4 Questions I’m sitting with before 2026
Hey Reader,
12 days till 2026.
Ouch.
You’re probably already thinking about your 2026.
Most people go into January with a list of things to ADD.
More goals to hit. More habits to build. A newer, better version of themselves to become.
But here’s what I’ve learned after doing this for over a decade: the best years of my life didn’t start by adding more, they started with what I was finally willing to subtract.
So here are the four questions I’m asking myself before 2026.
1. What goals do I need to let go of?
When I was coaching full-time, I worked with people who genuinely believed they were failures. When I drilled down to where that belief came from, it was almost always the same thing: old goals they set and never hit.
That business they were going to launch by 30.
That book sitting in their notes app with three chapters written.
The problem is that most of us set goals with big round numbers and arbitrary targets that are five or ten years out. Then we just carry them, year after year, never once stopping to ask if we still want them.
Psychology calls this ‘sunk cost bias.’
I call it being stubborn as f*ck.
You ever had the experience of moving apartments? Most people pack everything up and haul it to the next place. Then you look around and realize you’ve been carrying the same crap through three different homes. Not because you love it, but because it’s just… yours.
Then there’s that moment you finally toss it, and you wonder why you held on so long.
Your goals work the same way.
And that goal you keep dragging into every new year… do you even want it anymore? If it hasn’t happened in three years, why is that?
I’m guilty of this, too.
People assume I hit every goal I write in my journal, and that couldn’t be further from the truth. Realistically, I check off maybe 40%. The difference now is I stopped calling that failure.
Because here’s what I’ve learned: three goals you actually want beats fifteen you feel obligated to chase. Three out of three feels like winning. Three out of fifteen feels like failure.
So before the year ends, you might want to ask yourself: what goals are you ready to let go of?
2. If I keep living exactly like this, where am I in 5 years?
You know that old Scrooge movie where the ghosts drag him through visions of his future? He sees what his life becomes if nothing changes, wakes up terrified, and resolves to be a different man.
There’s a reason that story still hits after all these years.
Five years ago was 2020. Felt like yesterday, right? Your next five will move just as fast.
And if you like the direction you’re headed, beautiful. Keep going. But if nothing changes, nothing changes.
I asked myself this question in my 20s about my business. Let me tell you, I did NOT like the answer. But it motivated me to shake everything up and make my first million within 18 months.
I’ve asked this question about relationships too. Sometimes the answer led to hard breakups. Other times it led to my engagement with Dani, where the answer was hell yes.
Don’t overthink this with words like “forever” or “life purpose.” I find those to be too abstract. Just look five years out. That’s a close enough timeline to feel real and far enough to actually matter.
Where do you end up if you keep going in the direction you’re going?
3. If I flash forward 12 months, what would make it a win?
Most people set vague goals like “be healthier” or “make more money.” No wonder they quit by February, there’s nothing to grab onto.
Here’s what I do instead.
I imagine it’s December 2026. I’m looking back on the year. What would have had to happen for me to score the year a…
(0-3) Failure (4-6) Okay (7-8) Win (9-10) MEGA win
For me? A 7-8 means launching my next program, getting back into drums seriously, maybe setting up a studio space to film in. A 9-10 means all that plus starting a family.
Yours will look completely different, and that’s the point.
This journal exercise forces you to define YOUR win. Not your parents’ version, not what social media thinks success looks like…YOURS. And once you see it clearly, you’d be surprised how much easier it becomes to move toward it.
So, what does your 7+ look like?
4. What sounds fun?
Okay, enough heavy stuff.
Somewhere along the way, we forgot that life is supposed to be fun. We got so obsessed with optimizing and achieving that we stopped asking the simplest question: what do I actually want to do?
Sometime last year, I realized I’d become a one-dimensional workaholic with nothing to talk about except YouTube.
So I Googled “improv classes near me” and signed up for the first one I found before I could talk myself out of it.
First class, I’m up on stage. Bombed completely…. but I felt ALIVE. Not productive, alive.
Not everything needs to be a goal. Some things just need to be lived.
What have you been wanting to try that you keep putting off?
Life Updates
What I’m Listening To
Somber
Been on repeat all month. Moody, stupidly catchy, and every song on that album feels like driving at night.
Ultimate Guide to Keeping a Journal (2026)
Dropping Monday. This video has become our unofficial Christmas tradition at this point. If journaling is something you’ve been meaning to start (or get back to), this will get you set up before 2026 even hits.
See you next Saturday,
CK
