Hiking the AT

Following my heart on the Appalachian Trail.

It’s 2am. This is the third night in a row that I’ve been unable to sleep. Conversations from the day’s meetings run through my head on an endless loop. Am I making the right decision? We’re so close – our investors are ready to write a check. Why am I not excited? Why does my gut tell me that this is the wrong path? I’ve worked so hard to get to this point – why doesn’t it feel right? Why can’t I sleep? What’s the right decision? What’s the right path? What’s the right answer?

My name is Jack Jones and I’ve spent the last four years pursuing entrepreneurial projects. I own a media company called The Healthy Gamer. In 2014 I opened a CrossFit gym.

The company giving me so much stress was founded in 2015 with myself and two partners. The core idea is to build character and teach social skills through video games. We experienced great early success and proved that there is a viable business model. The kids loved it. The parents loved it. The last few months have been spent meeting with investors. We’ve negotiated terms, the investors like the idea. They believe in the vision and are ready to invest $200k. It would be a guaranteed pay-check for the next two years. If successful we’d all be millionaires.

Last week I decided to walk away from the business and thru-hike the Appalachian Trail.

I won’t have a job when I return.  I won’t have a place to live. I’ll need to spend most of my savings to fund the trip. It’s a irresponsible decision. It is a reckless decision. And yet I feel excited. I feel alive for the first time in months.

What constitutes a good decision? 

Life at its core is a series of decisions. And I have a bad case of FOMO(fear of missing out). This has manifested in business as trying to take on every opportunity. Which then leads to overwork and burnout. I agonize over making the “right” decision. I’m afraid that picking one opportunity over the other will lead to disappointment and regret. In too many instances this fear of missing out and worry over making the “right decision” has lead to decision paralysis.

Not making a decision is a decision in itself. In the Army we were taught that in combat any decision is better than indecision. I think that axiom applies to life.

It’s been my experience that the heart is always clear on the path it wants to take and that it’s the mind which muddies the waters. I’ve known in my heart for months now that I didn’t want to build this start-up. Yet my mind has suppressed the heart. “It’s a great opportunity. It’s a great team. There’s capital. You won’t be living month-to-month anymore. It’d be stupid to do anything else.”

I think the mind gives itself too much credit. The mind thinks that it can see a clear path. Just follow A to B to C and then you will arrive and live happily ever after. But I think the reality is that the path that the mind sees is a fiction. That smooth A to B to C path is made up of your own wishes, assumptions, and hopes. Not reality.

I think your heart has a much more clear vision for life. The heart’s path is convoluted. It’s not straight or easy – you’ll go through the underbrush, back-track over mountains, walk through storms, and journey into the unknown. The path of the heart is filled with risk, uncertainty, and danger. But I think the heart has true vision where the mind is blind. And following the seemingly reckless and dangerous impulses of our heart may a more sure path to the fulfillment of our dreams than the safe and seemingly clear path built by our minds.

This Appalachian Trail journey is a test. A test of resolve. A test of heart. A test of mental and physical toughness. And a test of my new hypothesis.

The hypothesis: The surest path to happiness is to follow your heart.

What’s the end goal? Why hike the AT? Or build a business? Why exercise? Why do we want the things we want in life?

We’re all searching. Searching for feelings. Searching for happiness. Searching for meaning. I’m searching for LIFE. I want to feel ALIVE.

I’ve mostly taken the safe path. I attended college because that’s what you’re “supposed” to do. I graduated with an accounting degree because I wanted a safe career.

I made those decisions because at the time that’s what I thought would bring me happiness. Take the accounting degree. I pursued the degree because I thought that a steady pay-check and secure job would then let me relax and enjoy life. Hah. I wish someone would have told me at the time that accountants have one of the highest suicide rates of any profession.

“If you do what you’ve always done, you’ll get what you’ve always gotten.” – Tony Robbins

I need a fundamental change in how I make decisions. It’s now clear to me that safety and security do not bring happiness. A good career and a steady paycheck does not automatically equal contentment. It’s time to take the road less traveled.

It’s time for adventure!

Sure this hike is full of risk and uncertainty. But then so is life. Our ideas of security are just that – ideas. Fantasy. Make-believe. The reality is that all of life is uncertain. That at any moment we could be struck by illness, accident, or a CPA job. We are not guaranteed anything. Not one single moment.

And I think there’s real freedom in that idea. We are all destined to die. Nothing we do will last, or matter. So then really – there are no consequences. No people to please. No status to maintain. No assets to protect. Because with time all of those things lose their meaning completely.

If you want to wander the desert… wander the desert! Take up piano. “Waste” your time on video games! Drop those awful needy clients. In the end – It. Doesn’t. Matter.

Live your life. The only guarantee we have is that if we keep putting off to tomorrow what your heart wants today then one day it will be too late. One day it will be too late and you will die, surrounded by things that you don’t need, full of regret for the dreams that never were.

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