Reboot - Jerry Colonna
One-Sentence Summary:
A thought-provoking book on the value of radical self-inquiry for a person but also the organization he leads, through the coaching and story of the VC turned CEO whisperer.
Rating On Time Of Review:
A thinker. A reference book for the questions. It needs to be read at the right time, like most books. That’ll make the difference of whether it’s a 3/10 or a 8/10.
Book notes below. My thoughts are in italics. Opinions are mine during the time of review.
Date Reviewed: July 6, 2020
Introduction
“Take a random group of entrepreneurs, for example, and do a quick unscientific survey by asking them to raise their hands if they grew up in an environment where at least one parent had disappeared or left or was never present. Most hands will shoot up. Early promotion into adulthood is often painful and equally often a sign of an early promotion into leadership…… you may find that leaders who have built their company may have unconsciously stacked the team with other folks who experienced such early promotions.” / An anecdotal litmus test? It’s an interesting model to keep in mind when considering what drives people to take on the rough path of entrepreneurship.
**Powerful questions to be mindful of:
How did my relationship to money first get formed and how does it influence the way I work as an adult? What was the belief system around money and work that I grew up with?
How can I lead with the dignity, courage, and grace that are my birthright? How can I use even the loss of status and the challenge to my self-esteem that are inherent in leadership to grow into the adult I want to be in the world?
In what ways have I depleted myself, run myself into the ground? Where am I running from and where to? Why have I allowed myself to be so exhausted?
Who is the person I’ve been all my life? What can that person teach me about becoming the leader I want to be? What was the story my family told about being real, being vulnerable, being true?
Why do I struggle so much with the folks in my life? Why are relationships so difficult? What am I not saying to my co-founder, my colleagues, my family members, my life partner that needs to be said?
What’s my purpose? Why does it feel I’m lost while I struggle to move forward? How do I grow, transform, and find meaning?
How has who I am shaped the ways I lead others and myself? What are the unscious patterns of my character structure that are showing up in my organizations?
How might I survive my life of heartbreak? How might I live in peace?
What kind of leader and adult am I? What is enough? How will I know when my job is done?
Chapter 1
“I am not what has happened to me. I am what I choose to become.” - Carl Jung
What great leaders use radical self-inquiry to become more authentic. Become their true selves. They also: “…create the spaces for each of us to do the same, turning our organizations into places of growth and self-actualization. They infuse the profanity of work with the sacred duty of Work: the opportunities to lead, to grow into their whole selves while nurturing others, encouraging them to do the same.”
Chapter 2
“Learning to lead yourself is hard because it is painful. Growth is painful; that’s why so few choose to do it.” / one of the reasons it is painful is because there is no answer. People are always looking for answers and they come to Jerry for answers or some book that’ll give answers but there never are answers someone else can give you. It’s the painful process of figuring it out yourself.
“Self-doubt convinces us that there’s a magic path and if we can only find and follow the yellow-brick road, we’ll end up safe, warm, and happy - successful leaders, beloved adults, retiring in Millionaire Acres at the end of The Game of Life. And we’ll never be hungry, cold, alone or afraid again.” / the illusion.
“The goal is to buy low and sell high, not buy lowest and sell highest.” / Better to be approximately right than precisely wrong.
**Powerful questions: “..what do you really believe? What values do you hold? What kind of company do you want to build? And what kind of adult do you want to be?” / A continuous thread of examining the underlying beliefs/intentions that drove the error/mistake because it’s never about figuring out who was right/wrong from a decision but what needs to be learned from it.
Chapter 3
“By not standing still, I was able to be the object of everyone else’s projections of who and what I should be. Too busy to live my own life, I took direction from the affirmations of others.” / too often, people are afraid to stop and let their thoughts consume them. This sometimes leads to the desire to continuously be busy and doing things to never let hte mind rest and calibrate. This was a fault of my youth and is something many ambitious people will need to learn to hone in on. It’s important to not let the expectations of others impact/influence your decisions.
**The question to always ask yourself: “What am I not saying that needs to be said?” / A possible antidote to all the aches in your mind and heart. A forced question for honesty.
“… panting through work is a lousy strategy. It feeds the anxiety of never enough; it gets in the way of thinking clearly; and it convinces you to mistake motion for meaning.”
**“… things are always falling apart; always.” / the faster you accept it, the less it will surprise you when shit never works out.
Hard questions to ask yourself: “Who am I? What do I believe about hte world? What do success and failure mean to me (and not to everyone else)? What kind of adult do I want to be? And, most helpful, how have I been complicit in creating the conditions in my life that I say I don’t want?”
Chapter 4
“Until you make the unconscious conscious, it will direct your life and you will call it fate.” - Carl Jung
Chapter 5
“It’s absolutely irrational to try to argue rationally with someone who is being irrational.” / same could be implied with trying to convince people of a view you hold. Most will not want to be convinced. It’s silly to think that… they will agree with you when they realize what you were trying to convey. But they’ll tell you how they saw it all on their own without you. Such is human nature.
**Jerry goes through his troubled childhood to dissect meaning and purpose that was embedded in the conditions of his childhood. He uses that as a way to share how one must come to understand the causes and conditions of his childhood to gain an understanding for how that has shaped his current belief systems as an adult. This was quite an important chapter for me as I ended up deeply examining my own childhood. The estranged relationship I’ve had with my father, the period of immigrating to Hong Kong without my mother, and how the continuous feedback I received of being told I’ll never amount to anything may have all contributed to my detest for authority and a possible ‘need’ to prove people/society wrong.
Questions to find habits/patterns for radical self-inquiry:
What parts of me are being projected onto the other person?
How do I reclaim those parts of me?
What do my reactions say about me?
Why do I do what I do?
Why do they do what they do?
What need for love, safety, or belonging might they be trying to meet with their irrational behaviour?
This entire chapter is probably worth re-examining over time. It looks into what Jerry calls the “Irrational Other”. It’s the embodiment of all the negative self-talk/doubt we have in our minds. Most of us, I think. The negative beliefs that were instilled in us by people in our childhood. This Other not only influences our decisions but also impacts how our relationships form with people around us. Hence, it becomes important to look deeper into it and resolve it. For me, telling my parents about all the trauma from my childhood was the first step.
Chapter 6
“… no one knows if they’re doing the right thing. No one.” / an excerpt from Jerry’s discussion with a colleague who felt tortured by not knowing what he should do with his life despite being at an age (44) where he left like society demanded he should know.
More powerful questions: “Is it supposed to feel this confusing? Where do I belong? If my life isn’t unfolding as I expected, then what am I doing?”
**“We’re all so desperate to move up and to the right. We’re convinced that any motion that isn’t straight, direct, up and to the right is somehow not part of the path. What if being lost is part of the path? What if feeling lost, directionless, and uncertain of the progress is an indicator of growth?What if it means you’re exactly where you need to be, on the pathless path?” / This is a crucial point. The pathless path. Not some graph going up to the right for some linear progression. There is no proper path.
**“…a map is a poor substitute for a life lived. The truest guide isn’t the mind of a guru but your broken, scared and scarred, lonely heart.” / focus on being present. And enjoy it. Also, it’s this realization that probably is an indication that you’re entering a new game. One where you can’t live a life of ignorance anymore. Instead of making maps and detailed plans… Jerry brings up a point of focusing on incremental progress that was directionally correct. The approximately right approach…”… where the meaning of your life was a function of the meaning of each day. And each day, an expression of your life.”
“If I allow myself, than I can have an infinite number of do-overs.” / embracing the ‘beginner’s mindset’. It’s your life. The regret one way have of not taking the most optimal path in the past, and the subsequent desire to be perfect for the future path….. it’s all so irrational but so real. A hard but necessary mindset that can help is to realize that you are the judge of your life and you can give yourself a do-over whenever. It only seems ridiculous if you impose the ridiculous values of society on you with limitations like age, education etc…
“What stopes you from building the life you really deserve?”
**“Work - our careers, our professions, our jobs - is neither the blissful expression of deep purpose nor the dreadful obligation that stands in the way of being ourselves. Work is an opportunity for a daily realignment of the inner and outer, a daily do-over of life expressed with integrity.” / instead of focusing on purpose… what if what you do every day defined you? What if instead of trying to discover a path, you focused on a way of being. Where each day is a new opportunity. A do-over every day. As long as we make incremental progress to an approximate direction… every step becomes purposeful.
Chapter 7
**“The pain of hating our own creation is a consequence of our investing too much of our sense of being into the company, the product, the creation. When we hang our sense of self on the whisper of an idea; when we unwittingly insist that our love, safety, and belonging depend on what we do and, most important, how others feel about our feelings, our actions, and our work; then we leave little space for anything other than bitter, existential suffering.” / the trap of making work your identity.
“For those who hold power, the price of unsorted baggage is paid by those with whom they pass their days - their coworkers, peers, direct reports…. the toughest, most intransigent, most troubling aspects of the collective unconscious blithely referred to as culture can more effectively be worked when the leader commits to doing self-inquiry work.” / the impact a leader can have. Why leaders need to focus inwards and address the beliefs that are limiting them for the better of everyone else.
“The commitment to sort the unsorted baggage turns leadership into a journey of self-actualization. With that, work becomes not the impediment to our lives… but the way we can live out our lives as they were meant to be.”
“May leadership be for you / A true adventure of growth.” - John O’Donohue
Chapter 8
“Resiliency isn’t the goal; it’s the path. The goal is the equanimity of a warrior.” / It’s never the goal to be hit in the face with all kinds of curve balls and tragedies. It’s just what we encounter and we need to be able to get through each painful experience. We are not trying to experience pain.
“True grit, the capacity to stick with something to the end, stems from knowing oneself well enough to be able to forgive oneself. To have inquired deeply and steadily enough to find the deep sense of purpose that is beyond a personal mission.” / I equate this with the feeling of ‘there’s nothing else to do with my life other than what I am doing now’. Jerry notes how resiliency and grit are different. Even with grit, most people misunderstand. False grit is akin to the stubbornness of just pushing onwards to prove something to your underlying fears or to prove to other people. That is brittle.
Chapter 9
“What makes hard things like running a business complicated is leaders avoiding doing their work. When we don’t do our work, we stand in the way of our growth. When we fail to grow, we hold back others, and we warp and twist the organizations we seek to serve…... What makes all of life complicated, and not just hard, is this unwillingness to do the work that’s ours to do; our unwillingness to live the examined life.”
Critical questions: “What am I not saying that needs to be said? What am I saying that’s not being heard? What’s being said that I’m not hearing?”
**“Each of us is an artist of our days. The greater our integrity and awareness, the more original and creative our time will become.” - John O’Donohue / great writers write amazing pieces that are their own stories. Stories of themselves. It’s through reading these stories that we can discover our own. Hence why people needs to read wide and often.
“I can’t think of a sadder way to die than with the knowledge that I never showed up in this world as who I really am. I can’t think of a more graced way to die than with the knowledge that I showed up here as my true self, the best I knew how, able to engage life freely and lovingly because I had become fierce with reality.” - Parker Palmer
Great questions are ones that are open-ended and honest. Ones you don’t have know the answers to.
**“Tell me what success and failure mean for you and we can use your answers to chart a path. Tell me if, after imagining your children working for your company, you feel shame, fear, or pride, and I’ll tell you if you’re building a worthwhile company.”
Disclaimer - I’m writing this for myself. For my past, present and future self. Much of what I write is my opinion. If it somehow ignites agreement in you then great, I’d love to hear about it. If it sparks disagreement in you, don’t reach out because I don’t care for it. There always are obvious exceptions and the flawed person in me hasn’t considered them all.