See if this sounds familiar: You’re miserable in your job. You’ve been “quiet quitting” (or thinking about it) for months. You’ve concluded it’s time to quit for real and the boss’ office is just a few steps away.

But hang on a minute there.

Don’t miss

It’s not about what you’re about to do but how you do it. So says a wealthy stay-at-home dad who retired at 34 and credits a healthy severance package he negotiated as a key driver.

“If you are going to retire early, you might as well try [to] negotiate a severance since you have nothing to lose,” writes Sam Dogen on his Financial Samurai website. He did it when he left his executive director post at Credit Suisse in 2012 — landing a package he says was worth about six years of living expenses — and has spent the last dozen years trying to teach others how to do the same.

Here’s what else Dogen has to say about having your farewell cake and eating it too — and we’re not talking about that stale sendoff sheet cake in the break room, either.

Questions of how (and when) to do it

Dogen’s advice doesn’t come cheap. If you want to part ways from your company the Dogen way, you’ll first have to part ways with a whopping $97 for his book (though he also offers a free newsletter).

Still, he gets pretty granular about how to negotiate the exit strategy. First, he stresses that you have to be a high-performing employee to get the maximum leverage. From there, he outlines five steps key to any successful severance. They are: know your worth; set clear expectations with your superiors; get to a point where regret disappears; stand firm on your demands; and propose a win-win solution.

He also advises naming a number of perks, from cashed-in vacation time to extended health insurance coverage, that will allow you to suggest different package variations.

Yet the question, especially now, is whether the overall timing might be right.

Any advice on negotiating a fat severance comes as the U.S. job market has hit a decided downturn. The Bureau of Labor Statistics reported on Aug. 21 that the U.S. economy created 818,000 fewer jobs than originally reported in the 12 months through March 2024 — a result of statistical revisions.

Story continues

The BLS also reports a lower level of job quits compared to several years ago: currently 2.1% nationwide as of June, compared to 2.4% a year ago. Six states seem primed for a Dogen bus tour, as their quit rates topped 3% earlier this year: Alaska, Florida, Idaho, Montana, South Carolina and Wyoming. (New Jersey and Massachusetts tied for last at 1.5%.) The reasons have remained constant over time, from lack of any chance for advancement to that perennial favorite, the Bad Boss.

Read more: These 5 magic money moves will boost you up America’s net worth ladder in 2024 — and you can complete each step within minutes. Here’s how

Not for every person or situation

As outlined above, Dogen’s samurai plan of attack isn’t for everyone — and not because they have preferable alternatives. Much like a coach telling you how to hit a major league fastball, he offers advice for a select (and arguably elite) audience in a position of privilege. A corporate finance vet, Dogen reportedly retired with $3 million in the bank and $80,000 a year in passive income.

Negotiating a severance is likely a no-can-do even among the most valued service workers, for starters. Just imagine a star barista hitting up an indie coffee shop owner for six weeks’ pay.

What’s more, Dogen’s shoot-for-the-moon approach can easily backfire. In a dysfunctional corporate culture a stab at negotiation — no matter how deserving you think you are — could yield a gun to the head rather than a pen on the contract. Even if your supervisor adores you, the buck often stops with a mercurial CEO. In a 2023 survey by the American Psychological Association, 19% of workers said their workplace “is very or somewhat toxic.”

At worst, a departing employee who thinks they’ve done an excellent job and thus holds a strong bargaining position could easily fool themselves (file under: distracted boss cuts their losses). That’s why those who can pull off the layoff-over-quitting option need to do their homework, step back, and do even more homework. It helps to know, for example, whether others have tried this tack and how they fared.

You will also want to make a case — quantitatively and qualitatively — why you deserve to be taken seriously. Who knows? An understanding boss could give you more than you asked for and as Dogen points out, return with a counteroffer that boosts your pay and betters your working conditions.

Enter your other best negotiating partner: the romance novelist Nora Roberts. This quote, attributed to her, might just say it all: “If you don’t ask, the answer is always no.”

What to read next

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.