Ten Crucial Entrepreneurial Lessons I Learned Skydiving

I jumped out of a plane.

When my daughter turned 21 my husband and I wanted to give her an adventure for her birthday. She’s always wanted to go skydiving so it seemed like the right thing.

I have never had any desire to jump out of plane. Skydiving wasn’t even close to being on my bucket list. But then Paul decided that if Sammi was going to go, he would like to jump too. I was sure I’d be happy cheering them on from the ground.

I’m not quite sure how or why, but one day I found myself sending this text message to Paul and Sammi.  

As you can tell from their reactions, my text wasn’t what either of them expected.

Guess what I found out? You learn as much about yourself on the journey to 10,000 feet as you do on the way down and it has the potential to impact every aspect of my business and my life.

Here are key lessons I learned:

1. Be careful who you let into your inner circle. I was scared to go skydiving. I also knew that many people would rightfully tell me that jumping out of a perfectly good plane 10,000 feet above the ground is stupid. Some people would have tried to protect me, some would have told me that skydiving terrified them and wished me well, others would have cheered me on. I decided not to trust anybody. I didn’t tell my Mom, friends, or clients. I told one of my sons the day before we went, only because he was home. I was scared enough for everyone, I didn’t need any help with that. And besides that, I knew that someone else telling me how wonderful it was for them or that I would be okay wouldn’t have helped me.

In your business it’s the same. It’s risky to be in business for yourself. You need to put yourself out there every day, it’s called marketing, but when you’re trying to figure out a new idea, or you’re working hard to do something new, be careful who you let into your inner sphere. Even though people may care about you, it’s vital that you protect yourself. Pay attention to what you need and put up whatever walls you need to in order to keep yourself safe. Don’t let other people’s opinions sway you or scare you away from your goal.

2. Be open to new experiences… don’t sit on the sidelines or you’ll hate yourself later. I was going to watch Sammi and Paul skydive. Skydiving was Sammi’s dream and Paul  wanted to go. It had never occurred to me to go. Then I realized I had an opportunity. There was no reason to say no. I decided to take advantage of the unexpected opportunity. And, if I am being totally honest, if I just watched I always would have wondered what it would have been like and been angry with myself for not doing it.

In business, opportunities present themselves everyday. Clearly you can’t do everything but be on the lookout for things that stretch you beyond your comfort zone. Things that fit within what you’re doing and help you take yourself and your business to a new level. Ask yourself how you would feel in the long run if you pass up the opportunity.

3. Capture the moment and ask for what you need. I decided that if I was going to skydive, I wanted to share it with everyone (after the fact!). I shot a short video before we left home and planned to shoot two more, one before we took off and the second right after. Then we were in the moment, suddenly we were heading to the plane. There was no time to grab my phone to get the second video. I started to say something and then said “Never mind”. Fortunately, the person who was going to jump with me asked me if I needed something. I said I wanted to shoot a video. Since we had paid for someone to video the jump he made sure to give me the time to do it.

In business and in life nobody other than you knows what’s important to you. Ask for what you need. Capture the moments that are important to you, they will be gone before you know it.

4. Get help. Hire someone who’s done it before. Trust them. As it turns out the skydiving facility we went to is owned and operated by Don Kellner who holds the world’s record for most skydives with over 42,000 jumps (super cool side note, he was in the plane with me and jumped out shortly before I did which means that I was in a record making flight). I am sure that there are other well-qualified people who would have been just as good but it felt great knowing that Above the Poconos has a 100% safety track record.

Clearly, I couldn’t expect to jump out of a plane and survive the experience without expert help. I also made sure to listen to and follow every direction they gave me. It’s the same in business. Get help from an expert who has been there. They know what you need. They know how to help you make it happen. Trust the advice they give you. Don’t second-guess them; it’s why you hired them in the first place.

5. The three bite rule stands. When my kids were growing up we had a “three bite rule” at the dinner table. If there was something on their plate they weren’t sure of the rule was that they needed to take three bites before they could decide if they liked it or not. I jumped out of a plane. As we were driving home Sammi asked me what I thought. I realized I didn’t know. I wasn’t even sure if I remembered it. There were so many new experiences coming at me so quickly. So much to absorb. Before I can definitely say I like it, or I don’t, I would need to go again.

In business too, when you try things or take an unusual risk you are hit with so many sensations that it’s overwhelming. If you’re not really sure about something don’t give up after trying once. You’ll likely need to do it again or even two more times, before you can make a fair assessment

6. Stop the mind chatter. Just do it. The only reason I was able to stay sane during the month leading up to our jump is because I refused to think about it. I made myself ignore the fear. Not telling anyone I was going definitely helped. And I kept not thinking about it as we flew 10,000 feet above the ground. I just did what I was told to do. I followed directions and did not allow myself to scare myself out of the experience.

It’s so easy to think about all the things that can go wrong when you push yourself in your business. It’s time to stop. Stop thinking. Stop giving yourself excuses. Just do it.

7. Expect your legs to shake when you’re done. We free fell for about 30-seconds and then floated down for about 2-minutes once the parachute opened. When we landed I tried to walk. My legs were wobbly and my stomach was a bit queasy. I was back to normal quickly, within 30 seconds or so, but I had to give myself a bit of recovery time. I had just achieved a major accomplishment and my adrenaline was flowing. And during those few seconds I was forced to stop, take a breath and recognize what I had done.

Business is hard. It’s important that we recognize that after we finish things it’s normal to feel a bit funny inside. Stop, take it in, breathe and celebrate.

8. If you’re not scared you’re crazy. After our jump I spent a few minutes speaking with Don Kellner. He told me that even after over 42,000 jumps he is scared every time. He went on to say that if you’re not scared you’re crazy.

It’s true for our businesses too. We take risks every day. Some things are easier than others. The trick is to be scared and do it anyway. Trust in your experience, the experience of others and your equipment. You can do what seems to be impossible if you take the leap.

9. Our bodies give us many signals. It is up to our brain how we interpret them. Fear and excitement feels exactly the same in your body. It is up to you to choose which one you decide to feel. I was terrified of skydiving. I decided to be excited instead.

Look around at the things you can do in your business. The options and opportunities are all around you. What are you afraid to do? What would happen if you decided to be excited about it instead?

10. There is only one thing stopping you from doing anything…a decision. When we first decided to give Sammi the gift of skydiving I knew I would watch. Then in a single text message, written without letting myself think through the consequences, it all changed. I put it out there. I made a decision. I gave the thumbs up. I decided to do it.

There is nothing more powerful than a real decision. Making a decision is about more than thinking that something would be nice if something happened or that you’d like to do something. It’s about deciding that no matter what happens you will do whatever it takes to see that decision through and then doing it. I made a decision. I made it happen. What decision is it time for you to make in your business?

Looking back on what I’ve written I realize that I need to be on the lookout for things that push me more often. What do you need to push yourself on? Which of these lessons can you bring into your life and business? Share your thoughts in the comments section below.