Entrepreneurial Lessons Learned

6 Quirky Entrepreneurial "Lessons Learned" from Trail Running

Recently, I started trail running on the weekends. Let’s say, it’s currently more of a run, walk, run walk. And, that’s OK. It will take a little time to master the trails. This Sunday, I started thinking about the lessons I’ve learned from my first few weekends on the trails. Ironically, those lessons applied to entrepreneurship as well.

Let me share my lessons with you. If you agree or disagree, I’d enjoy hearing your thoughts.

1. Pick up your feet and keep moving forward

Trail running is challenging. Sometimes we find ourselves tripping over bumps in the road. We jump from one rock to another, trying not to slip … stubbing our toe on a rock, root, or anything else in our path. All the while, a little thought lingers in the back of your mind … when will it happen? When will I finally fall flat on my face?

You know what? The more you do it, the better you get. Your skills increase. Recognize that most stumbles are caused by dragging your feet. Pick up your feet! You’ll get faster, stronger, and more confident. Keep going and push those little thoughts aside. If you fall, get back up and keep moving forward. Sure, you’ll have some bumps, bruises, and scrapes ... but that won’t stop you.

In entrepreneurship, pick up your feet and keep moving forward. Learn from your stumble, bruise, scrape. Gain skills and agility. Get out there and do it! You got this!

2. Have the right equipment

When I first decided to run trails, I put on my street running shoes and headed to the park. I mean, there’s not that much of a difference between running on streets vs. trails … right? Let me tell you, for the trails I run, there’s a huge difference! However, starting out with street running shoes helped me. You could say they were the Minimum Viable Equipment to my trail running venture. Through trial and ERROR, I learned what needed in a trail running shoe.

Traill and error brought me to my current trail running shoes. I love them. But, I’m glad I jumped onto the trails, pushed forward, and learned from my experience. Now, my trail running shoes have the right amount of comfort, traction, support, and protection.

In entrepreneurship, the most critical step is to get out there and go fast. Learn from trial and error. Then, find the right equipment to support your business.

3. The path less taken provides the greatest learning

If you want to play it safe, stick to the well-beaten path. The safe path could be the most appropriate route for you at that time. The path you choose depends on a few things:

  • How you’re feeling?
  • Your level of preparation?
  • How hard do you want to push yourself?

Once you’ve answered those questions, decide on which path to take. When starting out, there is nothing wrong with taking the main trail. It provides you the opportunity to test your new (ad)venture. You can take the time to learn a few things but remain more on the safe side. As you run, take note of the trails peeling off into the wilderness. Where do they go? What is the landscape? Who's traveling along those paths? Do they meet back up with the main trail?

Once you’ve gained some insight and learned from the main trail, find a time to jump off that path. Go rogue! Take a path less taken. Explore! Say WTF and go for it! I guarantee the speed and depth of learning from this (ad)venture will pay off 10-fold! You’ll experience new things at a very rapid pace. Your senses will heighten. You’ll adjust, adapt, and dig deeper than ever before. When you reach the end, you're worn out, but exhilarated! You’ll crave taking on more (ad)ventures … more rogue paths.

In entrepreneurship, don’t be afraid to choose the rogue path. Take a little time to prepare, but say WTF and go for it!

4. There’s beauty in disconnecting

Disconnect the moment you step into the woods and hit those trails. Your mind clears and focuses on nature. You smile when you see animals interacting in the wilderness. Or, laugh when you stumble. You might even say hello to a new face, fellow hiker, runner, and their cute puppy.

Trail running allows you to disconnect from technology. Sure, we bring some tunes, fitness trackers, or other technology like that, but it’s not the everyday grind. We unplug from our computers, emails, TVs, crazy politics, and all other junk. On the trails, we are enjoying the moment. We disconnect and decompress.

Last Sunday I came across a squirrel. The silly little guy was right on the path with his/her head buried in a pile of leaves foraging for food. When I ran within a foot from this guy, he looked up at me. Dude didn't even care I was there. He went right back to the leaf pile. I couldn’t help but laugh. A simple interaction with a silly squirrel, yet I enjoyed every moment of sharing the path with this little guy.

In entrepreneurship, always find time to disconnect. It’s a whirlwind of adventure filled with stress, ups, downs, and all around. Disconnecting allows you to clear your mind and decompress.

5. Be aware of what’s around you

I run trails 15 minutes from my house. Turkey Mountain is a beautiful urban wilderness area. On the weekends, it’s packed! The remarkable part of this park ... it’s open to all kinds of people, animals, and ways to enjoy the park. 

When you’re trail running, you must be aware of what’s around you. Sometimes a mountain biker will sneak up from behind. If you aren’t mindful and they aren’t kind enough to inform you ... this could be trouble. Most of the time people give you a heads up ... Most of the time. Luckily, I haven’t had any incidents other than a few close calls. Sure, we are all out there to enjoy the trails. But, you could call them "trail competition.” The paths have limited space and resources. We are all competing for the same area and resources. You must be aware, adapt, and adjust at a moment’s notice. Don’t get run over!

In entrepreneurship, be aware of what’s around you. Don’t chase the next shiny object, but don’t get run over either. Be ready to adapt and adjust your path to continue your path forward.

6. "When you come to a fork in the road, take it."

Yogi Berra had it right, “When you come to a fork in the road, take it.” When I’m out testing the “rouge” trails, sometimes I have no clue which way to go. Which way takes me home? Which way leads me off to never-never land? I’ve experienced both outcomes. Two Saturday’s ago, I planned a quick 30-minute run. When I came to a fork in the road, I went for it. My “quick run” ended up taking 1.5 hrs. But, you know what? It was awesome! I found an area of the park I didn’t even know existed. The landscape changed. I captured a few funny moments on Snapchat and Instagram. I learned my current strength and limits. Plus, I went back to that trail the next weekend. (YouTube)

On the trail, you can find many different paths. Sometimes you don’t know which one to take. My advice, take "that" one and go for it!

In entrepreneurship, sometimes you won’t know which path to pursue. Don’t get to analysis paralysis. Follow Yogi’s advice, “When you come to a fork in the road, take it.” Learn, have fun, and keep going.

[PSA / Safety Moment: My Urban Wilderness Area isn't crazy large. A short walk in any direction brings me to civilization. Please know your situation. Don’t go rogue when it’s not safe.]

Thank you for reading this post. I hope you enjoyed it and can apply these lessons to your journey. If it helped you, please share with your friends, colleagues, and families.

- Stewart Swayze

Follow me on Instagram / Snapchat: stewart.swayze  

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