We love it when a retirement plan comes together—when the equity is vesting, the calendar lines up, and the runway to exit is clear.
Sometimes, the stock doesn’t cooperate. This is especially true for executives who have built significant equity compensation positions. When you’re sitting on unvested equity, options, or milestone triggers, we need to be ready to pivot when the variables change as you approach your exit.
Start With How Much Is Enough
We like the phrase, “What are you optimizing for?” In the financial planning context, it can be tempting to optimize for “max returns,” whether it’s investments or career decisions. The problem is that we can easily prioritize more money and sacrifice optimizing for life.
For many of our executive clients, they’ve already got more money than they’ll need this side of the grave. Walkaway money? Covered. Retirement? Funded.
The Golden Handcuff conversation needs to become about getting the financial value you want but not being so tied to maximization that we wear the handcuffs longer than we need to.
All of this to say – we have to start by figuring out how much is enough. Once we are grounded in the financial goal posts, we can optimize for life, not for pure ROI.
Explore and Understand the Terms of Your Compensation
Just this week, I spoke with a client in the pharma industry whose company's stock has dropped 50% over the past six months. That wiped out a huge portion of what we expected to vest in early and mid-2025. There was so much vesting in the near term that it didn’t matter if some longer-dated options expired post-retirement. We weren’t worried.
Now? We had to revisit the variables.
The good news is that we were able to go through his compensation terms and identify a key distinction:
If he left tomorrow, he’d have 90 days before those options expire, likely requiring him to sell before the stock could rebound.
Instead, we found that if he stayed for about 3 more months, he would reach a critical point where he could hold those options for 6-7 years post-exit, allowing more time for a potential recovery.
Even if that stock only recovers to its original value in that time, it’s an easy 7-figure swing.
If your stock has taken a hit—or even just gotten bumpy—you need to revisit the plan. Not to panic. Not to blow it up. But to pressure test it.
Ask:
Are the numbers still doing what we thought they’d do?
Do milestone rules or policy cliffs kick in if I delay?
Is the “clean exit” worth more than the equity I’d be walking away from?
This is the part where we get into the weeds: HR policies, option expiration timelines, garden leave possibilities. It’s less glamorous than a big-picture financial plan—but it’s where the real money gets protected.
Don’t Just Go with the Original Plan
It’s tempting to say, “Well, we already decided.” But the market doesn’t care about your calendar. And neither should you—at least, not blindly.
Sometimes, the difference between walking away and waiting 90 days is the difference between leaving money behind and building a longer-term cushion.
If the market has moved, rerun the analysis. Revisit the dates. You might not need to stay longer, but you need to know what it would mean if you did.
Bottom Line
Executives experience both the benefits and volatility of executive comp. Few industries can experience the range of outcomes like pharma, in particular. We don’t want you to wonder if you’ll be able to retire based on how your company is doing at the exact window you wanted to exit.
If you’re exiting under less-than-ideal conditions, let’s have an honest conversation about a set of tradeoffs. They only come into focus when you pause and run the numbers—honestly and specifically.
Our aim is that by having you well-positioned ahead of an exit, you can have maximum flexibility to choose the option that most benefits you and your family with less dependence on ideal conditions.
We’re here to help you Envizion More for your life, lifestyle, and legacy. It’s decisions like these that we can help you navigate with an experienced partner on your side of the table.
Reach out if you have questions around this topic. We’re always here to help.