Don't ask what you want. Ask what regret you can't live with.
A good friend of mine reached out a few years back. We hadn't seen each other in a while. I was buried in a long project at work and told him as soon as I wrapped it, we'd get dinner and catch up on everything we'd been up to. I really meant it. My first day off for Christmas holidays arrived. I opened my phone to tap out a message to him, and that was when I learned I was too late. He'd been ill, and I hadn't known. And the dinner we were going to have now existed only as something I'd promised and would never deliver on.
Back then, I was a workaholic in the most complete sense of the word. It wasn't just long hours, it was core to my identity. I was the guy who always delivered, could do everything, the go-to. At the time, it felt so important to me. I didn't know who I was without the work. Every now and then I'd get the thought that the balance was wrong. That I should see my family more, meet my friends more, experience more. But I couldn't picture what a different life actually looked like for me, and because I couldn't picture it, I didn't really try. I kept grinding. I told myself this was just what it took, that this skewed work-life balance was normal.
What happened with my friend didn't just sadden me. It forced me to reckon with something I'd been avoiding for years. Not the question of what I wanted (I'd been stuck on that forever) but the question of what I absolutely could not bear to live with the regret of. And that question, it turned out, was much easier to answer.
I wish I'd had the courage to live a life true to myself, not the life others expected of me.
I stopped obsessing over work. I figured out what actually mattered to me and made time for it. I got healthier, spent more time with the people I loved, became a better partner, a better friend. And, you know what? I didn't even slightly impact how I was perceived at work. The thing I'd been sacrificing everything to maintain didn't actually need that sacrifice. It never had.
What struck me later was the question of why regret worked when desire hadn't. I'd wanted to change for years. I'd known what a better life might look like. But wanting something is a surprisingly weak motivator when the path is unclear. Regret is different. It's specific, it's visceral, it arrives with a face, a name, a moment you can point to. It bypasses the vagueness that makes desire so easy to put off.
I started to read into it more and stumbled across Bronnie Ware, a palliative care nurse in Australia who spent years sitting with people in their final weeks. The same regrets kept coming up, and the most common one wasn't about money or career or status. It was this: I wish I'd had the courage to live a life true to myself, not the life others expected of me. Not a dramatic fork-in-the-road regret. A slow, accumulated one, built out of hundreds of small moments where they chose the safe thing, the expected thing, the thing that kept everyone else comfortable. They've stayed with me, because the people saying these things weren't guessing about what they'd regret. They already knew.
Not huge actions, but they compound.
Most people talk about regret minimisation as a big-decision tool. Should I quit? Should I start the thing? But what Ware's patients were describing is something smaller, but just as powerful. Whether to pick up the phone. Whether to be present at dinner or half-somewhere else. Whether to let another week pass without seeing someone who matters. Not huge actions, but they compound. And one day, the sum of all those small choices is what you're living with.
The practical move is a reframe. Instead of asking what you want (which is genuinely hard, because what we want is often vague and shapeless) ask what regret you couldn't bear. What would you be unable to explain to the version of yourself looking back? Start there and work backwards. The path forward gets clearer when you're moving away from something specific rather than towards something you can't quite describe.
We tend to think of regret as something that arrives after the fact, the price of a wrong decision. But it can work the other way. Used early enough, it's one of the clearest signals we have. Sometimes the most honest answer to what do I actually want is just: not this.
The Editor's session
I'd take this one to the Motivator. It finds what's actually blocking you when you already know what matters but aren't moving on it, and that's the whole point of this piece: I knew what I was losing, I just wasn't doing anything about it.
There's something I keep putting off that I know I'll regret. I can see it clearly. But I still haven't started, and I don't fully understand why. Help me figure out what's actually in the way.
When you say you haven't started, is that you don't know where to begin, or that you can't make yourself take that first step?
Something to think about
What are you putting off right now that could quietly become a regret you couldn't live with?
If something here landed, or opened something you'd rather not work through alone, I'd genuinely like to hear about it. The best issues come from real stories, so if this one stirred something in yours, write to me at desk@thinkfurther.uk.