Expert Insights for High Earners escaping Golden Handcuffs


This is where golden handcuff planning gets tactical.
Our articles are written for VPs, Directors, and senior professionals navigating equity, taxes, and the emotional weight of leaving corporate life. If you're ready to build your exit plan, or just curious how close you are, you're in the right place.

All blog posts

How to escape your golden handcuffs, exit the corporate world, without a big tax bill
How to escape your golden handcuffs, exit the corporate world, without a big tax bill
How to escape your golden handcuffs, exit the corporate world, without a big tax bill

How to Build a Tax-Smart Exit Plan From Corporate Life

Leaving corporate life without a tax strategy can cost executives hundreds of thousands in lost wealth. Learn how to design a tax-smart exit plan around RSUs, options, and deferred compensation.

an image of the author, Zach Ashburn CFP®
an image of the author, Zach Ashburn CFP®
an image of the author, Zach Ashburn CFP®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

An Expert in Golden Handcuffs discusses the risks of staying put in a corporate job too long
An Expert in Golden Handcuffs discusses the risks of staying put in a corporate job too long
An Expert in Golden Handcuffs discusses the risks of staying put in a corporate job too long

The Hidden Risks of Staying Too Long in Corporate Golden Handcuffs

Golden handcuffs can seem like a reward for loyalty, but staying too long in them carries hidden risks. Learn the financial, career, and personal costs executives face — and how to break free on your own terms.

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Don't Let AI Take Your Job, Leverage it Instead

How I Made a Viral AI video and how other's can leverage this idea to break their golden handcuffs

a photo of Zach Ashburn CFP® the author
a photo of Zach Ashburn CFP® the author
a photo of Zach Ashburn CFP® the author

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Exit Planning Checklist for Executives: Are You Ready to Leave Corporate Life?

Thinking about leaving your corporate role? Our Exit Planning Checklist helps executives with $2M+ in assets navigate stock options, taxes, and lifestyle changes before making the leap.

a photo of the author, Zach Ashburn CFP®
a photo of the author, Zach Ashburn CFP®
a photo of the author, Zach Ashburn CFP®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Reach Media Mentions

Links to our firm and advisors featured in the media

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

"Signs it's time to leave your high-paying job – golden handcuff planning guide"
"Signs it's time to leave your high-paying job – golden handcuff planning guide"
"Signs it's time to leave your high-paying job – golden handcuff planning guide"

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

Tired of corporate life but unsure if it’s time to leave? Learn the signs that show it's time to exit golden handcuffs—and how to start planning your move.

an image of the author, Zach Ashburn CFP®
an image of the author, Zach Ashburn CFP®
an image of the author, Zach Ashburn CFP®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

"Graceful exit from golden handcuffs – how to leave a high-paying job smartly"
"Graceful exit from golden handcuffs – how to leave a high-paying job smartly"
"Graceful exit from golden handcuffs – how to leave a high-paying job smartly"

How to Unlock Golden Handcuffs Without Burning Bridges

Ready to exit your high-paying role? Learn how to unlock golden handcuffs with a smart, graceful plan that protects your wealth, network, and next move.

An image of the author, Zach Ashburn CFP®
An image of the author, Zach Ashburn CFP®
An image of the author, Zach Ashburn CFP®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

"Golden handcuffs cost calculator – high-paying job trade-offs explained"
"Golden handcuffs cost calculator – high-paying job trade-offs explained"
"Golden handcuffs cost calculator – high-paying job trade-offs explained"

How Much Do Golden Handcuffs Really Cost You?

Think you're winning by staying in a high-paying job? Learn the true financial, emotional, and opportunity costs of golden handcuffs—and how to exit wisely.

A picture of the author, Zach Ashburn CFP®
A picture of the author, Zach Ashburn CFP®
A picture of the author, Zach Ashburn CFP®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

5 Types of Golden Handcuffs (And How to Unlock Each One)

Explore the five most common types of golden handcuffs and how high earners can break free from each one without risking their financial future.

An image of the author, Zachary Ashburn CFP®
An image of the author, Zachary Ashburn CFP®
An image of the author, Zachary Ashburn CFP®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Graphic titled “What Are Golden Handcuffs?” showing planning tools and symbols for stock options and corporate benefits
Graphic titled “What Are Golden Handcuffs?” showing planning tools and symbols for stock options and corporate benefits
Graphic titled “What Are Golden Handcuffs?” showing planning tools and symbols for stock options and corporate benefits

What Are Golden Handcuffs? (And How to Break Free)

Golden handcuffs keep high earners stuck. Discover what they are, how they work, and how to break free — without blowing up your finances.

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

Zachary Ashburn, CFP®, EA, AFC®

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Reach Strategic Wealth LLC (RSW) is a registered investment adviser offering advisory services in the State of North Carolina, State of Connecticut, and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training. The presence of this website on the Internet shall not be directly or indirectly interpreted as a solicitation of investment advisory services to persons of another jurisdiction unless otherwise permitted by statute. Follow-up or individualized responses to consumers in a particular state by RSW in the rendering of personalized investment advice for compensation shall not be made without our first complying with jurisdiction requirements or pursuant an applicable state exemption.

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Reach Strategic Wealth

Based in North Carolina & Connecticut

© 2025 Copyright

Reach Strategic Wealth LLC (RSW) is a registered investment adviser offering advisory services in the State of North Carolina, State of Connecticut, and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training. The presence of this website on the Internet shall not be directly or indirectly interpreted as a solicitation of investment advisory services to persons of another jurisdiction unless otherwise permitted by statute. Follow-up or individualized responses to consumers in a particular state by RSW in the rendering of personalized investment advice for compensation shall not be made without our first complying with jurisdiction requirements or pursuant an applicable state exemption.

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Reach Strategic Wealth

Based in North Carolina & Connecticut

© 2025 Copyright

Reach Strategic Wealth LLC (RSW) is a registered investment adviser offering advisory services in the State of North Carolina, State of Connecticut, and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training. The presence of this website on the Internet shall not be directly or indirectly interpreted as a solicitation of investment advisory services to persons of another jurisdiction unless otherwise permitted by statute. Follow-up or individualized responses to consumers in a particular state by RSW in the rendering of personalized investment advice for compensation shall not be made without our first complying with jurisdiction requirements or pursuant an applicable state exemption.

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