Tag: Annie Duke

  • The Worthwhile Endeavors

    “Optimism makes you less likely to walk away while not actually increasing your chances of success. That means that being overly optimistic will make you stick to things longer that aren’t worthwhile. Better to be well calibrated. Life’s too short to spend your time on opportunities that are no longer worthwhile.” — Annie Duke, Quit: The Power of Knowing When to Walk Away

    In all honesty, last night I was planning to make this my last blog post. To end with a bang on the 4th of July seemed poetic. I’ve thought this before, but talked myself into sticking with it for a round number or a date with particular meaning for me. The 4th has particular meaning for me and so it felt appropriate to roll out the Annie Duke quote and wrap this thing up.

    Naturally, this is why I write in the morning, with a fresh mind not yet beaten down by the realities of the world. This is why I read poetry and listen to music with the ear of a philosopher. This is why I travel to places that leave me gobsmacked. And this is why I favor quiet conversation with the smallest of circles, that we may each be heard. The well was empty last night, it’s not quite so this morning.

    No, I’m not ready to stop writing just yet. But the thought was a red flag for me that I must pursue other worthwhile endeavors to ignite the kindling before it floats away in the winds of time. There’s a whole world out there awaiting our graceful experience with it. So frequently asking ourselves whether we should stick with things opens up the possibility that maybe we shouldn’t. Recalibrate. And in the absence of obligation to that thing other opportunities may open up before us.

  • A Series of Outcomes

    “Perseverance is not a long race; it is many short races one after another.” — Walter Elliot

    “The future we have bet on unfolds as a series of outcomes.” — Annie Duke, Thinking in Bets

    The journey of becoming what’s next never stops, does it? We just move from one version of ourselves to the next, and then the next still, until we reach the end of our days. The trick is to build off each, creating something bigger than our current selves in the process. Life is reinvention and renewal, but it is also fragile and fraught with danger. We must be bold in our choices and tough in our resolve.

    “The thing about life is that you must survive. Life is going to be difficult, and dreadful things will happen. What you do is move along, get on with it, and be tough. Not in the sense of being mean to others, but being tough with yourself and making a deadly effort not to be defeated.”
    ― Katharine Hepburn

    Being hyper-aware of the race we’re currently in is essential to savoring a life well-lived. So too is being hyper-aware of the direction we’re going in, that we might stay on course for who we aspire to be in the next version of ourselves, and the one after that. We must play the long game even as we deal with the cards we’ve been dealt in this hand.

    There is no other way to progress through this life than one step at a time. Sometimes we leap, sometimes we take smaller steps than we’d like. Sometimes we go sideways around an obstacle. But we must feel the urgency of the moment and act. Life is urgent because life is so brief. We simply have no time to lose if we are to reach the places we’ve set our course for. And yet we must take the long view, even as we deal in today. Life is now, with an eye on whatever we can make of then. We must get on with it.

  • 11 of My Favorite Books Read in 2020

    Looking back on this maddening year, I found I read a lot of poetry that inspired and a lot of page-turner novels that distracted. It would be easy to make half this list collections of Mary Oliver poems, but I subtracted poetry from the list altogether to focus on the craft of the written novel or book. Still, I like to bend the rules, so in making my list of top ten favorite books for the year, I chose eleven. This was a nod to Charlie Mackesy, who spun a bit of magic in a year where it was essential. Illustrating the timeless nature of books (or perhaps how far behind I am in catching up), only four of the eleven were released in 2020. These eleven books are listed in no particular order, largely because there’s a bit of wonder in each of them. Each informed and delighted me.

    Breath: The New Science of a Lost Art by James Nestor
    “The more oxygen life can consume, the more electron excitability it gains, the more animated it becomes. When living matter is bristling and able to absorb and transfer electrons in a controlled way, it remains healthy. When cells lose the ability to offload and absorb electrons, they begin to break down.”

    I find myself thinking often about breathing after reading this book. Waking up with a dry mouth reminds me I need to be better at nasal breathing, when hiking I try to control my breath and focus on how I’m taking in oxygen, and when I chew almonds I crunch with satisfaction, knowing it helps release stem cells and increase bone density. This book is highly informative and strongly recommended for anyone, well, breathing.

    The 80/20 Principle: The Secret to Achieving More With Less by Richard Koch
    “Equality ends in dominance: that is one of the messages of chaos theory. The 80/20 Principle’s message is different yet complementary. It tells us that, at any one point, a majority of any phenomenon will be explained or caused by a minority of the actors participating in the phenomenon. Eighty percent of the results come from 20 percent of the causes. A few things are important; most are not.”

    This was the most highlighted book of the bunch. Honestly, there were chapters I skimmed over because they didn’t sing a tune I wanted to hear, but the theories here are sound. I wish I’d read this book at the beginning of my career, but it’s not too late to implement the core principles in many aspects of my life.

    The Splendid and the Vile: A Saga of Churchill, Family, and Defiance During the Blitz by Erik Larson
    Hitler wanted still more force applied against Britain. America seemed increasingly likely to enter the war but would do so only, he reasoned, if Britain continued to exist. On March 5 he issued another directive, No. 24, this signed by Field Marshal Wilhelm Keitel, chief of the High Command of the Armed Forces (OKW), aimed mainly at how Germany and Japan might coordinate strategy under the Tripartite Pact, which both had signed with Italy the preceding fall. The goal, the directive said, “must be to induce Japan to take action in the Far East as soon as possible. This will tie down strong English forces and will divert the main effort of the United States of America to the Pacific.” Beyond this Germany had no particular interest in the Far East. “The common aim of strategy,” the directive stated, “must be represented as the swift conquest of England in order to keep America out of the war.”

    We all grew up sort of knowing about The Blitz. This book neatly sums up just how tenuous the situation was. I fancy myself well-informed about World War II, but I learned far more from the The Splendid and the Vile than I expected to. For all our complaints about the pandemic, most of us have no idea what real sacrifice is. Larson brings us closer to understanding with this book.

    The Boy, the Mole, the Fox and the Horse by Charlie Mackesy
    “What do you want to be when you grow up?” asked the mole.
    “Kind,” said the boy.


    A beautiful, simple book. I picked this up for my daughter as a gift and read it quickly before wrapping it up. If 2020 kicked you in the ass, read this. Then read it again. The Boy, the Mole, the Fox and the Horse is art, meditation and a warm hug disguised as a book.

    Longitude: The True Story of a Lone Genius Who Solved The Greatest Scientific Problem of His Time by David Sobel
    The zero-degree parallel of latitude is fixed by the laws of nature, while the zero-degree meridian of longitude shifts like the sands of time. This difference makes finding latitude child’s play, and turns the determination of longitude, especially at sea, into an adult dilemma—one that stumped the wisest minds of the world for the better part of human history.

    I’ve danced around this book for years, never getting around to reading it. And then I went to Greenwich and saw the chronometers ticking away in their plexiglass cases and resolved to get right to it when I returned home. This is a story of perseverance solving what was believed to be the impossible. A delightful book.

    Mayflower: A Story of Courage, Community, and War by Nathaniel Philbrick
    No longer mindful of the debt they owed the Pokanokets, without whom their parents would never have endured their first year in America, some of the Pilgrims’ children were less willing to treat Native leaders with the tolerance and respect their parents had once afforded Massasoit.

    Living in New England, you can’t really get away from the story of the Pilgrims. But the part we seem to forget with the Pilgrims is how much they relied on luck and the strategic kindness of Massasoit to survive at all. It seems I’m a descendent of a Pilgrim (or two), so I’m told, and that lineage makes me all the more indebted to the Pokanokets who assured that those first few years here weren’t the last for the passengers on the Mayflower. As the quote above suggests, that indebtedness seemed to skip the next generation, paving the way for the tragedy of King Phillip’s War.

    Draft No. 4: On the Writing Process by John McPhee
    That four-to-one ratio in writing time—first draft versus the other drafts combined—has for me been consistent in projects of any length, even if the first draft takes only a few days or weeks. There are psychological differences from phase to phase, and the first is the phase of the pit and the pendulum. After that, it seems as if a different person is taking over. Dread largely disappears. Problems become less threatening, more interesting. Experience is more helpful, as if an amateur is being replaced by a professional. Days go by quickly and not a few could be called pleasant, I’ll admit.

    Reading McPhee, like reading Hemingway, it’s easy to get just a bit intimidated. The beauty of this book is that he pulls back the curtains to show you the way. Great research, editors and fact checkers smooth out the rough edges and polish the story, but the work you put into it makes the finished product shine.

    Cape Cod by Henry David Thoreau
    The ocean there is commonly but a tantalizing prospect in hot weather, for with all that water before you, there is, as we were afterward told, no bathing on the Atlantic side, on account of the undertow and the rumor of sharks. At the lighthouse both in Eastham and Truro, the only houses quite on the shore, they declared, the next year, that they would not bathe there “for any sum,” for they sometimes saw the sharks tossed up and quiver for a moment on the sand. Others laughed at these stories, but perhaps they could afford to because they never bathed anywhere. One old wrecker told us that he killed a regular man-eating shark fourteen feet long, and hauled him out with his oxen, where we had bathed; and another, that his father caught a smaller one of the same kind that was stranded there, by standing him up on his snout so that the waves could not take him. They will tell you tough stories of sharks all over the Cape, which I do not presume to doubt utterly,—how they will sometimes upset a boat, or tear it in pieces, to get at the man in it. I can easily believe in the undertow, but I have no doubt that one shark in a dozen years is enough to keep up the reputation of a beach a hundred miles long.

    This book, like Philbrick’s Mayflower, informs the native New Englander about the places that once were the places that now are. I have a stack of quotes from this book that I’m saving for other blog posts, but the one above reminds us that the question of sharks has been around a lot longer than we might believe. Like Thoreau I’m much more concerned about undertow when swimming in the surf, but hey, you never know…

    Siddhartha: A Novel by Hermann Hesse
    “Were not all sufferings then time, and were not all self-torments and personal fears time? Weren’t all the difficult and hostile things in the world gone and overcome as soon as one had overcome time, and as soon as time could be thrust out of the mind?

    I’ve heard enough people recommend this book that eventually I had to read it, and I finished it in 2020. Amazingly, it feels like I read this a decade ago, for all that’s happened this year. Like The Alchemist, it’s a story that teaches you a bit about yourself as you wade through it.

    Thinking in Bets: Making Smarter Decisions When You Don’t Have All The Facts by Annie Duke
    What makes a decision great is not that it has a great outcome. A great decision is the result of a good process, and that process must include an attempt to accurately represent our own state of knowledge. That state of knowledge, in turn, is some variation of “I’m not sure.”

    How do you make decisions? How can you make better, more informed decisions when you don’t have all the facts? And what is a game of strategy versus a game of chance? This book uncovers some of these answers. As with anything, there’s book smart and there’s street smart, and reading about it and understanding it in real life are different things. Duke sprinkles in some street smarts hard won on the poker tables.

    Sailing True North: Ten Admirals and the Voyage of Character by James G. Stavridis
    “The contemporary malaise is the unwillingness to take chances. Everyone is playing it safe. We’ve lost our guts. It’s much more fun to stick your neck out and take chances. The whole attitude is to protect yourself against everything, don’t take chances. But we’ve built this country on taking chances” (Quoting Rear Admiral Grace Hopper)

    A quick, enjoyable read that offers lessons learned from some of the great “Admirals” in history. This is examination of character in ten short biographies, but also an unflinching look at racism and sexism in the Navy and how that battle continues to be fought to this day. And there’s no mistaking the Admiral’s feelings about character in certain political leaders we currently suffer through. A timely message for all of us.

  • Scenario Planning and Backcasting

    Consider a broad range of possibilities for how the future might unfold to help guide long-term planning and preparation…. The reason why we do reconnaissance is because we are uncertain. We don’t (and likely can’t) know how often things will turn out a certain way with exact precision…. By at least trying to assign probabilities, we will naturally move away from the default of 0% or 100%, away from being sure it will turn out one way and not another.” – Annie Duke, Thinking In Bets

    I was giving this book a few days to digest before coming back to this concept of scenario planning Duke writes about. To me this is the heart of her book (the title does give it away). I’m not a poker player, but I do think in future probabilities in my career, and found this concept helpful in how I’m looking at 2020 and beyond. This goes beyond the usual weighing the probability percentage on an opportunity you’re forecasting to close, and looking at the bigger picture. Will this tactic work on this project? Maybe. Will it hold up as sustainable for the next five years? Harder to determine. How will changes in the economy impact the probability of this outlook? Does living in the same house for the next ten years increase or decrease the likelihood of retiring with a big enough nest egg?

    These are the predictive exercises that clarify a vision for your future. When you combine it with another tool in your belt you can begin to identify actionable steps to get you there. Duke doubles down in covering the concept of backcasting, or working backwards from a positive future:

    Identify the reasons they got there, what events occurred, what decisions were made, what went their way to get the enterprise to capture that market share. This enables the company to better identify strategies, tactics, and actions that need to be implemented to get to the goal.” – Annie Duke, Thinking In Bets

    The timing of this book was good for me as I map out the year ahead. I’m familiar with both techniques, but I’m not proficient at either. That’s something to work on as I refine my business plan for the year, and equally important for the other objectives in my life. A call to action, if you will, to clarify the vision and the steps needed to reach that outcome.

  • Better Decisions

    In most of our decisions, we are not betting against another person. Rather, we are betting against all the future versions of ourselves that we are not choosing.” – Annie Duke, Thinking In Bets

    As we enter the first full work week of the New Year, I’m focused on this concept of Second Order Thinking and working to apply it better in my life.  In short, asking what will be the consequences of doing this versus that in the first order, the second order and the third order?  If I eat this donut because it looks delicious (first order), then I’ll add more empty calories and gain weight (second order), which will make me more stressed out in the future when my pants are getting too snug (third order).  Second and third order thinking is a way of fast-forwarding into the future as you decide on whether or not to do something in the present.  It gets you out of the self-centered immediate gratification of now and looking at the ultimate satisfaction of then.  Ray Dalio describes it as the lower-level you winning out over the higher-level you.  I haven’t been consistent with this in my lifetime, particularly when it comes to snacking.  I’d say it’s time to look up from the proverbial candy dish and think beyond the moment.

    “Decide what to be and go be it.” – The Avett Brothers, Head Full of Doubt/Road Full of Promise

    I didn’t believe I’d like the book Thinking In Bets.  I’m not a poker player and have no desire to immerse myself in the world of poker. They wear sunglasses indoors and pull their hats down low to cover expressions on their faces.  I mean, who wants to hang out with people doing that?  But this isn’t a book about poker, it’s a book about decision-making.  And making better decisions is something I’ve been working on in myself for some time.  It started with this idea of Second Order Thinking, where you weigh the consequences of your decision now and into the future.  I’ve made plenty of decisions in my lifetime that made sense in the immediacy of the moment that turned out to be bad decisions down the road.  And a few that I thought weren’t great early on that turned out to be brilliant (and lucky) decisions with hindsight.

    We’re the average of the five people we hang around with the most, as Jim Rohn would put it.  Applied to what I’m reading, I’m currently hanging around with stoics, poets and experts in creating and sustaining better habits.  And now I’ve invited decision-making experts to the party.  I’m okay with that mix, and will enhance it over time.  But reading about something isn’t doing something.  That’s a trap that you realize as you read book after book without applying the knowledge you pick up from all that reading.  No, the rubber meets the road when you take action.  Applied knowledge, repeated daily, leads to exponential improvement over time.  I’ve seen that working in all things over the course of my life.  The focus now is to improve the decision-making process so I spend that time on better, more productive activity.  Dance a bit more in the higher-level self.  Now is as good a time as any to get to it.