In almost 30 years of running a business, I’ve had a few periods where I genuinely didn’t know how we were going to get through.
The 2008 housing crash wiped out our U.S. pipeline. COVID undid a lot of what we had built in the years leading up to it. People have come and gone. Clients have changed. I’ve made mistakes and sometimes taken too long to adjust to things that were happening right in front of me.
I’ve come to call those periods “leveling up.”
I used to think going through something difficult was mostly about working harder. Put your head down. Climb the hill. Grind through it.
My experience has been different.
The really difficult periods are the ones where you encounter something you aren’t currently equipped to handle.
That is a very different feeling.
You’re anxious. You’re frustrated. You’re angry that it’s happening. You wonder why you didn’t see it coming. You can feel completely alone.
And sometimes, even if only for a moment, you genuinely think: I have no idea how I get past this.
I’ve learned that being hard on myself in those moments makes things worse.
How did I let this happen? Why didn’t I know better? Why can’t I figure this out?
There’s an arrogance hidden in those questions that I’ve had to let go of — the idea that because I’ve been successful before, I should somehow already have the answer to a problem I’ve never encountered.
Sometimes I don’t.
And sometimes I actually know what I need to do, but I haven’t found the courage to do it yet.
That has probably been harder for me.
My nature is fairly people-pleasing. Earlier in my career, there were times when I knew I had the wrong person in a role but delayed making the change. There have been other times when I believed strongly that the business needed to go in one direction, but I allowed other opinions to pull me somewhere else.
I thought listening to people meant their opinions had to change my decision.
I don’t believe that anymore.
I absolutely want people around me who challenge my thinking, point out blind spots and tell me when they think I’m wrong.
But eventually someone has to make the call.
And one of the strangest things I’ve learned is that I can often tell when I’ve finally made the right move by how the stress changes.
The stress doesn’t disappear.
Now I might be worried that I’ll look stupid. I might lose money. I might upset someone. The decision might not work.
But that is a different stress than knowing what I believe I should do and watching myself avoid doing it.
That second kind of stress eats away at me.
The first one feels more honest.
And then, eventually, you get to the other side.
The funny thing is how obvious everything looks from there.
I should have done that years ago.
Of course.
But it wasn’t obvious when I was in it. I had to go through the uncomfortable part to become the person who could see it that clearly.
That is what I wish I had understood earlier.
I don’t think every period of anxiety, uncertainty or discomfort means something wonderful is about to happen. Sometimes things are simply hard.
But I also don’t automatically see those feelings as evidence that something has gone terribly wrong anymore.
Sometimes they’re part of changing.
I’ve been doing this for almost three decades now, and there have been plenty of moments when I wanted the difficult part to be over much faster than it was.
Some lessons took months. Some took years.
Looking back, I wouldn’t pretend I enjoyed going through them.
But I’m incredibly grateful I kept going.
Because some of the things I’m most proud of in my life and business exist on the other side of periods when I wasn’t at all sure I could get there.