The Solitude of Being An Entrepreneur

Spencer Sheinin, CPA, CA
The Startup
Published in
9 min readMar 6, 2020

And Then the Float Plane Took Off

Everyone got a little more serious.

We had just been dropped off by a float plane in Buckley Lake in Mt. Edziza Provincial Park with the intention of getting picked up a week later, also by float plane, in Mowdade lake, some 80 km across the park. It’s about as far Northwest as you can be in British Columbia before you’re standing in either Alaska or the Yukon.

Mt. Edziza itself is a dormant volcano, almost 2,800 meters high (over 9,000 feet) surrounded by another 30 or so other cinder cones within the park (some extinct, some not) including the picture perfect Eve cone (pictured below) and Coffee and Cocoa craters.

The author in front of Eve Cone circa 2002. Photo credit: Kent Alekson

Starting at Buckley lake, our plan (“our” being me and my friends Kent Alekson, Mike Sileaka and Mike Walkinshaw) was to hike up to the Edziza Plateau (Day 1), work our way across the plateau to the base of Mt. Edziza (days 2–3), base camp and, weather dependent, summit Edziza (days 4–5), and then continue the last couple of days back down off the plateau to Mowdade lake where we’d be picked up by the same pilot (days 6–7). Combined, the four of us already had a reasonable amount back country experience, having done lots of week-long backpacking, back country skiing and paddle trips both together and individually.

We’d come well prepared with ample food, a stove and fuel, water purification filters, warm clothes, all the necessary camping gear, bear spray and bear bangers (a small charge that, when fired, sounds like a gunshot to scare away bears), first aid kit and the requisite amount of scotch (read: way too much). When the float plane landed and drifted up to the shoreline, there was the typical flurry of activity, unloading our gear and rescuing the fuel and bear spray stowed in the pontoon for safe keeping during flight. We were laughing and joking as we always do (mostly in the form of sarcastic insults at the size of each others manhood) and waved goodbye to the pilot before he took off.

“See you in a week” he said. With that, he took off. We stood quietly watching him go. The sound of the engine fading into the complete silence that is only ever truly experienced in the back country. It’s not until the complete absence of noise is it apparent just how much noise we experience in our daily lives. The biggest difference for me isn’t even the lack of traffic, restaurant bustle or other day to day noise in a city. It’s actually the lack of electrical buzz. It’s generally imperceptible when you’re in it. Really not even noticeable. For most people, the only time when that kind of silence is felt is during a power out (one of my favourite moments!!). There’s a remarkable peace that can be felt during a power out. The absence of that low hum of the countless digital devices, lights and wires running to our electronics all throughout the house. It’s more of a buzz than a sound. Yes, you can hear it. But even more so, you can feel it. Or, more likely, the absence of it when it’s not there.

When the plane’s engine sound finally faded out, that serene, silent, peaceful (lack of electric buzz) was in full effect. Occasionally, we heard a gust of wind. Maybe a trickle of water from the tiny ripples in the water washing up on the bank of Buckley Lake. Otherwise, pure glorious silence.

And that’s when things got a little more serious.

As I said before, we’d all done lots of back country trips before. That wasn’t unique. The big difference is for the first time we flew, rather than drove, to the start of our hike. In previous trips, we’d drive to the trailhead, pack our gear and head off into the bush. Usually, our trips are about a week and often are a loop or point to point. We either shuttle cars to the ending point, or send an emissary after were done to hitchhike back to our starting point to collect the car (said emissary is either the person who looks most presentable after a week in the bush, or Mike Sileika. That guy can talk to anyone!). The point is, doing a week-long loop or point to point, we’re at most 3 days hiking to civilization, or at least the car, and a relatively short drive to the nearest town. An in an emergency, one of us could likely get back to the car, and help, in a single big daylong push.

This was very different.

Mt Edziza is a very rarely visited park. So rarely visited, in fact, there are no trails in the park. It’s all just route finding, with some help from the occasional cairn (man-made pile of rocks) dotted along the plateau. We knew that before we arrived. We planned it that way. Our favourite trips are those where we don’t see anyone else during our time in the back country and we had high hopes this wouldn’t disappoint (and it didn’t. We didn’t see anyone else during our trip).

So why the seriousness all of the sudden?

For the first time in my (our) life (lives), I (we) felt entirely alone. Sure, there were three other people with me. All of whom I trusted and felt comfortable with in the back country. But collectively we were completely alone. We were all used to not having cell coverage or contact with the outside world during our trips, but we were always within one (or at worst) two days of help if we needed it. If we miscalculated our food, we’d go hungry for a day or two. So be it. Our biggest fear wasn’t bears (as most people seem to think it would be), it was usually running out of booze, which always required careful rationing to manage.

This time, we were several days from help. If something went wrong, we were entirely on our own. If the plane didn’t show up for some reason (when we got dropped off, we had a three hour weather delay due to low cloud. It’s conceivable that weather could also stop the plane from flying in to pick us back up), we were on our own. If someone got hurt, we were on our own. If we forgot a critical piece of gear, we were on our own. If we ran out of food, we were on our own. I could go on, but you get it, we were on our own.

Nobody had to say anything. We all felt it at the exact same moment. We stood silent for a moment, taking it all in. Experiencing the silence and the vulnerability of being completely reliant on ourselves for the first time in our collective lives. After a couple minutes, someone finally said “Well, I guess we should start hiking”. With that, we heaved our ridiculously heavy packs on our backs and started hiking.

It’s amazing to think how far removed we are from the sensation of true aloneness and self sufficiency. Have you ever really felt that way? I don’t mean feeling lonely after a tough break-up or moving to a new city where you don’t know anyone and Netflix is your best friend for a while. I mean being several days from civilization and 100% responsible for your own safety and well being. I mean really being alone (even if with other humans around).

The closest I’ve come to that totally alone and vulnerable is usually around 2am. Lying in my own bed. At home. Having an entrepreneurial melt down. A crisis of entrepreneurial confidence.

Loading up the float plane for the journey home.

It’s about as close to the exact opposite scenario to the back country isolation but amazingly results in pretty much the exact same feeling. At home, in bed, I’m completely safe. I’m in the middle of civilization. I have access to anything and everything I need and basically only a natural disaster would put me in any real harm’s way. I might be physical alone (whereas I was with three friends when the plane took off), but that’s not why I feel so isolated.

Despite a ridiculously supportive family, friends, employees, partners, senior executives, coaches, teachers, etc., in those moments of intense self doubt, I feel very lonely, just like when that plane took off. It’s not only when I’m in my bed alone at 2:00am. It sometimes happens to me in a crowded restaurant. It sometimes happens when I’m at work in a meeting. It sometimes happens in the hours leading up to giving a talk. It almost always happens when things aren’t going according to plan. In those moments, it feels like I’m days from safety (or, in some cases, forever away from the safety and security of a business living up to my vision). I’ve never been that prone to anxiety, but I suspect if feels very similar. A helpless spiral that seems impossible to break. Or, maybe it is anxiety?

Yet each time it happens, I make it though. The same way I picked up my backpack and started hiking until we got picked up a week later, I pick myself up and work through whatever the crisis du jour. I’ve since done other back country trips that were equally remote, and we didn’t see anyone else for the entire trip. Interestingly, I didn’t get that same vulnerable, alone feeling that I did in Edziza (blissful peace devoid of electric buzz, yes. That’s what keeps me coming back. But alone, vulnerable feeling, no). Success breeds confidence and having successfully and safely completed the Edziza trip, I was way more comfortable and confident in the truly remote wilderness. Of course, not so much so to get overly confident or arrogant. The remote back country still demands much respect.

Same goes with entrepreneurial crises. The good news is each time I work though it, the spiral is a little less intense. Each time I add another skill and or tool to handle the loneliness of being an entrepreneur.

As weird as it seems, it starts by making sure I’m not hungry. That’s totally #1. If I’m hungry, everything seems overwhelming. Something as simple a protein bar can snap me out of it (I’m in a bit of a keto phase right now. Don’t hate me). I’ve literally felt that what I was up against was impossible, recognized that feeling of overwhelm that I now associate with hunger, stop for lunch and have the issue solved within minutes of taking it back up again. Sometimes it’s that simple.

But sometimes is not and I can stuff myself and still feel lost. For those moments I’ve adopted other tools to help me through like re-framing the problem, getting curious about where this crisis will take me (“A crisis is a terrible thing to waste” — Paul Romer), journaling, working with my coach or starting with small tasks and working my way up. I’ve tried meditating, but that doesn’t seem to get me anywhere (not yet, but I haven’t given up on it). Exercises is critical, but for me, it’s more of an escape then part of a solution.

I won’t get into the various tools and mechanisms of dealing with the crisis of loneliness here because there are just too many options, I’m not an expert and everyone has to find their own path.

The point is each time I work through an entrepreneurial meltdown, I have a better toolkit to deal with the next one. Each one gets a little easier.

The last time I got dropped off by a float plane in a remote corner of British Columbia (which was last summer), it was pure bliss with none of the loneliness and seriousness of Edziza. Imagine how life would be as an entrepreneur if we could approach each “crisis” with a sense of excitement and bliss for where it will lead, rather than foreboding of what’s to come.

Some questions to ponder:

  • When do you feel most alone or most vulnerable?
  • What are the most effective tools you use to cope?
  • What tools don’t work for you?
  • What would life look like if you experienced those moments as unique moments of entrepreneurial solitude, rather than loneliness?

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Spencer Sheinin, CPA, CA
The Startup

Founder & CEO of Shift Financial Insights, Keynote Speaker, Best-Selling Author of Entreprenumbers — The Surprisingly Simple Path to Financial Clarity.