Recently, Ryan Holiday, a bestselling author on Stoicism, outlined twenty-four of his regrets.
A therapeutic thing for a Stoic (or anyone) to do.
One was about saving and investing. He writes:
As far as saving and investing money goes, there are so many different automatic transfers I should have set up earlier. I don't know what my block was, but I stuck with doing things by hand for too long. Meanwhile, every account I have and did eventually set up scheduled transfers for–for my retirement, for my kids college, rainy day fund etc–constantly surprises me with how large the balances have been. Set it and forget it…the sooner you do it, the more you'll have. You won't regret compound interest.1
What are you regretting financially?
Debt? Lack of earnings? Lack of savings? Lack of investments?
Do something about it and make it automatic or habitual.
Start somewhere: increase that debt payment, get that side hustle, start saving today, begin investing now.
Why? Because regret, like interest, compounds too.
While compound interest increases wealth, compound regret increases stress.
One of the worst things about regret is how sticky it is. It's so hard to escape. Don't let regret win by staying stuck—but know that this is one of its most debilitating side effects.
Regret broods.
One way through regret is to get out of inner self-talk. Talk to someone else.
This could be a close friend. Or it could be a financial professional like us.
Either way, the first action step toward doing something different is this: talk about it, then develop an action plan.
Action doesn't wipe all the regret away, but it does shrink its power.
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Source:
- Ryan Holiday, “24 Things I Wish I had Done Sooner (or my biggest regrets)” (April 13, 2026), https://x.com/RyanHoliday/status/2043719821607448912