AI Can Help You Make Big Life Decisions

Have you ever wished you had a crystal ball? One you could use to peer into the future and know that those major, life-altering decisions were the right ones? The decision to start a family, to move across the country, to leave one job for another? In this piece, first published in March, Dan Shipper explores how artificial intelligence might ease the burden of these big decisions—and how it might have helped him make one about Every. Plus: For paying subscribers, we’re sharing the exact chat that Dan had with Claude to build our new prompt tool, Spiral. Check it out. —Kate Lee

---

We all want to know how we’ll feel in the future. If we had perfect information about how decisions in our lives would affect our emotions, we might do a lot of things differently. That’s why, as they say, youth is wasted on the young.

I remember dancing in a glass-enclosed conference room when we got our first acquisition offer. It was 2014, and the company I’d started, Firefly, was a small team and had just started to bring in meaningful revenue. I hung up with Public Live Chat’s (a pseudonym) corp dev guy, queued up AWOLNATION’s song “Sail” on Spotify, and wriggled as un-self-consciously as a Hasid in prayer. Suddenly, at 22, I was faced with one of the biggest one-way door decisions of my life.

Six years later, I remember deliberating endlessly in late-night phone calls with Nathan about the decision to raise money for Every. It was the heady days of the creator economy, we were growing like crazy, and startups were pulling down massive seed rounds. Did we want to put the company on a venture path? Or should we heed the blood-soaked history of venture-backed media companies and stay bootstrapped?

Most decisions in life are reversible. But some are one-way doors. Jeff Bezos talks about these:

“Some decisions are consequential and irreversible or nearly irreversible—one-way doors—and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation.”

If you’ve lived any length of time you’ve probably faced a few of these one-way-door decisions yourself. Sometimes you’re choosing between two new options: Get a job or travel the world. Sometimes you’re choosing between the status quo and something radically new: Stay in a relationship or leave; climb the corporate ladder or quit to go all in on a startup. 

The decisions we make are the lives we build. One-way doors are the entrance to an entirely new and unfamiliar part of our paths.

In business, there are many inputs to a one-way-door decision. There are practical considerations, strategic considerations, and economic considerations. But an important variable in any decision is: How will we feel, personally, when we cross the threshold of that door? Will we regret it? Will we be happier?

Predicting how we’ll feel about a decision is something that we repeatedly get wrong. We think things will make us happy when they won’t. We miss opportunities that would change our lives because we’re too afraid to try them out. 

Worst of all, our projections about what might make us feel happy or satisfied are key inputs to our economic and strategic decision-making. How many people raise money or sell their startups expecting to feel happier, only to find a deep depression on the other side? 

In short, refining our ability to predict our future state is critical. 

AI is an incredible tool for this kind of decision-making. It can simulate us—our personalities, our thoughts, our emotions—and reveal what that simulated version of ourselves might feel and think in different circumstances. It allows you to walk through a one-way door like a caver: wearing a sturdy harness knotted to a rope tied to a rusted stake. You explore the darkness fearlessly and follow the fastened rope back out.

I’ve been using AI to help me make one-way-door decisions and predict my future state. For obvious reasons, I don’t want to talk about present-day decisions. But I do want to walk you through how it could have affected one of my historical one-way-door decisions, so you can see how powerful it might’ve been. 

AI-assisted one-way-door decisions

When we were deciding whether or not to raise money for Every in 2020, I was doing a lot of journaling in the then-red-hot note-taking app Roam Research. I was writing about things like: What are the pros of raising? What are the cons? What are my fears and how realistic are they? What could work about raising money for this business? 

The nice thing about this journaling habit is that I have all of the entries. I know exactly what I was thinking at the time. So I grabbed a bunch of them, threw them into Claude, and asked it to pull out the patterns:

“Here are a few journal entries about whether or not to fundraise for Every. Can you help me find patterns that can help me make a breakthrough? Be honest and direct. Be specific, use examples.”

Here’s what I got back (lightly edited for clarity and privacy):

“Based on the journal entries you provided, there are a few key patterns and themes that emerge:

1. Fear of losing control and autonomy by taking outside capital. You worry that having investors will make you feel obligated to hit metrics and strain for growth in ways that make you uncomfortable. You want to avoid feeling terrible and being "behind the curve" constantly. The idea of taking investor money is triggering a strong "NO" reaction in your body. You seem to want to maintain control and optionality, focusing on craft and writing. 
2. Desire to build something on your own terms. You are drawn to founders like Andrew Wilkinson, Nathan Barry and the Basecamp founders who built profitable businesses they own and control. You want to create your own "weird wonderland company" and having too many investor expectations feels at odds with that.
3. Changing and uncertain feelings. Your feelings seem to oscillate a lot on this topic and you acknowledge not being 100% sure how you feel. The VC-backed vision sometimes resonates but other times feels off to you. You are trying to stay open while also listening to your intuition.

In summary, the conflict between an investor-driven, high-expectation growth path and a more organic, craft-driven, founder-controlled approach is the core tension causing you stress. At the same time, you acknowledge that company-building inherently involves some discomfort and that investors aren't necessarily bad. Staying open to paths where you maintain sufficient control/autonomy while still having support to build something great seems wise.”