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How to Get Comfortable Being Uncomfortable as an Entrepreneur


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I’m 47 years old. I still feel like I’m 21, but I now “enjoy” a host of aches and pains that have no discernible cause. I’m also moving towards needing reading glasses. And yet, for the first time in my life yesterday, I strapped on a snowboard and tried something completely new. Let me give you a little background.

Twenty-six years ago after college, I moved to Summit County, Colorado with my great friends Davin, Ted and Dan. We lived the quintessential ski bum lifestyle. And I was pretty good. Good enough to become a ski patroller at Keystone (full disclosure, I was still the worst skier of all my roommates). Good enough to ski basically anything in Colorado. I loved it, but after two years, I left for law school.

Fast-forward 24 years. I was an attorney living in Chicago when the pandemic hit. Crime skyrocketed. Chicago languished. So, my wife and I made the decision to pack our stuff and move back to Summit County, Colorado with our son. We’ve been here for almost two years now, and we ski every weekend in the winter.

Related: The Lasting Benefits of Getting Comfortable With Discomfort

The challenge

Several weekends during the ski season, we head out with our friends Connor and Laura. Laura is a skier (an outstanding one) and Connor is a snowboarder (a spectacular one). While Laura and I use the same medium, watching the speed and power that Connor can generate on snowboard is really impressive. To be honest, I never had a massive interest in snowboarding, but when you see someone who is really good, well, I couldn’t help but think: “I gotta try that.”

Now, let’s go back to the beginning. Once again, I’m 47 years old. Snowboarding is legendary for being crushingly hard on your wrists, back, butt, shoulders and knees when you’re starting out. So, when I mentioned I was thinking of trying it, the majority of my friends told me I had lost my mind.

Still, I couldn’t shake the interest, and I wanted (maybe needed) an excuse to give it a shot. Fortunately, my buddy Chuck and his family were headed out to visit us, so I asked him if he’d be up to go snowboarding for a day. His exact response was: “Always down for an adventure.”

So, one brisk morning in early March, Chuck and I got snowboards and headed over to the mountain. Did we take a lesson? Of course not. Too headstrong. And both being strong skiers, we figured “How hard can it be?”

Well, I won’t keep you in suspense. It’s hard. Really hard. The minute I clipped one foot in, I realized I could barely stand. As we sat in the lift line, I began to sweat profusely. I realized that for all the comfort I have on skis, I was basically helpless on a snowboard. But off we went.

Here are the results: (a) I didn’t get off a single chairlift without falling; (b) I couldn’t make a toe edge turn to save my life; (c) literally, I fell more in one day on a snowboard (probably 30-40 times) than I have in the past 30 years combined on skis; (d) on skis, I’m confident, really to the point of cocky. On this snowboard, “Paddington’s Easy Way Home” looked like K2; and (e) the next day, I assessed my injuries … two jammed thumbs, two sprained wrists and two severely bruised knees.

Related: Want to Be an Entrepreneur? Get Comfortable Being Uncomfortable.

The rewards and the application to entrepreneurship

So, you’re probably thinking it wasn’t a very successful day — the exact opposite. It was absolutely amazing, and I can’t wait to do it again. Here is why:

  • As you get older, there are very few things that you can do that are truly brand new and challenging. Particularly as an entrepreneur, your life becomes discomfort. The more you are able to thrive under those circumstances, the better.

  • Fear is not a weakness — it’s a strength if you decide to overcome it. Taking the leap into entrepreneurship necessarily entails fear. But if you never leap, you never fly. Embrace the fear, and take the leap.

  • Being humbled reminds you that you’re never as great as you think you are. We can all use a dose of humility now and again. As an entrepreneur, you are going to fail. Over and over and over again. And that’s okay. Failure teaches you. Learn from your failures and improve.

  • Your friends have both the power to inspire you to do new things and to join you on the ride. Both are an absolute gift. As an entrepreneur, you cannot accomplish your goals on your own. Create a great group of colleagues and friends. Let them inspire you. Lean on them for help. And enjoy the ride with them.

  • Pain is temporary, but self-improvement is not. When starting a business and running a business, you are probably going to experience metaphorical pains that will make you want to quit. It’s going to happen often. Pushing through those pains and marching forward is the only way to succeed. Remember, take one step forward each day, no matter how bad it may hurt, and eventually, you’ll reach your destination.

  • Lastly, being an entrepreneur means you NEED to get comfortable being uncomfortable. Life is full of routine, often to the point of monotony. When you jump outside the routine and truly get uncomfortable, you can be recharged in a way you never expected. Moreover, if discomfort isn’t your bag, starting a business may not be either.

Related: Why Getting Out of Your Comfort Zone Is the Best Thing You Can Do as an Entrepreneur

When I recover from this adventure, the first thing I will be doing is buying a snowboard and boots and going again. I’m sure it will hurt … again. I’m sure I will suck at it … again. I’m sure I will fall … again and again and again. But there is a new mountain to conquer. A new goal to achieve. And it will be very uncomfortable getting there — and I’m completely comfortable with that.

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