3 things I’m bringing into 2026

I did my reflecting, but I'm not ready to share… yet. But the teaser is: 2025 definitely wasn't as "good" a year as 2024. 

If 2024 was me celebrating 40 years and having a big bash, 2025 was more of a transition year. More to come on that next week.

I'm writing this as I fly off to a multi-day meditation retreat.

As I mentioned a couple of weeks ago, I love YearCompass. This year it was tougher because all the reflections weren't rainbows and unicorns, but I'm working on seeing the good in it.

While you wait for my reflections and the coming big announcement for the new direction of Gateway X… I want to share THREE "new/different" intentions I'm taking into 2026 and why:

Let's face it: my history has been one of bootstrapping. I have not ever built a unicorn (maybe by design?) — Ampush was >$50M exit. 

I think GrowthAssistant and Aux will be bigger. But they are similar stories. If I'm being honest, they were all businesses I started where I felt confident they would succeed.

"What's wrong with that, Jesse?!"

Nothing. In fact, I think it’s the right way to do your first business (and maybe your second).

Also, marketing/ads is a favorite first biz of many successful founders. I always remind people that Elon Musk’s first business was a "small" exit in marketing (Zip2), as was Tony Hsieh’s!

But I'm 41. I think I have another 10-20 "good years" to go hard at something. I've been blessed with success.

So, I want to THINK bigger and SWING bigger. What does that mean? You'll see soon. 

But it’s not just what I do… it’s a mindset. I think it shows up most in taking risks or doing things WHERE YOU’RE NOT SURE YOU’LL SUCCEED.

Both inside the companies and the platform as a whole, we're embracing this mindset in 2026.

Acceptance is a funny word. And not a word often associated with entrepreneurs.

By definition, we are supposed to REJECT the status quo and agitate for change. "Unacceptable" is a common refrain from high-standard-having founders.

If you ask most founders, "Can you accept yourself and your company for where they are?" They will say:

HELL NO. If I do that, then my company will just keep all its problems, stop growing and, ultimately, fail.

Sound familiar?

I think this can be an effective way to motivate yourself and your business… and I've used it for a decade-plus. But… it’s MISERABLE.

So, what's the other way?

Accept what it is. Now. Don't make it wrong. And then decide (from joy or creativity) what you want to do next. This is subtle and nuanced, so here's an example:

You're hiking up a mountain. You’ve got your map and a great game plan. You're fired up. Then, one mile into the hike, a boulder rolls down the hill right into your trail.

What do you do? Do you start beating yourself up for not anticipating it? Do you give a speech about how it's unacceptable? Do you berate your hikers for missing the mark? Do you give up?

Probably not. What you’d probably do is express a little frustration, but then say, "It is what it is…” NOW, let’s find a different path to get up the mountain.

That frustration and "it is what it is" is ACCEPTANCE. And it’s something I want to practice more.

Less judgment, less digging into "who’s to blame" (that's different than a retro) and instead, accept it. Then decide what's next.

It’s lighter, happier and more energized.

This is a weird one at first, but it ties in quite nicely with the other two.

I am a type 7 on the Enneagram. I highly recommend taking it if you haven't. It’s my favorite self-awareness tool.

7s avoid "difficult" emotions like sadness and fear. Your first thought might be, “LUCKY you, Jesse!” And, on the surface, I can see that way. Happy, energetic, etc.

But there are costs to this. It makes me less joyful, keeps me stuck and just generally less "human" (emotionally available and empathetic). 

I can write another newsletter about those in the future.

One of the biggest "business" costs, though, is it’s kept me playing small. 

Why? Because if you want to avoid sadness, you avoid failure (or the possibility of it) and so you end up doing things where you feel confident you can succeed (see 1).

Also, when something is truly sad, say we lost a big client or a great employee quit, rather than feeling it (they say sadness is the feeling of what to let go…), I will go into denial or try to spin it.  (See 2).

Denying any emotion denies all of them. I'll leave you with a quote from my coach, Dave's, favorite coach,

There you have it. Three things I'm taking into 2026 that are new and uncomfortable.

What's on your list and why?

jesse