Taking Risks

This article is for my children. It will probably be ignored, as is most parental advice, but I need at least to do my part to communicate the power of taking risks in life.

How much you enjoy life is due to your comfort level with risk. If you live a life with the impossible notion of having zero risk, you may be happy but you won’t know how much happier you could have been if you explored new experiences with some risk attached. Risk is the opposite of comfort. If you feel comfortable at all times, the risks you’re taking aren’t stretching you—and everybody has different comfort levels. I’m very comfortable looking out a window of a jet flying at 40,000 feet, but put me on a 10-foot ladder that shakes a bit and I’m freaking out. Another person might think I’m crazy for boarding that plane, but cleaning the gutters on their house is no big deal.

The key is that fear can drive decisions. Decisions affect what happens in life and those experiences shape people. In my life, I have more regret over the times I played it safe than the times I took risks. When I started my first company, I was just 19 years old. To some it looked like a risky decision, but there was very little risk involved because I was a college kid, living with my parents and had relatively low expenses. I didn’t have anything to lose with this venture since it was bringing in more money than my illustrious job wrapping burritos at Taco Bell.

Looking back, the business I created was the safe route. My company wrote custom software for local businesses. We would agree on an amount for a project, sign a contract, and they would pay me 50 percent up front and the remainder on delivery. Incredibly low risk. A higher risk option would have been to sell my software in computer stores—the way apps were sold before the internet. Selling packaged software was tempting because I wouldn’t just get paid once like contract work, I’d get paid over and over again for that time I spent building it. This might have been a lucrative business, but I was too afraid that my software wouldn’t be good enough and, in addition to the months of unpaid coding time, there’d only be a handful of sales. The prospect of making little or no money for my effort was terrifying.

In hindsight, I can see how foolish I was to let fear drive my decisions. That was the Wild West of the personal computer industry, before Microsoft was a household name, and would have been the perfect time to take that risk. Instead, I let this time slip by and two years later was married, buying furniture, paying rent, and collecting stuff. It would take 25 years for me to realize that more stuff wasn’t the key to a happy life. Taking risks and challenging myself to step out of my comfort zone was the answer. When I finally summoned the courage to risk building and selling apps on my own, it opened a whole new world for me personally and professionally. Many of the friends I have today—and my current job at Apple—are a direct result of taking this risk.

Speaking of Apple, I had another opportunity to dramatically change my future during the second-coming of Steve Jobs. I had just sold all my shares from my most recent startup and was deciding whether to invest in AAPL stock or buy a bigger house. Our old house wasn’t tiny and we could easily have stayed there, but the short-term comfort of a bigger space was very appealing. The new place was very comfortable, but if I had used that $20,000 down payment to invest in AAPL at around $10 before several splits… well, let’s just say that I would have had my choice of any house I wanted today. I don’t allow myself to do the math anymore because it’s too depressing to see the cost of choosing comfort over risk. Additionally, buying the bigger house meant buying more stuff, which made it even harder to risk moving or expanding our universe.

No one can guarantee that a risky decision will turn out better than a safe one, but there is a theme in my life. Every time I allowed my fear of the unknown or the uncomfortable to guide my decisions, I delayed advancing my life. In each instance, I can recall my gut telling me to take the riskier path and my head talking me out of it. Some of my most daring moves—the “trusting-my-gut” moves—have been in the last 15 years. I was almost 40 before I really started seeing how many opportunities I lost because I didn’t want to be uncomfortable or fall hard due to a big failure. This means I took a lot of risks in my life when I had a lot more to lose—when the decisions to give up comforts and security are dramatically more difficult.

I wasted so much of my youth playing it safe.

So here’s my simple advice to you: Take as many risks in life as you can while you have less to lose.

You are young and single with more of a job than a career—you can afford to experiment. Focus on finding a position that offers learning and experience over income and stability. Grab the job that lets you travel and explore other cities around the country and the world. Rent a furnished apartment instead of anchoring yourself to bulky, expensive couches, tables, and chairs that have to move with you. Expand your horizons before your vision is blurred by familiar surroundings. Check out cities with diverse cultures, magnificent museums, exceptional landscapes, and opportunities to broaden your views.

What you understand today as fun and enjoyable is limited by what you have experienced. Your comfort is a trap that keeps you from seeing and fully experiencing this beautiful world. Exploring it on the internet is nowhere near the same. Also, being comfortable is highly overrated. Some of my fondest memories were the times when we had no plans and just decided to go on an adventure and see what would happen.

It took a few trips to London and Paris and a move to San Francisco after five decades of life for your mother and I to understand how cool it is to shake up things and try new experiences. Our world is bigger and better now and we’ve barely scratched the surface of what is out there culturally. My hope is that you don’t wait as long as we did to step out of your comfort zone. I never knew that I’d like so much of what I like now and never would have if I didn’t push myself to take risks throughout my life. My wish for you is that you surpass my accomplishments, and the best way to do that is to start embracing change now while you’re young and free.

The place (or person) that you love might be out there right now, but you’ll never know it if you don’t go for it. Stretch yourself. Find a bigger, deeper happiness than you could ever imagine having today. Make yourself uncomfortable. Take risks.

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