Should you marry that person? Quit a steady career to retrain? Move across the country, away from ageing parents? Sit with any of these and watch your mind spin. You weigh what you’d gain against what you’d lose. You run the numbers. And still no answer arrives.
Big decisions do this to us. They are rare, life-shaping, and hard to undo, and they refuse to be solved like a sum.
Researchers recently used AI to analyse more than 100,000 real dilemmas posted online. They found choices pulled in dozens of directions at once, far from the tidy two or three variables we imagine. Big decisions are messier than they look.
I study how people make life’s biggest decisions. In research, I asked more than 600 people to describe their ten biggest decisions. Thousands more have since mapped their own choices in an ongoing study. Marriage, children, career changes, house purchases, and relocations come up again and again.
My study didn’t hand me a checklist you can use when faced with a big decision. But it did show what separates the decisions people are later glad of from those they regretted. Read alongside the wider research, those factors fall into a rough order worth trying.
1. Choose, don’t drift
Start by admitting you are deciding. Many of us never quite choose our biggest paths. We move in with a partner to save on rent, sliding into a relationship rather than deciding on one. We take the job that happened to be offered. We stay in a city because leaving never quite comes up.
Bit by bit, life feels less like a choice than a current we floated along. A decision you never consciously make is one you cannot make well.
2. You’re choosing for a stranger
Standard guides tell you to list what you want. But a genuinely big decision is transformative. It changes the very person making the choice. Parenthood, marriage, or a new career reshape your values, so the “you” on the far side may want different things than the “you” choosing now.
So don’t only ask what you want today. Ask who you want to become, and whether the experience itself is one worth having. And don’t assume the goal is happiness. Some big choices trade comfort for a richer, stranger life, and people choose them anyway. A good life can be interesting rather than easy.
3. Try before you commit
Resist the two-option trap: “take it or leave it”. Instead, run a “vanishing options” test: ask what you’d do if none of your current choices were allowed. New paths will appear – to wait a year, do it part-time first, rent before you buy.
Then, test what you can. No big choice allows a full dress rehearsal: living together isn’t marriage, a weekend with a niece isn’t parenthood. Sample the edges anyway. Take the secondment before you quit. Spend a month in the new city before the move. A rough taste beats a pure guess.
4. Borrow some hindsight
Ask people who know you, and people who have done the same thing you’re considering. In my data, decisions made with more advice were judged more positively years later.
One catch: don’t tell them which way you’re leaning. Reveal your hunch and advisers tend to echo it back rather than test it. Ask first, share your view later. Other people’s hindsight is the closest thing you have to your own foresight.
5. Some things won’t add up
Now, the hard part. You will crave a single score, a spreadsheet that ranks each option. But the things that matter most share no common currency. How do you convert love into the same units as money? You can’t – and forcing them onto one scale just hides the trade-off you’re trying to discern.
So, stop trying to compute the odds. Instead, build a story. Weighing that move abroad, you can run the years forward – the work, the friendships, the life that might grow there – and choose the version you believe. When the sums can’t be done, a story is what’s left to act on.
6. When in doubt, leap
How do you choose between options that won’t rank? Watch your hesitation. In my data, the decisions people felt sure about were the ones they later judged well.
Confidence may act as a signal that you’ve searched enough – and when it won’t come, more spreadsheets rarely summon it. When you are truly on the fence, the odds favour the braver move.
American economist Steven Levitt had more than 20,000 people flip a coin over choices they were stuck on; those the coin pushed towards change were happier six months later. Staying can be right, but our thumb presses too hard on the status quo. Research suggests the road we regret longest is usually the one not taken.
7. Commit, then plan to be wrong
Make the call, then commit. A good decision is a good process; the outcome is never fully in your hands. So, build the process. Before you commit, run a “premortem” and a “backcast”. Picture it’s a year on and the choice has failed, and list why. Then, picture it’s gone brilliantly, and list why.
Together they show the risks to guard against and the upside to chase, while you can still act on both. Then set tripwires – the dates or warning signs that trigger a rethink – so a slow drift never hardens into a sunk cost.
The deciding is the point
The worst way to make life’s biggest decisions is to not quite make them. To slide into a marriage, a career, a city, then wake years later wondering who chose. So, choose. Even imperfectly. The deciding is the point.
