As the saying goes, “Winter is coming.”
Entrepreneurs and “high achievers” seem to have only one season: spring.
Growth! Launches! New things galore!
We generally suck at winter…
But in winter, roots grow steadier. The nutrient budget shifts to repair. Strength comes through the subtraction of the non-essentials.
I’ve always wondered, “Don’t trees need jackets?” but it turns out that while the outside temp gets colder, the soil temp matters more: above roughly 40°F (4°C), roots slowly grow and repair.
Wintering at Work
At work, winter can show up as a “meh” energy toward your calendar. Not necessarily toward the people you work with – you might still like them.
It’s more the work itself: the subject matter, deliverables, goals.
“But Mike, being great at anything means being willing to get bored doing it… shouldn’t I keep going?”
I’m talking about a deeper blandness, as if you’ve outgrown the soil but keep watering it out of respect for the past.
I’m not saying, “Burn everything down” …an idea that my friends like to toss around to make veiled threats to themselves.
These people (including me) just suck at wintering. We’d rather go full pyro than calm down for a damn minute and learn to sit with ourselves.
Wintering can make things look dead to the naked eye. For those who have careers built on buzz and social, we hate that but…
May I suggest that we, like nature has done for eons, identify what roots are most important and re-direct energy there?
In September, I cut nearly all of my retainers, leaving $25,000 in MRR on the table. That hurts still… and it won back 20 hours a week.
I stopped taking interviews on my podcast and won back 8 hours a month.
That’s 80+ hours a month I’ve re-directed to the roots of clearer thinking, stronger writing, and closer relationships with fewer clients.
Personally, the wintering has helped me outgrow myself from the inside.
I’ve cut drinking by 70% (tracked it) and my nights mostly consist of workouts, cooking, watching Star Trek: The Next Generation (I thought this show sucked as a kid, it’s good), reading, and maybe sketching.
I just chalked this up to “getting older.”
Then I realized it was just me saying to myself, “Hey. It’s time to be with us.”
The Exhausting Battle of Persona vs. Person
Again, those of us whose businesses (or personal need for affirmation) revolve around Instagram flex are privy to a special kind of hell:
Trying to live up to whoever people think we are online.
Know where I’ve seen this the worst in my life? Dating.
If I land a date from an app (I’ve deleted them) it’s usually because of persona.
One picture of me on the roof of a van racing through a safari? I look like an outdoorsman (I am not).
One scuba diving pic? I must spend my days spearfishing snapper in the Maldives while I write bestsellers on the beach as my catch roasts on an open flame.
The most common question: “What do you do for a living?” (I have terrible answers.)
The real question we’re all trying to find the answer to: “Who are you, really?”
Day to day, I live in a box in the suburbs. I walk my 12-pound dog on a pink leash so other owners know it’s a girl.
There’s a jacked dude who lives behind my building who also walks a small dog. I’m convinced he believes my dog belongs to my (non-existent) wife.
We’ve never said hello. We share a tacit agreement to never acknowledge each other, much like men in the part of the store holding their wives’ bags while they’re in the changing room.
Posts are posts, image is image. You can make anything now with AI. For years, I’ve keep social media off my phone. I now refer to Instagram as “tabloids.”
If I get the urge to re-install it, I literally say out loud, “I am choosing to download this brain-rotting app so I can trash out on digital tabloids.”
It works like… 8 out of 10 times.
The hardest ones to work with are the ones who have not wintered. They still believe the pretty leaves and radiant colors are what matters.
Persona vs. person.
If you’re wintering right now, good on you. Do the deep work and you’ll probably like what you find underneath. Or you’ll at least know what to adjust.
If you aren’t, but you’re feeling something from what I’ve shared, it might be a sign. Don’t be afraid to shed.
Earlier I mentioned redirecting my energy to closer relationships with fewer clients.
In December (first time in three years) I’m opening ONE spot for 1:1 advisory in 2026. This is for established multiple 6-figure to 7-figure+ business owners, done in an intensive capacity. Also includes two in-person VIP days throughout the year.
In January, I’m opening ONE spot in my Private Mastermind. This is a carefully curated group of 6-7 figure+ entrepreneurs. Access a collective mind that challenges your thinking, opens doors you didn’t know existed, and holds you accountable to who you’re becoming.
Join the Private Mastermind waitlist »
Join either waitlist and you’ll be the first to know details.
Til next time,
Mike