Scrambling to Pay Taxes Every April?


SAVING FOR TAXES, UGHHHHHHHHHHHHLYYYYYY.

Let me just put that in big ol' caps up there, because we all know that saving for taxes when you work for yourself is right up there on the task list with "drinking slimy brown mildew sludge straight from a dish drying rack that hasn't been cleaned in 3 months."

(You know that 🤮 film I'm talking about? If you don't empty that thing out constantly and clean it? NOTHING makes me want to vom more. Which is why Clorox is now my BFF. Sorry, vinegar people.)

Anyway, so taxes and mold. 🦠🧤🧽 Should be the name of my next book.

HOWEVER—I'm thrilled to tell you that, after much trial and error, I have now developed systems, my friend. Systems.

These are two things helping me conquer "Saving-for-taxes-itis."

Way No. 1: The Relay Bank App.

I LOVE, LOVE, LOVE (did I say love?) Relay. It's a modern online banking app specifically for business, and it's soooooooo much more enjoyable to use than your average, stuffy, "we made this website in 2004" bank. Its UX is demonstrably much slicker than any other bank I've ever tried (and I can send wires without having to drive 508 miles to the nearest bank branch to confirm my damn identity), but most importantly?

It has this new genius, life-changing "split incoming deposits" feature:

Relay: split incoming deposits setting, sending a percentage of every deposit to a tax savings account

Oh, yes.

This means that you can automatically have a percentage of every single deposit go into a separate tax savings account in Relay, so there is no doubt you'll be set at tax time (and won't have to do questionable, demoralizing things come April).

I love Relay so much. Even their debit cards are adorable. And you can set up virtual cards at the drop of a dime, or even temporary physical cards with a set limit (perfect for giving to an employee or contractor to spend at a conference).

And, they also have slick invoicing tools, too. 💵

Howevah.

You may also be one of those people who CANNOT SEE aforementioned tax savings account, or else you will use it. Next thing you know, you're selling your plasma in a dark, urine-stained laboratory off the freeway.

Alas.

Enter one of my favorite "unorganized money person anonymous" hacks.

Way No. 2: Set Up a Claude "Save My Ass" Task

What's a Claude "Save My Ass" Task, you ask?

It's when you set up a recurring, scheduled task with Claude, and Claude saves your ass. Obviously.

In this case?

I use it to report the previous day's revenue to me, and then tell me how much money I should transfer from my (other Chase business bank account) into the tax savings account. (Based on my own 30% rule.)

It DMs me the number every morning at 7am in Slack.

And then I manually execute the transfer.

Now, obviously this is hugely granular and OCD and totally overkill—most people would probably do this every week or month, not every day—but, that kind of frequency really helps me with clarity + control. And, who doesn't love control?! 🤣

Quarterly taxes are this abstract number that feel totally made up. But, daily taxes are a concrete, real-time number that you have visibility on. Also? You will price differently. Fact.

To set it up: make sure you set up a project specifically for this first (I call mine "Joe" - Bookkeeping + Taxes). (Joe is my real CPA, hahaha, so I call my AI employee Joe, too.) Then, make sure you add the scheduled task under that project. This will keep everything under one memory, give Claude the context it needs (e.g. I'm an S-Corp, fiscal year is calendar, use accrual basis, etc.), and won't force Claude to start every single run from scratch. (That's the difference between three robots who've never met and one employee who keeps a file. 🗂️)

If that sounds DELIGHTFUL but you also have no idea what I'm talking about?

This is exactly the kind of thing we'll be learning how to do in October inside of Claude for Business Owners.

Because I don't want you scrambling around at tax time for money like a helpless little fish.

And I don't want you drinking slimy brown mildew sludge straight from a dish drying rack, either. 🤷‍♀️

Share this one

LinkedIn  ·  X  ·  Threads  ·  Facebook  ·  Email

Extraordinary Work

AI is going to be what divides businesses in the future. Get my 17-years-and-counting unconventional work newsletter on the smartest, most interesting ways to stay relevant in 2026.

Read more from Extraordinary Work
How to Get Things Done When Your Brain is a Pile of Unseasoned Linguine

Every time I stare at the screen like a dummy (like I am right now), I have to remember: IT'S BECAUSE I DIDN'T SLEEP LAST NIGHT. That's always the reason. Zero creativity? Zero original thoughts? Zero ability to, like, get things done? I have to remember it's because I was up since 2am thinking about Discourse. Yes, the forum app. (What do you think about in the middle of the night, lol???) And also the wallpaper I bought for the guest cottage. There are VERY LARGE CRANES. Will the cranes be...

Boo-Yah! How to Show Up in ChatGPT (It Took Me 4 Minutes, and I Didn't Write a Word)

You know what's weird? The only things I Google anymore are the hours for restaurants and, like, antique shops. (Okay, fine: and probably wine shops.) Like yesterday. In the Catskills. This ******* place didn't open until noon. (And then I was so disappointed, because it was less antiques and more "here are some vinyl records that will make you look very, very Brooklyn cool.") (I mean, I want to look very, very Brooklyn cool, too, but I ALSO want a vintage oak apothecary cabinet that smells...

Photoshoots are SO MUCH FUN. 📸 That said, they are also one of those things you put off like you put off writing your will: not that you don't need one, but you're always waiting for some imaginary far-off time in the future when you have the gumption, the time, the headspace. Ha. And yet! Amateur headshots are still one of the #1 things that absolutely murder conversions on small business websites. They totally drag the whole thing down to the pits of hell and wreck all your hopes and...