"How will you know you have won at life?" My speech to the UCT Graduates of 2019

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Good afternoon soon-to-be graduates, and your impressive support team - the mothers, fathers, grandparents, extended family, spouses, partners, academic staff, and the broader UCT community that made today possible.

First, let me say that I was milling around outside while you were taking pictures, and I noticed what a good looking graduating class you are. Of course, as I climbed the hundreds of stairs leading up to this hall, broke into a spontaneous sweat and had to catch my breath, I realized why - you have daily exercise built into your curriculum!

But really, look around you! Your radiance is palpable today.

Of course, I’m not here to pay you superficial compliments. No, my objective for the next 9 minutes is to leave you with just one question that I hope sits with you for a lot longer than that. And if you choose to answer that question, I am going to share two pieces of guidance that have served me well. More on this question and my guidance for answering it later.

One of my great takeaways from studying here at UCT was learning to appreciate a good theory - a conceptual thinking tool to help us make sense of the world and, naturally, a prerequisite for thriving in it. I now refer to these thinking tools as “mental models”. I’m not exactly sure why I prefer this term over the more traditional notion of a “theory”, but the naming helps me keep clear that these are models to help me do better thinking.

One of the universal models of the world is that it is driven by competition. We can see this dynamic at play in most contexts we find ourselves in - first and foremost the natural world but, equally, while studying, in the world of business, academia, not for profits, families... everywhere. To see the world as competitive is by no means totally accurate nor sufficient. “The map is not the territory”, which is to say that mental models are just models of the world and not the actual world. Nevertheless, I find it useful to see the world in competitive terms and today I’d like to talk about winning.

Today you celebrate winning. Winning at University.

How do you know you have won? Well, you passed your exams by achieving a satisfactory, if not exceptional, result. And therefore Africa’s leading University has endorsed you as one of their very own alumni. It means a lot to you and your careers to be given this honour. Employers take note. Peers take note. Most importantly, you take note.

The most useful definition I’ve come across for self esteem is that it is the story you tell yourself about yourself. It’s the reputation you have with yourself.

Well, today you have a new powerful part to the story you tell yourself about yourself.

You are about to become a UCT graduate.

And as you leave this hall today, you look forward to the next chapter of your life.

The question I want to ask of and leave with all of you is this: how will you know you have won? Won at your life?

I feel like there’s an Instagram hashtag here - #winningatlife. Of course, it’s a lot more serious than that.

Here’s one way to think about this question: how will you know you have won at life?

You know what it means to win at University because there are very clear criteria for passing exams. You know the number of credits you need to graduate, and today you celebrate this achievement.

The new challenge you have for this next phase is that you now have to define your own criteria for winning. No one sets these criteria but you. Gone are the days of Professors setting papers. You are now both the student and the Professor, if you choose to be.

But most of us don’t take the time to play this new role of Professor for ourselves.

It took me 7 years and a crisis after leaving University to clearly state my criteria for what it would mean to win at life. I did this through writing my own one page personal plan, a personal manifesto of sorts. And before then, I did what most people do and inherit whatever murky, generalised set of criteria society hands to us. Get a job, get married, keep up with the Joneses, go on holiday once a year, have kids, post it all to Insta - you know the story. It’s astonishing to me how few people take the time to be clear about who they wish to be, why they exist, what they will and won’t do. And even fewer of us write this down so we can hold ourselves accountable, share it and evolve it over time.

It’s hard to change this. In the challenging words of Maria Popova: “A world which, in the sobering words of E.E. Cummings, ‘is doing its best, night and day, to make you everybody else.’ Try as we might not to be blinded by society’s prescriptions for happiness, we are still social creatures porous to the values of our peers — creatures surprisingly and often maddeningly myopic about the things we believe furnish our completeness as human beings, habitually aspiring to the wrong things for the wrong reasons.”

One day it struck me that I wasn’t going to thrive if I didn’t take the time to be very clear about who I was and how I wanted to win at life. Our best plans are our plans - one that we have a strong hand in shaping. We make them personal, we make them so they reflect our authentic selves, in line with our strengths, and in support of our purpose and reason for being.

It was a crisis that got me there. It was 2011, I was 29 years old and had reached my own ceiling. GetSmarter, the business I had poured by professional life into, was 60 people in size, our complexity had spiralled, and because I wasn’t a good enough leader it felt like every day was an uphill battle. I had relational issues with the people closest to me and it was hurting them and me.

I’m reminded of the age old wisdom from Confucius: “What has one who is not able to govern himself to do with governing others?” I wasn’t governing my life according to my own set of criteria for success. How was I to expect to be able to govern a fast growing business if I wasn’t doing it right even for myself?

That changed. I did the hard work, got clear on who I wished to be, and what it meant for me to win at my life. And it changed me first and the business second. It wasn’t so much a once off event as it is a way of being - committing to an explicit statement of self and then doing the hard work of holding myself accountable to it, failing, trying again, refining, building trust in myself to be myself.

You know, we’re all so very different. My path to crisis was the path of business. Your paths will be different and uniquely personal. What will be the same, for sure, is that your life grows both in potential and complexity. And to thrive, you need to be both the student and the Professor - setting the criteria for winning and then going out there to do the hard work.

You wouldn’t be sitting here today if you didn’t have the mental speed to win at University. But what I’ve learned is that what you’re really looking for isn’t just speed, it’s velocity. “Speed versus velocity” is a great mental model. We’re all clear on what speed is. But velocity is different - it is defined as speed with direction. As the saying goes, if your ladder is against the wrong wall, it doesn’t matter how hard you keep stepping - you just get to the wrong place faster. Harnessing the speed you have today by guiding it with a strong direction is what I’m talking about.

So, now that you are both student and Professor, what are your criteria for winning at life?

  • Who is it that you want to be?

  • What’s your why? Why do you exist?

  • How do you think about passing the relationship exam - relationships with your partner, your children (if you have them), your broader family, the society around you? Which of these relationship exams are most important?

  • How do you think about passing the career exam? What will you and won’t you do for your careers? Too many of us don’t answer the second part of that question.

  • What would it mean to pass the money exam - lots of it, or strive to live within your means?

  • How do you think about your personal development exam? This might be better thought of as a weekly tutorial with yourself.

  • Your spiritual exam?

  • The animal exam?

  • The nature exam?

  • The ethical exam?

  • The health exam?

  • The whateverisimportanttoyou exam?

I have only two pieces of guidance for you in the way you think about these deeply personal questions:

  1. Don’t accept societies generally accepted criteria for winning at life as your own. It’s the safest but also the surest way of ensuring you don’t reach your full potential. Do the hard work of getting clear about who you want to be. Better yet, write it down so you can share it with others, get feedback, evolve it, and hold yourself accountable. The best kind of competition is competition with yourself for yourself.

  2. The longest ever study of human happiness, conducted by Harvard University, has one conclusion and one conclusion only. Your happiness is based on the quality of relationships with the people closest to you. That’s it. Nothing else matters as much to your happiness. Therefore, be sure to set clear criteria for what it will mean for you to pass the relationship exam. For your relationship with yourself and the people closest to you. It’s not the most popular subject because it’s hard, vulnerable work. But it’s the one that will best equip you to win at your life.

Onwards and upwards, class of 2019!

Thank you.