If you’ve ever been on a roller coaster, you know that moment right before the first drop – you grip the bar, your stomach tightens, you take a deep breath, and you wonder what the heck you just got yourself into.
Welcome to entrepreneurship.
Except this ride lasts years instead of minutes. There’s no operator doing safety checks. You can’t see the track ahead. And the drops? They’re steeper than anything at Six Flags.
After 32 years of running my own business, I can tell you this: The roller coaster never really smooths out. You just get better at riding it. That’s what I want to share with you today – how to not just survive the ride, but actually thrive on it.
Build Your Reserves (Both Kinds)
First things first: You need cushions for the falls. I’m talking about two types of reserves that most entrepreneurs overlook.
Financial reserves are the obvious one, but let me be specific. You need at least six months of operating expenses, plus personal savings. Not the optimistic spreadsheet version where everything goes perfectly. You need the realistic version where your biggest client ghosts you or that investor pulls out at the last minute.
I run my business on a ten-month year. Not because I take two months off, but because I know things will fluctuate and some months will be lean. Building in that buffer keeps me from making decisions out of desperation.
Here’s what most people miss: Emotional reserves. This is your hobbies, your relationships, exercise, meditation, therapy – whatever fills your tank. The entrepreneurs who burn out aren’t the ones who work hard; they’re the ones who work hard with an empty emotional tank. When you have people you can talk to, activities that restore you, and a life outside your business, you create an emotional cushion that lets you weather the storms.
You can’t pour from an empty cup, so protect both reserves like your business depends on it because it does.
On Low Days: Do ONE Thing That Moves the Needle
There will be days when you wake up convinced you’ll never get another client.
When the weight of it all feels crushing.
When you question everything.
On those days, forget your massive to-do list.
Pick ONE thing that will actually move the needle and do that.
Not busy work. Not cleaning your desk or organizing files. One meaningful action: Make that scary sales call, have that critical conversation you’ve been avoiding, fix that tech bug that’s been haunting you, send that partnership proposal.
Here’s the magic: Mood follows action. We’re often waiting for the mood to hit us before we take action. But it works the opposite way. You don’t need to feel motivated to act; you act and the motivation follows. Take the action first, and watch your mood improve.
After a Win: Attack, Don’t Relax
This might be the most counterintuitive advice, but it’s critical. Your most dangerous moment isn’t after a failure; it’s after a success.
You just closed a major client. You just hit your revenue target. Every instinct tells you to take your foot off the gas, to relax a little, to enjoy the moment.
Don’t.
Celebrate that evening, absolutely. But the very next day? Double down. Already in a good mood? Take more action. Make another call. Close another client. Do something that makes a difference while you’re riding that high.
Here’s why: Wins create momentum, open doors, and boost confidence. You’re never more attractive to potential clients, partners, or investors than right after a visible success. Use that fuel. Don’t let it evaporate.
Know the Difference: Dip or Dead End?
Not every low point is worth pushing through. Seth Godin talks about “The Dip,” that valley between starting something and mastering it where most people quit. Winners push through strategic dips because there’s something valuable on the other side.
But dead ends are different. A dead end is when the market fundamentally doesn’t want what you’re selling, when the economics will never work, when there’s nothing pointing to it coming back.
The hard part? They feel the same in the moment.
That’s why you need trusted advisors – friends, coaches, mentors – who can help you see clearly. People who will tell you the truth when you need to hear it because it’s really hard for us to know the difference between a dip and a dead end when we’re the ones on the ride.
Hold On Tight
The ride is terrifying.
The ride is exhilarating.
For those of us crazy enough to strap in, it leads to something incredible: freedom.
You get better at riding it.
You build your reserves.
You take action when you’re low.
You attack when you’re high.
You surround yourself with people who help you know when to push through and when to pivot.
Buckle up, buttercup.
This is what you signed up for, and it’s worth every twist and turn.
The most important skill for weathering a storm isn’t strength; it’s presence.
Pause and accept what’s happening. No sense in ignoring the symptoms. Denying it only makes things worse by trying to overcompensate.
As well as a time for thinking back over the past year, facing your missteps, asking forgiveness, and considering how you may become a better person in the year ahead.
Building anticipation: