 I used to be young and ambitious. Now, I guess I’m just ambitious.
Over the last 25 years, I have had the great fortune to work with hundreds of highly ambitious people across all walks of life and work. From fellow athletes to fellow artists, from community organizers to the marginalized young people we worked with, from startup founders to investors, from ministers to gang members, from teachers to doctors to politicians to parents, I have seen ambition in seemingly infinite forms. And yet, it dawned on me recently that despite the many topics in leadership I have studied and lived and taught over these 25 years, I have never put much thought to ambition. So, I tried to categorize people throughout my career to see if any patterns might emerge on ambition and where it comes from and to what end. Through this reflection, I discerned 4 archetypes of ambition that are not mutually exclusive, but the people I have known who I would call ambitious are driven predominantly by one with typically a clear second coming in behind it. Acquisitive People driven by acquisitive ambition look out into the world and seek to acquire what’s in front of them. They are effectively ambitious consumers of opportunity. They want to win, but they also really want others to acknowledge they won. At work, they may look for the promotion with their contribution or value creation a secondary notion. Their ambition is the position. Their purpose and goal are the external reward. Their ambition can serve them well in highly structured career paths. Advancing People driven by advancing ambition are trying to get somewhere and their drive and reward system are deeply rooted within. These are the people who live and work from their values and internal drivers and their work persists whether anyone recognizes them or not. They may be seeking a better life. They may be seeking to create more opportunity than they had. They may just be doing the thing they love. Their ambition can serve them well in creative or entrepreneurial settings where they make their own path. Altruistic People driven by altruistic ambition have something deep within that drives them to do right by the world. They are motivated and rewarded by the success of others which ties fundamentally to their sense of self. These are the people who always step up to help, to give, to mobilize, to engage even when they may not be directly affected by a situation or circumstance. They often sacrifice personal benefit for the sense of contributing to the greater good. They tend to give credit for success more than claiming it. Their ambition can serve them well in purpose-driven communities and organizations. Associative People driven by associative ambition want to help others but they also want to be recognized and known for it. They often do good in the world but can come across at the same time as self-promoters. They want to be seen doing good work and seen and associated with people and organizations that do good work. For them, the good deed is made better by the recognition that they were part of it. Their ambition can serve them well in societal and political settings built on social or economic standing and status. As I mapped out these quadrants, I realized again that we all possess a bit of each of these ambitions. I also recognized that my ambition has changed over time as I have aged, started a family, and changed careers. While my dominant ambition hasn’t changed, the degree to which it drives me has. So, what’s your ambition? Can you guess mine?
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 I was asked recently how you teach strategic thinking. The actual ask went something like this: “You’re a good strategic thinker. How do you do it? And, how do you get others to think like you do?”
To be clear, I’ve taught a lot of things, but never this topic specifically. So, I thought it was a great prompt to think more about my thinking and my practices – which I admittedly don’t always understand. And, I’m sure some of these are solidly based on proper strategic thinking frameworks I don’t know about, or have read about and forgot I read about them. I do know they are all rooted in how I learned to think and work as an artist, an organizer, and an entrepreneur. So, here are my 10 tips for getting more strategic in your thinking: 1. Look two steps ahead and one step behind. - Two steps ahead: Where could this go? What are the possibilities? What are the probabilities? What are the pitfalls? What are the next questions that will arise as a result? What are the next challenges it will expose? - One step behind: How did we get here? To the current state? To the current mindset? To the current decision? What is guiding our thinking today? And, back to two steps ahead: is this what should be guiding our thinking into the future? 2. Define your assumptions (so you can keep testing them). This is our business. This is our ideal customer. This is our value proposition. These are our markets. These are our products and services. These are our points of difference. I’ve worked with hundreds of team members from the executive level to the frontline, and it’s rare they can confidently define these much less do so in full alignment with each other. 3. Be strategic about what your being strategic about. We can think strategically all day about how to solve a problem or seize an opportunity but if that’s not the right strategic problem or opportunity then we are still not being strategic. We must distinguish between presenting problems and latent problems, today problems and not-today problems, opportunities and the right opportunities. 4. Align on “The Why”. If you, your team, and any other stakeholders aren’t aligned on “the why” of whatever it is you are doing, then when it gets hard, things are going to fracture. Back to #2, we must not assume alignment. We should do the work to put “the why” into words so that it can consistently be shared across stakeholders and over time and not morph as a function of memory or interpretation. 5. Align on why. “The Why” is about purpose. Aligning on why is about rationale. Why is this the right move? The right direction? The right investment? The right time? The right team? A good idea is only good in as much as you can provide these answers and convey them to others. 6. Treat everything as a tradeoff. Every choice we make to do something is an implicit choice of what we won’t do. We must discuss and make decisions based on both sides. 7. Assume you are wrong. Assume they are wrong. But, be nice about it. It is the opposite of strategic thinking to assume we have it all figured out, we’ve asked all the right questions, and we have all the right data. Poke holes in everything as a matter of strategic process, not judgment. 8. Stop nodding in agreement at blur words and vague ideas. I mean, strategy…who disagrees we should be strategic? Everyone nods for respect and teamwork and synergy. I don’t know what any of those mean to you and certainly not to your business. Be wary of too much agreement when you haven’t even made sure you agree on what you’re talking about. 9. Focus on the system. What part of the system are we not thinking or talking about? What are we missing? What stakeholders have we not aligned? How does energy, investment, effort, and/or required skill shift within the system if we go this way or that? A system with one underperforming part is an underperforming system. A strategy with one underperforming part is an underperforming strategy. 10. Understand your starting point. Strategy doesn’t matter unless you have the people to execute it. Your teams will determine if your intended strategy becomes your delivered strategy. Be honest about who you have and if they are ready, or what it will take to get them ready. Strategy is useless without execution.  I sometimes get asked about the ROI on the work that I do. Whether I am talking about leadership, emotional intelligence, empathy, communication, trust, developing others, conflict management, or decision-making, it’s all a function of building relationships that build teams that connect with customers that build businesses.
So, let me flip it around a bit and pose the presumed, if underlying, question: what is the ROI on a relationship? How much is your spouse worth to you? Your kids? Your friends? Your neighbors? What’s the dollar amount you expect to get back from loving them, caring for them, cultivating them? What are they worth? What’s the return on investment for your time, energy, and effort in these people? Just asking these questions stirs a kind of queasy feeling. It feels almost perverse because we don’t look at these relationships as transactions, as quantifiable. Most of us do, however, look at them as the investments that create the most value in our lives, the most joy, the things that mean the most to us, that motivate us, give us purpose, connection, and belonging - and yet, they have no consistently defined return on investment. When you convert the potentially transformational into the transactional, the relational into the purely functional, you’re destroying value in the name of capturing it. At some point, we have to remember we are just humans working with other humans in human-created systems trying to serve other humans. We just call it a business. If you aren’t actively cultivating relationships because you can’t defend the cost, then good luck defending the cost of not cultivating them.  One of the reasons I write is for my daughters. I want them to know me at some point, perhaps when I’m gone but hopefully before that, in a way I can only write about and can’t always express otherwise - thoughts from my more intimate moments of personal reflection. I try to capture funny anecdotes about the shit-show times of parenting. I try to capture the sweet moments I don’t want them or me to forget. I talk about my own life and particularly the loss of my Dad to suicide in ways I just want them to understand but can be difficult to verbalize.
Just a few minutes ago, I wrote in a reply text to an old friend who was just checking in that I was "drunk on being Dad" right now. I wrote it, read it, and it seemed like something I should be sharing with my girls. So, here we are. Lately, I’ve found profound and irrational joy in the young women they are becoming – which includes the flashes of the little girls they used to be, glimpses of emerging teens, and flash-forwards to the women they will be. And, even as I write this, I realize I should really be speaking to them, telling them directly the things that have me feeling a little woozy. Girls,
Parenting is hard and it is relentless. Sometimes, it helps to stop and have a drink of the good stuff. Cheers!  Just because the clock strikes midnight, and the calendar turns to January 1 doesn’t mean some magical transformation happens in our lives or that we’re suddenly ready or able to make such a transformation happen for ourselves. Pretending the passage of time is somehow also automatically the turning of a page is a setup for disappointment, self-doubt, and lingering unease. Suggesting that this mirage of an annual milestone called New Years is magically the time for starting things anew and changing course in our lives explains why most of the stuff we start in January as a year-long resolution has stopped by February.
I don’t mean to sound negative. I mean to sound honest, to be realistic about growing and changing rather than merely being hopeful or delusional we will grow and change. I suspect, if you are like me and like most humans, 2024 wasn’t all peaches-and-cream, and that didn’t change on January 1, 2025. My friends (4) from their 30’s to their 80’s are all still dead, and I am still mourning. My family member is still fighting cancer and managing a difficult recovery. I’m still raising my children in a world that many days frightens me, and most days frightens me for them. What I am reflecting on as I enter this new year is that it’s ok to let the New Year inspire goalsetting. In fact, it’s a good, symbolic moment for it. It’s ok for a New Year to be a time of optimism and planning for something better. But, it’s also a great time to look back at all the stuff that sucked about the previous year, to evaluate the scars we earned, to see what we can control and what we can’t, and to name the stressors and anxieties we are carrying into the next year. Knowing what past we need to let go of or what present we still need to work through is the only way we know what future we can honestly and freely run toward. If we are resolved to work on these things first, our New Year’s resolutions will become a lot more resolute. So, I want to offer a few atypical tips on New Year’s resolutions with the understanding that they will likely be far more meaningful than magical.
May we all be resolved to find peace and love and hope in the New Year knowing that it starts within us. Image: https://www.fastweb.com/student-life/articles/a-college-student-s-guide-to-new-year-s-resolutions  Life is full of stuff we can’t control, both big stuff and little stuff that can create chaos in our lives, work, and relationships. This reality just makes it that much more imperative that we avoid creating more chaos-inducing stuff for ourselves – that we control what we can control knowing that little choices today can create (or help avoid) big chaos tomorrow.
The goal is not to pretend we can avoid chaos altogether. I don’t think that’s life. The goal is to keep our chaos “resting state” at a level that gives us capacity to manage when the uncontrollable things hit. Managing our resting state then demands daily diligence and discipline around the little, controllable things. So, here are 10 ways you may be creating chaos today for your self tomorrow: 1. Not taking care of your mental health: Whether it’s managing stress, anxiety, Depression, grief, trauma, or otherwise, if you’re not managing it (or at least giving your best effort), it’s managing you and all of your relationships and work. 2. Not taking care of your physical health: Whether it’s exercise or sleep or what you eat, it impacts how you relate and respond to the world - adding chaos or neutralizing it. 3. Avoiding difficult decisions: Decisions that need to get made but don’t only get bigger and more complex in time. And, they don’t get easier or less necessary. 4. Avoiding difficult conversations: Conversations that need to be had but aren’t only get bigger and more complex in time. And, they don’t get easier or less necessary. 5. Not monitoring and managing your relationships: Relationships are dynamic and need tending to. Some relationships need more investment, some need less, and some you probably need to just let go of. 6. Cutting corners: When you sacrifice quality or completeness whether in work, relationships, or otherwise because you think you don’t have time or the energy to do things fully, it will almost always pay you back with a chaos flywheel. 7. Not defining and keeping your boundaries: People who can’t say “no” eventually create chaos for everyone around them. 8. Needing to be a fixer: Helping others is good. Enabling their chaos creation is not. Thinking you can fix their chaos only ensures you are now a part of it. 9. Being vague or ambiguous about your needs: Uncertainty in relationships or expectations breeds behavior, investment, and performance that are uncertain. 10. Failing to relentlessly prioritize: There is never enough time and yet we all have the same amount of it. We don’t find time or create it. We only prioritize it. Image: https://www.freepik.com/premium-vector/chaos-mess-circle-continuous-line-drawing_346070449.htm  I finished a leadership training a couple of weeks ago and paused to thank the participants before we wrapped up. I thanked them for their engagement and their participation. And, I explained to them that I had lost a friend and team member just two weeks before to a tragic and untimely death. After two days of adrenaline facilitating and actually enjoying it, I was clearly and quickly coming down off the high. Through tears, I thanked them for helping me find joy in my work again during such a terrible time. I explained that getting back in there and doing the work was one thing, but I hadn’t yet figured out how I would find joy in it.
Fast forward to today, about a month later, when I was out for a run in one of my sacred places, Shelby Park. I’ve been running lately without music because I recognize how noisy my head has been since he died. When I run, I just let my head be noisy until it gets tired and finally quiet. I just let it run while I run. I passed a woman going the other direction whose t-shirt said in bold letters: BRING JOY. I instinctively complimented her and after she’d passed thanked her somewhat to myself. That shirt planted a new thought path amidst the other noise in my head. It quickly dawned on me that I needed to reframe where I am and how I have been thinking about it since my friend’s passing. I need to stop looking for joy, trying to find joy, and instead concentrate on bringing it. Looking seems an endless, outward journey. Bringing feels like an empowering, inward prompt. (That’s a helluva t-shirt.) Over the last month, I’ve been looking. During my search, my “good mornings” to my team were practically non-existent for several weeks. They weren’t “good” mornings. They were shitty mornings. And, I’m shitty at faking it. I just needed to get through the day and get some stuff done and put one foot in front of the other. No more. No less. No joy. This last week, I somewhat unwittingly returned to the “good mornings” but still a bit half-heartedly. I’m trying or perhaps I’m just progressing and it’s not really about effort. I don’t know. I know my “good morning” is not insincere, but it’s also not what it used to be. Better, but joy would be a stretch. This is what was running through my noisy mind thanks to that t-shirt. And then, a bicycle approached going the opposite direction and it had two little girls in some sort of contraption on the back with a dad driving. The girls were facing each other, meaning one of them was looking forward in the direction the bike was going and one looking back to where it had been. As I passed, the girl facing forward broke into my noise with an enthusiastic “hello!” And, by the time I was responding in-kind, the other little girl said “goodbye!” It was cute and funny and kind of brilliant. I kept running now pondering these two little girls and slowly realized something important from that interaction: every moment is both a hello and a goodbye. It passes as quickly as it is acknowledged, often more quickly. This is a simple fact of life. It’s fleeting. Now, to connect that with my previous noise on grief and my t-shirt prompt to “Bring Joy”… Not every moment is joyful. Not by any stretch and not just in the midst of tragedy. Life is complex and always will be. Joy is a function of sorrow and sorrow is a function of joy. But, every moment is, in fact, passing just as certainly as it approached. Hello. Goodbye. Another moment is there waiting. We don’t have to look for it. The shirt didn’t say “be joyful” or “be happy”. It said to “bring joy”. So, what’s the difference? Fundamentally, one is about a state of being we often can’t control. The other is a choice of an action that we usually can. Even in the midst of loss, I can find joy in what my friend/colleague and I created together and bring that joy to new work. I can bring the joy of the memory of his laugh as I face an office full of other friends/colleagues who are laughing but aren’t him. I can bring the joy resonating in the echoes of our absurd jokes and his goofy impersonations as I listen to others joyfully bantering among themselves. I can bring those joys to my current work and the opportunity I have to build on what we started. The joy of what we had. This doesn’t mean it is easy, but it means I have agency and not just aspiration. I can bring joy and not just look for it, not merely hope to find it. Image: https://greatruns.com/nashville-shelby-bottoms-greenway/  Pain is inevitable. Suffering is optional.
This teaching from Buddha changed my life and put me on a healing path after my Dad’s suicide. And, as I was thinking about what to write on this the 18th anniversary of his death, April 27, the day before his 62nd birthday, April 28 – the celebration of his life, I was blindsided by a sudden and devastating death of a young coworker and friend. (That’s his picture of totality above.) What the fuck do you do with this? Why the fuck? How the fuck? So young. What happened? He didn’t seem that sick. It can’t be. It is. It just is. Pain. I am suffering for him, his family, his wife, my other coworkers, myself. And then, there’s this word – totality – that has been agitating my brain ever since the solar eclipse a few weeks back when we were all consumed with the “path of totality” – millions packing up their families and their cars with totality as their destination. What a word! Totality! I couldn’t decide if I feared it, or I was seeking it. Whether it is closed and final and finite or the key to transcendence and the eternal. Totality. What is the lesson to be learned beyond a neat, stellar phenomenon for a couple of minutes? Surely, it’s more than cosmic entertainment, cheap cardboard sunglasses, and a media bonanza! It wasn’t coming to me though. But, that word – totality - wouldn’t leave me alone. And then, Andrew died. His photos of totality still in my texts from him. He had flown home to experience the path of totality with his family. Is death totality? I don’t think so. Or, at least, that’s not what has been bothering me with that word for all these weeks. What is totality in life? In the living? And, while I was running yesterday trying to burn off the overwhelming suffering energy that has had me wrecked since I heard the news of my friend’s death, it suddenly became clear to me again, like it did when Dad died, and I read those words the first time from Buddha. Totality is just the sun and the moon together. Both light and shadow. Source and reflection. Love and loss. Joy and sorrow. Fullness and loneliness. Presence and absence. Life and death. Totality is not a celestial moment that happens once in a generation. It is existence. All of it. In totality. And, in human existence, pain is inevitable. Suffering is optional. Thank you for the light. It will always be part of my darkness.  I’m doing the dishes. I like to listen to music while I do the dishes. Tonight, I needed some Pearl Jam. Alexa hit me with “Yellow Ledbetter” out of the gate. So, I obviously asked her to turn it up! The luxury of hands-free Alexa when your hands are covered with dish suds! I am almost immediately sing-mumbling at the top of my lungs about a porch and a wave and a boxer or a bag. Who knows what the hell that song says, and who really cares! Just sing! And, do it loud! Like I’ve been doing it for 30 years!
My sweet and lovingly spiteful younger daughter in defiance of the volume of both my music and my voice – which could never be mistaken for music – decides she suddenly wants to practice her piano and asks if I will turn the music down. I politely decline. I return to my vociferous sing-mumbling: “Ohhhh….ohhhh….yeah…yeah…can you see them…” She turns and heads to the piano. I turn it up more. Still, I start to hear her piano notes through the grungy wash of Pearl Jam at its most melodic and confusing and wonderful. I can tell she’s playing as loud as she can, pushing my grandmother’s ivory piano keys to their limit. But, she will be heard. She’s playing Taylor Swift. “All Too Well.” Taylor will be heard. Pearl Jam or no Pearl Jam. Oh shit. Alexa follows with “Alive”. I am a teenager. And now, I actually know all the words and all the badass air-guitar riffs. But, I’m down to my last dirty bowl. My time and excuse for extremely loud Pearl Jam on a Thursday night, a school night, are running out like the sudsy water down the drain. Taylor via my daughter via my grandmother’s piano keeps audibly peeking in as I reach 1990’s musical euphoria. “Oh, I, oh, I’m still alive.” I reluctantly stop Alexa at the end of “Alive.” I didn’t want to stop. I could have kept doing dishes and jamming all night. Just as Pearl Jam soothed my angsty, teenage soul, so can they soothe my wrinkly, dishpan hands. But, alas. The dishes were done. Taylor takes over. But, just for a few more bars. With the good-spirited spite of my singing and Pearl Jam diminished, my daughter suddenly decided she had practiced enough. Little shit. I love it. I love her. So grunge. But, in the end, I suppose Taylor wins again. So be it. As Eddie Vedder mumbled: “I don’t know whether I’m the boxer or the bag.” It doesn’t matter. Postscript: I decided to look up the lyrics to “Yellow Ledbetter”. It doesn’t make any more sense than the glorious mumbles I hear clear as day in the music. But, for what it’s worth: Yellow Ledbetter Unsealed on a porch a letter sat Then you said I wanna leave it again Once I saw her on a beach of weathered sand And on the sand I wanna leave it again, yeah On a weekend wanna wish it all away And they called and I said that I want what I said And then I call out again And the reason oughtta leave her calm, I know I said I don't know whether I'm the boxer or the bag Oh yeah, can you see them Out on the porch Yeah but they don't wave I see them 'Round the front way, yeah And I know and I know I don't want to stay Make me cry I see I don't know, there's something else I wanna drum it all away Oh, I said I don't, I don't know whether I'm the boxer or the bag Oh yeah, can you see them Out on the porch Yeah but they don't wave I see them 'Round the front way, yeah And I know and I know I don't want to stay I don't wanna stay I don't wanna stay I don't wanna stay, oh no Yeah Oh, oh Oh, oh Images: https://lifeonacocktailnapkin.com/eddie-vedder-in-the-house/ https://www.pinterest.com/pin/taylor-swift-live-performance-in-st-louis--785174516257828659/  But, don’t tell anybody, or it won’t come true.
I was recently at my 90-year-old aunt’s belated birthday party and as they brought out the cake and candles, my cousin reminded her: don’t forget to make a wish! My aunt is 90. She has dementia. She lost her husband a year ago. She can’t walk freely. She can’t manage all body functions. She sits mostly. And, laughs. Some days sharp as a tack. Others, not so much. And, somehow she is still the same old, crazy, wonderful aunt we have all always been crazy about. What did she wish for? This is the first time I’ve ever really wondered much about someone else’s birthday wish - and then almost immediately feared my wondering. What do you wish for at this stage of life? At this stage of health? At this stage of loneliness? Only the day before, I had my own birthday, so my wish was still fresh in my mind as it’s the same wish for every birthday, coin in a fountain, blown dandelion, or clock striking 11:11. I wish for my girls to be happy in their lives. That’s it. Whatever that means. That’s honestly all I wish for. I’ll just have to trust that my wish can still come true despite sharing it here. And, this week, turning 12, my daughter will be prompted to make her own birthday wish. And, like a thousand others before, I won’t really wonder or care too much about what’s in her heart and her mind and in her wish. She’s a kid. Her birthday wish is not for me. But, there was something about my aunt. Something I’m still not settled with, or I wouldn’t be sitting here writing. What do you wish for when life is in its final chapters? Do you wish to see your spouse again, to be reconnected with the love of your life? Do you wish to see your parents? Do you wish you were healthy enough to get around on your own again? Do you wish you could still drive? Do you wish you could still live alone? In the home you built for and with your family? Do you wish you could talk to the friends and family you’ve lost? Do you wish for more years, more life? Or, are all of those wishes really out of the realm? Unreasonable wishes? Lost causes. So, you wish for something that might actually be possible? Do you wish to be done with this life in hopes of moving on to the next? I think I’m troubled by the question because I fear that if I learned my aunt’s answer, somehow it would provide some prescient insight about life that I may not want to know. It’s like being able to predict the future or read someone’s mind. When you’re a kid, maybe it sounds fun. As an adult, it sounds horrifying. I don't fear death, but perhaps I do fear wishing for it. There’s simply no doubt that I would do anything I could to support and help my aunt realize her wish. She’s earned whatever it is. And yet, what can I do? Almost nothing. And, this may be exactly why she shouldn’t share her wish and exactly why I don’t want or need to know it. I’ll just wonder for myself – if I am lucky enough to live to 90 years old and to have lived the life and loved and lost the people that she has, if my mind is fading, if my body has faded, and yet I still love, and yet I still laugh, and yet I’m still alive, and yet…what will I wish for? Please nobody tell me. |
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