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What does winning in your XXs look like?

Picture of a sign with the word "WIN".
Danny Howe on Unsplash

[select the age group for you from 20s, 30s, 40s, 50s, 60s and replace XX]

I have a confession to make, I didn't ask myself this question when I turned forty, but I wish I had. I just continued, head down, doing what I was good at, what I had succeeded at doing previously. And what paid me a lot of money. Money that was no longer making me happy at work.

And then, after spending over twenty years working for other people, full-time, within corporations, I started to explore what I would do for the next twenty years. It was at this point that I realised something had to change. That was six years ago.

And now, as I approach the big 5 0, I feel fortunate. I get to think for a living.

What does that mean?

Basically, I get to do what I love. I have designed the second half of my career, which is full of the following:

  • Coaching amazing people.

  • Continuous learning.

  • Reading and writing.

  • Spending time with my family.

  • Healthy living.

The money sucks compared to investment banking. And, of course, I don't always get everything right. But I view myself as wealthy. I guess it depends on one's definition.

And yet, to avoid the trap of automatically embracing the status quo, I will still answer the question about winning in my 50s.

Enough about me. What about you?

Too few busy, successful people get the chance to stop and think when it comes to planning the next steps in their careers or the changes they should make to their existing jobs to make them more enjoyable and more fun.

If you can't find a way to make it fun, perhaps you should not be doing it.

So, for you, what does winning in your XXs look like?

I want to help you ask and answer this question proactively rather than reacting after some unexpected external event acts upon you. Being proactive gives you a better chance of operating from a position of strength.

So this month's challenge includes some exercises I have used with successful professionals who have hit a point in their career and asked, "What's next?" and "Is it worth it?" Their reasons often differ, but common themes that are catalysts for exploration are:

  • The new opportunity - a more significant role, with more responsibility - but "is this really what I want at this time?"

  • The workplace conflict - where the boss was wilfully blind to their adverse impact on their team, demotivating the A-players who were now questioning "whether it was all worth it?"

  • The lost mojo - repeated restructurings, downsizing and missing out on a promotion is draining. "How to redefine the relationship with work to be more effective and, at the same time, more enjoyable?"

🏋️ Challenge: What changes should you make to move forward intentionally?

Complete one or more of these exercises for your monthly challenge.


Reflect on the past year and set goals to make your life better. It sounds obvious, but how many people have written their goals outside their employer's formal annual appraisal system? The most successful people do this consistently.

Download the template for my 3-step system to help set your goals.

The Odyssey Plan

Write out in detail your answers to the following three questions. Write fast and write whatever comes to mind. Reviewing and refining come later. Grab a glass of wine or a cup of tea if it helps:

  1. What your life will look like five years from now if you go down your current career path.

  2. What your life will look like five years from now if you take a completely different path.

  3. What your life will look like five years from now if money and obligations are not a factor.

Coaching for fulfilment

An exercise using personal constructs to tease out our values and belief systems:

  • Identify ten meaningful relationships from the past - family, friends, and work.

  • What attributes, characteristics, attitudes and behaviours have you observed in these people?

  • What is the opposite word for each one of these common elements?

  • For each pair of elements, put both words under the headings "desirable" and "undesirable". So, for example, if the common attribute is "trustworthy" and the opposite is "untrustworthy", then the first would be placed under desirable, while the second becomes undesirable.

  • How would you score yourself for each pair of elements if the maximum desirable is a ten (out of ten)? In contrast, the maximum undesirable is one out of 10.

  • Using the insights, ask what changes (stop doing, start doing, do more of) you will implement in your life.

These exercises can be deeply reflective experiences, especially when you work with a coach to delve deep to identify what is common, what surprises you, and what you are willing to do differently. Use these exercises to answer the big question to help you know whether you are winning as a vicenarian, tricenarian, quadragenarian or, in my case, soon-to-be quinquagenarian.


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