On August 21st I had the unique privilege of skydiving during the total eclipse in Wyoming. Being under a parachute at 11,000 feet in the middle of a total eclipse is something only a few people on this planet have experienced, and it was the most awe-inspiring and spectacular experience of my life to date. I have applied many of the lessons I learned from skydiving directly to business, with great success. Below are a few of those lessons:

Do not let fear keep you from moving forward.

I know this sounds so cliché, but skydiving has taught me that everything you want in life lies on the other side of a wall of fear. When I was first learning how to skydive, over a decade ago, my main parachute malfunctioned. It was my 13th jump. I opened my reserve and landed without incident. Once I was safely on the ground, I was overwhelmed with a level of fear I had never experienced before in my life. I knew I needed to jump again, as soon as possible, or I would never get back on the horse. On our climb to altitude for the next jump, my heart was beating so hard I felt like it was going to come out of my throat. I couldn’t formulate words. My knees didn’t work. I literally had to crawl over to the exit and roll out the door. Once I was out of the plane, I immediately went into a normal skydive and the fear went away. I landed without incident. It was a very real turning point for me in my life. I learned that you can be scared to death, and move forward toward your dreams and goals anyway. If had let fear hold me back, I would have never experienced the most amazing moment of my life by jumping during the total eclipse. I applied that same lesson of fear when I started my business. I was so scared. Scared of the unknown; scared of failing; scared of losing everything. When I stepped out on my own, I kept going back to what I learned about fear on that skydive. I used that lesson to move through the wall of fear, and found happiness and success on the other side. Everyone’s tolerance for risk is different. I have found that you should never let fear prevent you from taking risks in business or your career.

If you wait until everything is “perfect”, you’ll miss the opportunity for the incredible.

Before our eclipse jump, I was extremely nervous. Even though I had been building my skill set for years, there were still so many unknowns. There were an extra 900 aircraft per hour in the air for the eclipse. We had three planes full of skydivers that would all be jumping at the same time (more than I had ever experienced). It was going to get dark, but we didn’t know how dark. The eclipse was going to cause the temperature to drop as much as 20 degrees on the ground (which could equate to a 60-degree temperature drop at altitude), which makes your canopy fly much differently (in addition to making your fingertips go numb). We heard the winds could drop during the eclipse, but no one really knew if they would increase, decrease or stay the same. We were landing in a completely unfamiliar place that had never seen skydivers before. It was far from perfect. However, if you wait for it to be perfect, you’ll miss a once in a lifetime opportunity. The same goes for business. It will never be “perfect”, but when a once in a lifetime opportunity comes along you have to seize it. When I started my business, it was far from perfect timing, but I knew it was now or never. So, I seized the opportunity, took the jump, and never looked back. Business and your career advancement will never present you with a great opportunity at the right time. In fact, I’ve learned that incredible opportunities usually come at the most inconvenient times (but they don’t come twice). When you take one of those unique opportunities, accept that you won’t know all the answers when you start. You just have to trust yourself, and trust that you have built the skills you need to allow you to figure out the answers when the time comes. In skydiving and in business, don’t miss out on an amazing opportunity because it’s not “perfect.”

Trust the people around you, even when they make mistakes.

When my parachute failed on my 13th skydive, I then did my 14th jump and learned how to move through fear. At this point in my skydiving training, I didn’t know how to pack my own parachute. After my 14th jump, I went over to the parachute packer who packed the canopy that malfunctioned on my 13th jump…and I asked him to pack my parachute for me. Another parachute packer asked me, point blank, if I was crazy. I looked at her and said “do you really think he’s going to make that mistake again?” She understood. There was no way he was going to let that happen to me again. He was a good person, with the right skills, who made an honest mistake. I knew that was going to be a perfect parachute pack job (and it was). I’ve applied that same lesson to business. Your people, as good as they are, will make honest mistakes. When they do, you don’t have to remind them of the mistake. They know. Instead, use it as a learning opportunity to make them better, build trust, and make sure it doesn’t happen again.

Only surround yourself with good people that you trust completely.

In skydiving, as in everything in life, there are different types of people. If you want to have a long and safe skydiving career, it is very important to surround yourself with others who are safe and who you trust, and trust completely. At one of my old drop zones, there was one person I knew was extremely unsafe. I wouldn’t even get on the same plane with him. I’ve applied this lesson directly to business; if you even have to ask yourself if this is someone you would trust your life with on a skydive, then you shouldn’t do business with them. My team and I have walked away from some potentially lucrative deals, because we all knew the person wasn’t trustworthy on the other side. I have seen some of my closest fellow entrepreneurs lose everything because of the actions of one or two people who were close to them. In hindsight, they said they knew something was off, but they didn’t listen to that little voice in the back of their head. As a result of the actions of a few select people at critical points, their businesses failed. In skydiving, the actions of a few select individuals can be catastrophic. If your gut is telling you something is off, listen to it and, most importantly, act.

Have accurate, verified data and reporting.

As you progress in skydiving, you have to demonstrate more advanced skills. One of those is the ability to skydive and land safely at night. Night jumps are completely different than jumping during the day. The lights on the ground don’t provide a point of reference for your altitude. Your brain starts to think you’re too low (even though you are not), and tells you to open your parachute. During night jumps, you wear a glow-in-the dark wrist-mounted altimeter. As a back-up to the wrist altimeter, you also have two audible altimeters in your helmet. These audible altimeters beep in your ear at certain preset altitudes. There are two audible altimeters, in case one fails. There are back-ups for the back-ups. When you skydive at night, you are completely dependent upon your instruments and the data they provide. You have to learn how to trust that data. In business, as in skydiving at night, it is crucial that you have good data to make the right decisions at the right time. Without good information, you have no point of reference and you are just falling through the dark sky without any idea of what you need to do. In business, as in skydiving, spend the money on good reporting tools. Be able to verify your numbers, and trust the data to make the right decisions at the right time.

Learn from the mistakes of others.

I have lost some people that I cared about very deeply due to skydiving. It’s an unfortunate and real part of the sport. Whenever something goes wrong in our sport, it is thoroughly investigated by the FAA (the regulating body for skydiving). The reports are published in the monthly skydiving magazine that every jumper in the US receives. These “incident reports” are studied thoroughly. We use them to learn from the mistakes made by others, so we can avoid those same mistakes. Often, it is the same mistakes made again and again, that cause us to lose a friend in skydiving. In business, I have seen several of my fellow small business owners fail. As in skydiving, it seems to happen because of repeated mistakes (overestimating demand, underestimating resource requirements, poor financial controls, etc.). Everyone writes books about what you need to do to succeed in business, but success isn’t just about doing what is right. It’s also about making sure you don’t make a big mistake. Just as losing friends is an unfortunate part of skydiving, seeing your friends lose everything as their businesses fail is also part of being an entrepreneur. The biggest difference is that I can still hug my friends who lost their businesses. I can’t hug my friends who made big mistakes in skydiving (I wish I could…every damn day). Study the mistakes of others, so you know what to avoid.

Get up. You will get knocked down. Get up. Dust yourself off, and do it again.

On one of my jumps several years ago, I didn’t take my own advice. I didn’t learn from the mistakes of others. As a result, I hurt myself very badly and required several months of surgery and rehab to learn how to walk again. When I was learning how to walk again, I remember feeling sorry for myself. One day I could walk, then next day I couldn’t. “How could this happen to me?” “I’m a good person, why me?” etc. Then, one day, someone close to me looked me right in the eye and said “You’ve never felt sorry for yourself ever before, so why are you doing it now? You can either keep crying about what happened, or you can do what you need to do to get better.” She was completely right. I immediately shifted my energy from feeling sorry for myself, to doing whatever I had to do to get better. I applied the lessons from those months of rehab and surgery directly to business. In business, if you go out on your own, there is a very high probability that you will get knocked down. When the IRS decides to audit you in your first year in business, and the resources you have to devote to the audit cause you to almost go out of business before you’re even up and running (cough cough). When you’re unable to sleep at night, because you realize you won’t be able to pay your rent if your client doesn’t pay on time (more coughing). When your credit cards are maxed out and they are shutting them down (still coughing…). When your savings accounts are drawn completely down (and…more coughing). When these things happen all at once during the startup phase of your business…that is when something will really go wrong. That’s when you will get knocked down. In business, as in a skydiving injury, you only have two choices. Feel sorry for yourself, or do whatever has to be done fix it. When I started my business, I remember the desperation and thinking that I couldn’t get through it. But then I remembered skydiving when I had to learn how to walk again. I remember telling myself that I got through that injury, so I could get through this. When things go wrong in business, don’t feel sorry for yourself. Accept where you are. Figure out what you need to do fix it. Then do it. If I had quit when I got hurt skydiving, I never would have experienced a total eclipse at 11,000 feet. If you quit when you get knocked down in business, you will never experience the happiness and success that comes on the other side. When you get knocked down, get up.

Surround yourself with influencers.

In skydiving, I had a choice between a few drop zones. One was a little less expensive, but I chose to jump at the drop zone that was better known. I chose this drop zone because they were involved in all the exciting events. Those who jump there are the ones who skydive into NFL games. They are the ones who fly American Flags into events. The best jumped there, and I wanted to jump with the best. As a result of being around that network of people, I put myself in position to be invited with a very select group of individuals to fly to Wyoming to skydive during the total eclipse. The same happens with business. You need to work your way into the right crowd of people; those who are connected and make things happen. Our company is currently based at a shared office space. There are plenty of them popping up everywhere. We chose our shared space because the people who started that space are very networked in the business community. Other shared office spaces are just buildings (even if they are cheaper). We set up our business in a way that placed us around the people that make things happen. Being around those people has had an enormouspositive impact on our business, that far outweighs any additional costs. These people have introduced our company to some of the biggest decision makers and influencers in our city, which has led to some incredible successes. In skydiving, and in business, keep putting yourself in positions and around people where the incredible can happen. It may not happen right away, but if you’re constantly in the right place, eventually it will happen.

You’re preparing for something big, even if you don’t know it.

In skydiving, I was building a skill set that came together perfectly for one spectacular moment. I didn’t know I was building towards something special, until all of the pieces came together for one perfect eclipse jump. I’ve learned that business is the same. All of the skills you have developed throughout your career will suddenly become incredibly useful, all at once. Even a skill that might seem mundane, like learning how to talk comfortably on the phone as a customer service rep, suddenly becomes incredibly important when you start your own sales business and need to make cold calls. Throughout your career, you are building skills. You will know when that once-in-a-lifetime opportunity comes along and puts all of your skills together at once.


Just like being given the opportunity to skydive during a total eclipse, when that once in a lifetime opportunity comes along in business or your career, you have two choices; stay on the ground or jump. If you jump, there are risks. It could go wrong. Or it could lead to the most incredible experience of your life. As I said before, everyone has different tolerance for risk. However, I would encourage you to push through your fear. Surround yourself with good people who you trust. Get the information you need to make the right decision. Learn from the mistakes of others. Keep putting yourself in positions where there are opportunities for success. Trust that you can figure out the unknown. Then, when life or business hands you that once in a lifetime opportunity, even if you’re not sure if you’re ready, don’t be afraid to jump.

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