My New Year's challenge to you
A simple, achievable -- maybe even fun -- way to get 2026 off on the right foot
Happy New Year, my friend!
I don’t know about you, but I will definitely not miss 2025. It was a year of immense personal loss — I went to three funerals between October 16 and November 6, including two in four days — and just a seemingly never-ending parade of crappy news involving my family, friends or colleagues.
Yes, I made some amazing memories, which I’ll touch on further down in the post, but seriously, 2025 can’t go the hell away soon enough.
Here’s hoping that 2026 is a year in which the joy, laughter, good health, gainful employment and love you experience far outweigh the bad stuff.
One way to start 2026 off on the right foot
This time last year, I proposed something I called The Ask Questions 2025 Challenge.
The Challenge was simple: “Sometime in January, contact a business you work with and ask them to change something.”
It was designed to be simple, achievable, relevant, quick and maybe even fun. No year-long, suffocating commitment. Just one single step that may or may not lead to something more.
Well, I still love this idea and I’m proposing it again… Welcome to the Ask Questions 2026 Challenge!
Here are a few possibilities:
Ask your cellphone provider to lower your monthly bill
Ask your credit card issuer to lower your interest rate, waive a fee or give you a bigger credit limit
Ask your gym to lower your monthly rate
Ask the furniture store or appliance store to waive a delivery fee
Ask a hotel to upgrade your hotel room or a rental car company to upgrade your rental
Ask your medical provider to reduce a recent bill
Ask a mechanic for a lower price on a car repair
Ask someone at the garage sale down the street for a lower price on something they’re selling
Ask your boss for a raise or a promotion
Ask your realtor for lower closing costs
Ask the car salesman for a cheaper price
All I’m asking is for one request sometime between now and the end of January. That’s it.
If you get your request granted, amazing! Good for you!
If you don’t, it is still awesome that you gave it a try.
Either way, it might even inspire you to want to try again. And wouldn’t that be amazing, too?
If you do it, tell us in the comments below!
2025 wasn’t all bad, y’all
As much of a stinker as 2025 was, I’d be lying if I said it didn’t have some amazing parts, too. In tough times, it can be hard to admit that there’s good stuff sprinkled into (or to even recognize good stuff as it happens) but it is incredibly important.
I took my first trip to Yellowstone, where my wife, son and I got to see a buffalo up close (but not TOO up close).
It was also the year I discovered that I really enjoy rock-climbing gyms, though I’m kinda terrible at climbing.
I got to sign more copies of my book out in the wild — everywhere from Bozeman, Montana, to San Marcos, Texas, to Fifth Avenue in New York City (pictured below).
And, of course, I dived fully into “Ask, Save, Earn.” It really has been one of the bright lights of my year. Since I joined Substack in March, my subscriber base is up about 60% and my overall audience has more than doubled, up about 160%. A massive thank you to all who’ve come along with me through this nutty year.
This was my most-read post of the year..
This was my second-most read…
And this was one that I loved that might’ve flown under the radar a bit.
Some of my goals for 2026
In the nonstop insanity of the past year, some of the things I hoped to do ended up having to take a back seat, and that’s OK. Life is about prioritization, and sometimes life just takes your plans, crumples them up, tosses them away and laughs.
There are a few things I know I’d like to do in 2026, though, including:
Another small book tour
More collaboration with Substackers, friends and colleagues
More meditation and reading
Giving people more ways to access my content
And so on.
Some of these things are already in the works. Some of them may be soon. For now, however, we’re just focusing on taking the next step forward into a year that will hopefully be better than the one that just passed.
To the promise of a new year!
Until next time,
Matt