How to Unlock Golden Handcuffs Without Burning Bridges

Golden handcuffs keep high performers stuck: great pay, solid benefits, maybe even prestige. But when it’s time to go, how you exit matters just as much as when.

This guide breaks down how to create a smooth, strategic departure that protects your relationships, your reputation, and your future.

Step 1: Know What You're Walking Away From

Before you exit, get clear on the financial benefits you have and what you'll leave on the table when you exit:

• Vesting schedules for RSUs/ESPPs

• Bonus payout timing

• Deferred compensation and 401(k) match timing

Pro move: Run scenarios with your advisor to see if waiting 3 months could mean keeping an extra $50k+. If you aren't sure what happens to your equity when you leave, checkout our Golden Handcuffs Resource Library for more info about leaving your job.

Step 2: Build Your Personal Runway

Whether you're retiring, launching a consulting business or taking a break, you need a clear plan for:

• Monthly spending needs

• Business ramp-up time (if consulting)

• Health insurance coverage

• Tax planning for variable income

Most people underestimate how long it takes to replace their W2 paycheck. Don’t wing it. Consider creating a Stoplight Plan to help you know when it's time to pull the ripcord.

Step 3: Protect Your Reputation

Even if you're done with your job, you aren't done with your network. In fact, it's probably best to use the 6 months before your exit to shore up your network contacts both in and out of your current company. There's no downside to having people in your corner.

• Give proper notice

• Document your work

• Leave systems organized

• Thank your team and mentors directly

People remember how you leave. Make it classy.

Step 4: Be Strategic with Timing

Some exits are triggered by burnout or frustration. But if you can pause long enough to time your departure, you'll benefit.

Smart exit triggers:

• After key vesting dates

• After performance bonuses hit

• After your replacement is trained

Don't let emotions make expensive decisions. It's often best to burn some vacation days to get enough space to make a plan rather than burning bridges with an explosive exit.

Step 5: Have a Post-Exit Plan

Without a plan, freedom can quickly feel like floating.

• What will you do the first week after you leave?

• Who will you meet with in month 1?

• What will success look like after 90 days?

• What's the goal for the next year?

You don't have to know all of the specifics but the exit isn't the end, it’s the beginning of your next chapter. One of the ingredients for a confident exit is knowing what you're moving to along with what you're moving on from.

Use Our Exit Planning Checklist to Plan Your Jump

We built our Exit Planning Checklist specifically for people like you:

• High earning professionals with equity

• People who want to consult or pivot

• Those who want a smart, strategic transition

> Download the Exit Planning Checklist