The Are No ‘Supposed-to’s, and Other Thoughts on How to Live

[Just realized that this, from my old blog circa March, 2010, was really my first annual commencement address, though I didn’t know it at the time. That puts my run at three.]

I love meeting people in transition: graduating students, travelers, career switchers. It is such a tense moment of life, crawling with uncertainty, opportunity, and risk – there is no better time for the type of conversation that shapes lives.

Here is what I like to tell people going through such transitions, and what I like to tell myself as I navigate the ceaseless transition of living.

First, there is no such thing as ‘supposed to.’ There is no predetermined path through life that we must divine; no secret map to fulfillment that, if missed, will leave us floundering. We have a profound freedom as human beings to assess the options presented to us, and to choose those we believe are best. Are we going to make mistakes and have false starts and change our minds? Of course! But what greater joy than to chart one’s own course, and what better map than our own constantly developing sense of purpose?

Second, as Westerners we face a challenge almost entirely unique in human history – an over-abundance of options. The typical college graduate is halted not by a lack of opportunity, but by a wave of it. Not that we all have our choice of highly-paid positions, but we can pursue almost any field or profession or interest we like, in almost any country in the world! And the kicker is, we never know which option is best. We can’t. We don’t get a trial run. The best we can do is apply all the experience and knowledge and sage advice that we have access to and dive in, and be ready to learn along the way.

Third, once you’ve chosen your pursuit, there are three principles to bring to it in order to maximize it. One, Commitment. Every successful pursuit I have seen has come from a deep commitment to that pursuit. If it’s not worth committing to, don’t do it. If it’s worth doing, commit. Two, Enthusiasm. Get excited and enjoy the ride! If you can’t have a little fun at it, it’s probably not for you. Three, Flexibility. This is the balance to Commitment. Remember, you didn’t get a practice run, and you made a decision with incomplete information. Don’t let one decision shape the rest of your life if you don’t want it to. Always be ready to learn and course-correct.

Fourth, failure is always an option. I’ve heard it said that if you want more success, increase your failure rate. I’ve personally set out on a good number of failed adventures, and learned a ton along the way. Of the several projects I currently have going, most will likely fail. And that’s fine! The point of it is the journey and the things you learn and the people you meet along the way. And if the end of a particular path is failure, that does not erase one experience or conversation or relationship you had in getting there.

Fifth, have a little whimsy. My friend Bob first introduced me to whimsy, and the idea is simple: just do some stuff. Have an idea? Do it, see what happens, don’t worry so much about the outcome. And when I looked at the people that I most admired I found that they all seemed to have some whimsy in them. They weren’t the ones sitting back doing cost-benefit analyses of each new idea, they were out doing stuff, with commitment, enthusiasm and flexibility, not bound by the outcome of each experiment, but enjoying every bit of the journey along the way.



  1. James, this is one of the best pieces of writing I’ve read in ages. There are several posts in here, and I will certainly come back to this.

    The whimsy bit is brilliant. I am learning to not take myself seriously. And I’m trying to quit living for the legacy. Just whimsy. Man, I really enjoy that.

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