Inspiring talk by Professor Irving Grousbeck, delivered as part of the 2023 last lecture series for graduating students at the Stanford GSB. I have included my paraphrased notes below (these are for personal reference only and any mistakes in transcription are my own).

Regret for what you have done can be tempered by time, but regret for what you have not done is inconsolable. A quick story: a former student of his from a number of years ago recently made a Zoom appointment with him. He was pleased as they hadn’t been in touch for quite some time. The former student appeared on the screen looking like a million dollars – well dressed, confident and with a big smile. But after exchanging some pleasantries, there was a pause. “I’m an imposter” he said, “and I’m miserable at work.” His story then came pouring out: 42 years old, happily married with 2 wonderful children, earning a 7 figure income, spending most of it, living well, respected by his partners and other professionals. He is considered a domain expert but he knows he is neither as wise nor as knowledgeable as people think and, more importantly, he hates to get up in the morning and go to work. It is boring, repetitive, what he does has no impact to speak of and he can’t point to anything that is truly his. Until recently, he thought he would become an entrepreneur, truly leading and making a difference, but now that dream has died and he feels trapped. 

That story raises a few questions – when the counting is done in our lives, what will be left? Will what I have done matter? Will who I made the journey with matter? What about the quality of my relationships? What about my prominence? What about my legacy? And since he mentioned it earlier, how can I avoid living with regret? These are daunting questions. So, on a lighter note, here is one formula for living: “work like you don’t need the money, love like you’ve never been hurt and dance like nobody’s watching.” Those were the words of Bojangles Robinson, who was a tap dancer and friend of the legendary musician Duke Ellington.

Let’s take a step back. These are extraordinary times. Despite the recent market downturn, the economy is generally vibrant, new employment opportunities are being created, and those jobs arise largely from entrepreneurial efforts. They arise because some people had visions they pursued and people in the marketplace were willing to buy the products and services flowing from those visions. Yet most of us feel like we may be destined to become observers – highly paid managers, investors and advisors, sitting just outside this wave of entrepreneurialism.

Many of us have hoped that someday we might become entrepreneurs, yet statistically, most [Stanford GSB] graduates don’t pursue entrepreneurial careers. Fewer than 35% of graduates 25 years out classify themselves as having pursued something entrepreneurial or having been self-employed. Yet some 90% of entering first-year MBA students express a strong interest in owning their own businesses. So, what happened to derail these ambitions? Well, reality intervened. How can I think about being my own boss – I am focused on getting a good job, having some kind of life and paying off the student loans I have incurred.

He offers for consideration two of his very favorite quotes. They describe sharply contrasting attitudes that are likely to lead one into very different careers and lives. The first is from TS Eliot’s The Love Song of J. Alfred Prufrock:

“No! I am not Prince Hamlet, nor was meant to be;
Am an attendant lord, one that will do
To swell a progress, start a scene or two,
Advise the prince; no doubt, an easy tool,
Deferential, glad to be of use,
Politic, cautious and meticulous;
Full of high sentence, but a bit obtuse;
At times, indeed, almost ridiculous—
Almost, at times, the Fool.

I grow old … I grow old …
I shall wear the bottoms of my trousers rolled.

Shall I part my hair behind? Do I dare to eat a peach?
I shall wear white flannel trousers, and walk upon the beach.
I have heard the mermaids singing, each to each.

I do not think that they will sing to me.

I have seen the moment of my greatness flicker,
And I have seen the eternal Footman hold my coat, and snicker,
And in short, I was afraid.”

TS Eliot uses some penetrating words – “attendant lord”, “advising the prince”, “deferential”, “cautious”, “glad to be of use”, “afraid”. Elegant, evocative lines, but a sad portrayal indeed. In contrast, hear the words of WH Murray, who led the Scottish Himalayan expedition:

“Until one is committed, there is hesitancy, the chance to draw back. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favor all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamed would have come his way. Whatever you can do, or dream you can do, begin it. Boldness has genius, power, and magic in it.”

Well, one might say, how would I become an entrepreneur if I wanted to? Are they born, like .300 hitters are said to be in baseball? Or can they be made? Before talking about steps to take, he would like to identify one thing you should not bring if you aspire to have your own business: capital. How can capital be anything but an advantage to an entrepreneur? One of the things he teaches is that the functions of the entrepreneur and the capital supplier are very different. Nowhere is it written that an entrepreneur needs to supply capital. The disadvantage of having some money is one tends to define the scope of one’s venture according to the size of one’s resources. His working definition of entrepreneurship is the pursuit of opportunity without regard to resources currently controlled. 

If you think you might want to own your business, match your outlook with the 5 attitudes observed in most entrepreneurs. One is an unending dissatisfaction with the status quo, which has two elements to it: you are not happy with the status quo and you think you can do something about it, something better than what is now being done and build a business around that notion. Two is a healthy self-confidence, a willingness to be lonely, make tough decisions, stand on a level of the organisation chart with no peers, have the buck stop with you, sometimes be wrong in a big way. Three is what he calls responsible competence. You feel good about what you do. You think you can do more and you’re willing to stretch. Four, a concern for detail. There are very few successful entrepreneurs he has seen that are broad-brush people in all aspects of their lives. They may be broad brush in some areas, but in critical areas they are meticulous. And if they are not meticulous by nature, they are astute enough to find a partner who is. Critical details do matter. Finally, perhaps most importantly, a tolerance for ambiguity. That should not be confused with a love of risk, because the best entrepreneurs are constantly asking themselves how to shrink risk out of a situation. Rather, it means a willingness to accept an uncertain future – you are not sure you have a job tomorrow, you are not sure you have an income. You are willing to give up the corporate environment that you know, the peer group, the routines etc. and you will take on the ambiguity of attempting to buy or start a venture. 

Assuming you generally match the attitudes just described, how would you begin to become an entrepreneur? How does one get from here to there without an idea, capital and the knowledge of how to start? You have to be determined to own your life, not lease it out in sections. Your life is not for sale. When you go to work everyday, you should not have to leave your heart at home. The future is uncertain but the best way to predict it is to invent it. Don’t be afraid to take a big step, you can’t cross a chasm in two small jumps. There is only one basic requirement in terms of the process and that is how to buy yourself some time to be able to establish yourself apart from your present job, so that you can use the morning of your energies on your new venture. If you are going to work full time and want to have any life outside of your professional endeavors, you are only going to be able to give the evening of your energies to your new venture, if you remain employed. But new ventures demand first class, morning energies. So you need to be able to leave your current position and live for some period of time while you translate your dream into reality.

Stepping back, he holds firmly the belief that entrepreneurship is a reasonable career alternative. Not for all, but for any who might choose it. You don’t need to be impulsive, headstrong, bombastic or flamboyant. You need no operating experience though it usually helps. In short, to be an entrepreneur, there are no external barriers, only those we internally impose. Ask yourself this question – what would I do with myself if I knew I wouldn’t fail? He is reminded of Seneca’s words: “it is not because things are difficult that we do not dare, it is because we do not dare that things are difficult.” A principle for charting your career path is will I be in someone else’s organisation, or in my own? 

In many courses at the Stanford GSB, they are in one way or another examining the risks of entrepreneurship. But just for a minute, let’s examine the risks of employment. While the company you work for will hopefully challenge you, promote you, compensate you well, flatter you and give you buttons to push and increasing numbers of people to manage, it may also insinuate you into its culture and envelop and consume your entrepreneurial ambitions, energies and perspectives. The uninvited intruder in your lives that does not knock before entering is risk aversion. It creeps imperceptibly into your consciousness and decision making over time. Many, although not all, large company executives are anything but free. Many of them would love to leave but don’t know how to, where to go, can’t afford it etc. He has rarely met an unhappy successful entrepreneur but he has met many unhappy successful executives. 

Your career should not only be fun, it should serve your life – not the other way around. We have discussed a few of the risks of people not following the entrepreneurial path: tilling the soil in their various locations, creating further value for their shareholders, often not being challenged and not having much fun. Wouldn’t you like to wake up when you are 40, 45, or even 55 and go to work with a skip in your step? Someone else’s company is more than a matter of where you will spend your workdays, it will reverberate to every facet of your life. And yet the decision to become an entrepreneur is made even more difficult because each of us labors under the burden of high expectations: of close friends, of family, of ourselves. Each success in our career puts more chips on the table. With each victory comes greater expectations, and in order not to disappoint others or oneself, a “safer”, more customary, lower risk career course is often charted. But surely we recognize there is no absolute career safety and that risk can be avoided. There is no right career choice. Where are the guideposts? What am I supposed to be doing? Most of us realize that intellectually, but find it hard to accept emotionally. Certain risks must be assumed consciously or not. The operable question to ask is what set of risks can I best control? He doesn’t like exogenous risks, but can he make them execution risks? That way, if I perform, I’m rewarded.

He starts with the premise that one of our goals in life is to die young as late as possible. Therefore, what are some of the important questions to be asking oneself if the door to an entrepreneurial career is to be left open? How would I define my ideal work environment is a good place to start, in terms of partners, ambiguity, risks, peers, status, power, smaller vs. larger enterprises, culture, structured vs. unstructured, importance of money. As you sort through these variables, which are more or less important to me? What skills of mine need supplementing? Do I think of supplementing them by recruiting a partner or making myself more ready to go at it alone? Regarding the jobs now offered or potentially available to me, let’s look at the daily routine I would follow, avenues of advancement, availability of a mentor and two very important things: what doors are opened or closed in my path by assuming this job? Some of them produce awkward transitions to places I might want to go. What are the natural transitions out of the job and what are the ones that are more difficult, larger leaps? How will you keep your perspective and entrepreneurial dream alive when you are working for someone else? How difficult will that be for you? He has learnt that the easier a change is to make, the less it usually matters. And the older we get, the harder it gets to choose change. Change is one form of hope. To risk change is to believe in tomorrow. So it behoves us to set a course whereby any job we take moves us closer to our career goal by building our skills, but the path must be visualized in advance. 

Now back to the question of how to get from employment to self-employment? The most difficult part of any task, as Plato said, is the beginning of the work. And that means both beginning the search and sustaining the search for one’s entrepreneurial venture. Maintaining a search is in a sense like maintaining one’s spiritual beliefs. They die if not nurtured, atrophy sets in. If you don’t freshen the entrepreneurial mentality by reading and staying in touch with other entrepreneurs, atrophy will indeed set in and the quest for one’s venture will be abandoned as that naïve idea you once had. One of the really important guidelines is don’t spend 5 years getting 2 years experience. You require alternatives to be in a strong position to make good decisions, so you need to look at a lot of opportunities in order to refine your judgment. 

What are the risks of entrepreneurship? Failure, perhaps. But in the event of failure, you don’t lose your reputation or your money (he hopes not!). Do you lose other people’s money? Yes. But that is where the term risk capital comes from. They are set up to take the risk, they are throwing mud at the wall a lot of the time and hoping some of it sticks. You are not, you are investing yourself, which is a huge difference. Will a company not hire you after a failure? That is absolutely wrong. The biggest risk is that you might become constitutionally unemployable, you just don’t want to work for somebody else again. But you may have to go back somehow and reestablish your credentials in order to try again. There are many first time failed entrepreneurs who were subsequently wildly successful.

When are you ready for your own venture? In his book Psycho-Cybernetics, Maxwell Maltz said you are ready to do something when you can visualize yourself doing it. But there is a relatively short time window, and it is ideally sooner rather than later. In percentage terms, not many entrepreneurs start or buy their first ventures after the age of 40-45. Entrepreneurs are just like you and me in ability, but what they have that is distinctive is vision and conviction. Remember also that the warm sense of everything going well in your career may only be the body temperature at the center of the herd. Keep in mind that many people who waited at the platform for just the right train while life passed them by, only to be saddled by so many responsibilities and financial constraints that they eventually couldn’t get on any train. Don’t let that be you.

What are the rewards of the entrepreneurial path? Top of his list would be freedom – to stretch one’s capabilities, to put an imprimatur on a company, to create something, to have an ethical impact on others and to have financial independence. On money, here is a comment he offers without apology. There is a big difference between being rich and being wealthy. Being rich is having money, being wealthy is having money and time. There is a fundamental difference between income and capital. Financial independence when you’re young enough to enjoy it might be something worth working for. It gives you an opportunity to have a second and third career, as well as psychologically set out in a new direction in mid-life. Thus, if you stay with a successful organisation you created, you do it out of choice not necessity.

A short story. His ninth grader teacher once gave the class an algebra test. The last question worth 25% was what is the custodian’s name? Though it was December and they had seen him everyday for 3 months, no one knew his name. He became a person that day, not just a functionary. And their attitudes were permanently affected. There is a confluence of the ethical and the practical in life. So resolve to win from the high road. And in your quest, pause now and then to ease the burdens of your fellow travelers. It has been said we have all go though life with partly broken hearts. Any definition of success must include service to others. We have all drunk from wells we didn’t dig, and been warmed by fires we didn’t build. He rejects the prevailing notion the pursuit of selfishness has overtaken the possibility of compassion. Not just by giving some money to your local charity or taking a titular position on a hospital board, but by devoting your time and abundant skills to something worthwhile. Really pulling on the oars and making a difference in areas where you are best qualified to do so and are most passionate about.

Returning to TS Eliot’s image, at the end of his days, he doesn’t want the devil to snicker and hold his coat. If he has led well and stood for something noble, he will not have to worry. At school, they teach lots of things they know you will soon forget. The reason they do that is because they don’t know how to teach you what you always need to know. Compassion, commitment, concern, involvement, love. Don’t risk looking back on even part of your life and realizing you suffered from a failure of kindness. It has been said that the only difference between love and friendship is the degree to which we can hurt each other. The saddest phrase of middle age is “I wish I had.” That regret is inconsolable. How much better to say with open eyes “I have dared and cherished no regrets.” It is undeniably tougher to create your own opportunity than to be part of someone else’s but he has been down the entrepreneurial road and it offers unparalleled exhilaration. If you choose to take that path, ignore the naysayers, because very likely your only supporters will be other entrepreneurs and those with blind faith in you. So do it, if you will. 

He offers the words of Ben Johnson written in the early 17th century:

It is not growing like a tree
In bulk doth make Man better be;
Or standing long an oak, three hundred year,
To fall a log at last, dry, bald, and sere:
A lily of a day
Is fairer far in May,
Although it fall and die that night
It was the plant and flower of light.
In small proportions we just beauties see;
And in short measures life may perfect be.

That venerable, elegant poem tells us that the lily that lived only one day in May might have made more impact than an imposing 300 year old tree. Impact on others is how you will be known, remembered. In this world, it is not given to us to lead perfect lives, but we can attain perfection in short bursts of altruism, kindness and compassion. And what should we strive for? Not for a legacy. Buildings all over the world display the names of benefactors in bold letters and 40 years later who knows who they were or what they did and few people really care. He does not question the spirit or utility of the gifts, only the durability of the name recognition. So let us think of the impact we have on others, of standing for a set of values or principles and really living them. Did I listen? Did I invest? Did I care? Was our interaction a transaction or a small step in the deepening of a relationship? Did I freely express my love?

Turning back to the topic of careers, each of us is equipped with everything we need to experience a powerful life, full of success, incredible passion and joy. The difficult part is giving ourselves the permission to live it. Those are the words of Deborah Rosado Shaw. Or, as said another way by May Sarton, “now I become myself, it’s taken time, many years and places; I have been dissolved and shaken, worn other people’s faces.” Paraphrasing Robert Frost, while the woods are lovely, dark and deep, you have promises to keep and miles to go before you sleep. So go out, touch the skies and be special because you are.