I just sent this note to my future self

February 2026 version of me says this...

Author

Diana Kelly Levey
March 09, 2025

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Does anyone else ever write a note to their future selves?

I used to do this a few years ago with some aspirations of where I wanted to be, which included some things I wanted to achieve in personal and professional pillars.

Now, it’s usually putting a calendar reminder in December to order my January son’s birthday supplies or gifts early because the new year will be too late.

Not super exciting stuff, I know.

Recently I put a reminder on a February 2026 calendar date that says “This time of year makes you feel broke.”

I’m not really broke.

But I remember feeling this way in the beginning of the year last year, too.

Why do these feelings crop up?

I look at “how much I earned” the previous year. I may even pat myself on the back and bask on those feelings of pride for a few minutes.

Then, I look at my bank accounts and wonder why most of that money I earned isn’t in them. (I think a lot of people feel this way at tax time.)

I add up all of my business expenses. (Ahh, that’s where a lot of it went.)

I also send everything to my accountant.

The accountant tells me how much I owe in taxes to the Federal government and state since I earned more last year, they feel they should have been getting higher amounts during quarterly tax payments. (Of course they do.)

Those payments are due somewhere in between March 15 and April 15.

Also, Q1 estimated taxes are due around April 15th.

You know what also happens this time of year?

»Many of my annual business subscriptions for software, websites, newsletter services etc., renew.

»I try to toss extra savings into my retirement funds which can also lower the tax bill a bit.

» Work tends to be slower in January and early February. So that “steady income” that flows in a bit easier in spring, summer and fall is slower in the winter. Combine that with December and early January being expensive for our family and it can seem like money is flying out the window.

Losing Dax Shepard GIF by SpinTheWheel

Gif by SpinTheWheel on Giphy

In reality, it’s not.

I’m fine. My business is fine. My husband and I have a healthy savings. (He doesn’t work in this industry.)

I have to remind myself that this is also the ebb and flow of my business.

I know it’s usually slow these months and I mentally and fiscally prepare for that (I think) but I tend to forget the other expenses that renew around the same time.

This is why I put a reminder in my calendar for next year. So if I start to feel like I’ve done something wrong, that I didn’t earn any money, that no one wants to hire me or question why I pursue this career, to take a deep breath and say, “Oh yes, you felt like this last year.”

Rant over.

I just wanted you to know that running a business is frustrating at times.

It can feel like two steps forward and four back — especially at tax time.

So if you’re a little bit of a salty sister or brother this time of year, you aren’t alone.

If you are looking for some freelance tax tips to streamline your processes, check out this guide.

Thanks for being a reader.

Diana

P.S. Want to know how I ramped up marketing efforts to close over $8,000 worth of business in February? Get my 2025 Freelance Marketing Calendar with specific strategies to implement to find high-value clients. (It also includes three BONUS PDFs to help your marketing efforts.(

P.P.S. Missed last week’s newsletter or a recent post? Check them out here.

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