2. Learning Uphill

The first time I realized I might not be cut out to run the chocolate cafe I had just launched was behind the cocktail bar during service, reaching for a liquor bottle when my sleeve, long and gapingly oversized, caught onto the bottle and nearly flipped the liquor onto the floor.

I was messy and scrambling, throwing my sleeves back like they belonged on a character at Disneyland.

I had taught myself how to serve drinks behind a makeshift bar in an old Mexican restaurant-turned chocolate factory, where we offered free drinks to our friends for a short, 2-day popup. Talk about crash course.

I didn’t know how to dress for the job.

I also didn’t know how to manage people.

Within five weeks of opening the cafe, I made one of my first employees cry. She was slow to acquire the pace of service, and I didn’t realize how much efficiency made me a ticking-time bomb of anxiety.

If you didn’t speed up, I was going to explode.

I seethed at her, attempting to direct her efforts more productively, but there was no veil for my frustration. She bolted out the back door.

That was six years ago.

I’ll never forget that feeling. Watching someone else be impacted by my emotions, expectations, & execution. I had no idea what I was doing. I — and the people around me — had to learn the hard way. Some of us are like that though, that’s the only way we’re really willing to learn. Uphill.

I was listening to the latest Armchair Expert podcast episode with Dax Shepherd and organizational psychologist, Adam Grant. They talked about the two different methods of getting out of your comfort zone. One is where you test the waters by dipping your toe in, then your ankle, etc, until you’ve submerged yourself. The other is to throw yourself into the deep end. Holding nothing back.

When I was in my mid-twenties, I was ready for the deep end. I just wanted to be thrown in. I mean, I hate cold water. Don’t do that to me in the cold Ionian Sea, even in summer. But like many entrepreneurs, I love to start things from scratch, to fly a plane with no training – just give me enough runway. Somewhere along my childhood I learned to value myself most from what I could contribute intellectually. I have little patience for myself working with my hands. Things are too tedious, and take too much time. I feel most valuable when I think and think and think. My husband and I will be reading books, and he’ll look over at me after about five minutes and ask, “Lauren, how is that book?”

And I’ll fire a glance over at him, smirking. He knew I wasn’t reading.

I was staring into space, thinking.

About the next brand to launch, a new financial model for the business, an excel projection I should run on inventory, a design project - laying out tiles in my head.


Other times I’m replaying the mistakes I’ve made. Re-remembering all the scenarios where I could have or should have done something different to be a better person, a better leader, a better business owner. It’s often a replay loop. I have had to learn, through years of practice, how to take the “off ramp” from the mental merry-go-round. Because it will repeat incessantly like a horror movie.

I can never escape hardship no matter how many times I play it again in my mind.

Good people remind me, welcome to being human Lauren. We can’t outthink our past, no matter how hard we try. The replay loops? It’s usually our body’s way of reminding us, hey – do this part differently next time. If we learn how to listen, we won’t make the same mistake twice.

Jumping in the deep end has felt a lot like treading water for the better part of a decade.
Or like climbing uphill, forever.

Whichever metaphor you choose, the path of learning always results in a kind of transformation.
“We cannot become what we want by remaining what we are.”

Fortunately for me that means these days I’m spilling fewer bottles and making even fewer people cry.

To grow, we have to take the leap. To submerge ourselves (whether toe-dipper or cliff jumper).
We have to be willing to look like fools, to walk with anxiety ridden stomachs, and do the internal work.
Allowing the uphill climb to render one tiny transformation after another.

Then one day years later, we just might meet a version of ourselves we’re proud of.