The biggest risk to your career isn't failure - it's regret
How mental time travel can help you make better career decisions
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I've been thinking a lot about regret lately.
Not in a gloomy way, but because I’ve just re-released my 2022 conversation with Dan Pink on the Future Work/Life podcast. Dan had just published his book on regret, and one insight from our chat keeps rattling around in my head:
The overwhelming majority of us regret inaction more than action.
This struck me because I see it playing out constantly. Whether you're weighing up starting a business, changing roles, or pushing for that promotion, most of us get stuck obsessing over the perceived risks - financial uncertainty, lack of experience, or what others might think if we fail.
But here's the thing.
Failing to be bold is far riskier in the long run than failing in a new venture.
Let me explain why.
Most discussions about pivoting your career focus on the risks - some real and some perceived. If you're like me and have a mortgage and young children, you worry about the financials. If you've only ever worked for someone else, you wonder how you'll handle all the unfamiliar tasks. And then there's that nagging voice asking "What if I look like an idiot?"
But Dan's research, drawing on nearly twenty thousand people's greatest regrets, reveals something fascinating. People overwhelmingly wish they'd adopted more of a bias for action. And the greater the time that passes, the more profound the sense of regret becomes.
As Dan told me:
"We have a very good sense of what future-you is going to regret. Future-you is going to regret not building a stable foundation for your life. Future-you is going to regret not taking an appropriate risk. Future-you is going to regret not doing the right thing."*
This insight led me to explore how other experts approach this challenge of making better decisions and they identify similar patterns. And advise similar approaches to decision-making and taking action.
Adam Grant: Fast-forward to reframe regret
Adam Grant puts it perfectly:
"The purpose of learning isn't to affirm our beliefs; it's to evolve our beliefs."
When we're paralysed by fear of failure, we often catastrophise. Our minds spin worst-case scenarios and amplify potential downsides. But mentally projecting ourselves into the future provides distance and perspective. That terrifying leap doesn't seem quite so scary when viewed from years ahead.
Grant's research shows that when people look back on their careers, they rarely regret the chances they took - even the ones that didn't work out. What haunts them are the opportunities they were too afraid to pursue. By fast-forwarding in your mind, you can tap into that future wisdom today.
Ethan Kross: Quiet the mental noise
Ethan Kross suggests something brilliantly practical - talk to yourself in the third person:
"Use distanced self-talk. When you're trying to work through a difficult experience, use your name and the second-person 'you' to refer to yourself."
This isn't just a psychological trick. Kross's research shows that when we step back and view our situations from the outside, we access the same wisdom we'd offer a friend. We become better at distinguishing between legitimate concerns and anxiety-driven overthinking.
I use this technique regularly. Let me share a real example:
"Ollie, if you decide to up sticks to Ibiza, you'll be creating unnecessary disruption in your kids' lives"
"I know that, Ollie, but imagine how amazing it will be for them to learn Spanish and be able to go straight to the beach after school every day."
"Yes, but what are you going to do when a new client asks you to come to the office to see them the next day?"
"I'd probably say what century are you living in, and, anyway, my aim is to have a business that can be run from anywhere in the world, so this is the perfect way to test it. And besides, if it doesn't work out, we'll come home having experienced something new as a family."
This kind of self-talk helps you gain perspective and often reveals what you really want.
More importantly, it helps you see what future you might regret not trying.
Laura Carstensen: Focus on what truly matters
Laura Carstensen from Stanford's Center on Longevity offers perhaps the most profound insight:
"When we recognise that we don't have all the time in the world, we see our priorities most clearly."
Her research reveals something fascinating. As people age and their time horizons shorten, they naturally focus more on what brings genuine meaning rather than surface-level success. But here's the key - we don't have to wait until we're older to adopt this perspective.
By imaginatively constraining our time horizon, we can access this clarity of priority at any age.
Carstensen's work suggests that when we adopt a longer-term view, we make decisions that align better with our values and lead to greater life satisfaction. It's not about being morbid - it's about using the power of perspective to make choices we'll be proud of.
An exercise in mental time-travel
Here's a practical exercise combining all these insights:
Picture yourself a decade from now. Be specific - where are you, what are you doing, what matters to you?
Have a conversation with yourself about the decision you're facing, using your name. Write down both sides of the dialogue.
Ask yourself: "What would I tell my best friend if they were in this situation?"
Consider what you'll regret more - taking the risk or wondering "what if?"
Does mental time travel work perfectly?
Well, I haven't moved to Ibiza yet. But that's mainly because there have been decisions I'd regret more that have stopped me from doing so. But if I keep asking the question…who knows?
What I love about this approach is how it cuts through the noise.
When you're trying to decide whether to take that entrepreneurial leap or push for that promotion, your future self often has surprising clarity about what really matters.
Want to hear more?
Listen to my full conversation with Dan Pink. He shares fascinating insights about regret, decision-making, and how to build a life you'll be proud of when you look back.
But before you go, I'm curious. What would your future self tell you about the decision you're weighing right now?
Reply to this email and let me know. I read and respond to every message.
Until next week,
Ollie
P.S. If you found this helpful, share it with someone who's facing a big career decision. Sometimes we all need a reminder to think bigger.