How Long We’ve Been Doing This

One day, we’ll be talkin’ about how long we’ve been doing this.

It’ll be in the quiet moments, like me cooking a lazy Sunday dinner while you’re working on a jigsaw puzzle nearby.

Or in the loud ones, like cheering on the sidelines at a soccer tournament, because it’s one of ours out there.

There’ll be days we’re just listening to country radio, holding hands as we drive to the coffee shop.

One day, we’ll be talkin’ about how long we’ve been doing this.

We’ll reminisce about getting a night out with old friends at Mario’s—the cozy restaurant we went to once, and it became ours.

And I’ll think of how you always bring the Fage Greek yogurt recipe we love for biscuits and gravy to brunch, in that cast iron pan that’s turned into “that old cast iron pan.”

There’ll be the quiet, spontaneous moments too, like you wrapping me in a hug while I’m sitting at the table writing a blog post (just like you did today).

Some things will stay the same, like family dinner at a crowded table with bumpy cake for a birthday—or pineapple, if it’s June.

There’ll be walks with the dog who still insists on taking us out at lunchtime.

And, of course, our family meetings that always seem to end with a cleaner house—or our temperature checks that always end with a kiss goodnight.

I know the years ahead will bring big changes—retirement, new adventures, and more gray hair than we have today.

But I hope that through it all, some things stay just as they are now. I hope, God willing, we’ll still be talking about how long we’ve been doing this, and how long we’ve been building this life together—one little tradition at a time.

How to Make Selflessness Joyful

To my friends of the mind,

Lately, I’ve been thinking about time and what we leave behind — not just for our children or our children’s children, but for those far down the line.

A generation, they say, is about 30 years. Ten generations? That’s 300 years. It makes me wonder: what could I pass on that lasts for one generation? And, more curiously, what could endure for 10?

One of the biggest lessons I learned while writing Character by Choice was this: to truly be good people, we need to think beyond ourselves. It’s not just about what we accomplish in our lifetimes, but about listening deeply to the call of something greater — something that stretches far into the future, beyond what we’ll ever see or experience. In fact, I’ve come to believe that selflessness becomes joyful when we shift our focus far beyond the present. When we know our actions aren’t ephemeral, but rooted in something that will last for generations, it deepens the sense of purpose and fulfillment. It’s this depth that sustains us, guiding us to work on things that really matter, even if we’ll never see the results.

Let’s say we’ve done the hard inner work, the kind that builds empathy for those distant future generations — the ones we’ll never meet but whose lives we still want to impact. So, what then? What do we actually do with that kind of perspective? How do we spend our time, knowing that we’re playing a much longer game?

I started asking myself this question and even opened it up to some friends on Facebook. Together, we came up with a list of ideas — some lighthearted, some heavy, but all worth considering. What I’ve realized through this process is that I want to focus more on the long game — the 10-gen stuff — instead of getting caught up in things that might only matter for one generation.

So, what might last for 10 generations? Here are some things that came to mind, from the obvious to the unexpected:

• Inventions

• Great companies and institutions that do the right thing

• Values and moral principles

• Beautiful heirlooms

• Novel, simple mental models

• The effects of unconditional love

• Trauma

• Recipes

• Wisdom

• Practical knowledge (e.g., how to can vegetables, how to lay a brick)

• Waste (e.g., plastics, radioactive material)

• Art

• Genetics and predisposition to disease

• A well-built house (or other very well-built things)

• Big beefs

• Spiritual beliefs / Religions

• Culture

• General-purpose technologies (e.g., electricity, the internet)

• The earth and climate

And then there’s the stuff that might burn bright for just one generation before it fades — things we invest time in but maybe shouldn’t overvalue in the long run:

• Inherited wealth

• Reputation / Fame

• Debt

• Status

• Most possessions

• Little beefs

• A “career”

• Incremental innovations

• Politics (for the most part)

• Pop culture

• Gadgets

• News

So, what do you think? What would you add to these lists? More importantly, do you believe the 10-gen stuff is worth striving for? Is it even something we can shape? I’d love to hear your thoughts — let’s keep the conversation going.

Always,

Neil

Imagination is a Foundational Leadership Skill

I define leadership as the act of taking responsibility for something.

However, one crucial element that underpins effective leadership is frequently overlooked: imagination. From my experience, both personal and professional, I have learned that taking full responsibility for a project or goal requires the ability to vividly imagine its realization. This power of imagination is not just a lofty concept but a practical and essential skill for leaders.

To inspire a team to bring our vision to life, we must articulate it clearly and compellingly. This act of sharing our imagination is what we commonly refer to as having a vision. Whether you are a CEO, product manager, entrepreneur, artist, politician, or parent, the ability to communicate your vision is fundamental to effective leadership.

Imagination operates on three distinct levels when we take responsibility for a project. To illustrate, consider the creation of a running shoe. The first level involves envisioning the product itself. What does the shoe look like? How is it designed? What makes it unique and special? This product vision is the core of what we aim to create, whether it’s a shoe, a family, a city, or a store.

The second level of imagination is what I call the market or cultural vision. This involves envisioning the broader impact of our product or project on the world. For our running shoe, we must consider who will be using it. Are they solo runners or part of running clubs? How does running with our shoe change them as individuals? What new stories do they tell themselves because of their experiences? How do these runners interact with others differently? Envisioning this broader impact helps us understand how our efforts contribute to making the world a slightly better place.

The third level of imagination is the internal vision, which focuses on the process and team dynamics required to bring our vision to life. For the running shoe, this means imagining the manufacturing process: How will the shoe be made and designed? Who will be part of our team? What kind of culture will we cultivate within our team? What will our interactions look and feel like? If a documentary were made about our journey, what key moments and values would it highlight? This internal vision ensures that we have a clear roadmap for achieving our goals.

In essence, a leader is someone who takes end-to-end responsibility for a project or goal. To do this effectively, the ability to imagine and share what’s in our mind’s eye is essential. Without this, we risk merely replicating someone else’s vision instead of creating our own.

This brings us to two key “how” questions: How do we get better at imagining, and how do we assess imagination in others?

To improve our imagination, we need practice. However, imagination cannot be practiced in the abstract. We must engage in the act of creation—whether it’s building a custom shelf, writing a book, painting a picture, or organizing a street festival. The process of imagining often unfolds naturally as we commit to building something. We don’t set out with the intent to imagine; instead, we follow our instincts, commit to the project, and let the imagination flow.

Assessing imagination, particularly in an interview setting, is relatively straightforward. Ask candidates to share their dreams—whether for their current company, their family, or their community. Encourage them to elaborate with follow-up questions. If, within 5-10 minutes, you can vividly see what they envision and feel excited about it, they likely possess a refined ability to imagine and communicate their vision. Chief James Craig, who led the Detroit Police Department while I was there, emphasized this principle: “We have to talk about our dreams.” I wholeheartedly agree.

To ground this discussion, which may seem abstract, let’s envision a world where people are committed to making their corner of the world a bit better by bringing their dreams to life. Achieving this requires the ability to imagine and clearly communicate what’s in our mind’s eye. How do we cultivate this capability? By building things and talking about our dreams.

Doing Strategy in Politics

Here’s my thought experiment for how we might do political visioning in America, grounded in the aspirations of the entire polity.

The first bit is a good illustration of how I think about the American Dream. But for what it’s worth, I mean this post more as an exercise in how to “do” politics differently than just having a platform on 50+ issues that matter to the polity and shouting about it as loud as you can - not an unpacking of my own vision.

My main consternation as a citizen is this: I don’t want a policy platform unless you’ve shared a bona fide vision first! Rather than just griping, I figured I’d actually explain how I think things could work instead.

And, for what it’s worth, this is how I’ve seen great organizations function across sectors. This sort of discipline around strategy and execution is one of the things I most wish the public sector would adopt from private sector organizations and business school professors.

To start, let’s assume a visionary political leader believes these are the three overarching questions that unify the largest possible amount of our polity:

1. On average, do people have enough optimism about the present and future to want to bring children into this world?

2. On average, once someone is brought into this world, do they flourish from cradle to grave?

3. Overall, the simplest and most comprehensive way to measure the health of a society is Total Fertility Rate vs. replacement rate. Is our long-run population stable, growing, or declining?

Thinking about the fundamental need gripping the polity is key. I think whether or not people want to reproduce is a good bellwether of a LOT and therefore a good framework for contemplating political issues at a national level.

A vision statement based on these questions could be:

I imagine a country where our citizens believe it’s worth bringing children into the world and have reasonable confidence that those children will flourish during their lifetimes.

A vision statement statement has to describe the world after you’ve succeeded from the POV of the citizen, not the work itself.

A pithy slogan / mission (which does sharply focus and describe the work itself) to capture the essence of this vision statement could be:

“Families will thrive here.”

Let’s assume this is a vision / mission statement that the polity believes in. If so, then the political leader can translate their rhetoric into action by asking two simple questions:

1. Is the vision true today?

2. If not, what would have to be true for the vision to become reality?

From there, a political leader can create an integrated set of mutually reinforcing policy and administrative choices that they believe will allow the polity to make disproportionate progress toward the vision state.

Put another way, by working backwards from the vision, you can place bets on the initiatives that are more likely to succeed rather than wasting resources on those that won’t get us to where we agreed we want to go.

The problem with this approach is that you actually have to articulate a vision, understand the root causes that are preventing it from happening without intervention, do the extremely abstract work of forming a strategy, and then communicate it clearly enough so that people get behind it. That’s really hard, and you have to have major guts to go through this exercise of vision -> strategy -> priorities -> outcomes.

This is quite different, I think, than simply articulating a pro-con list of policy preferences across a widely distributed set of issue areas that aren’t contemplated in an integrated way. But the thing is, having focus and priorities tends to work much better than “boiling the ocean” or “being all things to all people.”

To be fair, I’ve seen some contemporary politicians operate this way. Not many though.

In a nutshell, one of the biggest lessons I’ve learned from observing the leadership of private-sector companies is that it’s a big waste to just start doing stuff in a way that’s not integrated and focused—as if every possible initiative is equally impactful. It works much better when you start with a specific end state in mind and work backwards. It’s an idea that’s useful for political leaders, too.