I’ve been working on my fitness lately, and it taught me a surprising lesson about money.
For the last 12 weeks, I committed to lifting weights. I’ve been a cardio guy for a lifetime, but it’s been a good thirty years since I seriously lifted. Knowing that I’m in my fifties and need muscle mass for stability and a longer healthspan, I decided to go all in. I started aggressively lifting six days a week, progressively overloading my muscle groups exactly the way the YouTube fitness gurus recommend.
At first, it felt great. My muscles were getting bigger and I was getting visibly stronger.
But about six weeks in, the wheels started coming off. I developed a new injury every single week. First it was my shoulder. Then my back. Then my pecs. My joints throbbed constantly. On top of the physical pain, I was completely exhausted, to the point where I was spontaneously falling asleep at six or seven o’clock at night—something I had never done before.
I was hobbling through my days feeling significantly worse than before I started.
I realized my approach was completely unsustainable. The goal of lifting was to feel good and improve my health, but I was making myself miserable. So, I changed the routine. I cut back from six days a week to every other day. I switched to full-body workouts just three or four days a week.
The result? The injuries healed. The constant aching stopped. I felt stronger than ever, and my body actually continued to change the way I wanted it to. I was simply overtraining, and taking my foot off the gas was the cure.
It hit me a few weeks ago: we do the exact same thing with our money.
We go completely down the personal finance rabbit hole. We use frugality as a weapon. We track every single cent we spend. We obsess over our investments, constantly maximizing the tax code, and agonizing over the minor differences between traditional and Roth accounts. We become so hyper-focused on the efficiency of our financial machine that we forget why we built it in the first place.
You’ve probably seen the symptoms. It’s the person who makes a great living but feels acute stress over buying a cup of coffee. Or the millionaire who checks their portfolio balance three times a day, terrified that they haven’t optimized their safe withdrawal rate.
I know people who are totally on top of their money, worth millions of dollars, yet they are visibly stressed all the time. They are financially secure, highly optimized, and entirely unhappy.
Financial overtraining happens when we get so deep in the woods that the process itself becomes a source of pain. We get so efficient with all the tips and tricks that, instead of getting the results we actually want—peace of mind, freedom, security—we just feel worse. We become penny-wise and pound-foolish with our own well-being.
Most of our financial journeys follow a similar arc to my fitness journey. In the beginning, we need to do the heavy lifting. We need to put the spreadsheets together, learn to save, and build the foundation.
But eventually, you have to accept good and “good enough” over perfect.
If your financial plan is causing you daily anxiety, you might not be failing because you lack discipline. You might be overtraining. The solution is to take a step back. Take some time off from checking your balances. Put the spreadsheets down. Let your compounding do the work, and give yourself permission to actually enjoy the life you’ve been saving for.
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I think people are always Pennywise and pound foolish.Something I discovered in the mid 1990s.Thinking I was clever I placed a buy order at around 3 cents under the price,then left it. I didn't get the dividend but owned the shares without checking the date they were bought. They were bought 2 months after the original order,after going XD and the price had fallen .Did it again 2 or 3 years later,then after that every order was at market. Buying at say $10.10 cents rather than say $10.06 doesn't make the slightest bit of difference 25 years later when the shares are at say $70.
The most important thing is we have enough,a 50% drop in capital value doesn't change the dividends we get.The dividends are fairly stable and rising annually.The value of the portfolio is volatile,so look at it perhaps once a year.Most years the value of the portfolio goes up,from 2016 to present there has been a good increase,7 years it has gone up,and 3 years it has gone down. Through COVID and everything else that has gone on over that period.