#42 - The 3 Biggest Regrets of Retirees
Greetings!
First, I enjoyed sharing some thoughts with The Wall Street Journal this week on staying calm amidst endless market noise. Read full article here.
On This Monday’s Episode of the new podcast, Your Money Guide on the Side:
What happens when a former English teacher becomes a CFO and decides to teach everyone around him how money actually works?
In this week’s episode, I sit down with my longtime friend Andy Schneider, a career educator and current CFO, for an honest, funny (maybe?), and deeply practical conversation on what we do and don’t teach about money. From the real cost of college to the myth of the “money expert,” we dig into the overlap between education, finance, and finding purpose in a world that keeps getting more expensive.
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The 3 Biggest Regrets of Retirees
As some of you know, I spend a lot of time talking to people who’ve done well financially: retirees, high earners, business owners, and even those who are still making millions in their respective professions. Regardless of financial well-being, here’s what I hear from all of them:
Pangs of Regret.
Not about the markets. Not about their success in the professional world. And certainly not about their retirement portfolio. But about how they thought about money during the years they were earning it, and how they’ve come to think about money (and life) now that they have achieved what they were taught to achieve.
Here are three common regrets I hear over and over in my conversations with you:
1. “I don’t know how to shift from saving to spending.”
After decades of accumulation, and after having spent a life being told by everyone (including yours truly) to save, invest, save, and invest, it turns out that switching into “it’s okay to enjoy this” mode is much harder than expected. Many retirees never fully make the leap, and they continue to check balances daily, worrying about market dips, and whether or not they should buy that new vest. (Hint: always buy the vest.) :)
Money is the tool to get you there; it was never meant to be the there in and of itself. Personally, this is easily my biggest money vice: I’m great at saving and investing, yet I experience extensive anxiety when I make big purchases and always feel immediate buyer’s remorse. I’m working on it. :)
2. “I focused so much on accumulating wealth, I didn’t prioritize taking trips and creating memories when I was physically and mentally in my prime.”
Not to say for even one second that any of you are not in your prime as of today. I fully plan on getting better with age (if I can), but the consistent pressures of deferred life have many of us sitting on the metaphorical sidelines waiting to play a game we may never have the opportunity to play as optimally as we’d like.
If you haven’t read Bill Perkins’ Die With Zero, I would encourage you to pick up a copy today, particularly if this one concept resonates deeply with you.
3. “I invested too much time chasing a future version of happiness.”
Start by reading Cavafy’s Ithaka. Note that we’re all, in some way, waiting for that elusive “there” to start living and spending and enjoying. As Cavafy reminds us: there is no Ithaca that will ultimately complete you; there is the journey, the experience, and the tools we use along the way to take the next step.
As I note in this past week’s short video content, if you always find yourself saying, “I’ll be happy when X,” hate to say it, but odds are, the attainment of X is not going to do the trick. If you can’t find a way to be happy today, odds are small that you’ll magically find a way to be happy tomorrow.
If you’re still in the saving years, let this serve as a gentle checkpoint. Money’s important, and it can smooth the ride. But, it’s not the end game; it’s not the Ithaca.
As always, hope this gives you something to think about throughout the week.
Tyler
Your Money Guide on the Side
