The Day I Learned the Difference Between Fear and Risk
From summit pushes to leaving Apple - how I learned what real risk actually is
06/12/16 ~1am PST
Ingraham Flats - 11,100 feet - Mount Rainier, WA
I woke up to somebody shaking our tent. It was cold. Really, really cold.
“Let’s go guys, it’s time.”
I wasn’t sure if I’d actually slept. I do know that I heard an avalanche while trying to force myself to. That didn’t help.
Our guide Paul signaled to the group that it was time to meet in the main tent. I grabbed my headlamp and shuffled over in the dark.
It was Day 3 - Summit day on Mount Rainier, one of the most iconic peaks to climb in North America.
“Sit down and get yourself some coffee and some oatmeal.”
I still remember the steam rising off the coffee so thick I could barely see him across the tent.
“Today is going to be the hardest day of your life physically and most likely mentally. And most of you are going to quit on the mountain today.”
Paul had guided on Denali, Aconcagua, and completed an Antarctic Traverse. He had seen the movie before. He knew what was coming.
“My job is to convince you otherwise. Right now, I want you to think of all the hours you’ve trained. All of the friends and family back home who are pulling for you. You need to make a decision right now - ahead of time - that you will listen to me when I tell you we are pushing on.”
Oh shit.
My stomach dropped. My brain immediately started generating every reason I should back out.
Dammit, Kevin. Why do you always do this. Why don’t you just take up golf?
And then, like a deck of cards scattered in the wind, the group spilled out of the tent into the darkness. Each person nervously fumbling for their gear, trying to remember how to put their crampons on.
I didn’t know it at the time, but I would feel this exact feeling many more times over the next decade.
I felt it when rising sunlight revealed a thousand-foot dropoff while standing on a ledge the size of a shoebox on the Grand Teton. I felt it in the car driving to the head of the Ocoee River, windows down, hearing the rapids before I could see them.
Always at my own doing. Always because I had chosen to be there.
When Fear Met the Mountain
I have been anxious my entire life.
Extreme high standards and a fear of failure resulted in me over-worrying about everything.
If I thought through everything that could go wrong and had an answer for all of them, I could never fail.
Or at least that’s what my brain always told me.
Before that morning on Mount Rainier in 2016, I had never been exposed to real risk.
Then I saw the crevasses.
Massive cracks tore through the mountain’s surface, revealing hollow, blue-shadowed abysses that swallowed the light. A simple slip would be a permanent descent into the mountain’s heart.
Something unexpected happened when I was finally on the mountain: the anxiety disappeared.
Not because the situation wasn’t scary - it was the most terrifying thing I’d ever done. But my brain had no choice. Real risk demands full presence.
There’s no room for hypothetical worst-case scenarios when the actual worst case is six inches from your crampons.
I’ve spent most of my life worrying about things that don’t matter.
The big presentation at work. Whether my net worth is trending in the right direction. The DMV tag I’ve been putting off for three months.
On that mountain, every single one of them disappeared.
Not because they got resolved. Because my brain finally had something real to focus on.
For the first time I could remember, it was completely quiet.
The Summit
Summit day was 14 hours.
I thought I knew what I was getting myself into. I was wrong by a factor of ten.
The winds were relentless, resulting in sub-zero temperatures. I had never been so cold in my life and I haven’t been since.
Every time I thought we were close to the summit, we were hours away. The mountain kept moving the finish line.
At some point I screamed Paul’s name at the top of my lungs. I wanted a break.
The ripping wind swallowed my voice whole and he never heard me.
So I kept going.
I remember standing on the summit at 14,410 feet, being confused about where I was. The altitude, the exhaustion, the cold - it felt like being drunk. Our guides told us we had ten minutes on the summit. It wasn’t safe to stay longer.
The descent took as long as the climb.
When we finally stopped back at our tents - twelve hours after we’d left - I collapsed on the tent floor and ate an entire bag of Snickers minis without stopping. The entire bag, gone in a instant.
Hours later, I pulled Paul aside.
“I kept waiting for you to ask me if I wanted to keep going or stop. Honestly, I think if you asked, I would have given up.”
He smiled.
“Why do you think I didn’t ask?”
Reframe on Fear
My perspective changed that day.
Suddenly the everyday annoyances of life mattered a little bit less. The issues at work that would have stressed me out became almost laughable. Nobody was going to die if their iPhone delivered a day late.
But the feeling faded.
Within a few months I was back to my old ways. Worrying, planning, coming up with solutions for problems that didn’t exist yet.
I wanted permanent change, but one mountain wasn’t enough to produce it.
So I went back.
Every year since, I committed to a massive outdoor adventure I wasn’t sure I could complete. Every year, right before going for it, the same feeling arrived.
I remember climbing Casaval Ridge on Mount Shasta - our most technical route - and being punched in the face by the immediate exposure. We were in over our heads big time.
My buddy asked the guide if it got easier from here - “We’re just scratching the surface, bro.”
Oh shit.
I remember standing at the start line of my 50 miler. Wind whipping, rain coming down, the race director standing on top of a car with a megaphone just to be heard. Then he told us to go to the start line.
Oh shit.
I remember standing on the bank of the Ocoee River before our first whitewater kayaking run, listening to the rapids barreling past us.
Our guide turned around: “Alright guys, get in your boats.”
Oh shit.
Different mountains, different rivers, different starting lines.
Same feeling, every single time.
Fear Is a Muscle
Overcoming fear is a muscle and the reps compound.
Each time I did something that genuinely scared me, the effect bled into my personal and professional life for months afterward. The everyday fears got quieter, the imaginary problems got smaller, and the real problems got more manageable.
But eventually it faded. So I went back.
That’s the whole system. You don’t do One Big Thing once and walk away changed forever.
You do it every year because your brain needs the reps. The ROI on a single week of genuine fear is enormous, but only if you keep making the deposit.
When the moment came to leave Apple after nearly 13 years, I was scared. I hadn’t made a life altering decision in over a decade.
But it wasn’t the crevasse field on Rainier. It wasn’t a ledge on the Grand Teton with thousands of feet of dropoff below.
I had spent a decade learning the difference between fear and actual risk.
Leaving a career with a financial runway and a clear vision of what came next wasn’t actual risk. It was hard, it was outside of social norms. But it was also survivable. If I was wrong I could recover - you can’t recover from the crevasse.
I trusted myself and jumped.
I like to think a decade of voluntary terror had something to do with that.
Why You Need Your Own Mountain
You don’t have to climb Rainier. But you need something that makes you truly question your ability and decision making.
Something with real consequences that demands full presence. Something that forces you to make a decision ahead of time about what you’ll do when the fear peaks (it always peaks).
One major outdoor adventure per year. That’s it.
Because the person who walks out the other side of genuine fear is different from the person who walked in. Quieter in the head, clearer on what actually matters, and less rattled by the things that used to derail them.
The presentation at work, the difficult conversation, and the big career decision. They aren’t real risk.
They just feel that way because you haven’t had anything real to compare them to yet.
One Big Thing changes that.
Drop your answer in the comments - I read and respond to every one.
What’s the adventure you’ve been putting off until life slows down - and what would change if you stopped waiting?
Hmm very interesting. I anxiously worry a lot but did not make the connection between that and my big outdoor adventures. As I sit here a week out from my Azt section, and people are telling me it's going to be too hot and water sources are drying up, and that I should flip farther north, it's tempting to take the easy way out. Don't think I will though. My big dream is for my 5th book to sell better than my other 4. It takes a lot of courage to keep sending it out to agents.
This is great.