When we hear the phrase “midlife crisis,” we tend to picture a certain kind of story: the sports car, the dramatic career pivot, the person who suddenly decides to blow everything up. But there’s another kind of midlife crisis that’s far less dramatic, and in many ways far more costly. It’s the quiet reckoning that happens when you look up one day and realize you’ve been living someone else’s version of your life.
Sari Botton has spent decades asking people what it really means to age. The editor and writer behind Oldster Magazine joined Jean Chatzky on the HerMoney podcast to talk about the financial cost of people-pleasing, finding peace with your financial past, and why a midlife crisis might actually be the beginning of something better.
The Financial Cost of People-Pleasing
Here’s what doesn’t get talked about enough when we discuss people-pleasing: it costs money.
When we defer to a partner on financial decisions, we lose years of financial agency. When we don’t negotiate our salaries because we’re afraid of seeming difficult, we leave thousands of dollars on the table that compound over decades. And when we stay in jobs too long because they feel “safe,” we sacrifice not just our happiness but our earning potential.
Sari’s own career journey is a testament to this. Ghostwriting, gossip columns, copywriting, naming pantyhose colors for New York & Company, writing injury profiles at a law firm. She did a lot of things for money that weren’t exactly her dream. “I’ve had to juggle my entire career,” she told Jean Chatzky. “I put myself through college and often was working three part-time jobs on the side.”
The turning point, she says, came from learning to pause. “I try to count to 10 before I say yes to things because I have a knee-jerk tendency to just say, ‘Oh, do you want me to do a good thing for you that will make you like me? Oh yes, sign me up.'” Sometimes, she adds, she gives herself a full 24 hours before responding to an opportunity, just enough time to figure out if it’s actually right for her.
On Regrets, Wrong Turns, and Finding Peace With Your Financial Past
One of the pieces in Oldster Magazine that resonated most with Chatzky during their conversation was novelist Ann Hood’s essay on regrets. Hood is 67, looking back at a life full of wrong turns, including an apartment on Bleecker Street she sold for $125,000 that’s now worth $1.2 million, and arrived at a beautiful conclusion: she has no regrets at all, because every bad decision led her exactly where she was supposed to be.
That’s a hard place to get to. Especially when it comes to money. So many women carry real shame about their financial mistakes; the investment they didn’t make, the career they stayed in too long, the savings they didn’t start early enough.
After hearing from hundreds of people through the Oldster questionnaire, Botton has found that about half of respondents to the question about their biggest regret say some version of “Yes, that was a bad move, but it led me here, and I’ve learned from it.”
Botton agrees: “I am so certain I am where I am supposed to be,” she said, “and I don’t know that I could have landed here without the twists and turns.”
It’s Never Too Late
Perhaps the most powerful takeaway from Botton’s work is the reminder that, rather than viewing a midlife crisis as the end of something, think of it as a new beginning.
When Jean asked which Oldster questionnaire response has stuck with her most, Botton mentioned Elizabeth Gilbert, who wrote about in her late 50s returning to who she was as a nine-year-old, to the essence of herself before she started changing to fit in. “So many women write about that,” Botton said, “that they have returned to who they were before they started trying to change who they were.”
Whatever a midlife crisis looks like for you, the message from Botton is clear: you are not behind. You are exactly where you are supposed to be. And the next chapter is yours to write.
MORE ON HERMONEY:
- Life Over 50: The Top 3 Midlife Myths
- Ask Jean: “How Do I Find A Good High-Yield Savings Account?”
- Stop Keeping Up With the Joneses in Retirement
Pre-order Jean’s new book, The Forever Paycheck. It’s the guide to building the retirement income you need, so you can stop lying awake wondering and start actually living.
