TEXT: Hi, your dad’s friend Bill here. He mentioned that you’re freelancing now, and that you may need some help with your taxes.

SUBTEXT: Hi, your dad’s friend Bill here. Neither your father, nor I, knowing very little about you, have any confidence that you can be expected to handle filing your taxes by yourself.

TEXT: Please be sure to update the spreadsheet with your writeoffs for the year.

SUBTEXT: What did you waste your money on that we can try to justify as a business expense?

TEXT: Time to get organized again!

SUBTEXT: I’m really trying to help you, though I’m not sure why.

TEXT: So, I see that you’ve decided to spend another year as a freelance writer.

SUBTEXT: Have you considered doing something more practical, like being a C.P.A. in the nineteen-seventies? Worked out well for me.

TEXT: Whenever you receive income that will result in a 1099, you should take twenty-five per cent and put it in a separate account. Don’t touch that account except to pay taxes (estimated or at year’s end). That way, you will have money to pay your taxes!

SUBTEXT: You have the financial acumen of a fifth grader.

TEXT: Is this the total income for 2025?

SUBTEXT: It would take you three lifetimes to amass the wealth that I have accumulated, even though I did everything pretty normally. I know that you can’t help when you were born, your gender, or the economic circumstances created by my generation that your generation now suffers under, but I am going to judge you harshly for all of it anyway.

TEXT: Happy Passover.

SUBTEXT: Happy Passover.

TEXT: I’m still waiting. Please send details by April 1st.

SUBTEXT: It’s times like these that I wonder, Maybe I shouldn’t have let your father save me back in Vietnam.

TEXT: I have several trips planned for the end of March, so I’d like to prepare your returns sooner rather than last minute.

SUBTEXT: God, I hope you don’t want kids.

TEXT: Please read this Financial Times article. It summarizes a tax-court case regarding a writer who got in big trouble with the I.R.S. for taking deductions that the I.R.S. said lacked a profit motive.

SUBTEXT: Did you ever stop to think that your minor indiscretions could lead to jail time for tax evasion, and how embarrassing that would be for me, to have a friend whose daughter went to jail for tax evasion?

TEXT: It looks like you had a good year!

SUBTEXT: I am well aware that this message will be the exact validation that you desperately seek from an older authority figure, and, because I have been withholding any kind of praise for the work you have done, it means that much more to you. I did not think about this sentence until I typed it, and I will not think about it again, ever, after I am done typing it. I will pretty much immediately go back to thinking that all of your life choices are wrong.

TEXT: You can’t write off rent on your taxes.

SUBTEXT: Damn. I should’ve bought in Williamsburg when I had the chance. ♦