Originally published on Medium, refreshed for 2026 with new thinking on AI, inclusion and the mid-career moment.
Let’s talk about regrets. Rewinding the clock might not be an option but it’s never too late to learn from the past.
Looking back, most people wish they could have done something differently. We spend just about one-third of our lives at work, so there are bound to be some bad decisions and missed opportunities along the way. The hope is that we recognise our biggest disappointments and take steps to fix them while we can.
To that end, I regularly ask my coaching clients three questions:
What do you wish you’d known earlier in your career?
What would you change if you could magically rewind the clock?
What would you regret not doing over the course of your life or career?
While answers vary between age groups, professionals in the middle or later stages of their careers are remarkably consistent in their regrets, no matter what industry or organisation they’re in.
Five key themes stand out. I’m sharing these with the hope that organisations, managers, and individuals of all generations can draw insights from these experiences and take proactive steps to achieve what’s possible, before it’s too late.
