Days 3 and 4: The Headwinds We Choose and the Ones We Don't

In my book EntreThrive, I wrote about a 55-mile Alaskan river trip: seven days on row rafts through remote tundra, no lodge, no hired guides, just my friend's 20-plus years of experience keeping the rest of us alive. Every day of that trip taught me something different about the entrepreneurial journey, and looking back, I can map the whole thing out.

Days 1 and 2 were the honeymoon. We were on a narrower tributary, the trout fishing was decent, and the newness of it all carried me right past the discomfort. This is every founder's early season — the excitement of finally doing the thing you've been dreaming about is enough fuel on its own.

Then came Days 3 and 4. We moved onto the main river, wider and rougher, and the weather turned on us. Hard wind, constant rain, casting became nearly impossible. This is where the real entrepreneurial headwinds live, usually somewhere between year two and year five of a venture, though sometimes as early as month three. This is where I've watched so many good ideas die, not because the idea was bad, but because the founder got beaten up by the wind and rain and didn't have what it took to keep rowing.

Days 5 and 6 weren't easier. The weather still gave us grief. But we were finally into the part of the river where the salmon were plentiful, our reward for sticking with it through the first few days of floating. We were still pushing through discomfort of rain, mosquitos, and unpredictable weather, but we were catching so many salmon, we hardly noticed. Day 7, we went home with stories that will last a lifetime. Even the hard parts had become good memories by then.

Sometimes You Call the Float Plane

Here's a piece of that trip I didn’t include in my book: sometimes the weather turns so drastically that pushing forward isn't a sign of grit but rather a sign of stubbornness. Sometimes it’s wise to call in the proverbial float plane and find another river entirely.

As entrepreneurs, we're taught to romanticize perseverance, and rightly so, days 3 and 4 require it. But there's a difference between the headwind that's testing you and the river that was never going to get you where you wanted to go. Not every river leads to good fishing, no matter how hard you row. Sometimes the wisest move isn't more grit, it's admitting you're on the wrong water and finding a different one.

That's a harder call than it sounds. It means admitting the plan might be wrong, not just the weather. In entrepreneurial terms, that “new river” could be a business model that needs to change, a product that needs to be shelved, a partnership that's run its course, or even a relationship or career that's quietly been the wrong fit for a long time. It takes wisdom and humility to make that call. Yet if you want to get to Days 5 and 6, sometimes changing rivers is exactly what's required.

Presence Is What Lets You See the River Clearly

So how do you actually know which one you're facing; a headwind worth pushing through, or a river worth leaving? This is where I think most of us get it wrong, me included. We try to answer that question by replaying the past or projecting into the future. We ask, “How did I get here?” or “What if this never gets better?” Both are useful questions at times. Yet neither one is where the decision actually gets made.

The decision gets made in the now. Being present, fully attentive to today's water, today's wind, and today's fish, is what actually sharpens your judgment. When I was in that raft on Days 3 and 4, the moments we made the best calls, where to steer, when to hold the line, when to pull over and wait out the worst of the wind, were the moments I was locked into what was directly in front of me. The moment I started spiraling about how many days were left or how good Days 1 and 2 had felt, I got worse at reading the river, not better.

Presence isn't just a feel-good practice for gratitude journaling. It's a decision-making advantage. If you're always rowing while looking backward or forward, you lose sight of the one thing that's actually giving you real-time information: right now. 

The Gap and the Gain

This past week I had the privilege of being coached by my 10x coach, Chad Johnson, and Dan Sullivan, founder of Strategic Coach, in my FreeZone group. Dan introduced a new tool for coach members, called Yesterday Creates Tomorrow, built on a concept he developed years ago and more recently made famous in his book (co-authored with Benjamin Hardy) The Gap and The Gain.

Here’s the main them of The Gap and The Gain: we measure ourselves against one of two things. Against an ideal, where we always fall short and live in the Gap. Or against where we started, where we can actually see the Gain. Entrepreneurs default to the Gap. We're wired to chase the next milestone and discount how far we've already rowed.

A couple of newsletters back, I shared the experience of getting Dan Sullivan and Dr. Martin Seligman, my former professor and the father of Positive Psychology, on a Zoom call together. What connected them was this: Marty's book Flourish, which introduced PERMA, shaped Dan's thinking years before The Gap and The Gain was written. Two of the sharpest minds I know, pointing to the same truth; our capacity to flourish depends on where we choose to focus.

The Headwinds We Bring on Ourselves

Some of our hardest days are self-inflicted. Poor choices. Habits we know are hurting us. Relationships we keep out of guilt or comfort long after they've cost us more than they've given. These headwinds are quiet ones, because we're usually the only person who can name them and often the last one willing to.

I've had my own version of these. The instinct is to keep rowing and pretend the wind isn't there. It rarely works. Naming a self-inflicted headwind honestly and then seeking proper help to get us through it or onto another river, is usually the best course in these headwinds.

The Headwinds That Choose Us

Then there are the days that arrive uninvited. For our family, that day was December 15th, 2025, the day we learned our son Jantzen had cancer. No amount of preparation sees that one coming. It doesn't care about your quarterly goals or your view of Days 5 and 6. It changes everything, instantly, and there's no float plane and no other river. You just have to row.

What I've come to believe is that what separates the people who make it to Days 5 and 6 isn't the absence of these headwinds, self-inflicted or otherwise. It's what they choose to do with the day itself, and later, what they choose it to mean.

Making Up a Better Yesterday

Dan has a phrase I've carried for years: “Your past is mostly made up.” Not made up as in false, made up as in constructed. We decide, after the fact, what a day meant. That's not denial. You’re taking ownership over the meaning of each day.

I could have let Days 3 and 4 on that river shut me down. I could let December 15th be nothing but the worst day of our lives. Instead, I choose, deliberately, and not always easily, to remember it as the day our family leaned all the way in. We got present for Jantzen in a way we might never have otherwise. It's still one of the hardest days I've lived. It's also one I'm proud of.

That's the Gain. Not pretending the hard day wasn't hard, but refusing to let it be defined only by the distance between what we hoped for and what we got.

Your Days 3 and 4

Wherever you are right now, battling a headwind you brought on yourself, facing one that chose you, or wondering if you're simply on the wrong river, the way through starts with getting present.

Days 5 and 6 are still coming. Keep rowing or find the river that actually leads there.