Jab Till It Hurts - Chapter 8: The Unintentional Pilot

I started this book with a question: Have you ever flown an airplane? About that question...

For many years, I joked that if I wrote a book, it would be called The Unintentional Pilot, the story about how I overcame my fear of flying. Entrepreneurship often comes with a nice big side of fear, regardless of when in life you start your business, so it’s worthwhile to address it here. What are you afraid of? What are you doing to overcome it?

Before I dealt with my fear, flying was a big problem for me. For many years of my life, getting on an airplane was the single most horrifying thing I could do. I would have panic attacks, arrhythmias because I was so freaked out. I would have to take Valium, Vicodin, or something to be able to actually board. My hands would sweat. I would sit in silence on the airplane, I was just a terrified passenger. My heart was racing the entire time; I wouldn’t eat or drink, let alone move out of my seat. It was debilitating.

Back when I was a creative director in the broadcast world, I was working with a great talk show host Preston Westmoreland. He came in one day and said, “Spanky, I gotta take you up in the plane, go up for a flight, to get over this fear you have. Because once you get up there, it’s great.” He and his wife Nancy spent all of their free time flying. They would do fly-in camping where they would fly to these fields in the middle of nowhere, and the lifestyle seemed like so much fun. But I would never do it, because the thought of getting in a plane that small? I already have problems getting into a commercial jet. No way.

Reluctantly, I agreed and we set up a date.

I felt if I could just go up in the plane once, maybe that would get me over my fear. I got in the plane, we took off, and I was holding on for dear life, I was white knuckling it. This thing had seats, it had power. It was a Piper Saratoga. The airplane was named the Christine 2, after the Stephen King book. So, great, I’m now in a possessed airplane. There was room for six, it was comfortable, but I was green and sweaty immediately. All of the things that raced through my head in a commercial jet were now racing through my head, and here I am sitting only six feet away from the propeller. I’m watching the controls move right in front of me.

As we were flying toward the Superstition Mountains, Preston said, “Spanky, take the controls.”

I froze, but I eventually grabbed the controls. I was so nauseous and I could feel my heart beating in my throat. I could feel the sweat. As I’m talking about it, I can still feel it, I can still remember that pure terror. There was nothing worse.

I had the controls, and I started to porpoise the airplane. That’s what a lot of rookie pilots do—they correct a little too much, nose up, they correct a little too much, nose down. If you’re looking at from the side, it resembles a porpoise swimming.

I was green and struck with fear, exhausted from the mental fatigue. I handed Preston the controls and we got back down on the ground at Williams Gateway airport, and he looked at me and said, “To get over this fear of flying, Spanky, you need to get with an instructor and go for a couple of lessons and get over that fear.”

I said, “I have no intention of flying an airplane! Why the hell would I see an instructor?”

“It’s not about flying,” he said. “It’s about getting over that fear of crashing or of dying, or whatever. You gotta go.”

I discounted him, but a couple of days passed, and I realized my life was so limited by that fear of flying. There were so many places I wanted to go, and I had flown everywhere, but it took a lot to get me on a plane, and the night before I could never sleep.

So, I took his advice and ran with it. I found a flight school at Chandler Municipal Airport, and I made a phone call. This very nice gentleman, Butch Casdorph, answered the phone. He was retired from the Air Force and had just opened his flight school. I explained the situation and he said, “Okay, no problem.”

We scheduled the appointment, I went to the airport, and we get into this Cessna 172, which is a really small plane compared to Preston’s. I still remember the tail number: N734GY. We were ready to take off and he radioed the tower. We started rolling down the runway and off we went. We were up in the air and flew toward a practice area a few miles from the airport where there was no traffic.

As we flew, we chatted. I was in the left seat, the pilot seat.

He found out I was a creative marketing guy and said, “You know, I just opened my flight school and I could use some help with marketing.” He proposed a nice way we could both help each other. “I’ll help you get over your fear of flying, you help me with my marketing.” It turned into a really cool relationship because I was just paying for fuel. Engine time and instruction were on him. It was really nice that I fell into that. Everything happens for a reason.

He asked me what my biggest fear was regarding the airplane. I told him it was crashing, that the engine would die and so would I. So, he pulled the power to the throttle back. The propeller was just wind-milling. There was no thrust.

The plane started to descend, and I’m screaming like you would hear a little girl scream when she sees a scary movie. That’s me, as an adult, screaming at the top of my lungs.

The plane started to tilt nose down at a very gentle slope. We were in a controlled fall. Butch said, “Where could we put this thing down? Is there anything down there that looks like you could land the plane on it, should you need to in an emergency?” I looked down and saw a dirt strip.

“A runway is just a dirt road with lights,” he said. “Let me show you what this looks like.”

Pointing to a dial near the throttle he said “There’s this thing in a plane called a trim wheel.” He made a simple adjustment to the trim, dialed it in until our airspeed was 73 knots, and said, “I want you to take your hands off the controls for a second. Are we falling out of control?” We weren’t. We were just gliding, slowly making our way down to the ground.

All of a sudden, he was touching down on this farm field, he gave it fuel. Then he lifted the flaps and we took off again. You have to understand that, physically, I was nauseous again, but I survived that moment in time. That ended my fear of, If the engine fails, we’re going to crash.

Butch asked, “Did you have fun?” “Not a bit,” I answered.

We did a couple of these different maneuvers where I would tell him what I was afraid of, and he would do them—including a spinning descent. That ended my fear of crashing that way. When I got out of the plane, I literally kissed the ground like the Pope.

I started enjoying it and, with Butch’s help, I continued to fly. I wanted to get on a commercial airplane and not have a single ounce of terror overcome me. One day, in early September, we were doing some landings and takeoffs, and he said, “Next landing, take it in.” In other words, the instructor was telling me to solo: “You’ve got this.”

We landed and I took the plane to an area of the airport called the “run-up” area. Butch grabbed my log book, signed something in it and said, “Now give me five takeoffs and landings, and I’ll watch you from here. You don’t need me, you’ve got this.” The terror came back because now it was just me. He was telling me to take the airplane back up in the air and do this takeoff and landing sequence five times...by myself.

It was hard as shit, but I did my takeoffs and landings. When I landed the plane and met Butch on the tarmac, he was standing there with a pair of scissors. It’s common practice in aviation for your instructor to clip the lower back portion of your shirt off as a sign of their newfound confidence in your piloting abilities. Butch cut the back of my shirt off. I soloed that day and it felt so amazing.

I had taken something I was so terrified of and turned it into a win.

Then I flew what’s called a cross-country, at Butch’s urging. It was going to take me to Yuma, to Blythe, California to refuel and eat a crappy lunch, then back to Chandler. The day came and I did it. Air traffic control communicated with me; there was traffic coming in and they vectored me around it. Two minutes later, I saw a jet fly by me at lightning speed. I thought to myself, Wow, I didn’t panic!

Butch encouraged me to take the test and the check ride. So, I did it, and I became a pilot.

I never intended to become a pilot. I think sometimes people let their minds have so much control over what they do with their lives. My kids and I would fly to Sedona, I took some buddies for a guys’ weekend in Vegas. I took my family to Bisbee, Prescott, I would fly wherever I wanted to for breakfast with the kids. Fear turned to fun.

I got over my fear by pushing myself out of my comfort zone. You can overcome what you’re afraid of.

This is what it’s like when you step out on that edge, that edge of What the hell am I doing? It’s facing that same old fear that’s been holding you back. It’s irrational, it’s scary. But if you push yourself, you just might find that you’re piloting your own ship.

Let’s Talk about So-Called “Security”

Many people are terrified to walk away from their corporate jobs. One of the things they think is, “Well, I’ve got job security, I’ve been here a long time, and I’ve got health care and 401k...” But the reality is, no job is safe. None. Zero. I have had friends who work for companies, and all they talk about is what they do, how critical they are, and yet they’re not safe. I had one friend who was recently let go from a tech company he’d been with for 20 years. This was a guy who helped the company save millions and millions of dollars in their accounting, year after year, and yet was beached. You’re going to give up your health care immediately when that happens unless you want to pay their COBRA fees.

None of those are reasons to stay stuck in a job you hate. Health care is a necessity for all of us. Everybody needs medical care and health insurance to protect themselves should they fall ill. But the truth is, we have insurance options. Are they all great? No. In the U.S. we have a marketplace, you can go buy insurance if you need it. We have the ability to go to any health care provider and be seen. If we pay cash, great. I’m not advocating not having insurance, but don’t let something as simple as health insurance drive your decision making and keep you stuck in a place that you hate. Other countries have their insurance options, you’re not married to your employer. Because, at the end of the day, working at a job that you don’t like robs you of valuable years of doing your own thing, of being you, of finding happiness.

You can find health insurance and you can have your retirement plan roll into your own IRA or BizK. I’ve done it. All my 401k money from my corporate days is in my BizK. And, by the way, if you start your business practically and not fancy, you won’t spend your retirement money building your business. You shouldn’t do it. If you do that, I’m going to find you and beat the crap out of you because, in this day and age, it doesn’t take much to start a business. A smartphone, a Squarespace website and a few Facebook Groups are all you need to launch. You don’t have to dig into your savings to do this.

Shit, you don’t even need business cards. If you want business cards, create the design on Canva and download it to your phone. When someone asks you for your card, just send it to them digitally and share your contact information.

What if you didn’t take the chance? Will you be sitting there at the end of your life regretting that you didn’t believe enough in yourself? Regret is a horrible thing. I can’t imagine, at the end of my life, regretting that I didn’t try something, didn’t do something. That I didn’t step off the ledge and take that chance, not knowing what was in front of me. Just because you’re approaching retirement age doesn’t mean you need to approach everything like you’re frail. Approach it with gusto! Supercharge your retirement. Bring in more money than you’ve ever brought in before, in your life. The only regret you’ll have is that you didn’t do it sooner.

Overcoming Business Fears

You already read about how I overcame my fear of flying. The same rule applies to business. You put your head down and you hit the GO button.

But the fear that I have most is failing my family. What does that look like? It looks like not being able to feed my children, or not being able to provide for them a life that is better than what I had. Failing is letting them down and has nothing to do with me and has nothing to do with the business.

I have this deeply rooted need to be the Tarzan of my family. I am the hunter, I am the gatherer. It is my job to do that for them. After my first two children were born, my wife and I became foster parents. We went on to foster 19 children. Our three youngest were adopted by us. I have this deeply personal need to provide for all of my kids and to make sure that their needs are met. Failing, to me, is failing them. That’s my motivator every day, my driving factor. My family will never starve. My family will never want for the things they need to survive and live. For me, that’s the only thing I think about and worry about. It helps that I live practically. We don’t have debt; we have a house. We don’t live above our means.

Most people have fear over things they have no control over, or things they make up in their heads before they even take a chance on it. They’ll talk themselves out of even starting a business because they think “What if it fails? I’ve always wanted to do my photography business, but what if it fails?”

And? What if it fails? Then what?

Would you rather have the fear of failure, or would you rather have a failure? I’d rather have a failure— because that means I’m 0 for one and not 0 for 0. At least I tried. I did something. I stepped out of the comfort zone, I took a chance. I’ll gladly fail six times as long as I get up seven times.

That’s how you overcome those fears. It’s just like flying. Get into the cockpit and start to control it. The outcome is based solely on you and the decisions you make. It’s easy. Fear shouldn’t control you. It should be the motivator. It should be what makes you tick.

Key Points from Chapter 8

  • Be honest with yourself about your fears, and be willing to confront them head-on.

  • There’s no such thing as “job security.”

  • There are ways to secure health insurance and put together a workable retirement plan without a regular salaried job. Don’t let your attachment to your benefits stop you from starting a business.

  • Don’t let fear control you.

  • There’s no reason to spend a lot of money

    when you start your business. Be practical.

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Ken 'Spanky' MoskowitzJab Till It Hurts, Gary Vaynerchuk, Spanky Moskowitz, TYC, Best-Selling Author