After I wrote my last blog “What are you seeking?” a young man reached out with some questions. He liked the blog and was really trying to be thoughtful about his early career but wasn’t sure how to put this idea of “seeking” into practice.

When we met, he started by telling me he wants to be an investor and wondered how he should be thinking about “seeking” given his aspiration.

I simply asked him why. Why do you want to be an investor?

He had answers ready. He talked about the kind of work it is, the pace of it, the way it stretches you, the arc of the career, the people you get to be around, the chance to have impact. He was thoughtful. He had clearly given it real consideration. But as I listened, I heard exactly what I expected to hear. None of the reasons he gave as to why he wanted to be an investor was a unique attribute to a life or work being an investor.

So I asked him the next question: So, do you want to be an investor, or do you want those other things?

He looked at me confused.

I explained: Every reason you just gave me for why you want to be an investor, you could find on a dozen different paths. And, maybe the right path is actually being an investor. But, the problem with defining what you are seeking by a single destination is that you end up focused on the destination - and stop paying attention to the criteria that made you want it in the first place.

I have seen this pattern throughout my entire career. When I worked in the nonprofit sector, I had young people seek my advice all the time and tell me that they wanted to work in nonprofit. It is a strange thing to say when you actually pay attention to those words. No one has ever told me they wanted to work in for-profit. Why do they say they want to work in nonprofit? What those people wanted was work with purpose. They wanted meaning. They wanted to have an impact. And, in their thinking and their declaration, they had simply decided that those things lived in one place and nowhere else: nonprofits. Before they had taken a single step in their careers, they had already narrowed the aperture not just for their work but for their lives.

This aspiring investor had done the exact same thing, just pointed in a different direction.
Here is the trouble with narrowing your aperture on a singular career destination: once you fixate on the one path you believe will give you what you want, you stop watching for what you actually want. You optimize for the destination and lose track of what you were seeking - the why behind that destination.

So, how do you put this thinking into practice early in your career? How do you keep the aperture open without losing focus? How do you focus without losing the breadth of your values and the depth of what you are seeking?

Here are four domains to pay attention to:

The Structure of the Work
I learned early that I didn’t just want unstructured work. I needed it. I needed ambiguity. I needed roles that did not exist yet or needed to be radically transformed. I needed to create. I needed to build. I did not need rules or clear pathways or promotion criteria. The blank canvas is oxygen for me. For someone else, it would be a nightmare. Plenty of people do their best work inside clear boundaries, defined expectations, and a clean picture of what good performance looks like. That is not in any way a lesser way to work. It is merely a different one. Neither is right. The only real mistake is not seeking to understand where you are and what drives and excites you along that broad spectrum of work structures. Not noticing early can mean not noticing when the answer starts to shift as your life priorities and work evolve. The structure that fed you at 25 might suffocate you at 35, or the reverse. Pay attention to whether your needs and your work are still moving in sync. When life happens, this sort of self-awareness is your biggest source of resilience.

The Context of the Work
This is about what you are doing and where you are doing it. Every context has culture and process and people and impact. Some contexts will feed you and some will not. Some may become your true vocation, and some may just be a step along a bigger exploration. Part of the work is learning where context sits on your own ranking of what matters most to you. I figured this out early when I was working with youth. I loved this work. I gave everything I had to it, and it was some of the most creative and meaningful work of my life. But, when I looked at my colleagues who were equally invested and committed to the work, I saw that their commitment was often about a life’s commitment to young people. Mine, candidly, was not. And, I made that clear. I was all in. The context of youth work was deeply engaging. But, at the end of the day, if the work stopped being innovative and creative, I was going to need to find my next thing. Sometimes you learn the most about what feeds you by standing next to people who are fed by something you admire but do not exactly share.

The People You Work With
Early in your career you are told to build your network, and you should. But it’s far more important in your seeking journey to learn from the people around you – and not just what they do or how they do it, but who they are, how they learn and grow (or don’t), how they treat each other, how they see the world, how (and if) they live their values and if those values align with yours. You will never be content in your career surrounded by people you don’t like, trust, respect, or care for. That’s just being human. And, when we think of our career merely as the mechanics of industry, of promotion, or of financial progress, we may find ourselves having achieved all our goals on paper but feeling lonely, unfulfilled, or even a bit sick in our stomachs as we head into work every morning. People matter. They always matter. If you learn early that they do not, that lesson has a way of sticking. It hardens into a way of working, then a way of leading, and it shows up as an unrecognizable version of yourself down the road, long after you have forgotten how you got there.

The Impact of Your Work
Why does your work matter? That question has three parts. Why does it matter to you? Why does it matter to others? Why do you matter to it? When you start a career with ambition but no eye on purpose or impact, you should not be surprised to look up one day and find you’ve built a real career, earn a good paycheck, and feel a deep unsettled feeling you cannot quite name. This is your midlife crisis even if it hits earlier or later in life for you. The absence of purpose and meaning compounds quietly. It sits under or behind the wins, waiting for a slow enough season, a significant enough loss, or a large enough accumulation for you to finally feel it. You do not have to change the world in your first job or any job. But you should be asking, early and often, what your work is for. The habit of asking matters more than any single answer.

None of these four domains are things you find or assess once and check off the list. They are dimensions you keep evaluating, over and over, as you change, life changes, and the work changes. They are the criteria that keep your aperture open so you see when changes must happen before you hit a crisis – or, you are more ready and able to change when crisis hits you. They enable you to keep becoming, to keep seeking, to stay intentional in every step along the pathway rather than simply chasing the destination.

I spent years as a visual artist and teaching art before I ever started a nonprofit or even later started a business. People typically think of those eras like they were two separate lives or that I wasted my time in art and somehow came to my senses and got into business. What they don't understand is that art is precisely what gave me my senses. Nearly everything I know about starting companies, leading teams, and developing leaders, I first learned standing in front of my own canvas or analyzing someone else’s painting, drawing, or sculpture.
​
Here are ten of those lessons just to get started.

LESSON ONE: Facing the blank canvas (starting a business) is hard and it should be. Making something is easy. Making something that inspires you and the market is incredibly difficult.

It takes courage to make the first mark. It takes courage and creativity to keep adapting that first choice and iterating toward something whole and purposeful – especially when you know that no mark is perfect. When I started my first business, one of my developers gave me a book called Art and Fear. If you are building anything from scratch, go read it.

LESSON TWO: Business isn't just about building or selling more - or more disruptive - innovation. Sometimes it's about identifying and addressing a weakness in the market and providing a successful solution.

Look at the Degas painting. The whole scene is structurally precarious, which mirrors the psychological and physical presence of the woman at its center. She is barely there. Slumped. Slightly leaning. Not looking at anything. Now take your finger and block out the newspaper that connects the table in the foreground to the table holding the pitcher. The entire composition starts to fall apart. Everything hinges on that one fragile connection, and most people either don't notice it or find it merely curious but not important. The best opportunities usually live right there.

LESSON THREE: Every product or service you offer is being seen and experienced from different perspectives simultaneously.

Picasso painted time and perspective at once, capturing a face from different angles and different moments as if the combination were truer than any single view. His portraits make us ask questions. They keep us exploring. The moment we get comfortable with one perspective (typically our own), we tend to stop doing both.

LESSON FOUR: If you don't build your product or service with an eye on the whole, then it's going to fall apart when it interacts with the real world. No one uses it exactly the way you want them to.

Here are two still lifes painted a little more than a decade apart, in clearly different styles. The left by Cezanne, the right by Manet. 

​Now turn them upside down.

Something interesting happens. Cezanne's bowl of fruit becomes more of an abstraction, but it still holds together as a whole image. What we used to identify as the wall now holds up what we used to identify as a typical bowl of fruit. The cloth that used to hang off the bottom of the image with gravity now seems to cling to the top and hold things up. Manet's fish and pot, on the other hand, start sliding off the page. Cezanne didn't merely represent his objects in paint. He painted the whole, the relationship among the parts, their relationship to their environment. Those relationships still exist upside down.

And, it's not about being “done” or having every feature or bell and whistle complete.

Here is another still life by Cezanne on the left. The upside down version on the right. It holds together. It isn't even complete. Or maybe that's exactly the point. Maybe it is.

LESSON FIVE: If you put something out into the world, you open it and yourself to the world's interpretations and use.

Basquiat went from a cryptic street artist to one of the biggest names in art. He died of an overdose, and his images and his struggles are still being sold today. Do we understand what he was trying to say? Do we care? Did he want the fame he got? Was he playing the art establishment, or were they playing him? Setting aside the tragedy of a young life lost, the answer doesn't matter much. You open the door, and the world walks through it on its own terms.

LESSON SIX: Positive and negative are rarely as binary - or as obvious - as we have been taught to believe.

One of the first things you learn in art is the concept of positive and negative space. The point is to open the world beyond the surface – not to close it down to two options. Many of us spend our lives oversimplifying life into binaries, life in black or white. Customers buy or don't buy. Products work or don’t work. People are right for the job or they’re not. Kline's work – and I’d argue life itself - asks you to slow down and actually look, to be present with what you're observing and let it tell you something instead of imposing your own conclusion. Decisions and opinions are cheap. Learning, listening, and discerning are of a higher order.

LESSON SEVEN: Without leadership, people will take their next step based on what they see in front of them and what they understand their options to be.

Escher's drawings are often fun, like a puzzle, somehow both mathematical and controlled while joyous and free. But try to navigate them with unthinking logic and you end up somewhere (or nowhere) you never could have imagined. Years ago, I read advice about not following in a leader's footsteps but instead seeking what they sought. This is how Cezanne became Cezanne and Picasso Picasso. Follow Escher's stairs blindly and you dead end. Understand where he was trying to go, and you can chart your own path.

LESSON EIGHT: Sometimes you have to say things more clearly and obviously than you ever imagined you'd have to just to make your point. And, humor often helps.

Maurizio Cattelan wanted to make a piece about the loss of direction and challenges he saw in the Catholic Church. I'd say he made his point. Yes, it's profane, and it will offend some. It's also genuinely funny, and it is deliberate in every detail. Subtlety is a luxury you can't always afford when the message really matters. 

LESSON NINE: One member can set the tone for a whole team or even culture.

Look at the woman in the front with the sickly green glow. She defines the image. You can catch that same green off in the distance, but on her face, quite literally in your face as the viewer, it tells you this bar and this scene are a little seedier and less certain than you might otherwise notice. You may have someone on your team casting that glow. And you may have grown so used to it that you no longer recognize what's actually driving the sickness – even when it’s right in your face.

LESSON TEN: Rhythm and repetition are what build structure and flow.

You can hear Jacob Lawrence's paintings. You can hear the hustle and noise of the city. You can hear the back and forth of sawing and lifting and placing and building. You hear all of it because of his visual structure, his rhythm, his repetition. Do the scenes create the rhythm and repetition, or do the rhythm and repetition create the scenes? They are like jazz with individual actors moving freely within their space while contributing to the melody of the whole. This is how the best teams work – clear roles and contributions with the freedom to have some style and be human.

I hope you've enjoyed these. Obviously, the point isn't that art explains all of business. It's that the same attention, courage, and care that make an artwork come alive, communicate, and hold together are what make anything come alive, communicate, and hold together. It's the whole. 

​IMAGES:
Edgar Degas, “The Absinthe Drinker”, 1876
Paul Cezanne, “Dish of Apples”, 1876-77
Eduard Manet, “Fish (Still Life)”, 1864
Paul Cezanne, “Still Life with Water Jug”, 1892-93
Jean Michel Basquiat, “Guilt of Gold Teeth”, 1982
Franz Kline, “Untitled”, 1956
M.C. Escher, “Relativity”, 1953
Maurizio Cattelan, “La Nona Ora”, 1999
Toulouse Lautrec, “At the Moulin Rouge”, 1892/95
Jacob Lawrence, “This is Harlem”, 1943
Jacob Lawrence, “The Builders”, 1974

I was talking with a young, hungry professional not long ago, and he was laying out his dreams and aspirations to me. I have no doubt this young man can and will accomplish what he sets his mind to. And yet, I found myself at 50 trying to manage supporting him and encouraging him while also quietly carrying the life I know is coming for him, and for everyone else, from their early twenties to my age.

Priorities will change. The people you surround yourself with will change. Relationships will deepen. Relationships will be lost. People you love the most will get desperately sick. Someone you love profoundly will die. Maybe you have kids. Maybe you have your own health issues. Life is a lot, in retrospect.

Which is exactly why knowing what you are seeking matters so much. It’s about resilience. It’s about focus. It’s about making sure you wake up at 50, look around at a life that looks nothing like you pictured in your twenties, and still feel you accomplished all you dreamed of and more. Not less.

Talented, driven people often get what they want. Ask a driven person what they want and they’ll tell you before you finish the question. Ask what they’re seeking, on the other hand, and you’ll likely get silence. That gap is the whole thing. It’s the chasm that opens up over a life actually lived, and it has a way of telling you too late that your wants weren’t all they were cracked up to be. 

So I want to offer four comparisons worth examining. In each pair, the two can look almost identical from the outside, but they are not the same thing at all.

Happiness vs. Joy
When you seek happiness, you chase conditions. The promotion. The number. The recognition. The praise. You optimize your life to feel good, and you inherently tie that feeling to things going your way. It works right up until life stops cooperating, and life always stops cooperating. Happiness is a state of being you can’t fully control, so seeking it puts your peace at the mercy of circumstance.

When you seek joy, you bring something instead of chasing it. Joy is a choice and an action, not a mood you wait to receive. It doesn’t require the day to go well. It can sit right next to sorrow and hold its own. I’ve felt joy in the middle of grief, the fullness in reflection upon my father’s death, the echo of a lost friend’s laugh, in a good morning in the depths of sadness that actually means it. Happiness depends on the world. Joy depends on you.

Being Nice vs. Being Kind
When you seek to be nice, you are managing how people feel about you. You smooth things over. You want to be liked. You tell people what they want to hear and call it generosity, when really it’s about your own comfort. Nice can obscure a lack of depth.

When you seek to be kind, you are after the other person’s actual goodness, even when it costs you. Kindness tells the hard truth. Kindness sets the boundary. Nice can buy shallow approval and a pile of things left unsaid. Kind builds the kind of trust where someone knows they can come to you no matter how confusing or awkward it gets. Kindness is rooted in love.

Being Smart vs. Being Wise
When you seek to be smart, you want to be right. You want the answer first and you want the answer that wins the room. You collect knowledge and you make sure people see it. Smart is fast, and smart is often impressive. Smart also assumes it has already asked the right questions because further digging may make you look less smart.

When you seek to be wise, you slow down. Wisdom is less about having the answer and more about knowing which question actually matters, and when to stop giving answers and continue asking them. It knows what it doesn’t know or, at least, that it doesn’t know. It assumes it might be wrong and goes looking for the holes on purpose. Smart earns you admiration in the moment. Wisdom earns credibility and respect that still hold up years later, when the room has emptied, life has happened, and the applause is gone.

Being Seen as a Leader vs. Seeking to Lead
When you seek to be seen as a leader, you are chasing the title and the recognition that come with it. The position becomes the point. You manage your image. You want the credit for the win as much as you want the win itself. And the moment the spotlight moves, you feel it, because your sense of self was tied to being watched.

When you seek to lead, you are simply taking responsibility for something that needs doing, whether anyone is watching or not. You develop the people around you. You give the credit away and it doesn’t cost you a thing. Leadership is a team sport. The people who chase the appearance of it tend to be brittle and self-focused. The people who actually seek to lead become the ones others choose to follow.

Look closely and you’ll notice the same pattern in all four of these comparisons. One version points outward, toward how things look and how you’re received. The other points inward, toward who you are and what you bring. One is fragile because it depends on the world staying arranged in your favor. The other is durable because it doesn’t.

So back to that young man laying out his dreams. I believe him. I believe he’ll get there. I just hope what he’s seeking survives the life that’s coming.

I had been sensing it for a little while and then I got this note when my wife and girls went on a weekend trip without me. Dad. There it is. Not Daddy. Dad. And this from my younger daughter!

I wrote a blog back in January of 2020 titled “I am Daddy” as I came to the realization that this was no longer just a role I was compelled to play because I had children but a part of my identity – in fact, it was the primary way I finally saw myself despite years of having children.

Now, officially according to this note, I am Dad. So, what does this mean?

1. I am still Daddy, but I have to know when and how to use it. As both Dad and Daddy I toe a delicate line between being a doting father who desperately loves his girls and the man who needs to prepare them to be teens, to have the confidence to make their own choices, to recognize when rules and norms are important and when they don’t work for our family values and priorities.
2. I am the example and the standard of being a man. In one of the first conversations I had when we were pregnant with my first daughter, a colleague said: “you are the first man she will ever love.” Aside from any presumed preferences for who she will romantically love, the point hit hard and still holds profound meaning for me today. I am their most acute - if not only - example of what it means to be a Dad, to be a Husband, to be a Son, to be a man who respects the women in my life fully and completely and without compromise.
3. I am the hard conversation they don’t yet know they want or need. So, I must be the first to be vulnerable and say when I have made a mistake or mishandled a situation with them. In turn, I must also be the first to tell them the hard truth regardless of any awkwardness so that they can trust they can come to me no matter how confusing or awkward life gets to them.
4. I am the unconditional love that ends every night with the declaration that I love them always and forever, no matter what. I must be stability as the tumultuous teens take their inevitable toll.
5. And, if I do all of these things with any reasonable level of quality, I can continue to be safety. This includes the safety of Daddy but is deeper and more complex and more evolved to meet their growth and development as young women.

I am Dad. I am someone who sees them as beautiful inside and out in all the ways I used to think were cliché and corny. I am the one who must know and show them that their value is inside, that their inner beauty is controllable and not merely a function of surface perception or genetics. The beauty they control is the one that is most profound and can also last a lifetime. 

I am Dad. I am a man who must never and will never comment on women’s bodies, their weight, their looks, or demean them in any way. I have to know and accept and defy implicit gender bias including my own that they don’t yet recognize or have words for.

I am Dad. I am someone who genuinely finds them fun and funny to be around and am at my happiest when I am with them. I don’t want to experience new things without sharing them with my girls.

I am Dad. I am someone they miss on a weekend away and someone who misses them.

I am Dad. I am someone who allows them to give me the bird when I’m goading them about something in good fun because I know they are finding their confidence and showing their trust in me as they lightly test the boundaries (by doing something I undoubtedly taught them).

I am Dad. I am someone who above all else must show my girls that I am willing to listen without judgment or shame, no matter what the topic.

I am Dad. I am someone who must know the time for answers and the time for more questions to help them arrive at their own answers.

I am Dad, and I love it so, so, so much.

​

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?

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,

• I love hearing every sour note as you learn violin. It has been an inexplicable joy.
• I love your confidence at your piano recitals. I love that you chose to do that on your own and have kept doing it.
• I love your spirit of adventure.
• I love when you play together.
• I love when you play pretend with dolls and I love when you are too old to play pretend with dolls.
• I love that you’ve tried sports and performance and debate and art and you’ve found the good in each.
• I love that you are learning about yourself as you explore these things.
• I love the incessant dancing around the house.
• I love middle school dance and orchestra and chorus and musicals in ways I could have never possibly imagined.
• I love the new friends you are making and even that you are starting to let go of some.
• I love that you still want to dance with me (or at least act like it).
• I love that you still want to hold my hand (sometimes).
• I love that you still want to curl up on the couch next to me.
• I love that you have confidence I never had at your age.
• I love that you are funny.
• I love that you can laugh at yourself.
• I love that you can work through it when things don’t go as planned at school.
• I love that you are such a good friend to others.
• I love that you look out for each other.
• I love that you love to travel.
• I love that you love to read.
• I love that you make your lists.
• I love (secretly) that your room is so disastrously messy (like mine was).
• I love the boundlessness of your Taylor Swift fandom and your easy, self-assured dismissal of my Tay-Tay provocations.
• I love that you love our dog (Fitz) so fully.
• I love that you love your cousins and aunts and uncles and grandparents.
• I love that you are kind to everyone.
• I love that you are thoughtful.
• I love that you are creative.
• I love that you are inquisitive.
• I love that you let me be me.
• I love that you challenge me every day to become the Dad you need and deserve.

​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.

1. Talk or write or otherwise reflect on the parts of 2024 that sucked. Name them. Accept them. Then talk or write or otherwise reflect on the parts of 2024 that were wonderful. Name them. Accept them. Neither is right or wrong. Neither can be changed. Neither is controllable at this point. Both just are. And, both are now a part of us as we head into 2025.
2. Evaluate your wounds. Which ones are still active and open? We all hurt sometimes. It proves we love. It proves we care. It proves we are human. How can we allow those wounds to start to heal and become scars? How can we accept, as Buddha might, that our pain is what makes us human but our suffering is our choice? How can we carry pain, but not suffering into the New Year? Let’s make a resolution around that.
3. Own your scars. These are the wounds that have healed in some way, whether by time or deliberate effort. Can we allow them to become a part of who we are, a symbol of our strength and resilience moving forward, and not merely a marker of something that hurt us in the past? Can we own them and thereby claim the power from the life or events or people that caused them? Can we define which ones we caused ourselves and define a better way? Let’s make a resolution around that.
4. Define your next-best self – wounds, scars, and all. Plant a seed in all that newly fertilized 2024 soil. How might we be a better person in 2025? How might we be better at work? How might we be better to ourselves? How might I become the father, spouse, sibling, uncle, cousin, friend, and co-worker that I want to be? I know, for me, it starts with quieting the noise still swirling in my head from 2024. Let’s make a resolution around that.
5. With this foundation of honest, practical resolutions starting where we really are with life, with ourselves, with our relationships, with work, let’s define a goal that excites and stretches us, that defies any negatives and triggers our spirit, that gives us energy, that offers us something to run toward as we work on and through our other resolutions.

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