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

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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. 

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• The power of personality simulation in predicting future emotions
• Turning journal entries into actionable insights
• When raising money isn't the right move
• Plus: Get access to the AI chat that led to the creation of Spiral.