Resource Library to help you address your biggest planning questions.

You can also checkout the Exit Planning Checklist to see exactly how ready you might be to pull the ripcord on your current role.

• Feel financially ready

• Know exactly what your runway looks like

• Time your exit around equity and benefits

Download The Exit Planning Checklist here