Flow State

Sigh. Costly mistakes were made.

We’ve officially hit that time of the season—the period where my blood pressure does a slow, steady climb in tandem with the blooming tulips. It’s tax time.

Back in my pre-30s “innocence,” I actually didn’t mind this month. I worked for government entities, clutched my W-2 like a security blanket, and usually walked away with a modest refund. I’ve never been a fan of giving the government an interest-free loan (I’m perfectly capable of burying my own money in the backyard, thanks), so I never aimed for those massive, celebratory checks. But it was clean. It was simple.

Then came the law practice years. I’m not sure I’ve seen a “refund” since Y2K (my own personal disaster!) Instead, my life became a revolving door of estimated taxes and the soul-crushing weight of self-employment tax.

I’ve often thought that if every American had to physically write a check for their taxes every quarter—instead of having it stealthily siphoned away before it even hits their bank account—our tax rates would plummet within a week. I’m looking at you, Beardsley Ruml. You and your pay-as-you-go withholding system have a lot to answer for.

These days, the wife and I are back in the government fold, which simplifies things on paper. However, our finances stayed… “complicated.” In the world of adulting, “complicated” usually means “you have some means,” which is a blessing. But it’s a blessing that comes with a very sharp, very hidden edge. [Don’t misunderstand, it’s a blessing.  I’d rather have this issue than not. This isn’t really about the money and more about me being slapped in the face by a poor decision]

My particular brand of stupidity this year? Choosing the wrong “means” to pay for my kids’ tuition.

Imagine two accounts. Account A is a friendly, tax-neutral pool of money. Account B is a literal tax landmine. A smarter person—or perhaps a person who wasn’t rushing—would have pulled from Account A. Instead, I reached into Account B, triggered the landmine, and now I’m staring down a tax bill that requires a wheelbarrow to deliver to the IRS. [for reference, take about 40% of the tuition for two kids at college…that’s about what I owe]

So, on the 15th, I’ll be writing two checks: one for the “Oops, I’m Ignorant” fund and one for the 2026 estimated taxes. It’s a double-tap to the bank account that has me beating myself up. I’m all for supporting the infrastructure of society, but it’s hard to feel like a “proud taxpayer” when you know a healthy chunk of your hard-earned cash is destined to be swallowed by inefficient bureaucracy or lost to fraud [or both!].

Theoretically, I’m trying to be Zen about it. I’ve learned a “valuable lesson” (the most expensive kind). I know exactly how to pivot so that next year the pain is reduced by 90%. I am a wiser, more seasoned financial traveler.

But honestly? Zen doesn’t pay the bill. Writing these checks still feels like a kick in the teeth. If you see me wandering around Chicago looking slightly dazed this week, just pat me on the shoulder and ask, “But did you die?”  

No.  Just money.  [cue the crying]