Quitting Season Is Almost Here
The journey to this day began a long time ago at a publicly traded bank.
Her career navigated through four publicly traded companies and spanned nearly 4 decades. With each year, she became more valuable than those around her, and she developed the political/survival skills to always stay relevant.
Life in a bureaucracy can be as unpleasant as being a contestant on Fear Factor. Sometimes you have to smile for the camera after eating cockroaches.
It is hard to describe survival in corporate America. Base salary that barely covers family expenses after the menagerie of reductions for 401k, HSA, health insurance, and taxes, plus an annual bonus that is tied to metrics you can’t control, and then a stock price that hopefully appreciates to make all of this worthwhile.
Communications that are written by lawyers, managed by HR with the best of intent, but at the end of the day, are unreadable (unless you are an expert in tax, legal, and stock-based compensation(SBC)). And then a layoff that sends your friend packing for a reason nobody can figure out.
Those who make it to the finish line have developed a master class of survival skills.
Quitting Day is Vesting Day
As stock compensation has grown over the last 20 years, it has become the primary means of creating wealth for employees at America’s largest companies.
The unintended consequence of this trend is something that HR dreads every Spring.
Vesting day is quitting day. As Bruce Crumley highlighted in his Inc. article How Paying Bonuses Could Mean More People will Quit in Q1 2026, a new survey revealed that 48% of employees plan to quit once the stock vest.
A meaningful number of people are considering the exit. HR departments strive to retain talent, but it is hard to compete when the stock price makes your employees rich enough to do nothing.
Planning the Exit
She was debating about another year. The new RSUs are valuable, and the new package would add a very healthy sum to her net worth. “But life at the top is not pleasant here”, she said.
The new person that she just hired to replace her quit for a higher-paying job (more RSUs), and the Compensation Committee would not match the offer.
“Why am I doing this? I am over 60 years old. I don’t need the money. And nobody seems to care about longevity in this organization.”
Her Lifestyle Cash Flow was her metric, and she had it more than covered. The decision was made - she is out.
The stock vests mid-April, and she will provide notice once the cash is in her bank account. At some point in our lives, time becomes more valuable than money.
As Nassim Taleb put it in a blog or book, “I don’t run to catch the train anymore.” He has enough money and does not need to rush to do anything. He is now in charge of his own destiny.
How did she know the number?
Everything starts with Lifestyle Cash Flow.
Lifestyle Cash Flow is the money required to keep the family engine running. The annual cash flow required to pay the family bills, but also the trajectory of those expenses over the next 5 years.
A pro forma of your life, just like you were a CFO preparing the projections for an upcoming board meeting. Lifestyle cash flow is your family's pro forma. Once you know you can support the expenses without work, financial freedom is achieved.
We call that achievement – the Point of Independence.
Here is a hypothetical pro forma from our planning software – The BluePages.
Once you can replace the Lifestyle Cash Flow from other sources, you are free.
It could be a lower-paying, less stressful job.
You could have mapped the payout schedule of the deferred compensation plan to bridge the gap.
You could have enough money invested in cash-flow generating securities that provide 100% of the goal.
Or a combination of all three.
Each of us is different, and that is why it is so important to have someone who has been there and done that to guide the journey. Whether SBC is a good thing or a bad thing in corporate life, it is here to stay. It has been baked into the framework.
Being the beneficiary of these benefits is valuable, but don’t let the uncertainty of SBC control you.
Manage them wisely, and one day you won’t have to run for trains anymore either.
Looking Ahead
We’ll continue sharing patterns we’re seeing as these cycles unfold.
With the new year comes a natural opportunity to revisit the things we intended to address but may not have had a chance to last year. Target-date Funds has been a story I have wanted to write.
Next quarter, we will unpack the risks associated with Target-Date funds, especially for those nearing retirement. The set-it-and-forget-it investment approach is utilized by more than 59% plan participants, according to the Investment Company Institute.
We will do a deep dive into the hidden dangers of this very popular investment vehicle.
In the meantime, this is a good moment to pause, review, and make sure key details haven’t been overlooked.
A few areas worth revisiting:
Confirm your 401(k) beneficiary designations
Understand changes to catch-up contributions in 2026
Reassess the risk profile of target-date funds as retirement approaches
Review life and disability insurance elections
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