Too Soon Old, Too Late Smart: Thirty True Things You Need to Know Now by Gordon Livingston is a collection of thirty essays by a seasoned psychiatrist (he passed away in 2016 at age 77) who reflects on various lessons learned from his time with patients and also from the ups and downs of his own life. There’s a poignancy to his writing, especially when he mentions the deaths of his two sons over a 13-month period, one to suicide and the other to leukemia, but his overall outlook on facing challenges and living life left me feeling optimistic and hopeful, although a bit sad.

A few quotes that I highlighted and thought about throughout the book:

We demonstrate courage in the numberless small ways in which we meet our obligations or reach out to try the new things that might improve our lives.

Amen. Because I am a junkie for all things sports, I keep thinking of two maxims: “Do Your Job” (thank you Coach Belichick) and “Just Do It”. As trite as these may sound, I really do believe in the power of consistently doing what you’re supposed to do and being fearless when it comes to trying new things.

In general we get, not what we deserve, but what we expect.

This is a hard-learned lesson for me because at various junctures of my life, I would find myself resigned to thinking that I simply wasn’t good enough to achieve something and that I would fall short. This mindset inevitably became self-fulfilling prophecies. I think there’s a healthy way to confidently and optimistically believe in oneself and to support that with hard work, self-awareness, and discipline. This way, what we expect is not a delusion but just a point on the map we’re making our way to reaching.

The three components of happiness are something to do, someone to love, and something to look forward to.

I don’t get tired of reading about the various lenses/frameworks for thinking about happiness, and this simple lens by Livingston is a solid one. The “something to look forward to” is a component I actually hadn’t given much thought to, but is definitely important. I think for me personally, the “something to look forward to” is often something very simple and mundane, like anticipating a nice jog or a tasty breakfast, date night with Mel, or listening to a new episode of a favorite podcast. These small pleasures bring a series of happy moments that impact my overall happiness.

The point is that love is demonstrated behaviorally. Once again we define who we are and who and what we care about, not by what we promise, but by what we do.

This reminded me of a quiz I recently took with Mel, the 5 Love Languages (Words of Affirmation, Acts of Service, Receiving Gifts, Quality Time, and Physical Touch). I think Livingston would discount the “words of affirmation” and give more weight to the other languages. My quiz results weighted my love language heavily towards Quality Time and Physical Touch and very minimally when it came to Receiving Gifts.

The other thing that true love requires of us is the courage to become totally vulnerable to another.

Made me think about Brené Brown’s Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead, an excellent book on this topic.

Acquiring some understanding of why we do things is often a prerequisite to change. This is especially true when talking about repetitive patterns of behavior that do not serve us well.

If people are reluctant to answer “Why?” questions in their lives, they also tend to have trouble with “Why not?” The latter implies risk. Steeped in habit and fearful of change, most of us are to some degree risk-averse. Particularly in activities that may involve rejection, we tend to act as if our sense of ourselves is fragile and must be protected.

Change is hard. I know this because I’ve often felt like I was constantly learning and changing in a good a way, only to be blind or in denial about habits and behaviors I had a tough time letting go. I still struggle with this in various aspects of my life, and a big part of it is an unwillingness to examine certain aspects of myself more carefully, most likely due to fear.

This is the final and controlling paradox: Only by embracing our mortality can we be happy in the time we have. The intensity of our connections to those we love is a function of our knowledge that everything and everyone is evanescent. Our ability to experience any pleasure requires either a healthy denial or courageous acceptance of the weight of time and the prospect of ultimate defeat.

Sigh. I thought about John Mayer’s Stop This Train when I read this.

The most secure prisons are those we construct for ourselves.

I’ve mentioned a few times about how doing daily meditation has helped me in a number of ways. I think one of the biggest benefits has been the ability to shed and let go of miserable and unproductive thoughts. Feelings of being slighted, jealousy, self-pity, stress, and a host of other negative thoughts are indeed prisons we create for ourselves.

It is a primary task of parents throughout their lives to convey to the young a sense of optimism. Whatever other obligations we have to our children, a conviction that we can achieve happiness amid the losses and uncertainties that life contains is the greatest gift that can pass from one generation to the next.

Whether directly or indirectly, I think my parents have done a good job of instilling a sense of optimism in me. And I hope that when I, too, get the opportunity to become a parent, I can do the same.

One of the common fantasies entertained by those seeking change in their lives is that it can be rapidly achieved.

This is why I love running because it reminds me in a very physical way that change takes work and nothing comes easy. I’ve tried to take this mentality into business and any other endeavor I take on. I expect difficulty, challenges, and a slow slog. It’s the only way that real, meaningful change can happen. When you grow to love the toil, then change will come much more easily.

One of the things that makes us human is the ability to contemplate the future. If we are to bear the awful weight of time with grace or acceptance, we have to come to terms with the losses that life inevitably imposes upon us. Primary among these is the loss of our younger selves.

I know that with enough gray hairs and lines on my face, I’ll start to move into that phase of my life where I can no longer look in the mirror and fancy myself a young man. This would have troubled me in my late twenties, but as I approach my mid-thirties, there are more important and worthwhile things to care about. I’ll miss aspects of my younger self, but I’m optimistic that I’ll like my older self more.

As long as we measure others and ourselves by what we have and how we look, life is inevitably a discouraging experience, characterized by greed, envy, and a desire to be someone else.

I think about Warren Buffett’s Inner Scorecard and how you can live a truer and more fulfilling life by measuring yourself by your own standards. I used to compare the growth and progress of Barrel to other agencies, and it would drive me nuts that we weren’t keeping pace or not doing as well. I’ve gotten a lot better at focusing on an inner scorecard, and this has made work a lot more enjoyable.

Though a straight line appears to be the shortest distance between two points, life has a way of confounding geometry. Often it is the dalliances and the detours that define us. There are no maps to guide our most important searches; we must rely on hope, chance, intuition, and a willingness to be surprised.

This quote reminds me of my sister, who has traveled wide and far across the world, living a nomadic and adventurous existence. She has really embraced a life full of surprises. I used to think that this way of life was irresponsible, but I’ve come to appreciate her experiences and how it’s shaped her into a thoughtful and open-minded person, far beyond what I can imagine. For someone who has worked on the same business the past ten years in the same city, it’s a good reminder for me to open my mind to chance and some surprises.

The process of learning consists not so much in accumulating answers as in figuring out how to formulate the right questions.

I’ve given a lot of thought to the idea of formulating questions and how the ability to ask good questions can create a lot of value. At work, I often find myself evaluating the performance of employees based on the types of questions they’re able to ask. I evaluate my own performance in client meetings and calls based on the types of questions I’m able to ask. Questions reveal a great deal about how much someone understands and grasps certain subjects and concepts and also speaks to the person’s level of curiosity and intellect. Sort of related: the topic of questions also makes me think about a line from an old ESPN commercial with Chris Berman where he says, “There is no such thing as a stupid question. Just stupid people who ask questions.” Kinda mean, but it’s funny.

One of the things that define us is what we worry about. Life is full of uncertainty and random catastrophe. It is easy, therefore, to justify almost any anxiety. The list of fears that people carry with them is long and varied, and a function of the information with which we are bombarded.

I’ll mention meditation again. I worry a lot less about unimportant things by being able to let go quickly. The things I worry about, I try my best to process them into tasks I can work on. Anything outside of my control, I try my best to keep off my worry radar.

To imagine that we are solely, or even primarily, responsible for the successes and failures of our children is a narcissistic myth.

Here, too, I’m reminded of my parents and how hands-off they’ve been in my life. They only wish me happiness and good health and are unconcerned with any specifics of my successes or failures unless I want to share with them. I am eternally grateful, and I, too, will strive to be such a parent.

Nostalgia for an idealized past is common and usually harmless. Memory can, however, distort our attempts to come to terms with the present… What happens as we try to come to terms with our pasts is that we see our lives as a process of continual disenchantment. We long for the security provided by the comforting illusions of our youth. We remember the breathless infatuation of first love; we regret the complications imposed by our mistakes, the compromises of our integrity, the roads not taken. The cumulative burdens of our imperfect lives are harder to bear as we weaken in body and spirit. Our yearning for the past is fueled by a selective memory of our younger selves… Our constant challenge is not to seek perfection in ourselves and others, but to find ways to be happy in an imperfect world. We are impeded in this effort if we cling to an idealized vision of the past that insures dissatisfaction with the present.

One transformation that I’ve felt within myself in recent years is a distancing from the feeling of nostalgia. I was once fond of thinking and talking a lot about “the good old days”, often as an escape from whatever I had to face in the present moment. Part of the transformation has come from becoming more and more comfortable with embracing whatever stands in front of me. In fact, I get excited thinking about what’s next, whether it’s tackling a hairy problem or engaging in a strenuous activity. The other part is about repressing the tendency to wallow in regrets and what could have been. I try hard to block this out of my mind. I accept that I’ve made mistakes, that I’ve learned a great deal, and that what matters most is my next move. A great book that I think about from time to time is Ken Grimwood’s Replay, in which a man dies and wakes up as his 18-year-old self, “replaying” his life over and over again. The big takeaway for me was that the game is available to play every single day. But instead of going back 25 years to a younger self, I’m already in the game playing for my older, future self.

For most of us the process of nursing blame for past injury distracts us from the essential question of what we need to do now to improve our lives.

Breathe, let go, be productive. In living my life, I want to be the person who can consistently overcome “past injury” and work towards a better future. The right thing to do takes courage and discipline. It’s also a lot less taxing and drama-free.