I Thought I Would Always Earn My Way Out

The real retirement regret: not saving enough

There’s a piece of retirement advice making the rounds these days, and it sounds wise enough that most people nod along without checking it: spend the money. Take the trip. Don’t die with your savings intact, because you can’t take it with you, and the biggest regret isn’t spending too much — it’s spending too little. Research backs this up, as far as it goes. Boston College’s Center for Retirement Research has found that many retirees pass away with 80 percent or more of their wealth still sitting untouched. AARP has found that seven in ten retirees wish they’d spent more on travel and time with family while they still had the health for it.

All of that is true. It’s also, I’d argue, advice for people who don’t have my problem.

The advice I didn't take

My father told me, for as long as I can remember, to always save ten percent of whatever I earned. He said it the way fathers say things they believe but don’t examine too closely — a rule handed down, repeated on schedule, never quite explained.

He never followed it himself. He spent freely his whole life and accumulated no real savings by the time he was through working. I watched that contradiction longer than I heard the advice, and the contradiction is what stuck. A rule someone tells you but doesn’t live by doesn’t really land as a rule. It lands as a thing people say. So I filed it there, and moved on.

A glass jar with just a few scattered coins at the bottom.

I don’t think he was lying to me, exactly. I think he believed the ten percent rule the way a lot of us believe things we’ve never tested — sincerely, and from a safe distance. He wanted better financial habits for me than he had for himself. That’s a common enough impulse. What he never gave me, because he didn’t have it to give, was proof that the advice actually worked when someone lived by it. Advice without a demonstration is just an opinion wearing a father’s voice.

Advice without a demonstration is just an opinion wearing a father’s voice.

What I had instead of my father’s discipline was something closer to confidence: a quiet, mostly unexamined belief that I could always earn my way out of whatever hole I might eventually dig. Thirty-eight years in residential real estate will do that to a man. There’s always another deal, another client, another commission check if you’re willing to keep working the phones.

The pattern repeated itself often enough that I never stopped to question it. A long dry spell would stretch on, the pressure would build, and then a big payday would finally land — a closing, a commission check, something that would cover every living expense for the next ninety days, which at the time felt like forever. The relief was enormous. And the relief was also the problem, because it let me relax. I’d stop feeding the pipeline that was supposed to carry me through to the next payday, right up until the next dry spell arrived and the pressure built all over again. Saving felt almost beside the point when I could count on that cycle to bail me out. It always had before.

Where that belief runs out

I’m one of the majority, it turns out, and not the fortunate minority the “spend more” advice is written for. Research from the TIAA Institute found that 76 percent of retirees regret not starting to save earlier in their lives, and 71 percent wish they’d put away more overall. Wharton economist Olivia Mitchell’s research on adults over fifty found something even starker: a large majority wished they’d saved more, and only two percent wished they’d saved less. That’s not a close call. That’s nearly everyone looking back and wishing they’d done the one thing my father told me to do and never did himself.

I didn’t feel any of this until my mid-to-late seventies. Before that, the plan — if you could call it a plan — had always worked. I earned what I needed, more or less, when I needed it. What changed wasn’t the math. It was the body.

A worn antique pocket watch resting among brass clockwork gears.

Somewhere in my late seventies I noticed, without much ceremony, that I might not have the energy or the stamina to keep earning my way out of anything, the way I always assumed I could. That’s a sobering thing to realize at an age when there isn’t much runway left to correct course.

The regret nobody brings up at dinner

Part of why this particular regret stays quiet is that it’s an uncomfortable thing for a man to admit, especially one who spent a career being the person other people trusted with the biggest financial decision of their lives. Telling clients how to buy a house is one thing. Admitting you didn’t manage your own money as carefully as you managed theirs is another. There’s a real embarrassment in it — not the loud, dramatic kind, but the quieter kind that keeps men from bringing it up even with friends who are almost certainly carrying the same weight.

That silence is probably part of why the “spend more, you’ll regret holding back” message travels so much further than the more common, less flattering regret. Nobody writes an inspiring article telling you that you should have trusted your future self less. It doesn’t sell calendars or retirement seminars. But it’s the truer story for most of us, and I think it deserves to be said out loud at least as often as its more popular opposite.

The part nobody puts on a poster

Here’s what the “spend it while you can” crowd tends to leave out: that advice assumes you have a comfortable cushion to spend from in the first place. It’s a message for people who saved enough that their real risk is dying with too much left over. For a much larger group of us, the risk was never having too much. It was assuming, the way I did, that our own capacity to keep earning would always be the backstop, right up until age quietly retired that capacity without asking permission.

I don’t think my father was wrong to tell me to save ten percent. I think he was wrong to tell me and not do it, and I think I was wrong to let his example excuse me from doing it either. Advice you don’t watch someone live by is just a sentence. It took me most of a lifetime, and a real change in what my body could still promise me, to understand that the sentence was true whether or not the man saying it ever acted on it.

What I'd tell the man I used to be

If I could put one thing in front of other men my age, and the men still a couple decades behind me, it’s this: the popular advice about regretting a life too small, too cautious, too unlived — it’s real, and it’s true for some people. But it is not the more common regret.

An open desert road stretching toward a sunlit horizon.

The more common regret, the one the research keeps turning up again and again, is simpler and less romantic: most of us wish we’d saved more, started saving sooner, and trusted our own future capacity less than we did.

The more common regret is simpler and less romantic: most of us wish we’d saved more, started saving sooner, and trusted our own future capacity less than we did.

I trusted mine completely, for most of my life. It served me well enough, until it didn’t. I’d rather other men find that out from a study than the way I did — in my seventies, doing the arithmetic on how much runway is actually left, and discovering the tap I’d always counted on doesn’t run forever after all.

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Bill Leighty

Bill Leighty is the founder of The Encore Project, a platform for men 65 and older navigating life's second half with honesty, purpose, and a little hard-won wisdom. A former journalist who spent 38 years in Tulsa residential real estate, he built his career listening closely to people at life's pivotal moments — and started The Encore Project to give men the same honest space for the transitions after work ends: purpose, faith, friendship, and grief. A member of Tulsa's Edison High School Class of 1963 and a lector at St. Rita's Chapel, he lives in downtown Tulsa with his wife.

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