Season Three Finale!
Pretty Good Career Advice!
The Story
For years now, I have been ending the last class of my spring course with a self-indulgent and slightly presumptuous little bit I call my “last lecture.” By this time, we have already discussed answers to the final exam, and the “student rating of teacher” forms have been submitted, but there is still some time left, so, rather than letting everyone leave early, I use those last few minutes to share a little hard-won wisdom. More specifically, some career advice, some of what I like to call “dad advice,” and some more philosophical life advice.
For the career advice, I set the tone with a New Yorker cartoon showing a man lying on the psychiatrist’s couch saying, “I had the dream about meaningful employment again last night.” Then I say, in a conspiratorial tone, “I know, deep down inside, you are in a panic and thinking to yourselves, ‘I am about to graduate with a master’s degree in planning, and I don’t even have a plan of my own.’” To which I then say, “Relax, I have good news for you: it wouldn’t help.” Career planning should have a horizon of about 12-18 months, tops. Sure, you should plant some seeds, follow your curiosity, and develop and tend to some longer-term interests over the course of your career and life. But career management is less about planning and more about learning to recognize and seize growth opportunities as they present themselves. Then I move on to the comedian Steve Martin, who once said that you have to be “so good they can’t ignore you.” This also happens to be the title of a book by Cal Newport, who argues against “passion” and instead for building skills by practicing and getting very good at something that interests you. This will lead someone to notice how good you are and to say, “Hey, you are so good at that, how would you like to try this next?” From my own perspective, I can assure you that Cal is right, and that is how most careers actually progress. Next, I share the advice of both the ancients and the moderns: “Know Thyself” was inscribed above the entrance to the temple of Apollo at Delphi, while Oscar Wilde famously said, “Be yourself; everyone else is already taken.” I tell my students that knowing who you are and what you are about will help you make decisions that are good for you. I sum up by telling them to do the work, be useful, maintain a near-vertical learning curve, and know when it is time to start searching for their next opportunity.
My “dad advice,” is a very nuts-and-bolts list of things I wish someone had told me when I was graduating, including tips like, “pick a good life partner, live on one salary and save the rest, use debt…but wisely, buy used cars, start saving for retirement as soon as you get your first paycheck (compounding is a wonder!), don’t buy a home as a real estate investment but instead buy the home you want to live in. Finally, I say, “Learn to take risks while you are still young.” When very old people are asked in surveys what their biggest regret in life is, the number one answer is “I wish I had taken more risks.”
Let me be clear: I didn’t say it was THE best advice, I just said it was MY best advice. Anyhow, I end my talk by knitting these ideas together with some advice about how to live, and I’m going to expand on that part here, by offering three good ideas for people at all stages of career and life to think about.
The Theory
The Good Life or The Goods Life?
I start with Aristotle, the famous philosopher who lived, taught, and wrote at the end of the Greek Golden Age, from 384 to 322 BCE. Although the mere mention of the name “Aristotle” strikes fear into the hearts of many, his ideas aren’t as distant and inaccessible as one might think. His principle of the “golden mean,” for example, promoted moderation in life and finding balance between the extremes of excess and deficiency in all of the virtues: courage, temperance, generosity, magnanimity, patience, truthfulness, wit, and friendliness. So, in the case of generosity, you should strike a balance between the extremes of being miserly or a spendthrift. The same goes for eating and drinking: not too much, not too little. But my favorite Aristotelian idea is that of “the good life.” The Greek word eudaimonia means “happiness” or “flourishing,” and for Aristotle, the most important ingredients to flourishing were meaningful work, a life of personal growth and purpose, and relationships with family and friends. The Greek word arete translates as “excellence,” which means the fulfillment of purpose or function and the act of living up to one’s full potential. Combining flourishing and excellence, Aristotle believed “the good life” was one of happiness, and, indeed, that,
“Happiness is the meaning and the purpose of life, the whole aim and end of human existence.”
As intimidating as old dead white guys with names like “Aristotle” may seem, his ~2,400-year-old idea of what constitutes “the good life” remains fresh and relevant today.1
More recently, in his 2012 book The Unintended Reformation, religious historian Brad Gregory offered a contemporary, if darker version of what the good life looks like today, at least for some of us. Gregory explains how, since the Protestant Reformation, Western society has gone from the shared values that come from belief in one religion, to a more secular society and many religions, all but eliminating any consensus vision of what “good” is. He then argues that today’s societal ills stem from this loss of shared values and vision, and that the idea of “the good life” has been replaced by what he calls “the goods life”—a mere economic system where “the only thing anyone can agree on is the right to buy and consume whatever they want.” Gregory concludes,
“What sort of public life or common culture is possible in societies whose members share ever fewer substantive beliefs, norms, and values save for a nearly universal embrace of consumerist acquisitiveness?”2
How Will You Measure Your Life?
Clayton Christensen was a successful businessman and entrepreneur who coined the term “disruptive innovation,” wrote a bestselling book called The Innovator’s Dilemma, and finished his career at Harvard Business School, where he taught a popular course called Building and Sustaining a Successful Enterprise (BSSE). In the course, Christensen used business and management theories as “lenses” to explore why some companies succeed and why others fail. Then, on the last day of class, he asks his students to turn those same lenses on themselves and use the insights they gain to plan for a successful career and life. But first, he talks about what he noticed attending his 1979 Harvard Business School class reunions every five years:3
“At the fifth reunion – man, everybody was happy, most of my classmates had ended up marrying people who were much better looking than my classmates and they were doing well in their careers. But as we hit the 10th, 15th, 20th, and 25th anniversaries, oh my gosh, my friends were coming back not happy with their lives. Very many of them had gotten divorced and their spouses had gotten remarried and they were raising their children on the other side of the country, alienated from them. And I guarantee that none of my classmates ever planned when they graduated from the business school to go out and get divorced and have children who hate their guts and are being raised by other parents.”4
Christensen then asks his students to answer these three questions:
How can I be sure that I’ll be happy in my career?
How can I be sure that my relationships with my spouse and my family become an enduring source of happiness?
How can I be sure I’ll stay out of jail?
Next, he uses those business theories from his class to illustrate what went wrong.
“The reason why successful companies fail is they invest in things that provide the most immediate and tangible evidence of achievement, and the reason why they have such a short time horizon is that they are run by people like you and I. And we then apply that very same thinking process in our personal lives with sad results.”
To avoid those sad results, Christensen recommends that we take care in how we allocate our scarce resources. He explains that most of us operate several “businesses”—our career, our family, our role in the community—and the trick is investing time wisely in each. But many people invest in activities that provide immediate and tangible evidence of achievement, and careers give us that evidence, whether it is completing a project, getting paid, earning an award, or getting promoted. In contrast, investments in our families don’t pay off for a very long time. Christensen reminds us that kids misbehave every day, for years,
“And it really isn’t until 20 years down the road when you can look at your children and be able to put your hands on your hips and say, ‘we raised great children.’”
He also cautions his students against using the typical business mindset they are taught, which focuses on short-term, “marginal profit,” while excluding other important considerations and making individual decisions matter less in the aggregate. This is where we compromise, whether it be missing a child’s game or performance “just this one time,” or, in Christensen’s third question, about how to stay out of jail, stepping over some kind of ethical line, “just this one time.” Because after you have done it “just this one time,” it gets easier to do it a second time, then often, and in the end, your kid hates your guts, or you are in jail for securities fraud (as happened to his Harvard Business School classmate, Jeffrey Skilling, of Enron fame5). This is why Christensen says,
“It’s easier to hold your principles 100 percent of the time than it is to hold them 98 percent of the time.”
Christensen views management as a noble profession where the rewards come from helping other people learn and grow (I agree), concluding that,
“Doing deals doesn’t yield the deep rewards that come from building up people.”
The Second Mountain
Author and political and cultural commentator David Brooks begins his book, The Second Mountain: The Quest for a Moral Life, by remarking on how,
“Every once in a while, I meet a person who radiates joy. These are people who seem to glow with an inner light. They are kind, tranquil, delighted by small pleasures, and grateful for the large ones.”
What are these people doing right? Brooks then describes the traditional career and life trajectory that most of us embark upon. We finish school, start working, and then get married, buy a home, raise children, and continue growing in our careers, seeking both personal rewards and the economic success and achievement we need to continue supporting our families and lifestyles. This is our climb up “The First Mountain,” which Brooks characterizes as a selfish and individualistic phase of life. And then, if we aren’t knocked off the mountain earlier by a professional failure or personal or family challenge, sometime in mid- or late-career, we reach the summit and find ourselves triumphantly standing on top of the mountain. We have made it. We have been professionally successful, supported our families economically, done something of value, been recognized by our peers, and yet we still feel a little hollow. Then we look up, and out at the other mountains before us, and we realize, “I want to be on top of THAT mountain over THERE.”
Until this moment, we have been so busy climbing the first mountain that we haven’t taken the time to think about who we are, how we are evolving, what we have become, and what all of our toil has been in service to. Only when we lift our heads from the trail can we begin to see more deeply into ourselves, beyond the superficial and into a place where love and caring for others replace our ego needs. This is a rebellion against the mainstream and a lifetime of caring about what other people think of us. Whether it be a career change, starting a new venture, volunteering for an organization or cause we care about, engaging in a life of art, caring for family members or others in your community, this is where we begin our climb up “The Second Mountain,” which is all about joy, commitment, and service to other people. And this is when, after a lifetime of seeking independence, Brooks encourages us to embrace dependence by choosing a life of meaning and purpose through four commitments: To a spouse and family, to a vocation, to a philosophy or faith, and to a community.6
The Lesson
I have just compressed the thinking of three very different people into a summary of 2,000 words, and yet their ideas have so much in common that I suspect, if Aristotle, Christensen, and Brooks found themselves together in conversation, they would be in broad agreement about what we should all be doing with our lives. So instead of a lesson, I’ll just leave you with three questions, one from each, for you to ponder over the summer:
Will you choose “the good life” or “the goods life”?
Will you measure your life by career success, or by how many people you have helped?
And for those of you who are further along in your careers, can you see your second mountain yet, from where you are standing today?
The uncommitted person is the unremembered person. A person who does not commit to some loyalty outside of the self leaves no deep mark on the world.
- David Brooks
“God won’t ask how high you rose in the org chart. He’ll ask how well you helped other people be better people.”
- Clayton Christensen
“What is the essence of life? To serve others and to do good.”
- Aristotle
Bartlett, Robert C. and Susan D. Collins, translators, Aristotle’s Nicomachean Ethics: A New Translation, Chicago: University of Chicago Press, 2012.
Gregory, Brad, The Unintended Reformation: How a Religious Revolution Secularized Society, Cambridge: The Belknap Press of Harvard University Press, 2012.
Christensen, Clayton M., How Will You Measure Your Life?”, in HBR’s !0 Must Reads: Managing Yourself, Cambridge: Harvard Business Review, Boston: Harvard Business Review Press, 2012, pages 182-193.
Christensen later transformed the exercise into a book called How Will You Measure Your Life?, which was also the topic of a famous commencement address he gave to the graduating Harvard MBA class in 2010, and then a TEDx Talk in 2012. This quote about HBS reunions is from the 2012 TEDx Talk.
The third question, about staying out of jail, was particularly real for Christensen, as 2 of his Rhodes scholar classmates had spent time in jail and, most famously, his Harvard Business School classmate, Jeffrey Skilling, CEO of Enron, who was sentenced to 24 years in prison and fined 45 million dollars after being convicted on 35 counts of conspiracy, insider trading, making false statements, and securities fraud. Says Christensen, “These were good guys—but something in their lives sent them off in the wrong direction.”
Brooks, David, The Second Mountain: The Quest for a Moral Life, New York: Random House, 2019.

