One Week Off The Grid: Lessons for Entrepreneurship

One week off the grid. I mean completely OFF. No calls, no emails, no DoorDash. No use of electricity except for GPS. It gave me time to think about all the parallels between my annual trek, my life, and entrepreneurship.

For the past several years, I have taken a week off each September and headed to the mountains with two good friends. Just us, gear, some provisions, and hunting bows.

It’s a welcome adventure and respite from my business responsibilities. It’s far from what most would consider a vacation. This journey requires much preparation, starting 6 months in advance. Hiking several miles at an altitude of 11,000 feet in the wilderness requires the physical and mental conditioning to deal with everything nature can throw at you. One mistake could cost you your life.

It’s an arduous journey. If you don’t have the tools, the skills, and the guidance, you’ll get hurt or lost. You can even die.

While entrepreneurship won’t kill you, it requires much of the same preparation and fortitude as success in the wild. Below are some reflections on the parallels.

Don’t take success for granted

When you’re hunting for your own food in nature, nothing is guaranteed. Your chances of success are around 10%. Once you’re in the mountains, dealing with below-freezing temperatures, hiking up and down steep terrain through dead timber, you believe that you deserve to get the prize. When you don’t, frustration seeps in.

Don’t embark on a trip like this with a different expectation. But despite that, and after months of preparation, once you’re in the mountains dealing with below-freezing temperatures, hiking up and down steep terrain through dead timber, you get your hopes up. You believe you deserve to get the prize — you feel entitled— but when you don’t get it, frustration seeps in.

Entrepreneurs, likewise, usually know the odds are against them but inflate their expectations, leading to frustration and sometimes even hopelessness.

It’s during these moments that you as an entrepreneur need to check yourself. Just because you’ve worked hard and done all the right things, it doesn’t mean that everything will fall into its right place – certainly not right away.

Do your best, absolutely. This will increase your chances of success, but always remember: there’s no guarantee. Ever.

And regardless of outcomes – in hunting or in business – you can take the time to reflect, meditate, appreciate nature, and develop mindful awareness. I’ve found from my personal meditation practice that presence and awareness can be the foundation for unshakeable mental toughness.

Prepare, and manage risk

While hiking back to camp on a sunny afternoon during this year’s expedition, the weather changed drastically. A sudden temperature drop and a hailstorm! The hailstones were only a little bigger than a pea, but when they pelted my head, it hurt. My rain gear saved the day.

When you have to carry pounds of gear on an upcoming trek, it’s tempting to take shortcuts and remove items to make the load lighter. So the decision about how much you will push yourself and what risks you are willing to take becomes critical.

It’s the same with business: you need to be deliberate and calculated. Instead of pounds of gear, it could be seed money. Maybe you started tapping into your personal savings or started carrying debt. Decide if you will risk investing more before knowing what the upside is. Instead of having multiple services, you might go all-in on the wrong service and be left unprotected from a cash flow drought.

Always weigh risks carefully.

Constantly upgrade your skills

I’m a fair archer, but I’m no Robin Hood. I might not even place in an archery competition. I’m always aiming to hone my skills in archery and increase my knowledge of the game, its behavior, the terrain, the wind, ethical practices, survival skills, and dozens of other factors beyond pointing and shooting that are needed for a successful hunt.

Last year, I finally got my trophy (and with it a great deal of organic, free-range meat), but it was because I had constantly listened to the advice of my more experienced companions and had prioritized learning and deliberate practice.

Being an entrepreneur is no different. Whether it’s sales or negotiation or hiring and firing, each new challenge, win, or loss is an opportunity and grow.

Actively seeking out new skills is also critical. Ongoing success in business requires focus, but it also requires a some expansiveness, for yourself and your team.

Build camaraderie

There are those who go it alone in the same territory I go with my two friends. I’ve gone it alone on a few hunts, but I prefer hunting with others.

Going solo definitely has its advantages. You can move over terrain faster, make less noise, increase your stealthiness, and respond to changes with agility.

But I prefer to go with others. Going in a group increases your chances of getting your game and surviving the wild backcountry. In the woods, things can and do go wrong, and unforeseen challenges arise. For example, this year, we worked together to cross a swollen river; I wouldn’t have been able to do that had I been alone.

The same positives of solo backcountry trekking apply in business: not slowed down by committee-based decisions, you can move and respond with greater agility and complete autonomy.

I have, however, also preferred to rely on a team of partners or colleagues in business. Together we see and do more than we could ever do alone. Synergy is very real. But besides increased chances of success, it’s more fun to be on a journey with others who share your vision.

On the adventure, take people you trust and can rely on (and those you will show up for, too). The memories created, especially from going through very challenging patches, will strengthen your bond and stay with you forever.

Develop resolve, robustness, and resoluteness

I’m glad my hunting friends advised me to prepare for the high altitude and long treks before that first hunt. Though already pretty fit from martial arts, I found these long, strenuous days to be exhausting.

Doing something that’s very, very hard — pushing your limit — will get you prepared to take on other challenges. Crossing a river, climbing a 70-to-80-degree grade hill with full gear, or facing a fear.

And when I say do hard things, I mean in and outside of business. Yes, make that difficult prospect call, reach out to that intimidating potential partner, or give that first awful speech. You will only grow. But also do hard things in your personal life: exercise; build strength; seek new challenges to master.

In other words, become the type of person who welcomes and navigates additional difficulties. You’ll be better for it.

Cultivate gratitude

Remember your blessings… and there are always blessings.

During the past several hunting seasons, we’ve mostly come home empty-handed as far as game is concerned. But we were never angry about the outcome. We got to unplug from the hectic world, spend time surrounded by the glorious views of the eastern Rockies, and enjoy the stories we inevitably created together. We never know which hunting trip may be our last, so we treasure each one.

Early in my career, I didn’t have the resources to invest in a hobby. Not just the financial resources, but also the luxury of time. I certainly could not take a full week off and unplug. But I cherished the little things: the ability to sleep in occasionally, to take a midday break with my children, or to complete a big project and reward the family with a weekend outing.

Maybe you’re in the same boat. That’s OK. Look for gratitude in the small things you’d miss if they were suddenly gone: indoor plumbing, electricity, a hot cup of fresh coffee, clean clothes.

Even if you can’t fully unplug as I now am able to each year, you can take the time to appreciate the things – all the things – that bring comfort and meaning to your life. For me, appreciation enriches every personal and professional endeavor, and it’s reinforced each year when I’m in the mountains.