Never Enough

MANY FINANCIAL IDEAS are tough to embrace. But perhaps the toughest can be summed up in one simple word: enough.


Will we ever feel like we have enough and that we’ve accomplished enough? Accepting that we have enough and done enough might seem like worthy goals, a serene acceptance that’s possible for those at peace with themselves and the world around them. Indeed, for many, “retirement” and “enough” seem to be pretty much synonymous, a declaration that the pursuit of “more” is over.


But that isn’t where my head is. Even now, I’m not sure I’ll ever declare “I’m done,” which is weird, because I sure don’t have the time to do much about it.





And I don’t think I’m alone. In their 60s, and with decades potentially ahead, I suspect many retirees—and perhaps most—aren’t quite done, and I’m not sure it’s necessary. There’s great pleasure to be had in life’s striving. While we might want to temper our pursuit of more, I’m not sure we should seek to squash it entirely.


Amassing more. We spend our lives running on the hedonic treadmill, imagining the next accomplishment—the new house, the seven-figure portfolio, the promotion—is all that stands between us and happiness, only to discover that success soon leaves us dissatisfied and hankering after something else.


This desire for more doesn’t seem to disappear with retirement. Most of us spend three-plus decades amassing money to fund our post-work life and yet, when the time comes, we’re often reluctant to let our dollars go. How many times have you read HumbleDollar commenters gleefully note that their portfolio today is larger than when they retired?


Such sentiments are understandable. After a lifetime of saving, it’s hard to watch our money slip away. And if an ever-growing portfolio brings someone happiness, why should the rest of us object?


Still, the desire for more can create two key problems. First, consider the comment from financial author Bill Bernstein: “When you’ve won the game, stop playing with the money you really need.” In their pursuit of an ever-larger portfolio, retirees might take too much risk—and imperil their financial future.


Second, folks may shortchange their retirement by failing to spend in ways that could enhance their happiness during their final years. This, I think, is one virtue of Social Security benefits, pensions, immediate fixed annuities and laddered bond portfolios. All are designed to generate income, so folks feel they have permission to spend the money involved.


Struggling to let go of the dollars you’ve amassed? Consider making gifts to charity and loved ones. These aren’t just an alternative to spending. Such gifts are also an acknowledgment that we have enough—and the resulting sense of abundance may prompt us to be more generous with ourselves.


Scoring goals. Even as we struggle to accept that we’ve amassed enough, we’re also reluctant to declare that we’ve done enough.


Humans are a restless, relentless bunch, always looking to improve their lives in one way or another. This drive, I’d argue, is a good thing: It not only helps the individuals involved, but also it can spur economic growth and make society a better place for everyone.


Yes, retirees and those near the end of their career will often proclaim that they’ve reached the point where they’ve done enough, and they’re now happy to cruise through their remaining years. But I’m not entirely sure I believe them.


These folks might be content to step off the workplace hamster wheel, and they might fiercely resist my frequent suggestion that they consider working part-time during their early retirement years. Yet retirees often replace their professional aspirations with goals of their own choosing, such as reading a book every week, or visiting all 50 states, or pursuing their favorite hobby. And I see nothing wrong with that. There’s great happiness to be had from accomplishment.


Will we ever feel like we’ve done enough? I suspect not. We might be willing to declare that we’re done with career goals, but I doubt most of us will ever feel like we have nothing left to achieve.


Still, we might try to cut ourselves a little slack, especially as we age. How? I like to make a daily to-do list, preferably one that isn’t too long, so I know what success looks like for that day. Clearing each day’s list allows me to head into evening with a pleasurable sense of accomplishment—and the chance to recharge and reflect before tackling the next day’s list.


Check out the four earlier articles in this six-part series: Money Grows upTaking Center Stage, Mind Over Money and Taking It Personally.

Jonathan Clements is the founder and editor of HumbleDollar. Follow him on X @ClementsMoney and on Facebook, and check out his earlier articles.

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Published on February 14, 2025 22:00
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