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.
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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.