If you're excellent at what you do and the stars are in alignment, you will win. Of course, you may run out of time first, but, if you're excellent every day, you will have furthered your chances of beating the house as much as they ever can be. That should be your primary measure of success — excellence — not simply the spoils that come with good fortune. You don't want to entrust your satisfaction and sense of fulfillment to circumstances outside your control. Instead, base them on the quality of what you do and who you are, not the success of your business per se. Unless you understand what is truly outside your control, you are likely to make serious mistakes, misallocate resources, and waste time.
I ENCOURAGE PEOPLE to think about all the risks involved —personal risks as well as business risks. When I talk to candidates as part of recruiting outside management talent to the Valley, the issue of risk often comes up. Prospective managers usually fear that the venture won't be a blockbuster or, worse, that it will be forced to close its doors. Some recruits fixate on that business risk to the point of indecision. They strain to research all the facts, but at some point no additional information or assurances will offer them any further clues into the business's ultimate success or failure. Uncertain, they freeze and stay with the status quo, no matter how unsatisfying it is. After all, it's what they know.
But when I drill down, I inevitably find personal risks that need to be considered along with the business risks. Personal risks include the risk of working with people you don't respect; the risk of working for a company whose values are inconsistent with your own; the risk of compromising what's important; the risk of doing something you don't care about; and the risk of doing something that fails to express—or even contradicts — who you are. And then there is the most dangerous risk of all — the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.
Several years ago when I pondered the offer to join Apple, and I looked down that long corridor at my law firm, the answer was clear. I was not concerned with whether Apple's business would succeed or fail or whether my options would be valuable or not. What I had to weigh was whether I should remain on the well-defined path to professional and financial success as a lawyer or venture into a creative life in business, with no specific destination in mind. I was not hesitating because of business risk; I was wrestling with personal risk, a different game of chance in which we have far more control.
When I considered the risk of staying at my law firm, I had to face the possibility of an unfulfilled life, of working endlessly on things that did not matter and that at times violated my core values. I had to face subordinating my creativity in order to become a specialist, channeling myself too narrowly. To me these were graver risks than whether Apple succeeded or failed. Ultimately I chose to pursue what seemed most important to my life at the time.
In theory, the risk of business failure can be reduced to a number, the probability of failure multiplied by the cost of failure. Sure, this turns out to be a subjective analysis, but in the process your own attitudes toward financial risk and reward are revealed.
By contrast, personal risk usually defies quantification. It's a matter of values and priorities, an expression of who you are. “Playing it safe” may simply mean you do not weigh heavily the compromises inherent in the status quo. The financial rewards of the moment may fully compensate you for the loss of time and fulfillment. Or maybe you just don't think about it. On the other hand, if time and satisfaction are precious, truly priceless, you will find that the cost of business failure, so long as it does not put in peril the well-being of you or your family, pales in comparison with the personal risks of not trying to live the life you want today.
Considering personal risk forces us to define personal success. We may well discover that the business failure we avoid and the business success we strive for do not lead us to personal success at all. Most of us have inherited notions of “success” from someone else or have arrived at these notions by facing a seemingly endless line of hurdles extending from grade school through college and into our careers. We constantly judge ourselves against criteria that others have set and rank ourselves against others in their game. Personal goals, on the other hand, leave us on our own, without this habit of useless measurement and comparison.
Only the Whole Life Plan leads to personal success. It has the greatest chance of providing satisfaction and contentment that one can take to the grave, tomorrow. In the Deferred Life Plan there will always be another prize to covet, another distraction, a new hunger to sate. You will forever come up short.
Work hard, work passionately, but apply your most precious asset—time—to what is most meaningful to you. What are you willing to do for the rest of your life? does not mean, literally, what will you do for the rest of your life? That question would be absurd, given the inevitability of change. No, what the question really asks is, if your life were to end suddenly and unexpectedly tomorrow, would you be able to say you've been doing what you truly care about today? What would you be willing to do for the rest of your life? What would it take to do it right now?
On this hilltop I look left toward the Pacific Ocean, across the sloping fields where artichokes and poppies grow, where cattle and horses graze. This is rustic, rancher country. And to the right—all the frantic splendor of the Valley, a teeming maze of highways, bumper-to-bumper traffic, and business parks. Speculators, the Lennys of the world, still keep coming to this small patch of land, this boomtown settlement, and pay astronomical real estate prices for a chance to work their stake. Like the forty-niners 150 years ago, most will leave empty-handed. But some, a few, will amass fortunes and become the leaders of the New. This is a Valley of optimists.
Me, I like being on this ridge, one foot in both camps, one whole from two very different but equally compelling pieces.
In school I belonged to no particular clique, hanging out with a group of people both brilliant and crazy. These peripheral people were highly talented, with off-beat passions, like performing autopsies on busted televisions and computers, building telescopes, practicing ventriloquism, or painting watercolors of dissected animals. Wrapped in their passions, they stood outside the mainstream. I loved their talent and innovation, and I acted like a bridge, connecting them to everything else.
Now I work with inventors, entrepreneurs, and others highly skilled in their own right but not necessarily capable of bringing their ideas to the commercial light of day or achieving the impact their ideas could and should have. This is the creative edge of business — startups, working with a blank canvas to challenge the status quo and make change happen. I work with brilliant entrepreneurs who have a vision for how things can be better and who can't resist doing the next great thing. I am their consigliere.
THE LAST TIME I was in Amsterdam I spent an afternoon in the Rijksmuseum studying the Vermeers and Rembrandts. Rembrandt's The Night Watch particularly impressed me. Like many of the Dutch Masters, he painted it on commission for a group of well-heeled patrons. The work portrayed a dozen or so elaborately attired commissioners, reliving the past glory of their civic militia, arrayed according to their financial contribution and status. These were some of the many movers and shakers of Holland's economic Golden Age, affluent and prominent, seeking immortality on canvas. But I was struck that I didn't know any of them, nor did it matter. They were just characters in another man's masterpiece. The only person of importance, the only one whose fame had lasted beyond that period, was the eventually penniless artist— Rembrandt.