5 Entrepreneurial (And Life) Lessons from The Worst Hike of Our Lives
“This is NOT good, Greg.”
An Epic Hike Begins
Back when I first married my wife Kat, we LOVED to travel and explore the outdoors. We’d go all over the southeast in search of good trails. One fall, we decided to hike from Amicalola Falls (straight) up to the southern terminus of the Appalachian Trail on Springer Mountain in North Georgia. It’s an epic hike with a memorable visual finish at the start of the storied Appalachian Trail. It’s also a bloody slog and almost all uphill.
Don’t Think. Just Start.
I was anxious to get out there and on the trail and being a confident 30-something, didn’t really do much by way of planning. Kat trusted me, so we got up early, headed to Amicalola and without much fanfare, hit the trail with a small backpack, “enough” water and some snacks to get us through the hike. I wasn’t really worried. It was a pretty straight shot and we had a lot of experience hiking. Also. There’s this wonderful “hike in” hostel up there that is a fantastic mid-way point. They have food, snacks, water and a place to rest should you need it.
When Your Plan Goes To Shit
The “straight” hike was straight alright. Straight up. A brisk pace turned to a snails crawl. We passed the Inn on the way up and stopped in to say hello. We didn’t resupply because we thought we’d do it on the way back down. 5 hours into our hike, we reached the terminus. We celebrated with a few photos and started the trek back down.
That’s when things got worse. We were running low on water and had burned through our provisions. We also took a wrong turn near the top (and our navigation app didn’t work up on the mountain) so by the time we got back on track, our 15 mile hike was looking more like 19.0 miles. Kat was exhausted. I was fatigued.
Then things got a lot worse. We were desperately trying to reach the hike inn hostel and arrived ready to fall over. Trouble was…they had closed up early that day and the placed was locked up. So, we were out of food, running low on water (and light) and still had another terrible 5 miles to go. That was the longest 5 miles of our relationship. Kat was feeling terrible and nearly collapsed a couple of times. The only way we made it down the mountain was by playing word association games to distract ourselves from the hunger, thirst and fatigue.
We laugh about it now, but that 18 miles in 1 day hiking experience tested our relationship and our will/perseverance. And the worst part about it is that it all could have been avoided.
This IS The Entrepreneurial Journey (but, does it have to be?)
I feel like that hike is symbolic of life (and the entrepreneurial journey) in a lot of ways. We’re all scrambling to create opportunities, take risks with social or financial rewards and balance all the elements of our work and lives. Like everything else, we all:
- Have lofty, ambitious goals
- Feel eternally under-resourced, while being eternally optimistic
- Are gritting/willing our way through things
- Experience constant obstacles
- Have to come up with creative problem solving
Did you have lofty ambitions for this year? Were your sights set on big things? Did you hit the ground running? Charging up the mountain only to run out of water halfway up?
5 Painful Lessons I Learned
If you’re starting a new journey or evaluating the one that you’re on, I humbly submit some suggestions for your consideration based on our “wonderful” experience.
- Plan Ahead 🎯 – You can’t ever predict everything that can happen on a journey like this, but you prepare and plan for contingencies. The more you can de-risk a situation, the more likely it is that you’ll achieve success. Where are we going? What’s the journey along the way look like really? What do we need to pack (the right people, enough financial resources, tools that will help make the job easier, etc).
- Get a Freaking Map 🗺️ – Listen. It’s just stupid to launch into something big without a good map (read: clear game plan) for where you’re going, what stops along the way you can make along the way (read: milestones) and what alternatives you can take to reach the summit (read: backup plans).
- Pack The Essentials 🚰 – Knowing what really matters and focusing on those things can be the difference between achieving your goals and bailing with miles left to go. As Greg McKeown espouses in “Essentialism”, learn to quickly discern the trivial many from the vital few tasks that will help you achieve success.
- Check In Often ✅ – Stuff goes wrong. And I’ve never hit a goal that I wasn’t tracking and monitoring. Have some good KPIs that are meaningful. Check in often with those KPIs, your team and yourself.
- Correct Your Course 🧭 – Don’t be too proud, confident or stubborn to acknowledge when things are going off course. As Tyson said: “everyone has a plan until they get punched in the mouth.”
About The Author:
Greg Hilton is the cofounder and managing partner for SOCO, SOCO is a thriving platform and community focused on supporting creators, indie workers and entrepreneurs just like you. He’s an avid outdoorsman, creator and storyteller.
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