I need an irresistible vision to help me remember what I want most

I believe freelancers, consultants, and founders need an irresistible vision to help them judge which opportunities are well-aligned with the business and life they want and make confident decisions about what to pursue or ignore.

I have this conviction because I didn’t have an irresistible vision for the better part of the last seventeen years of entrepreneurship, and some of the “good” ideas, ventures, partnerships, projects, and priorities proved to be dead-ends, detours, and distractions.

Seneca, Yogi Berra, and other sages and wits across the ages have observed, “If you don’t know where you’re going, any place will do.” I’m not satisfied with going just anywhere even if I struggle to describe precisely what or where “there” is.

So an irresistible vision starts with an approximate destination. What do you want more of?

At times I’ve struggled to articulate what I want. I don’t mean the bottom bands of Maslow’s Hierarchy of Needs, which apply to me the same way they apply to everyone else who respirates. I want food, shelter, safety, clothing, and companionship or books or ideally both. (Why did Maslow leave out books? It’s mystifying.)

But once we’re fed, safe, educated, and relatively healthy, we ascend to the capstone of Maslow’s pyramid, self-actualization, where existential questions bubble up. Once artist-entrepreneurs like me have enough money to cover our basic needs and a swath of creature comforts, money stops being the goal. So we can’t help but ask, “What now? What comes next? What do I want?”

Poet Mary Oliver told me that I have "this one wild and precious life.” Okay, what should I do with it? What should I point my life at?

These questions can be especially hard to answer for entrepreneurs, and here’s an incomplete list of reasons why:

• We often have competing or conflicting desires.
• What we want collides with our obligations to other people.
• What we want changes over time, and almost as soon as we get it.
• The work we most want to do may not align with what the market will pay for.
• Being honest about what we most want, deep down, can be painful because hope and dreams and trying again can be painful.

Let me rub salt in the wound of that last bullet point because I think a nuance is important here. For many of us, it’s less true to say that we don’t know what we want and more true to say that we know what we want but getting it stopped seeming realistic or even possible. We stopped holding the dreams because they grew razor edges.

The subject of dreaming can land us in the most raw, tender, and tear-drenched of places. To talk about an irresistible vision for our lives can mean dredging up our most bitter disappointments. We can all point at scars and unhealed wounds where dreams used to be—infertility and miscarriages, infidelity and divorce, loneliness and mental illness, cancer and irretrievable loss, chronic illness and death, injustice and violence. Years spent paying the price of other people’s greed, lust, laziness, selfishness, and ignorance. Years spent doing the responsible thing. Years spent recovering from burnout.

What place do dreams have in that web of loss and grief and anger?

Hope hurts. Dreaming again causes our throats to close, our pulses to race. Do we even dare, knowing how often dreaming seems to invite disappointment?

I can’t speak for everyone, but I can speak for myself and say that I must dare for at least two reasons. First, I must dare because not dreaming causes regret, and regret aches more than the things I tried for and didn’t get. If I’m going to hurt regardless, then I prefer to have fewer regrets.

The other reason I must dare is because, at the practical, day-to-day level, I often must choose between Door One or Door Two, not prizes but priorities. How should I spend my time on a Thursday morning? What should I work on? What is more important?

An irresistible vision helps us make better decisions not because it has anything to do with the law of attraction, manifestation, or guaranteeing somehow that the universe-genie grants our wishes—bollocks to that—but because making better decisions assumes a clear sense of alignment or direction, and a direction assumes an approximate destination.

Defining an approximate destination starts with admitting what I want less of and what I want more of. I know I want more time spent honing my craft. I want to make more books. After I admit that, I can spend an hour on a Thursday finishing an essay that may become a part of a book and have a quiet mind while doing it. My anxiety isn’t thrashing under the surface with the question, “Should I be doing something else?”

The destination represented by an irresistible vision is always approximate. You and I both know that some of the things we think we want we may not end up liking as much as we thought. We may change our minds as soon as we get a taste of what it’s like to go on a book tour, be a digital nomad, or own investment properties.

I find myself returning to the “distant mountain” imagery that Neil Gaiman used in a 2012 commencement speech called “Make Good Art”. Here’s the full excerpt:

“Something that worked for me was imagining that where I wanted to be—an author, primarily of fiction, making good books, making good comics and supporting myself through my words—was a mountain. A distant mountain. My goal. And I knew that as long as I kept walking towards the mountain I would be all right. And when I truly was not sure what to do, I could stop, and think about whether it was taking me towards or away from the mountain. I said no to editorial jobs on magazines, proper jobs that would have paid proper money because I knew that, attractive though they were, for me they would have been walking away from the mountain. And if those job offers had come along earlier I might have taken them, because they still would have been closer to the mountain than I was at the time.”

A distant mountain or irresistible vision gives us a way to be directionally right—toward, not away; closer, not further, hotter, not colder. We cannot navigate our own lives with the certainty of a compass pointing to true north, and we do not need metaphorical latitude and longitude down to the degrees, minutes, and seconds. We do need, however, to check in with ourselves and quickly judge whether the new offer, morning routine, or collaboration is closer to north or east.

Another thing an irresistible vision does for us is clarify what our goals are apart from more revenue and growth. Conventional businesses behave like starved wolves. They will eat your life if you let them. If you don’t know the game you’re playing and set the rules for yourself, you’ll default to the conventional game with its values and monetary metrics, the game where higher revenue and faster growth are always good. More is always more.

Entrepreneurs with ambition knocking them forward like a big piston are particularly susceptible to this more is more way of thinking because we enjoy the creative and intellectual challenges, the adrenalin rush, and the delayed gratification—right up until we burn out. That is what happened to me when I was doing the startup thing from 2013 to 2017.

Check out this LinkedIn post from beehiiv’s co-founder and CEO Tyler Denk.

Though I’m 93.17% certain that Denk’s post is rage-attention bait, I’ll take the bait and say that my own “extreme sacrifices” are meant to avoid the very “lifestyle” and “intentional tradeoffs” that he describes. I’m not building a unicorn startup or corporation. I don’t want a large team. I’m not interested in mining the moon, putting a colony on Mars, or picking fights with other CEOs and public figures to drive shareholder value. That isn’t the game I’m playing.

I want a life rich with meaningful work and financial security, yes, but also one rich with community, connectedness, love, intimacy, friendship, art, simplicity, slowness, contemplation, and generosity.

I must write that irresistible vision down and revisit it. I must engrave it on the tablets of my heart because we builders can build our own prison without realizing it. The glittering empire I could build can’t love me back. Only people can. Wealth can’t bring me peace. Only a sense of my own belovedness can.

The picture below is of my Grandmother and me right before she passed away in June 2026. She is the single most loving person I have ever known. I got to have her for 44 years.

Nothing about her life is impressive on paper. But if you were to ask all the people who showed up to her funeral if she had a successful life, each of them would have blinked at you as though you were speaking an alien language. What could possibly be more important than giving yourself wholeheartedly to the people in your life even when it’s inconvenient? That is the ultimate regret avoidance plan.

We know this, we forget it, and when I forget, I drift back to the conventional game with its predictable mechanics of fear, obsessive building, money chasing, comparison, control, anxiety, and complexity. I’m in a fever answering emails when I might have called my Grandmother or thrown a ball with my youngest.

It’s worth noting that there’s time for building and for people. Some people will build their glittering empires, and the world benefits.

But is that what you want? Is that your irresistible vision? Or do you perhaps want more wonder and joy, more presence and beauty, more gratitude and frugality, more love felt and more peace made?

I’ll admit that I don’t know how to stop striving and make space for these things. Yet, I agree with Wendell Berry that not knowing means the real work has begun: “It may be that when we no longer know what to do we have come to our real work, and that when we no longer know which way to go we have begun our real journey.”

I don’t always know what I want. I can forget what I want most. I need an irresistible vision to help me remember what little I do know and move a little closer to the distant mountain.

Wendell Berry, "Poetry and Marriage: The Use of Old Forms," collected in Standing by Words: Essays (North Point Press, 1983).