What might you regret not trying?

This is the seventh and final exercise in this series designed to help you reflect on and gain perspective on the career choices you are making.

When people reflect on their lives, research shows they regret the things they didn’t do more than the things they did. Missed chances, unexplored paths, and untested ideas often weigh more heavily than the mistakes we made along the way.

Asking yourself “What might I regret not trying?” can be a powerful way to prioritise. It helps cut through the noise of fear, busyness, and short-term comfort to highlight what truly matters.

Reflection prompts:

• It's now 2040.  What career opportunity would you be disappointed you never attempted?

• What is a career decision that feels both scary and exciting?

• What have you put on the back burner, just waiting of the "right time"?

• Looking back on your career so far what turning points did you fail to take advantage of?  What can you learn from these?

• If you knew you couldn't fail, what bold steps would you take in your career?

• What dream or idea do you keep circling back to?

• If you were just a fraction braver what experiment would you try in your career?

As you complete this series of reflections, you now hold seven different lenses through which to view your career: flow, values, strengths, your legacy sentence, contribution, money-free passions, and regrets not taken. Each one is a doorway to deeper self-knowledge and wiser decisions. They are a toolkit to guide slightly more courageous career thinking. Career decisions rarely feel simple in the moment, but when you pause to reflect in structured ways like this, and you combine this with regular career maintenance, you give yourself the best chance of building a career in which you flourish.

As always, wishing you a flourishing career.

Katherine