How to price what you'd give up, what you'd get back, and the number that sets you free

Call her Lorraine, then. She is an invented composite, and she is neither a member nor a client. Fifty-four years old and serving as chief financial officer of a division, she has just done the very thing finance professionals are trained to do and that many of them quietly dodge. She has put a dollar value on her own golden handcuffs.

Scrawled across the top of her legal pad is a total of $410,000. That total combines her unvested equity, a retention bonus payable in nineteen months, and deferred compensation she would give up by quitting. These numbers are hypothetical, yet they carry real weight for her. Underneath them she has written the other number, the one she has never said out loud: four years of not being considered for the group CFO role, with an outside candidate brought in each time.

What she could walk away from

Remaining where she is means receiving the $410,000, holding onto her title, the team she assembled, and her Tuesday lunches with the general counsel. She also keeps the pattern. At this company, the division CFO role is a post for people it relies on but does not intend to advance. Two men have held that seat on their way up the ladder. Neither stayed four years.

If she walks out, the money remains with the firm. Nineteen months of pay would vanish, together with the equity. The headhunter who reached out about a CFO position at a publicly traded company made it plain that the base pay is in the same range. Everything else was murkier to her.

The turning moment

Lorraine works through the arithmetic again, just as she would for any member of her Milwaukee-area team. The $410,000 is not really $410,000. Stretched over the nineteen months she would have to remain, it comes to roughly $21,500 a month before tax. That monthly figure is what each month of waiting actually costs her. She then poses a question she has never before put to herself: what is one month of her career worth to her at 54? Not to the company, but to her. Next comes the question that shifts everything: which other employer might be prepared to cover that cost?

Buying out handcuffs is a routine expense for companies. Signing bonuses and make-whole equity awards are designed precisely for situations like hers. Her $410,000 is not a wall. It is an opening offer.

Why this reaches beyond Lorraine in Milwaukee

Per McKinsey and LeanIn's Women in the Workplace 2025, only 54% of companies place women's advancement among their high priorities. The remaining companies still allocate money for retention. A retention bonus is often what a company offers instead of a plan, and a generous check does not make it a plan.

Three points to carry away

Initially. Price the cuffs honestly. Total up what you would give up by leaving, then divide that sum by the number of months you would need to stay to collect it. The resulting monthly amount reflects the true cost of each month spent waiting, and it is far smaller than the lump sum makes it seem.

Next. Make the market cover that cost. "My unvested compensation is roughly X. What would it take to make me whole?" Raise this with the recruiter in your first conversation rather than your last. Reputable employers keep funds set aside for requests like this one. Employers who are not serious will make it clear by steering the conversation elsewhere.

Finally. Pick your walk-away number ahead of time. Record the sum that would make you switch, plus the date beyond which no sum would. With that in hand, you are bargaining from a concrete figure instead of a gut feeling.

Three numbers now sit on Lorraine's legal pad. The first is what it costs her to stay. The second is what a rival firm could be prepared to offer. The third is the amount she has come to regard as rightfully hers.