5 Things to Cultivate for the Future

I gave a short pep talk this week to a class of graduating Praxians. I had about 10 minutes at a coffee shop to prep, and asked myself, “What would I cultivate if I were just starting my professional career today?”

Interestingly, what I came up with varies somewhat from what I would’ve (and have) said for most of the last two decades. I think cultural and technological change have shifted the ROI for various skills and mindsets.

The most prominent shift is in the first item on this list. Not many years ago, I would’ve said the opposite.

  1. Idea generation. Ideas are more valuable than execution now. The ceiling on a great executor with few or weak ideas is lower than a person full of good ideas who is moderate but not great at execution. Why? Because there are more tools to handle more of the execution part than ever before. Generate tons of ideas, sort them later.
  2. Good judgement. Judgement is hard to define and I’m not entirely sure how to cultivate it, but roughly it could be described as, “Knowing what to say and do when.” Read the room. Understand motives and incentives. See the games.
  3. An entrepreneurial way of seeing. This is where the sorting of ideas comes in. Learn to see not just products or companies, but markets and business models. The order of importance in building a good business goes something like: Timing>Market>Segment>Problem>Distribution>Business Model>Team>Sales>Product>Innovation. When you look at products and businesses, ask yourself who their market is, what their model is, and whether it makes sense.
  4. Story finding. When you encounter facts, learn to tease a narrative arc out of them. Get curious about the story behind them. Seek it out. Find it. Humans (including you) are motivated by stories, and learn through stories. Turn data points into a connective tale.
  5. Story telling. Now learn to put those stories into a compelling format and deliver them. Story tellers can win partners, investors, employees, and customers. Start by learning to tell and retell your own story to yourself. Where are you in the grand arc? Knowing this will help keep you motivated and focused.

Don’t hold me to this as the definitive or absolute top five things to cultivate. They came to me top of mind at a coffee shop. But I’d absolutely tell my 20-year-old self, if he existed in 2024, to get busy cultivating these.

Categorized as Commentary

Value Above Replacement

One of the hardest things for people to understand is that they are not hired or paid based on the value they create in a vacuum, or compared to just anyone else. The value they create is compensated based on how much it exceeds the value creation potential of the next best alternative in their role.

It’s easier to see in sports. A good linebacker works his tail off and has a high injury risk. He creates a ton of value for the team. A mediocre quarterback may work less hard and risk fewer injuries and create only a little value for the team. But the QB is likely paid more.


Because the next best alternative for the LB delivers about the same value, or just a hair less. While the next best alternative for the QB delivers significantly less value. In other words, it’s easier to find a solid LB than a solid QB. Supply and demand rule.

Even if the LB creates 10 units of value and the QB only creates 6, the next best LB probably can create 9.8, while the next best QB can only create 5. So the QB generates a full unit of value above the next best alternative, while the LB only creates 0.2. They will be paid not on the total value they bring to the team, but the value above replacement (VAR, or VORP – value over replacement player). The QB is a net positive of 1, which is five times greater than the LBs net positive of 0.2. The QB might make five times more, all else equal.

In the real world, there aren’t easily measurable units of value so it’s not just a math problem. It’s really hard to numerically value leadership, upside potential, downside risk, fan appreciation, negative outcomes for the team for signing or letting a player go, etc. But the basic calculous is still being done, albeit more crudely and intuitively, which is why mediocre QBs make more money than great players at other positions.

This translates everywhere in the market.

It doesn’t matter your total value creation as much as how much higher it is than your next best replacement. This means you are best suited to finding an intersection of skills that are rare and hard to replace, in a market that values them.

There are lots of people who are great at spreadsheets. Being great at that won’t drive a high VORP. There are also lots of people who are great at surfing. Not a high VORP if you’re a great surfer. But I bet there are only a handful of people in the world who are great at both spreadsheets and surfing. If you find a market where both skills are valued, being a person with that combo probably makes your VORP very high.

Don’t get mad at this or see it as unfair! It gives you an advantage and the ability to command outsized returns for leaning into your uniqueness.

Categorized as Commentary

Humility and Offense

When you’re humble, you know that you make mistakes. If you know that you make mistakes, you don’t feel panicked and defensive about the possibility that you made a mistake. If you’re not panicky or defensive, you have no problem hearing or experiencing people who imply you made mistakes. If you’re able to dispassionately assess such feedback, you’re able to resolve situations, learn, and grow without burning bridges or creating fights.

This is one of the reasons humility is such a strength.

The humble person has nothing to defend or maintain when it comes to perceptions of their own failings. This frees them to focus on the things that matter, navigate to the truth, and take away anything useful.

Humility does not mean being a pushover or not having boundaries. Those result from a lack of humility. When you lack humility, you worry about what people think of you and this makes you avoid conflict, confrontation, and the need to speak strong words or draw clear lines. Those are liable to make you less liked, and when you lack humility, you place inordinate value in being liked.

When you’re humble, you are distanced from the opinion of others enough to do what needs to be done and speak what needs to be spoken, regardless of whether it makes them like you less. This makes you stable, reliable, strong, true, and worthy of respect (even if you’re not always liked).

True humility is in short supply, so we don’t have many good examples. But when someone is unthreatened and not compelled to make sure they get their due, you get glimpses.

Categorized as Commentary


It’s good that we never have enough.

“Enough” means “I don’t want any more.” While it’s true we reach this state in specific instances, say having enough steak or sleep, the reason we want to cease is to have more of the next thing.

And there is always a next thing.

We are directional beings. We move, as the arrow of time, always forward. We always seek more, better, upward, inward, new. The form of these desires change. A young boy wants more time before bed, an old man wants bedtime to come sooner. But we are never satisfied. If we were, we’d be in stasis. Human action requires a desire for more.

Even as we decline physically, we are still ever advancing and evolving in our desires. I suspect this continues right on after we pass from this plane. I think reality itself is engineered in an eternal, inexorable pull toward the inexhaustible vastness of God. Always seeking to get closer, becoming new at every step, perpetually in chase, making progress but never arriving at a point of stasis.

Categorized as Commentary

Chase the Fun

Work isn’t always fun. That’s perfectly normal and ok. But whenever you find work that makes you want to do it – where other stuff is getting in the way and you can’t wait to get back to your desk – find ways to do more of it.

Categorized as Commentary

Causally Stingy

If you practice generosity in your assumptions, it helps you be more useful to others.

If you’ve ever tried any kind of gratefulness practice, like thinking of someone to write a thank you note to or writing down things you’re thankful for every day, you might notice your logical brain raising objections.

“OK, sure, I could be thankful for this person doing this thing that benefited me, but in all honesty, I probably would’ve achieved the same outcome anyway. They weren’t really the causal agent in that outcome, I was.”

Life is too complex to reduce to a linear chain of causality. The path we take in life could be radically different if not for a few tiny variables. Yes, you are the dominant agent in your own life, and it’s possible many helpful people along the way were nice-to-haves rather than necessities. But if you try to parse it out and figure out exactly who gets what credit, you’ll develop a stingy view of causality.

Not only will this make gratefulness and generosity towards others harder, it will make you less capable of seeing your own goodness and ability to improve others lives and the world.

Look for excuses to thank others for even the smallest contributions. You’ll begin to see causality in a more expansive and generous manner, full of infinite contributors, mysterious, and joyful. This will be of great aid when you are at your lowest point. It will be easier to see the possibility of your own unseen contributions to the lives of others – the Remnant out there that you may be supporting in silence.

Categorized as Commentary

“Better A Hole”

I once met with an OG exec from Apple. I asked him how the company managed to maintain so much of its founding culture despite its immense growth.

He told me it was all about hiring, and in some cases NOT hiring. He said Steve Jobs had a saying, “It’s better to have a hole in the organization than an asshole.”

He also told me they had one role open for nine years before they found the right person.

I admire this. I’m not sure I’m patient enough, but I try to take at least something from it.

Categorized as Commentary

When You Know the Game but it Still Works

“You’ve been nominated to be on this list of top people!”

I’m a marketer. I know the strategy. Give awards to people you think will in turn want to pay you for things. Buy some goodwill with flattery.

I know it. But I’m still flattered.

Anytime you find games that still work even when everyone knows it’s a game, figure out why, tap into the principles at play, and do more with those principles.

Categorized as Commentary

Task-Based Creativity

There’s the short-term, action-oriented, task-focused brain. Then there’s the deep-pondering, less-contained, creative-focused brain.

Sometimes, they’re the same brain.

What I find troubling is how hard it is to separate them. When I have finally created that mythical perfect environment to create – no pressure for time, quiet, the house to myself, maybe a whiskey or a pipe – I can start a great many things, but rarely finish them.

I don’t just mean not finish them in that moment. That would be fine. I mean when I come back to what I started, I find it extremely difficult to finish. Yet starting and finishing something in one sitting, as I do these daily blog posts, comes very easy for me.

Task-checking mode seems to drive a completionist sort of creativity. While creative mode seems to allow me to start things, but the mere act of starting relieves sufficient creative pressure that I’m too relaxed when I return to finish.

Should I just accept this tendency, and determine all I’m good for are shorter articles that can be written in a single sitting with no forethought, or should I fight the pattern and try to learn how to have ongoing longer projects?

Categorized as Commentary

Patterns and Foundations

I’m an emergent order kind of guy.

I think most of the time, when we try to plot and plan processes for everything from the top and beginning, we waste time and get it wrong enough that it will change anyway. Better to nail down a very few principles, and let the processes emerge organically from the interactions of real humans within the broad confines of these principles.

These emergent processes can later be codified for easier scaling. But by that point, the codes serve mostly for new people to speed up the acclimation process, and to handle edge cases more quickly.

Starting with a fat foundation of coded culture feels fraught.

However, I will admit I sometimes take this too far and fail to setup a clear enough and defined enough foundation. I rely on a few principles, mostly unspoken or ill-defined, and wait for the emergent order to come. It does come, but sometimes along the way everyone is irritated and confused by the vagaries.

Part of me wants to just blame people for seeking too much guidance, trained by schools and states to be rule-followers who fear their own freedom. Whether or not this is true, it doesn’t help anything. We’ve got to deal with reality as we encounter it, so people’s desire for more clarity and definition demands some bending on my part.

I’m still working on that.

Categorized as Commentary

The Great Hybridization

It’s not contract work. It’s not full-time work. It’s not fractional work. It’s not project based work. It’s not consulting. It’s not agency. It’s not employee.

It’s not remote. It’s not in-person.

It’s not public school. It’s not private school. It’s not homeschool. It’s not unschool, or outschool, or alternative school.

Increasingly, the ways we orient our lives around learning and career are blurring all boundaries and creating things that are hard to name and categorize, but make solving our problems easier.

This is great news!

Categorized as Commentary

The Newness of the West

Whenever I’m in the American West, it feels new and fresh.

The air is crisp. The buildings and bridges aren’t very old. The culture is young and wide eyed, removed from the cynical and established coastal cultures.

The people aren’t many generations removed from those crazy frontiersmen that trekked out here and started cities. It’s big, open, naive, and simple.

I definitely crave the endless ocean horizon, but these elevated plains offer something I’ve not encountered anywhere else in the world. The land may be ancient, but the people are new.

Categorized as Commentary