Why Most Executives Delay Their Exit Too Long (and How to Avoid It)

The Psychology of “One More Year”

When we talk with executives about leaving corporate, the same theme comes up: “I’ll just wait one more year.” The logic feels sound — more stock vests, another bonus pays out, retirement accounts grow a little bigger. But behind that logic is fear. Fear of walking away too soon, of losing wealth, or of stepping into the unknown.

The Real Cost of Waiting

Delaying your exit can seem like a conservative choice, but in reality, it often carries hidden costs:

1. Tax Pile-Ups
   Holding out for more vesting frequently means higher taxable income compressed into fewer years, leading to steeper tax bills.

2. Concentration Risk
   The longer you stay, the more of your net worth sits in a single company’s stock. If the business falters, you could lose both income and equity value in one blow.

3. Lifestyle Burnout
   Waiting another year often means missing key family milestones, pushing personal goals further down the road, or compounding health and stress issues.

4. Market Timing Illusion
   Many executives wait for the “perfect” time — when the market’s up, when the company’s stable, when their portfolio feels untouchable. The truth? That perfect window rarely arrives.

Why Executives Delay Too Long

There are three big drivers we see again and again:

• Attachment to Identity: Stepping away from a prestigious corporate role feels like a loss of status.

• Financial Uncertainty: Without a clear exit plan, executives fear running out of money.

• Golden Handcuff Incentives: Stock grants and deferred comp are deliberately structured to make leaving feel too costly.

How to Exit Without Regret

The key is shifting from waiting by default to leaving by design. That means:

• Defining Your “Enough Number”: Clarity on what you need to live your life without work stress.

• Scenario Planning: Running multiple financial models to see the impact of leaving now versus waiting.

• Building Optionality: Setting up consulting, board work, or side ventures so you know you have income options.

• Reframing Wealth: Focusing less on “maximizing every last dollar” and more on maximizing time, freedom, and choice.

A Story We See Too Often

We've seen executives stay extra years to "hit their number" or for “one more vesting cycle.” By the time they finally left, life had happened. Stock prices dip, layoffs come through, and people get sick. There are no guarantees, but it's important to consider options in reality. Consider another who left a earlier, diversified, and built a consulting practice not only did they preserve more wealth, they gained extra years of freedom and road trips before their kids left for college.

Final Thought

Delaying your exit can feel safe, but the biggest risk is waiting too long. With the right plan, you don’t have to leave in fear — you can leave with confidence, on your own terms.

📍 Want to test your readiness? Start with our free Exit Planning Checklist — seven questions every executive should be able to answer before stepping away.