re: Do you max your annual 401k contribution?

I max and front load my workplace retirement account since 30. We had a SIMPLE IRA when I started, but I convinced my partner to swap to a 401k for the increase in headspace (seems to be worth the increase in price. SIMPLE was free, but $6000/y + ability to match ourselves up to 20% or a max of $57,500 vs 3% max match made it way more enticing).

I started practice at 29. I started practice in August and was a little stupid at first- I paid into a deferred compensation plan from residency the first half of the year and put into a traditional IRA in December. but I skipped the SIMPLE because the cash flow wasn’t planned for particularly well (got married, “lost” jobs on 7/1, started in August (me) and September (her), and bought a house. Both of us joined partnerships and didn’t exactly have full panels of patients waiting for us with high salaries right off the bat).

It’s a pretty decent regret I have in my financial life. The S&P is up about 50% from the day I started work, and about 68% from December of that year (when I would have had the cash to max it but put ~1/3 in the traditional IRA instead). It’s not going to be the one thing that moves the needle for me long term. But it’s a sore spot that I know is there.

So I put 1/12 the max in each month the next year and then moved to putting the full amount in each January the year after.