Aug 9, 2025
Exit Planning Checklist for Executives: Are You Ready to Leave Corporate Life?
Zachary Ashburn, CFP®, EA, AFC®
Introduction
Are you ready to trade the golden handcuffs for freedom?
Leaving a high-level corporate role is a big decision—especially if your compensation package includes stock options, RSUs, bonuses, or other perks that are hard to walk away from.
This isn’t just about quitting your job—it’s about setting yourself up for long-term financial success and peace of mind.
High-level executives often think they’ll sort of magically know when it’s time to make the leap. But the reality? The inertia of the financial, logistical, and personal questions they’ll face once they step away from a corporate paycheck keeps most stuck.
That’s why we created our Exit Planning Checklist a simple set of questions to help you see how prepared you really are. In just a few minutes, you’ll get a clear picture of whether you’re in the “green light” zone, need to make some adjustments first, or still have key pieces to put in place before you hand in your notice.
If you’re even thinking about leaving your role in the next 12–24 months, this checklist will give you the clarity and confidence you need to make the move on your terms.
Get your copy here: Download the Exit Planning Checklist
Read more
Understanding Your Stock Options: A Guide to Incentive and Non-Qualified Stock Options
A guide to understanding your Incentive Stock Options (ISOs) and Non-qualified Stock Options (NSOs)
Zachary Ashburn, CFP®, EA, AFC®
A Guide to Employee Stock Purchase Plans (ESPPs)
A Guide to Understanding and Maximizing Employee Stock Purchase Plans (ESPPs)
Zachary Ashburn, CFP®, EA, AFC®
What Happens to Company Stock When You're Laid Off
A review of what happens to your RSUs and Stock Options if you get laid off