5 Entrepreneurial (And Life) Lessons from The Worst Hike of Our Lives

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.  

  1. 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). 

  2. 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).  

  3. 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.  

  4. 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.

  5. 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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10 Women That Are Getting Sh*t Done

10 Women That Are Getting Sh*t Done

Introducing Some Badasses

We’re all surrounded by talented women in our lives. It just so happens that we’re super extra fortunate to be a part of a co-operative work community that is chock full of badass female creators, innovators and community builders.  They wear many hats.  They take on a bunch of responsibilities.  And they do amazing work.  So this post is for them.  

We want to celebrate their spirit, tell their stories and amplify their voices this month.  While we are fortunate to have many, many female members in our community…too many to list here.  But these are just some of the folks doing big, cool or interesting things worth noting.  Our challenge to you…read their stories, connect with them, follow them.  They have causes you can support, skills and knowledge you can hire and stories worth sharing. When women thrive…we all thrive.

PS: There are 12 actually…we couldn’t help ourselves. 😂

Amy Johnson Ely

Amy is the Executive Director for The Palmetto Cycling Coalition whose mission is to make South Carolina bicycle and pedestrian friendly, by improving safety through better access and education, to promote healthy lifestyles and livable and economically viable communities.  Amy is a huge advocate for bicycle and pedestrian friendly communities and livable communities; activating stakeholders, citizens and evangelists alike.

Bianca Shelton

Bianca is an entrepreneur, wife, mom and a  pizza and Prosecco enthusiast. Her favorite meal is brunch (check out her podcast Books, Brunch and Babes), a lover of all books (she still buys actual books), a branding photoshoot pro (check out her company, the Crawford Austin Agency) and a travel snob.

Dawn Dawson House

Dawn is fighting to preserve, celebrate and elevate African American cultural heritage in South Carolina and beyond. As the Executive Director of the WeGOJA Foundation, Dawn leverages her 20+ years as a tourism professional, storyteller and convener to document, preserve and activate African American heritage in South Carolina.  Their wildly popular and award-winning GreenBook of SC provided one of the first of its kind travel guide to SC African American cultural sites. (a co-operative project with SOCO members).   

Fiona Martin

Fiona is a competitive triathlete, founder of the worker-owned digital marketing agency FGM Internet Marketing, and an environmental activist.  When she’s not designing digital campaigns for companies and causes she believes in, she’s competing at the highest level in triathlons around the world (competing in the ITU World Championships for Team USA).  Fiona is a vocal advocate for the environment, sustainable development and equitable access for marginalized persons and cultures. 

Helen Johnson

Founder and creative director of digital powerhouse HLJ Creative, Helen Johnson is passionate about combining eye-catching design with data-driven marketing strategies to create brands and websites that make the right impression, accomplish your goals, and lead to long-term growth. She’s an entrepreneur and a super mom.  She’s seeing incredible growth and is evolving her team’s capabilities to serve the needs of a new generation of clients.

Jada Willis

A high energy and highly impactful coach, consultant and thought leader in organizational culture, talent attraction & retention and leadership…Jada built and sold her first company in late 2022 and is now working on empowering CEOs to build incredible cultures and companies with several new ventures in the works.

Kaleigh Cox

Freelancer turned creative executive.  Kaleigh Cox had a successful career as a freelance copywriter before she met fellow SOCO member Robert Gilbert in the early days of DxTEL. The two joined forces a few years ago and haven’t looked back. DxTEL is a fast growing managed services and platform company serving the rural broadband/telecom industry.  Kaleigh has built a reputation as a savvy storyteller and influencer in the space.  When she’s not evangelizing for access for everyone, she’s all about faith, family and community. 

Kassy Alia Ray

After losing her police officer husband in the line of duty, Kassy was moved to take action and founded Serve & Connect with the mission to help police and citizens work together as one community; Serve & Connect works to heal the relationships between police and the communities they serve and by doing so, creating a future where police and citizens work together as one community.

Katherine Swartz and Bre Spaulding

This dynamic duo is transforming entrepreneurial education and building the next generation of student entrepreneurs at USC through the McNair Institute for Entrepreneurialism and Free EnterpriseKatherine has been transforming nonprofits and shaping the next generation for 20+ years. “Bre” is one of Soda City’s most dynamic young leaders. Working with stakeholders from across the university, the McNair team successfully launched USC’s first ever minor in Entrepreneurship.

Shannon Franklin

Shannon is the Cofounder and COO of Consciously, a creative agency serving the needs of conscious brands including Akimbo (altMBA), B Lab, Black Wealth Data Center, and Planned Parenthood.  Consciously builds purpose-driven, inclusive marketing platforms that help companies nourish their business ecosystem.  In addition to being a mompreneur and a brand builder, Shannon has launched a life coaching business. 


Starlitt Miller

Starlitt Miller is blending a creative background with technology and data with her new startup Transity.  In 2022, Starlitt graduated from Visible Hands, a high tech accelerator focused on investing in and lifting up underrepresented founders.  She’s a vocal and active member of the Cola startup scene and the most recent Entrepreneur in Residence at the Richland Library.

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  1. Share it (please) and help us amplify their stories!
  2. Like, follow or connect with one of these badasses on the socials.
  3. Join us!  We’re a cooperative, workspace and community where people come first.  It takes a village