Why Entrepreneurship is Like Hiking

Dr. Lakeya Cherry
3 min readJan 24, 2022


South Fortuna (San Diego, CA)

Have you ever hiked? A real hike?

This past weekend I went on a hike 1094 feet in elevation and it took a lot of breaks and words of encouragement to keep going.

I wanted to do this hike well aware that hikes like this usually require more preparation.

I knew this, but I still wanted to try.

At one point, I stopped. I just couldn’t muster the energy to continue.

I sat on a rock breathing for dear life wondering if I should continue…wondering if I could continue.

And then it hit me, entrepreneurship is like hiking.

You may feel drawn to it without fully knowing what all it entails.

When you first start, your adrenaline is high and you’re excited.

You’re paying attention to the environment around you and you’re moving.

Then your shoe (business) hits a rock (an obstacle). Ouch. That kinda hurts, but you keep going.

You pay more attention to your steps, you perhaps change your pace.

Now you’re really moving. This is fun. You’re enjoying it. You feel alive. (Your business is thriving)

And then the first incline comes.

You’re still riding off the excitement and you push and pull your way up. You’re meant for this. (Your business is meant for this).

And then you realize the incline doesn’t seem to be ending any time soon. (Another hardship?)

Yikes…perhaps this isn’t as fun as you thought it was.

You can’t breathe. Everything hurts, which is now making the entire process more difficult. (Oh, entrepreneurship isn’t easy?)

People are passing you up. You’re self conscious. Can I do this? Am I capable? Maybe I should stop? (Will my business succeed? Why are others having more success?)

You give yourself the time you need to refocus (breathe), and get yourself together. Oftentimes with the encouragement of a friend, colleague, or partner.

You keep going. You almost slip, but you don’t. One foot at a time.

You tell yourself this isn’t a race. You give yourself compassion and words of encouragement.

You look down and see how far you come.

You begin to smile. You’re proud of yourself.

And then you realize that this isn’t the end. You still have a few more inclines to go.

You’ve come this far and you wonder if you should go back.

You can’t. You didn’t come so far to stop. You’re here for a reason. This is part of your journey.

You take the time you need, breathe in, breathe out, and over and over again…

You tell yourself you got this and you push, pull, push pull one step at a time.

It seems like this is never-ending, but you make it. You get to the top and wow!

You can’t believe you mustered the energy and courage to do it, but you did. You did!

And then you realize, this isn’t the end…

You have to go back the way you came to get home.

But now that you know what to expect, so you take your time, and then you go.

One step at a time.

You move with more confidence, more resolve, determined to get to the end.

And you know what, you make it.

You also have new information that will guide you for the next journey.

Entrepreneurship is like hiking.

It’s fun and thrilling in the beginning and then you’re met with your first challenge and it’s up to you to figure out what you’re going to do, how you’re going to navigate…

And then you succeed and everything is smooth sailing and the path seems clear again until you’re met with another hurdle…and yet again, it’s up to you to figure out what you’re going to do and how you’re going to navigate this challenge.

You feel some fear, some anxiety, and some dread.

But you keep going and you’re successful. You get to your destination. (Oftentimes with the support of those nearest and dearest to you).

It doesn’t matter who passed you along the way or how long it took you, but you arrive.

This was your journey. This is your journey. Whether you keep going or not, you’ll learn along the way and ultimately become stronger.

Are you up for the hike?

Read more about my entrepreneurial endeavors with Lakeya Cherry LLC here: Lakeya Cherry | Executive Leadership Coach



Dr. Lakeya Cherry

CEO | Partner, Evolution| Executive Coach| Thought Leader