Category Archives: Philosophy

Say you’re an ambitious person. You need to at once take seriously your aspiration for greatness and impact while also humbly laughing at the odds that your time on this planet will be very insignificant indeed. The smallest of dots on the map of human history, in fact. The task of reconciling these two opposing ideas I find a central struggle of the ambitious go-getter: without seriousness and without big dreams you will not fulfill your potential, without the broader perspective your seriousness becomes unbearable and you alienate others.

I meet young entrepreneurs all the time struggling with this. I’ve met teenagers convinced that intensity, relentless goal setting, and workaholism will lead them to the promised land. They have bet me with a stone-cold face that they will be president of the United States or the next Bill Gates. Part of me says, you go brother! But at times they display this ambition so nakedly that they turn me (and others) off. Their seriousness is suffocating. As any entrepreneur knows, you can’t do it alone — you gotta enlist the support and loyalty of others — so ignoring how you’re perceived is stupid. Likability matters.

I also meet student journalists searching for this middle ground. (I did when I ran my high school newspaper.)

The challenge of being a student journalist is that you want to stay away from well-covered national or international issues and focus on your niche (campus life), and you want to do so with a certain respectable seriousness as you’re trying to accumulate real journalistic experience. The problem is if you apply more than a modicum of seriousness to most campus issues the exercise goes from amusing to absurd pretty quickly. The trivial (how much is the party security budget? is vegetarian food served in the cafeteria?) gets transformed into matters of worldly importance. So you want to professionally tackle the reporting task at hand while also injecting your work with a healthy dose of awareness about the likely triviality of the entire enterprise. Which is why, in my view, the best student publications tend to be heavy on humor and satire and wit.

Bottom Line: Be serious about your brief time on the planet. Dream big. But also be self-mocking enough to dilute your earnestness to a level that makes you tolerable.

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Additional Note on Journalism: Since we’re on the topic. Cynicism is a cheap path to seriousness. I think this explains the negativity underlying most student journalism, a conviction that things at school are always getting worse not better and that exposing this decline somehow upholds a forsaken ideal as opposed to just feeding a throbbing self-obsession. Any student publication I’ve been a part of or observed thinks this way. Though maybe this tendency is built into journalism in general under the banner of keeping authorities accountable, not just student journalism…

Hat tip: Thanks Larissa MacFarquhar for inspiring the last sentence of the Bottom Line.

Business moves at the speed of trust. – Stephen Covey

Trust is one of the many things, it seems to me, that is best understood and appreciated by experiencing it in its failed state.

Ah, failure. Until you’ve failed as an entrepreneur, it’s hard to appreciate the entrepreneurial process. Until you’ve hired a wrong person, it’s hard to appreciate the importance of hiring the best. Until someone has been reckless with your heart or you with theirs, it’s hard to appreciate the criticalness of fidelity and honesty in romance. And so on. Like most cliches, “You learn more from a failed outcome than a successful one” reveals a terrifying truth.

Until someone has broken your trust, it’s hard to appreciate the essence of being trustworthy yourself to others.

When does trust break down? Sometimes trust is lost over time, a series of small divots adding up. But sometimes trust is lost in a flash: a single, meaningful lapse of judgment. What takes months and years to develop between people can be eroded in a matter of hours.

It’s not just the single lapse of judgment — say, the stressed CFO who unethically fudged the numbers the night before the earnings call, or the husband who had a one-night affair. The actions themselves cause some but not all of the damage.

What proves most damning in the end is the imagination of the injured: the retroactive (“Has employee Joe been fudging the numbers all along?”) and future suspicion of his activities and candor. Once this door of suspicion creaks open, it’s hard for it to close all the way and hard for trust to be established anew. (Though it’s not impossible — I have a couple relationships which have emerged stronger, in the end, after a rupture.)

I’ve let people down before. I’ve done things that have endangered the bond of trust I had with a person. What I’ve learned is that when I proactively and swiftly acknowledge that I fucked up, I can re-build the bond. When the other person finds out second-hand or if I shirk from responsibility for own actions, it’s much harder to repair.

Bottom Line: See the silver lining in failure. When someone breaks your trust, in the short term there’s pain and self-doubt about your own ability to size up character. In the long term there’s an opportunity to learn from the failure, deepen your own capacity be trusted and become wiser still in choosing who to trust in the future.

The best decision making tool I know of, and the framework within which I try to make most of my decisions, is the cost-benefit analysis.

The cost-benefit approach breaks down when you don’t have enough information to weigh all of the costs or benefits, or when the future costs or benefits are uncertain.

So my second framework is what I call “regret aversion.” My interest in the notion of regret started when I turned 18 and asked a few dozen adult friends what they regret not doing when they were 18. Interestingly, the #1 regret was not traveling more when they were younger. The regret question elicited an interesting set of responses and I followed up this idea with my post on asking questions in the negative.

Essentially, I have come to believe that many older people are haunted by the question “I wonder what would have happened if…” And that active 40 or 50 somethings regret not trying more things when they were younger. The regret can be as profound as “I regret not going to college” or as simple as “I wonder what would have happened had I mustered the courage to call that CEO I really respected and asked for help.”

While it’s no good being consumed with regret over a past you have no control over, it’s similarly no good to ignore the past and not try to learn from your decisions. Devoting an optimal amount of attention to the past is an elusive task indeed — I’m not convinced that complete detachment from the past is the best way to live. Most of the people I respect are reflective enough to have thought about their past and honest enough to harbor some regrets.

So, I regularly deploy the “regret aversion” rule of thumb: When in doubt, say yes. This will not eliminate regret from my life, nor is it a hard and fast rule (surely there are times when “No” is the right answer). But by doing more things, even relatively random things, if it doesn’t work out, at least I’ll know I tried (no “what if?”), and sometimes it actually does work out.

Let us remember in closing:

We regret the things we don’t do more than the things we do. – Mark Twain

I’m in the (freezing) midwest this week to keynote a couple of events and see friends. During Q&A someone asked whether I feel confused about what’s happening on the macro-economic and political front and how that affects how I plan for the future. Here’s the essence of what I tried to say:

I distrust anyone who says he can predict the future or anyone who is overly certain about anything. I am uncertain about most things that are going on around me — especially at a macro level, but also on a personal level, where almost daily some of my intuitions about what will happen get mugged by reality. I plan and think about the future a great deal, but no matter how much I plan, shit happens. As Mike Tyson once said, “Everybody has a plan until they get punched in the face.” I think we lie to ourselves about how in control we are. Chaos rules. Randomness rules. Emotions grip us. I’d like to think I posses a kind of inner calm that helps me make rational decisions day-to-day. I know I’m stable and confident (sometimes too confident) and, most of the time, relentlessly optimistic and happy. But I’d be lying if I said this amounted to a high degree of certainty about where the world is headed or even what in God’s name I’ll be doing in five years. I suppose I see the more enlightened among us as having achieved a certain comfortableness with uncertainty / confusion.

I would add that if you don’t regularly feel utterly confused, if you don’t occasionally feel like you’re treading just above water, if you don’t ever feel misunderstood, then you probably aren’t living in life — you’re just observing it.

The “living in life” concept comes from Joan Didion, whose quote to this effect I reproduce in the Introduction of my book. It’s from her UC Riverside commencement address:

I’m not telling you to make the world better, because I don’t think that progress is ncessarily part of the package, I’m just telling you to live in it. Not just to endure it, not just to suffer it, not just to pass through it, but to live in it. To look at it. To try to get the picture. To live recklessly. To take chances. To make your own work and take pride in it. To seize the moment. And if you ask me why you should bother to do that, I could tell you that the grave’s a fine and private place, but none I think do there embrace. Nor do they sing there, or write, or argue, or see the tidal bore on the Amazon, or touch their children. And that’s what there is to do and get it while you can and good luck at it.

The self-improvement industry rests on the proposition that with concerted effort you can become a better version of yourself and enact real change in your life. The cynic responds, “Oh come on, people don’t change! Go to your high school reunion — nobody’s changed.”

Both views are right. In some ways, a person will never change. Assholes at age 12 are usually assholes at age 30. Personality and core behavioral traits are largely heritable.

But in other important respects, people can absolutely change. Steven Pinker has suggested that if genes can explain 50% of complex human behavior, there’s another 50% attributable to a person’s “unique environment.” One’s environment is always changing — especially if you are young. Youth are more plastic, both biologically and in terms of their ever-evolving circumstances and adventures. Hence I never box in a person under age 30.

If I had to pick a side, I am on the side that people can and do change over a lifetime. This doesn’t always mean, in the face of dissatisfaction, I want to wait for it to happen — any entrepreneur will tell you, “Hire the right person on day 1, don’t try to change a person to fit the job.” True. But there are other times when investing in someone’s life as they evolve, grow, mature, age, can be enormously fulfilling. For example, it’s fascinating to see someone endure adverse conditions and as a result become more resilient, or sympathetic, or hardened, etc. There are also countless extraordinary examples of people who have turned their life around when it seemed they were stuck in the depths of misery (drug addiction, for example). This reason alone should force us all to be open to the possibility of someone changing in big or small ways.

We’ve heard a lot from Obama about America striving to become “a more perfect union.” I also think that within each person lies a capacity to better himself. This struggle to remake ourselves, to adapt to changing conditions, to develop new interests, to soften our edges and strengthen our cores, is a beautiful and uniquely human thing.

Bottom Line: Believing “people don’t change” simplifies the world but ultimately can sell short the experience of living even a basic life. The collision of one’s natural impulses with the dynamic, chaotic, unpredictable world of events can produce, in a lifetime, meaningful emotional, physical, and intellectual change.