I just want these two wolves in me to get along, even though one is a total poet and the other is a straight-up capitalist

And yikes, they're married

Alice and Milton

A few weeks ago, I said I didn’t have two wolves inside me.

They say inside you are two wolves. But not me. I just have a sheepdog.

I lied. I definitely do. Their names are Alice and Milton. And they have very different ideas about how to flourish.

Alice loves natural selection and competition. She believes these forces, though harsh at times, also refine us—pushing us to experiment, to revise, and to improve. She enjoys taking her ideas to the free market for immediate and brutally honest feedback. She loves rewards and works hard to earn them. She seeks prosperity and progress. She treasures efficiency and hates waste. She can be prideful, but she loves service and creating value for others. Alice, in short, is a capitalist.

The other wolf, Milton, seeks meaning above all. He spends his quiet moments reflecting on Life, Love, and the Big Questions. He yearns for self-expression and connection. He studies the rules of form, imagery, narrative, and aesthetics—simply because they’re beautiful. He believes that many of life’s greatest treasures—like friendship, faith, and feeling—can’t be bought or sold, much less priced or appraised. He would spend all day composing songs and sonnets if he could. He is pure in heart, but a little indulgent. Milton is a pure poet.

Trying to keep Milton and Alice happy has been a lifelong tightrope walk. But I think I’ve finally found the long-term solution. Milton and Alice need to do what any dysfunctional couple does to solve all their problems: get married!

No man can serve two masters (wolf edition)

Seriously though. I’ve come to the conclusion that marriage is the best option for them. I’ve tried a lot of alternatives.

My first idea was to keep them in separate lanes.

For example, when I was a lawyer, Alice ran the show. Deadlines, networking, interviews—these are her wheelhouse. She helped me get good grades, impress my employers, and serve my clients. We created a lot of economic value together.

Then, when it was time to go home, I would put Alice to bed and out would trot Milton, with my acoustic guitar in his mouth. The first year of law school is notoriously demanding, but I still probably practiced two hours of jazz guitar most days. It didn’t create any value for anybody. Anybody, of course, except me. Me, it was rescuing.

It worked all right for a while, but over time, this strategy unraveled. Being a lawyer kept Alice fat and happy. But law was demanding, and there was very little left over for Milton. A few years into my career, I found that Milton had wasted away. I wasn’t doing the work that I wanted to do, nor becoming the person I wanted to be. I was spending my best hours stuffing most of myself into a little cubby, so a shell of me could crank a big gear for a paycheck. It wasn’t right.

Partly for that reason, I left the law.

If you’ve considered quitting work forever, my story may interest you

Hoping to right the ship, I immediately began devoting what precious little TAP (Time After Parenting) I had to creative projects. Now, Milton had primacy. My first venture was a long-term dream—starting my own YouTube channel. In my excitement to be an Artist, I ignored all of Alice’s concerns about branding and SEO and just made every kind of video I could imagine. Essays, sketches, pop-punk covers in the style of bossa nova—it was a sandbox. I was so happy to see Milton thriving that I ignored Alice’s whimpers and signs of depression and malnourishment.

One day I looked up and realized that, once again, things weren’t right. I had been at it for over a year, but based on the numbers, my work wasn’t reaching people or resonating with them. I enjoyed the creative process, but it was also a tremendous amount of work, and I was starting to burn out. With no sign that my output mattered to anyone, I started to feel like creation had become consumption. I was using up my time and energy, and taking up bandwidth on a saturated internet. It was like running on a hamster wheel—good cardio, fun for a while—but was it really the best use of my talents and efforts?

I had neglected Alice for too long.

This experience taught me that I need to feed both of my wolves. I think it’s the only way to keep from drifting too far in either direction—and to do work that feels both personally fulfilling and genuinely meaningful.

But I have a family to care for, so I don’t have enough hours in my life to day-job one wolf and moonlight the other. So I think the best bet is to find a way to integrate them—to get them working together on something. Not turning a soulless crank, not running meaningless laps—I want to connect the two machines and create a turbine: a place where I can run with everything I’ve got and generate power for people other than myself.

What I’m saying is, the wolves need to get married.

But can that really work out?

We’re not leaving this conference room until we’re aligned on next steps, people

The good news is that Alice and Milton actually make a very complementary couple much of the time. Milton’s dreams and vision help me think big and keep my eyes on the things worth doing. He’s the compass. Alice is a realist, a doer. She’s thick-skinned, practical, and strategic. She’s the engine that moves us forward.

But theory is one thing, and practice is another. And integrating them hasn’t always been straightforward.

My latest attempt to get them to work together is on these weekly essays. In the planning stages for this project, I gathered my wolves for a meeting in my brain’s conference room. There, I invited them each to share their proposals for how to proceed.

Alice arrived early with a PowerPoint full of words like “value proposition” and “comparative advantage.” She talked about hooks, trends, and market research. She had immaculately designed slides about paywall strategies and leveraging industry contacts. She was polished and compelling.

Then Milton got up and unfolded a college-ruled piece of paper. On it was a poem he’d scrawled in swirly script, which he began to read aloud. The final stanza went:

You know you have something to say in your heart. So say it!

You are only truly free in this world if you act freely. So act!

Art is an act of love, and love is an act of letting go. So let go!

Dang, I thought—both these wolves are making some good points.

I can’t hear anything with you both whispering in each ear

I still struggle to know which voice to listen to, and when.

It’s tempting to go full poet-wolf. I believe in the value of art for art’s sake, and I think raw authenticity can yield amazing results. But the intrinsic joy of creating isn’t enough for me—not in a vacuum. I don’t know whether this is a moral failure, or a genuine desire to serve others—or both. Or something else entirely. But if I write, I want to be read. What can I say?

And that’s where my capitalist wolf comes in. Her no-nonsense approach is exactly the reality check I often need to head off my tendency for self-indulgence.

But some of what she says can be hard to hear.

For example, Alice would tell you that my YouTube channel was, if not a failure, then a non-success at best. She’d say it didn’t deserve to beat the competition. That I wasn’t ready for primetime.

And while it’s hard to admit, I think she’d be right. I didn’t stick to it long enough to achieve mastery. I didn’t do enough promotion to find my audience. I didn’t revise my work in light of the feedback I was getting enough. I really wasn’t ready for primetime. Ball don’t lie.

But wait, says Milton. Money and attention are not necessary or sufficient indicators of great work. The market is not perfect. Great art doesn’t always hit, and there’s certainly plenty of very popular garbage. Besides: sometimes it just takes time to catch your break.

Consider Van Gogh: he died in virtual obscurity, then posthumously was elevated to the pantheon of all-time great artists. I recently came across a quote of his from a letter to his brother Theo:

And this is why I say for my part, if I’m no good now, I won’t be any good later either—but if later, then now too. For wheat is wheat, even if it looks like grass at first to townsfolk— and the other way round too.¹

But that’s the million dollar question, isn’t it? Wheat or grass? Are these magic beans I just bought, or is it a handful of deer poop? And how long should I water them to find out?

Alice would say: iterate, fail fast, pivot. Milton would say: stay the course and trust yourself.

They both make some good points.

According to the legend, the wolf that wins is the one you feed. But I need them both, and I feed them both. And I’m really hoping that this marriage can work out.

The odd couple: a marriage of instincts

So that’s how I’m approaching this Substack: as a lupine marital experiment. A project where a capitalist and a poet try to create something together without tearing each other to shreds.

It’s a game of compromises. I try to meet my self-imposed deadlines² and edit ruthlessly. I make an effort to be active on the app and connect with other readers and writers. But I also follow my nose each week and write what I find interesting—without worrying too much about a theme, a brand, or a through-line.

Early signs are promising. Milton has been happy: I’ve genuinely loved the work for its own sake, even if nobody reads it. That’s a pretty big deal for me.

But Alice is also cautiously optimistic. Since I started this, there’s been a steady trickle of subscribers—255 of you at time of writing. That’s far more than I expected at this stage, and I’m grateful for each one. Every subscription, comment, and share votes yes on the proposition: “is this worth my time?”

An unknown gym bro's fist & an unexpected insight

And I guess that’s what this essay is really about for me. In the time I have outside of my family duties, there’s a lot I could be doing, both for myself and for others. I take the stewardship of that time seriously. These wolves—my instincts—are very different. Maybe even opposites. But listening to both has helped me spend that time more wisely.

Or maybe just less unwisely. Because I haven’t found The Answer yet, either. I’m still dreaming of that turbine, where the expression of my soul generates real electricity.

To find it, I think the best I can do is to keep listening to the wolves in my heart. Because if you ask me, they both make some pretty good points.

1. People love to abridge this into something like “If I’m considered great tomorrow, then I’m great today too.” But I can’t help noticing that the full quote also considers the possibility that “maybe I’m not so great after all.” It’s relatable, Vincent!

2. Never mind that this essay is coming out two days late. If I don’t say anything, I think no one will notice.