Hey there y'all! I hope everyone is doing well today.
I want to talk about something a little different than usual...not a tax rule, but a way of working. Every year around February I have the same round of exchanges with a lot of good people - I ask for a document, they send it, I ask for another one, they send that one four days later, I ask a follow-up question that generates three more questions, and somewhere in there two weeks go by that didn't need to.
None of that is anybody's fault...it's just what happens when one person knows what's needed and the other person is finding out one email at a time.
I've been thinking about this problem for a while and I keep getting a little better at explaining the fix (at least I hope so). So here's this round's attempt.
Here's the idea. You already have, sitting in your inbox, a nearly complete list of everything I'm going to ask you for this year. It's just scattered across forty emails from last February and March, in no order at all. And you now have a tool on your phone that is genuinely excellent at reading forty scattered things and turning them into one organized list.
You don't need to learn anything technical. You need about twenty minutes and a willingness to try it once.
That's the whole concept. Everything else is how to do it without doing something dumb with your personal information.
Which is exactly where we're going, because that part matters more than the productivity part. First the safety rules, which come before anything else and are not optional. Then the thing that actually saves the most time, which is mining last year's emails. And then the two other jobs AI is unreasonably good at that most people never think to use it for. Give me about five minutes and you'll have something you can actually run this week.
One: the rules, before anything else
I need to be direct here, because this is the part where enthusiasm gets people in trouble.
Do not paste your actual tax documents into a chatbot. Not your W-2, not your 1099s, not your K-1, not a bank statement, not a brokerage summary. The information on those forms is exactly what identity theft is built out of, and once you've pasted it somewhere you don't control it anymore.
Strip the identifiers before you paste anything. That means Social Security numbers, EINs, bank and brokerage account numbers, dates of birth, your home address, and your driver's license number. If you're pasting an old email thread, read it first and delete those pieces. It takes a minute and it's the whole ballgame.
Check the settings on whatever tool you're using. Most of the major ones have a setting that controls whether your conversations get used to train the model. Turn it off. If you're using something you got through work, check what your employer's policy actually says before you put personal financial information in it.
And the biggest one: AI is not your tax advisor. It is confidently wrong about tax rules on a regular basis, and it's wrong in a way that sounds completely authoritative. It will cite a publication that doesn't say what it claims, it will give you a threshold from three years ago, and it will do both in a tone that makes you believe it. Use it to organize your own information. Do not use it to decide what's deductible.
Organizing is the job. Advising is not.
Two: mine last year's emails
Okay...here's the one that actually saves time.
Go into your email and search for my name, or search for "tax" plus last year. Pull up the whole thread from last filing season - all of it, including the annoying back-and-forth where I asked for the thing you'd already sent.
Now read through it and pull out just the requests. Then hand the cleaned-up version to your AI tool of choice with something like:
Below is an email thread between me and my tax preparer from last year. Read through it and build me a checklist of every document and every piece of information they asked me for, organized by category. Include anything they had to ask for twice.
Clean the thread first. Names of businesses are fine. Dollar amounts are fine. Account numbers, Social Security numbers, and addresses come out.
What you'll get back is a document checklist built specifically for your situation, from the actual evidence of what your situation required. Not a generic list off a website that includes twelve things that don't apply to you...and misses the two weird ones that do.
That "asked for twice" line at the end is the sneaky-good part. Those items are your personal friction points - the things that were hard to find last year and will be hard to find again. Now you know about them in August instead of March.
Three: the two other jobs it's unreasonably good at
Turning a year of transactions into questions. If you keep your books yourself and you've got a pile of transactions you weren't sure how to categorize, you can export that list, strip the account numbers, and ask AI to group them by what they appear to be and flag anything ambiguous.
You're not asking it to categorize them correctly. You're asking it to sort a hundred confusing lines into eight groups...so you can bring me eight questions instead of a spreadsheet. That's a completely different and much more achievable job, and it turns a two-hour meeting into a thirty-minute one.
Writing down what changed. This is the one nobody does...and it's the one I'd most like to receive.
Sit down with AI and just talk through your year out loud - you moved, you started a side business, you sold some stock, your spouse changed jobs, you bought a house, you had a kid, you took money out of a retirement account. Then ask it to organize what you said into a summary of life changes that might affect a tax return.
Every single thing on that list is something I need to know and would otherwise have to discover by asking you twenty questions. You just answered them all in one pass, in your own words, before we ever got on the phone.
Send me that summary in January and I promise you our whole season goes differently.
What to do this week
Search your email for last year's tax thread and just read it. Don't organize it yet, don't paste anything anywhere - just read it and notice how much of it was me asking for things.
That's the raw material. Twenty minutes with it in August is worth two weeks in March.
And here's my honest ask: if you try this and it works, send me what you built. I'm genuinely curious what these look like across different people's situations, and if some version of this turns out to be useful I'd like to build a better starting point for everybody. If it didn't work, tell me where it fell apart - that's just as useful to me.
This is education, not advice, and reading it doesn't make you a client. And if you already are a client - this kind of general writing sits outside our engagement. Your engagement covers your return, your books, your situation. This covers everybody's, which means it can't really cover yours. So before you act on any of it, reach out and let's talk about your actual numbers. That's what the individual advice is for. Nothing here is a recommendation of any particular AI product, and you are responsible for what you put into one. Information current as of August 2026.
Varde Financial, LLC · Abel Scott, EA · vardefi.com