Before I went all-in on my first startup experience, I had the unique pleasure of selling access to Warren Buffett's fleet of private jets. My mid-20s were spent cold calling billionaires, celebrities, and athletes and every now and then, closing a deal that helped them avoid the TSA and arrive at their destination in style. It was an incredible job with some amazing perks, and in the process I learned a lot.
I didn't just casually observe how the wealthiest people in the world lived, I studied them and learned how they lived. I learned from my clients how they managed their finances, families, and business holdings. I learned from their teams of assistants and advisors how they delegated responsibilities and how they handled all of the numerous demands on their time. I learned how they were able to move multiple endeavors forward simultaneously and ensure they didn't succeed in one only to fail in another.
But one of the best lessons I ever learned while working in the private aviation industry was from my boss, John Daut. He told me that the most important thing I could learn from my clientele was how they defined wealth. Their definition of wealth was not about the amount of money they had in their bank accounts or the toys and material possessions they'd purchased. Their definition of wealth was that of increased options: whoever has the most options has the most wealth.
That is what we sold--optionality. The option to have a private jet on any runway in fewer than 8 hours. The option to be at dinner one night and decide to play golf the next morning with your son on the other side of the country. The option to take your four dogs with you in the cabin of the plane on your way to Mexico. Options to do what you wanted because you'd worked hard to earn them.
From that moment forward, I thought about my career and my "wealth" completely differently. Since that moment, whenever I've been faced with a decision, my first question is this: will I have more options or fewer options if I say yes to this? Am I increasing or decreasing my optionality?
The more I've developed this mindset, the more applicable it has become to me and to how I connect with others. At all stages of life, I've found it to be relevant. Senior in high school: the most acceptance letters to college means you have optionality wealth. Senior in college: the most job offers means you have optionality wealth. Two years into your first job: the most people recruiting you away means you have optionality wealth.
This line of thinking has served me well over the past decade. But I believe this line of thinking is going to serve me and anyone who owns it even more in the next decade because this line of thinking is at the core of the Creative Economy that is emerging faster than ever. The idea that you will be at the same job, using the same core skills five years from now is no longer the expectation. Everyone is going to be required to adapt and improve their creative skills to evolve in the world technology is changing.
I had the chance to see CNBC's Andrew Ross Sorkin interview AOL co-founder Steve Case about his new book The Third Wave. In the interview, Mr. Case explained that the over 30% of the American work force is now freelance and that number is only going to continue to grow in response to what he's labeled as the Third Wave of technology in our lives. As more and more systems and industries are disrupted and overhauled, more and more of our lives will be as well. I believe that developing the skills and the mindset of adaptability and optionality is the only way forward in the future of this Third Wave and the Creative Economy.
If you are not currently looking for ways to enhance or grow the capacity of your career, no matter what stage of life you are in, you will be left behind.
Think of it this way: the more skills you have, the more options. Whether artificial intelligence wipes out the industry you've been working in, or you simply get bored and want a change, the more diverse your capabilities, the more possibilities you can explore without giving up the core components of your lifestyle. Even if that lifestyle one day includes access to Warren Buffett's private jets.