My taxes are done! What I mean is, I filed and paid my taxes. Taxes are never done. And, I give up. My taxes weren’t done by me; my taxes were done by a professional. I’ve given up trying to figure out forms that evidently take professional expertise. I paid their fee. They saved me money. I think it works better this way.

Don’t forget the taxes! Don’t forget any of them. 

Write a book. Sounds laborious and simple. It is basically. But whether it sells or not, a flurry of paperwork follows. Royalties seem simple. Selling a copy personally seems simple. A bookstore sale may mean commission sales, and a different tax rate for each location. Already there are three tax categories to report. 

Give a talk? Another category. Track it too, if they paid you anything .

Oh yeah, and if you’re going to claim driving expenses, mark them, tally them, and prepare to defend them. Same for travel and entertainment. If you don’t make a profit, well, is doing paperwork good practice? Same for advertising, computer expenses, home office costs, etc. All good things, ideally, but there’s little tolerance for judging that recording an expense isn’t balanced by the income. Prove it. Sounds simple. Keep track of those simple things.

Got consulting clients? Good. Track them.

Made any money doing any business? Track it too. 

Pulling yourself up by your bootstraps comes with a lot of paperwork to prove that you didn’t make enough to cover expenses, yet. Don’t be surprised if you spend hours to zero is the true answer. 

At least this year I didn’t have a mortgage, or house purchase, or a major medical expense. Truly simplifying.

A pension? That doesn’t change, but must be tracked.

Social Security? Tell one part of the government what another part of the government did because for some reason it makes more sense to put us in the middle, two more opportunities to file a wrong number or put the right number in the wrong place. Simple? 

Add enough simplicity and complexity emerges.

Sell some stock. Make some money. Report it. Fine. Of all the numbers in my various incomes, stock sales are the simplest, assuming all of the paperwork exists. I sold some QBTS for more than the rest combined. That sale was the simplest. It’s almost as if the forms were made for people who only have stock sales. 

My effective 2025 tax rate ~3%. When I was working it was double digits. When I was only living off stock sales, the lowest was 0.15% as I recall. It’s enough to convince this experienced citizen that the American Way is not to work but to sell stock. An interesting incentive plan.

Hours of work chasing down documents that had low numbers because business is off. I won’t compare that to the value of my time working on inconsequential documentation.

I am entrepreneurial. The forms also work well for folks who have one job, one paycheck, and nothing happening outside work. There are probably incentives for entrepreneurs and creatives, but I suspect the forms are arcane, and the data is hard to obtain. So the incentive is to not be entrepreneurial and creative but to have one of the vanishing conventional W-2 jobs.

Which is why I hire someone to figure out my taxes. I still have to spend dozens of hours chasing down data and documents, but at least I don’t have to find the forms too, and keep track every year as deductions are added, altered, and eliminated.They do that. I fill in their still-long but simpler form, hand it to them, then a few weeks later they finish, we review, and I pay.

‘But, but, but,’ my frugal friends say. ‘Doing it yourself is cheaper.’ Yes and no. My tax preparer charges a few hundred dollars. That’s non-trivial. One year alone, they found a ~$3,000 deduction I didn’t realize existed. Every year they prove their value. For me, the most frugal thing to do is to let them do their work. 

Thanks, folks (though I don’t expect them to see this for months if at all because they have many clients, and some of them have businesses that benefit from all of those forms.

Now, pardon me as I celebrate by trying to take a nap.