The Scariest Day of My Life And How I Survived It

If I were to ask you what the scariest day of your life was, could you tell me? Take a moment to think about that.

If you were to ask me this same question, the answer might surprise you—because it happened on a day I thought would have been filled with pure joy.

It was a cold crisp December morning when I sailed out beneath the Golden Gate Bridge and turned south to embark on the journey of a lifetime. I had been planning my departure for years—I was going to sail around the world—something I had been dreaming of since I first stepped foot into a sailboat at age 13.

Why was that cold December day so frightening and not one of pure pleasure? Because that was the day I was leaving everything I had come to know as ‘my life,’ behind. Imagine with me what I felt as an inexperienced captain, with a crew of four inexperienced sailors looking to me for guidance, as we headed out to sea.

• I was sailing away from my career—in which I had spent 20 years building my reputation as an industry leader.
• I was leaving behind all future income from my career. I had enough money for a couple of years, and no plan beyond that.
• I was trading security for adventure. There would be no more local grocer knowing my name, and no car in the driveway.
• I was leaving my home and partner of 20 years, and the life we had built together. I didn’t know when or if I would ever see any of my friends or family again.
• I was leaving my identity as a successful executive with a stable life, to be an adventurer with an unpredictable future.

          I didn’t sleep much the night before our departure, and hopped out of my bunk at 5am. As we motored under the bridge at 7am, my throat was in my stomach, my heart was beating too fast, and I went back and forth between singing and crying. I was torn between priorities: from learning to use the navigation equipment to watching the land disappear behind us. My thoughts ranged from what we were going to have for dinner, to how much I already missed my partner. I thought perhaps I was crazy for leaving, and had lost my marbles. And I wondered if I could buy my car back from the bank. My mind was spinning. Maybe I was nuts, but I couldn’t help it. Once I had begun planning this journey, I was like a freight train careening down the tracks at unchecked speed. My passion to achieve my life-long dream of sailing around the world was so strong I was willing to sacrifice all in its pursuit.

          You will have scary moments in your life. You’ll wonder if you’re going in the right direction, and your confidence will be shaky at times. I’m living proof that if you stick to your convictions and stay focused, you will get through the scariest times of your life. I’m no different than you are. I’m just a regular guy—who really, really, wanted to sail around the world.

          So, how did I survive that day? Here are some specific takeaways you can use in your life. For starters, I was busy with a capital “B” and had so many tasks to do there was little time for reflection. There was so much to learn, so much I didn’t know, and I was consumed by the enormity of what I had begun. By immersing myself in the immediate responsibilities at hand, I was forced to focus on the present rather than the past or future.

          Was I afraid? Absolutely, but there wasn’t much time to be scared. Plus, fear, like all emotions is contagious, and I didn’t want to infect my crew. They needed reassurance that all was fine, so I gave it to them. And all was fine. My fears were unwarranted, but they did make me sharp and focused on the tasks at hand.

          Was I sad? Yes, I was so sad about leaving my partner, friends, family, and home that I almost turned the boat around. But that instinct to want the safe and known was countered by the excitement of new adventure. And I was feeling an enormous sense of satisfaction that I was finally going to make my dream come true.

          Was I nervous? Of course I was a bundle of nerves. I didn’t have the experience necessary for a voyage like this but if I had waited for that knowledge, I never would have left the dock. You don’t have to be an expert to try something; you can become an expert along the way. And since I was captain I figured I had better start acting like one; my nerves were overshadowed by my enthusiasm to be a good leader.

          More than anything, I not only survived, but thrived that day, and for the next six years and 40,000 nautical miles, because I was passionate about what I was doing. Passion drove me. Passion was my source of energy: my push, and my pull.

It surely would have been easier to remain at home with my good secure life and part of me ached to stay put. But I never would have experienced six incredible years of sailing adventure, completed a circumnavigation, or written my best selling book, The Boy Behind the Gate. I never would have become a motivational speaker, or a life coach. I would have missed out on an entirely new life.

Now, what about you? What fear is holding you back from the life you want? What past are you wrestling to let go of? What nerves are preventing you from moving forward? What imaginary future is preventing you from focusing on the present? Are you living a life filled with passion? Are you passionate in your speech, actions, beliefs, and engagement with others? Live with gusto, and allow passion to be a priority in all aspects of your life. Passion will guide you through any obstacles between you and the life you dream of living. Let passion rule, and you can survive any day.