Why the season you can't see through is the same one that's been guiding you all along...
We came around the corner to the top of the access road and hit a wall. White. Pure white. Not a haze, not a fog, not a flurry. A whiteout. Zero visibility. Nothing but a heavy squall hammering the top of Killington with everything it had. There was nowhere to turn because there was nothing to see. The road, the trees, the buildings, all of it swallowed whole.
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Now luckily I knew where we were. I’ve driven this stretch enough times that my hands could do what my eyes couldn’t. I could feel the road. I knew the condo was close, maybe a hundred feet ahead of me, but it was invisible. Completely erased by this zombie apocalypse level wall of snow raging across the peak. I crept past two, maybe three turns, second guessing every one of them, trying to figure out which entrance was ours. When the road started to pitch back downhill I knew I’d gone too far. So I turned around, retraced the route, and finally found it. We pulled into the parking lot where a fresh three or four inches had piled up in what felt like the last hour alone.
That kind of squall means something. It’s not just snow. It’s a signal.
The next morning the sun blazed through the curtains like nothing had happened. Bright. Clean. Beautiful. I checked the thermometer. Negative sixteen degrees. I looked over at my wife and said well, at least it’s sunny out. We made it through the day with the high topping out at negative seven, which believe it or not I’ve done before. I’ve played this game. Nobody at the resort wanted to talk about what the temperature was doing at the peak. They didn’t even publish it on the website because they were afraid of scaring people off. Can’t say I blame them.
But here’s where the story turns.
This morning I was standing in the kitchen and glanced over at the Alexa, the one that cycles through family photos on its screen. And there it was. A picture from just a few years earlier. Same mountain. Same base lodge. My wife and I sitting there in 45 degree weather with the biggest smiles on our faces like we had conquered the world. We looked like we owned the place. Not a care. Not a cloud. Just warmth and victory.
And now here we were, back in the same exact spot, with the temperature fifty degrees colder than that photo. That was really conquering the day.
It hit me standing there looking at that photo. Cycles. Seasons. Everything moves in them. The weather, the markets, the years of your life. There’s a coordination to it that we don’t always see when we’re in the middle of it. Times of harvest. Times of planting. Times of rest. I think it’s baked into the human condition, this continual rotation through phases that push us forward, pull us back, and push us forward again. Not everyone tracks it consciously, but I can tell you that for me the pattern has become almost impossible to ignore.
Here’s what I’ve noticed. My life seems to move in seven year cycles. Long stretches of growth and extension followed by a one to two year rollover period of reset. And they’ve always been there. Every single time.
I can trace it all the way back. I left college in 1990 and spent two years working in sub shops while playing in the band. That was the dormant stretch, the soil getting turned over before anything could grow. In 1992 I took my first real job in the business world and from there I grew my sales skills steadily through the explosion of the telecom industry all the way through the late nineties. Seven years of building.
Then came the transition. The next two years I spent relocating back to the New Jersey area, catching the wireless revolution just as it was taking off, landing my first real corporate role, and beginning to build out my real estate portfolio on the side. The soil was turning again.
Around 2008 I made the leap to entrepreneurship. From 2009 to 2016 I built my first agency from nothing and hit my first seven figure year. Growth. Expansion. Momentum. Then another transition kicked in. From 2017 to 2023 I pivoted to a niche based agency model, scaled it to a multimillion dollar operation, and eventually sold it. Reset. Harvest. Close the chapter.
And now here I am in 2026. Deep in the study of AI. Building the next business model. Standing at the starting line of what I believe is the next seven year run.
The pattern is almost eerie when you lay it out on paper. Your cycle might not be seven years. It might be three. It might be ten. The number doesn’t matter. What matters is that the cycle exists and it’s already running whether you’re paying attention to it or not.
I think we beat ourselves up for no reason sometimes. We look around during the quiet stretches, the dormant periods, the low seasons, and we think something is wrong with us. We think we’ve lost it or that the magic isn’t coming back. But what if you’re just in winter? What if the season you’re in right now is doing exactly what it’s supposed to do? What if it’s recalibrating you, letting the soil rest so the next crop comes in stronger than the last one?
I think that’s the truth of it. The cycles aren’t punishment. They’re preparation. They need to be in place so you can absorb what you’ve learned before the next wave of growth hits. And if you’re paying attention, if you’re honest with yourself about where you’ve been and where the pattern is pointing, you might actually be able to see what’s coming next.
So don’t be so hard on yourself if you’re sitting in a low season right now. These things come around like clockwork. There will be seasons of growth. There will be seasons of harvest. And there will be seasons of rest. They’re not failures. They’re functions.
It’s a lot like driving through that whiteout. You can’t see a thing. The road has disappeared. Everything in front of you is erased. But you’ve driven this stretch before. Your hands know what your eyes can’t confirm. And if you trust the feel of the road beneath you, you’ll make the turn. You always do.
Lesson Learned
The greatest lie we tell ourselves in the quiet seasons is that the growth is over. It’s not. You’re not stuck. You’re not falling behind. You’re in rotation. The same cycle that brought you your biggest wins is the same one that requires you to sit still long enough to understand what those wins actually taught you. If you can step back far enough to see the pattern, you stop panicking in the valley because you know the climb is already scheduled. The question isn’t whether the next season of growth is coming. It is. The question is whether you’ll be ready for it when it arrives. So look back. Trace the cycles. Find your rhythm. Because once you see it, you’ll never waste another winter wondering if spring forgot about you.
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