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Tax-time thoughts: now with slightly less incompetent accounting!

I have survived, I think, another tax season as a self-employed individual, and I’m increasingly convinced that if I keep doing this I will someday know what I’m doing. Once again, my worst enemy was...

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I survived doing our own taxes (I think)

Over the last few weeks, I did the one thing I was sure I’d never do after leaving the Post: prepare my own taxes instead of paying a tax professional to do the work. I’d outsourced my tax prep over...

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Five years of not having a real job

Monday marked five years since I’d last been on the clock for an employer. The continued absence of a salary still doesn’t bother me. A lot has changed since the day that started with my failing to...

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Year-end cash considerations

Yesterday, I forgot to invoice Yahoo for the last month’s worth of stories, and my stupid oversight may save me a little money next year. That’s because the odds of payment for November’s work at Yahoo...

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2018 in review: security-minded

I spent more time writing about information-security issues in 2018 than in any prior year, which is only fair when I think about the security angles I and many of other people missed in prior years....

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Here’s the Google spreadsheet I use to track my expenses

A friend of mine started freelancing at the end of last year, so I decided to give him a boring but useful present: a blank copy of the Google Docs spreadsheet I use to track my expenses. A systematic,...

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Tax-time thoughts, 2019 edition

It looks like we didn’t get crushed by taxes this year, even if we did owe money to the IRS. That’s nice, since we skipped the one step we were supposed to take to avoid an April 15 financial hit. I...

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I survived yet another year of self-inflicted tax prep

The annual exercise in accounting self-abuse that is me doing my own taxes ended three months later than originally scheduled and yet still on time, thanks to the IRS pushing Tax Day back to July 15 to...

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Ten years without a real job

I have now somehow clocked a decade of self-employment, and I won’t even pretend that was the plan when my status as a Washington Post employee officially expired on April 29, 2011. At the time, I...

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