Most of us, most often take the safer route, but we do it at a cost: “…our biggest regrets are not our actions but our inactions – the chances not taken.”

To explain the psychology of risk, I asked my college students yesterday to commit an hypothetical investment of $10,000, to either: an opportunity with a 5% probability of turning into $100,000, or one with an 80% chance of turning into $20,000. They could keep the difference, but had to give back the original $10,000.

10kThe choice I gave them was between a profoundly risky situation with a spectacular result, and one that carries a lot less risk but yields a less impressive return. If you flip it around and look at the risk side of the equation, they were weighing a 95% chance vs. a 20% chance of losing the initial $10,000.

In real life, we do this all the time. We choose between getting less than 1% interest on our savings with no risk to the principal and the possibility of earning five or ten times that annually in the stock market, the latter carrying the risk of losing our initial investment. We choose between taking the faster route to our destination on the interstate, with the likelihood (but not certainty on a busy weekend) we’ll get there faster, even knowing that taking the scenic route is more interesting and offers the chance of getting happily, temporarily lost. We choose a mate who might be easier to get along with over the firecracker who will drive us crazy (in both a good and bad way).


One of my students astutely observed that it’s where you are in life that determines the value and the meaning of the reward, because it directly influences how much risk we’re willing to tolerate. When I said they’d have to put up their own money, everyone was solidly in the 80% risk camp, but the same smart kid suggested this was because they are students and $10,000 is a lot of money at this point in their lives…and noted further that investors with a lot of money probably don’t see the world the same way. When I changed the equation to the possibility of getting a million dollars out of an initial investment of $100,000, several students moved over from the classes’ prior, unanimous decision to take the lower risk option.

There’s endless advice out there about following “the road not taken,” but you’ve got to factor in this matter of where you are in your life. Most of us, most often take the safer route, but (as Frost suggests in the poem that originated the phrase) we do it at a cost. The “safe” savings account at the bank pays so little interest it actually loses money to inflation. The “safe” corporate career path runs into the brick wall of “downsizing.” The “safe” interstate route misses all the peculiar, amazing sights and people we’d encounter along the byways. The “safe” relationship gets pretty dull over time.


As an inveterate glass-half-empty guy, I’d like to endorse another famous dictum, eloquently expressed by Adam Grant that “our biggest regrets are not our actions but our inactions – the chances not taken.” In other words, we are more likely to regret the harder/scarier things we did not try than the easier things we did. Previous generations, including I think boomers, bought into the idea of a traditional and linear progression: from high school to college to career, from infatuation to engagement to marriage to children, from your parent’s house to a crappy shared apartment to renting or buying your own place.


Have a look at any given group of millenials: this no longer computes, the sequence is all over the place. Kids first marriage later, group hang outs instead of steady dates, renting or boomeranging back home instead of taking on a mortgage, building a career with a single employer to a half dozen jobs before age 30. I don’t know if this is about a fundamental shift in the culture or individual risk tolerance, but it is different. Ask a roomful of college business students who wants to start their own business and it’s most of them. Ask the same room who wants to pay their dues on the road to the success and personal satisfaction of owning that business and it’s virtually none of them. They don’t and won’t necessarily process this as risk tolerance so much as about impatience to achieve their birthright. But I’d suggest it has an awful lot to do with wanting to upend the traditional equation and separate risk from reward.

Last Century

Elon Musk, the guy who used his gigantic windfall from PayPal to start Tesla and Space-X and is now pursuing the possibly crazy concept of hyperloop transportation, is at the extreme end of the risk-taking spectrum. He’s the ultimate entrepreneur, willing – no compelled – to risk it all because of the absolute surety that he can accomplish anything by force of will.

This Century

Most of us live at the quieter end of the spectrum, where we have a certain tolerance for taking chances, but once we’ve achieve security in our finances or career or relationships, prefer if given the choice to remain on the same path. I know a guy who turned down a job offer that carried a $30,000 increase in salary for reasons known only to him, but which I suspect had to do with the perceived risk of stepping outside the familiar.

I’m the last one to think you can do much about human nature in general, or about personal predisposition in particular. We are what we are, and change, if it occurs tends to be evolutionary rather than sudden. Most of the time I’m a lot less intense than I used to be, but push the right button and I’m rapidly, if less persistently the same impatient guy who demands destiny bends to his will rather than the other way around.


I used to be a change junkie, and while change continues to stimulate my synapses, I’m troubled about a creeping resistance that is actually a reversion to childhood form. I like new experiences but have to overcome the hump – for example, I’ve wanted to travel “down under” for a long time but tempered the impulse by thinking about 22+ hours on a plane, even if it is decorated with koala bears. I hate the occasional squabbles of any long-term relationship but know the true center from my underlying feelings and understand that I need to be with someone wicked smart and challenging.

So what and where is the right balance? There’s no generalizable answer, but I know this and return to it as an axiom to live by: I once knew a smart and accomplished woman who lived well, traveled the world, stepped into and ran a business with no formal training, and had in her forties a succession of successful and interesting suitors. Whatever it was, maybe just too much angst, maybe that encroaching resistance to change, maybe just a desire for some domestic calm, she ultimately remarried, to someone whose inability to deal with the world ultimately reduced her world to four walls of an apartment. It cost her everything to accommodate him, and while it affected other people that was her choice to make. But to my mind it was a bad one and it is my reference point when I feel I’m becoming too still to do something.   There’s no perfect balance point for risk and reward, but we probably all have a variety of object lessons in what not to do. Those lessons have provided me with a roadmap, and it’s served me pretty well in having the kind of life I wanted.




Wouldn’t it be great if we could have an intracontinental eclipse, or it’s equivalent, a lot more often than every few decades?

Social Media Today published a description this week of social media habits by age group. (Thanks to Mark D for the link.)  Two-thirds of people 50 to 64 but only one third of those 65+ use social media. By contrast, the overall rate of social media consumption is 86% for those under 30.

Those numbers aren’t exactly surprising, and no one’s going to lose sleep over a bunch of technologically tuned-out boomers, but the follow-on data give pause. The same article reports that while 9 out of 10 boomers are “interested in the news,” only half again as many are interested in the under 30 bracket.  More than half of those 60 and over vs. only 25% of people under 30 go “in depth.” Consumption habits show adults reading digital and online content and the “kids” predominantly watching videos.


So as bad as you thought the problem is with people getting their impressions of the world through sound bites, you have to wonder what will happen when those who can only consume information by video get their hands on the levers of government and industry. My observations as both a manager and an educator (not necessary at the same time) are that we’re becoming, or perhaps have already fully become, a transactional society.  That means acting on the basis of immediate, short-term outcomes rather than taking the long view. It means treating interactions with other people as discrete events rather than as parts of an ongoing relationship. It means losing of threads of human contact and experience which have historically been the ties that bind. Little wonder that someone who views the world as a purely transactional, zero-sum game is sitting in the oval office.

It’s not news that we’re living in a highly fragmented time, and just plain sad that we so infrequently experience common purpose or experience. This hasn’t always been the case; there as a time when it clearly wasn’t.


The last year in particular has seen families and friendships damaged, often irrevocably, by anger and politically-instigated intolerance. I’m not suggesting everybody ought to be friends, or that we normalize a bunch of vicious morons marching through their free country carrying the flags of mass murderers. Or that we act like a bunch of ostriches like a Facebook acquaintance who keeps celebrating her ignorance of world events like the objective is to have a nice dinner party. The damage is there, and it’s real, and I’m not ever going to pal around with a skinhead flying a confederate flag from the back of his truck. But I am happy to discuss substantive problems and solutions with thoughtful people, whatever their political persuasion.

brotherI have no idea how they teach it now, and shudder that there are lots of people who think of the Civil War as the “war of northern aggression,” but when I was growing up in Philadelphia they talked a lot about the Civil War being a “brother against brother” affair. As kids, we couldn’t understand how family members could end up figuratively or literally shooting at each other. It’s sadly not hard to see how that could come about through the dark lens of 2017.

So it was heartening yesterday, to watch the coverage of millions of people in cities across the eclipse’s path sharing awe and wonder, at the simple natural phenomenon of a celestial shadow. People clapped and hooted and exclaimed silly things, and in large measure fell silent as the moon fully “ate” the sun. Really, it was a spectacular day in so many ways. Apart from watching the real-time NASA footage, a lot of us got to play junior scientists with our homemade viewers, and a lot of others got to wear silly glasses that looked for all the world like a 1950’s audience at a 3D movie. It was all quite wonderful in a simpler time kind of way and revealed that there’s still some underlying visceral connection we can all spontaneously tap into…some shared humanity that, at least for a few minutes, renders us all part of the same whole.

watching 3

Maybe I’m a bit of a dinosaur in my thinking here (though 25 years ago I was incorporating leading edge technology into my startup company), but I think social media, an extension of electronic rather than paper or voice communication, has really screwed us up as a civilization. It enables the worst human instincts to propagate at the speed of light, it demands complexity be reduced to 140 character superficialities, it fractures personal interaction into impersonal fragments, it substitutes mass acquaintances for friendships, it causes us all to burrow deeper into isolation rather than collective experience. Wouldn’t it be great if we could have an intracontinental eclipse, or it’s equivalent, a lot more often than every few decades? Now that would be one hell of a totality.




Two Wheels and Freedom

I’ve resolved, at least intellectually, to stop wasting my time on activities that are not worthwhile, even if they are nominally gratifying in the moment. I’m going to try to move in another direction. To begin, I’m planning to raise some hell on two wheels this weekend.

I bought a motorcycle this summer. It’s a retro-styled Triumph, a “Bobber” in model name and vernacular. When I get off the bike after an hour or two I’m likely to be sore. But those couple of hours are joy. I think I’m younger, not 20 but maybe 40ish. I feel an affinity with Sons of Anarchy (absent the violence and incredibly vigorous sex.) I’m growing my beard back and my wife wouldn’t mind at all if I counterbalanced my diminishing feathering of hair on top with a ponytail in back.


This is aging for me. I’m not athletic and perhaps less adventurous than I was once, but I want to continue doing the things I’ve always done – like motorcycling since I assembled my first mini-bike at 10 and got my first Honda at 13. I feel guilty that my skis are leaning against my closet wall instead of strapped to my feet. I need to come to terms with this: if I do this stuff there will be a price to pay in aches and pains. I might even break something, hopefully nothing critical. But to do otherwise is to give up the flavor. And while there are days without an inclination to even taste it, there are others where the need is overwhelming.


I have been a CEO for many years, now of a lifestyle company but once of a large information company that I built out of a bedroom startup and fueled by raw ambition. It’s kind of a meaningless title now, unsupported by the scaffolding of employees and infrastructure, but it reminds me of whom I still am at some level. I don’t want the stress and burden of responsibility for employees’ livelihoods anymore, but I believe I still have the decision capacity and usually clarity of vision to realize important or at least personally meaningful things. If that’s a leather jacket and riding boots, well it’s something. I published a “business” book last year, and that was something else. It’s not the one I’ve wanted to write for 60+ years, which is a novel or collection of novellas, or something professionally informed but entertaining (along the lines of Oliver Sachs) – but the possibility is validated by the empiric evidence that I have done it.

My current conundrum is this: I’ve resolved, at least intellectually, to stop wasting my time on activities that are not worthwhile, even if they are nominally gratifying in the moment. I’ve been teaching occasionally for most of my adult life, and more regularly the last 10 years. I like smart college students, it gives me pleasure to be in a classroom and to tell them what it’s really like in business instead of spouting theory from a textbook. It’s gratifying to mentor and see those efforts pay off in new skills, a job obtained, a personal accomplishment. But I am firmly of a mind now that much of the student body politic has been allowed to morph into a “Confederacy of Dunces.” There are multiple causes of this – the idiocy of the Common Core curriculum in public schools, the overstimulation of an always-on electronic barrage of useless non-information, a generalized anti-intellectualism that has sprouted from the uncivilized discourse of politics – but that’s philosophical, causative and beside the point to my nominal decision. Too many students suck. They’re there because they don’t know where else to be, because there are no jobs if you don’t have a degree, because their parents want them to do well … whatever. But they really could give a rat’s orifice about actually learning anything, didactic spoon feeding is the pabulum they’re used to consuming, and creative thinking is a largely alien concept.

The fact that I get some satisfaction from being in a classroom is secondary to the frustration of trying to teach the willfully uneducable. So I’m going to try to move in another direction. Of which this blog is one piece. Like the first step in a twelve-step program. I’ll keep you posted as the other steps develop.

Meanwhile, I’m planning to raise some hell on two wheels this weekend.




Age Spots is a forum for anything and everything that details and reflects change. It’s dedicated to those of us in the second half, not the first.

Ah, the joys of waking up from a great dream about people you’ve loved, or things you’ve achieved … and feeling every joint you didn’t even know you had.

There’s nothing wrong per se with feeling a bit wistful about the past. It’s all true, we’re 60- or 70- or 80- something, and it’s not the same thing as being 20 or 30 or 40. But here’s the thing. What if, instead of bemoaning what’s in the past – interests, people, experiences we can’t replicate anymore – we spent more time focusing on intensity of the moment.

I’m not just talking about smelling the roses. I mean an alternative, a substitute if you will, for the mission that once drove us. Because that mission, however exhilarating, even fulfilling from a distance, cost us in proximity. Stress, interpersonal tension, willful or blithe inattention to people we could have been more in the moment with. They are the collateral damage of being driven.

I’m a recovering Type A and I know. Like the time I found myself completing a client project at 2 in the morning while my mother was in the last week of her life. Stupid. And for reasons better explained by social psychologists and evolutionary biologists, somehow unavoidable mistakes we all sometimes make.


I’m hardly stretched out on the gurney at this point in my life, but unmistakably diminishing capacities are real. (I went kayaking yesterday and it hurts this morning.)  I find myself hating aging. But the worst is not the change in body or muscle tone or speed of cognition. No, the hardest thing about this aging stuff is the loss of interest in some things that used to be interesting. It’s not that I don’t want to ski anymore, or that I rationalize it by saying my knees don’t like moguls, it’s that I can’t seem to get up the head of steam to go out and do it.

I was talking to my oldest friend about this. He’s struggled with change, and through losses I’ve been fortunate to avoid. But he’s found the only prescription I’ve heard that’s actually worth anything. I always chased something, and I’m persistent and bullheaded enough that I almost always achieved my goals. So not having something to aim for is absolute hell for me. But what if, as my friend suggested, I change the depth of field from that longer-range ambition (because really, the range has ineluctably shortened to maybe a couple of decades) to a very short focal point of here and now?

Again, I’m not talking about those damned roses, what I mean is concentrating the focus from the lighthouse in the distance to what I’m doing right now, today, this minute. You can’t force yourself to be happy, but what’s always made me happiest is doing something meaningful and with satisfying immediacy. The shift in thinking is it doesn’t have to be meaningful in anybody else’s mind field, just in mine. I don’t know whether I can successfully do this, but it’s sure worth a try.

So thanks to that conversation late last year, I finally sat down and executed on this idea I’ve been kicking around for months now. Age Spots.

Age Spots is a forum for anything and everything that details and reflects change. It’s dedicated to those of us in the second half, not the first. I don’t know what that means exactly, but I don’t think this is a space for 30-somethings to reflect on their transition from 20-somethings.

I’ll write a blog post, probably not daily but I hope a few days a week, and you’ll be able to post your own experience, emotions, perspectives – either in response to what I or someone else has written, or just as a personal reflection. I want this to be affirming, but I’m not going to set any rules other than civility and honest reflection. So if you’re having a bad day and just need to vent, well that’s obviously part of it too.

At the end of the day, I’m hoping that for you and for me, the opportunity to express ourselves, to those of us in the same stage of the journey, could provide just the intensity that defines and lifts us.