For years, I thought I knew what success looked like.

It was the title on my business card. The numbers in my bank account. The next rung on the ladder.

And for a time, that definition worked. It gave me direction, purpose, even a sense of security.

But over time, I realised something important – success does not only look different to each of us, it also changes depending on the season of life we are in. And if I am honest, I still have to remind myself of that truth, because it is easy to slip back into measuring myself against old ideals.

What once felt like the pinnacle can, in hindsight, feel hollow. The danger is clinging to those outdated measures and missing the fulfilment that comes when we realign success with who we are today.

Why Success Has Seasons

If we treat success as a fixed point – one single definition to carry through life – we risk chasing something that no longer matches what we truly value.

Life has seasons. And so does success:

• Ambition and Progress
  In some seasons, success means striving: climbing the ladder, building financial stability, proving yourself through achievement. These are periods of growth and momentum.
• Stability and Balance
  At other times, success is not about more but about enough. It means protecting time and health, prioritising family, or creating a calmer pace that sustains you.
• Impact and Legacy
  And in later seasons, success often shifts towards contribution: sharing wisdom, mentoring others, and creating something that outlasts you.

Each of these seasons is valid. Each carries its own form of success. The key is recognising when the season has changed – and having the courage to redefine what matters most.

The Cost of Outdated Ideals

One of the biggest traps I see – and have lived myself – is measuring today with yesterday’s yardstick.

We hold onto goals that once motivated us but no longer resonate. We compare ourselves to old versions of who we were or to standards that no longer fit our priorities. And when we do, we quietly set ourselves up for frustration.

Fulfilment rarely comes from more of the old markers. It comes from updating the definition.

Redefining Success in Your Season

So, how do you know what success looks like for you now?

1. Notice what feels empty. If the old markers no longer energise you, they are probably not the right definition anymore.
2. Pay attention to your values. What matters most today – growth, balance, contribution? Let that guide your definition.
3. Give yourself permission. Success does not have to look the same as it once did. It can evolve, just as you do.

A Question to Reflect On

What does success look like in this season of your life – and how will you know when you are living it?

Closing Thought

Success is not a single destination. It is a moving horizon. What fits in one chapter may feel restrictive in another.

The real challenge is not in chasing the old markers harder, but in having the wisdom to let them go and create a definition of success that truly fits the life you are living today.

If you are at a crossroads and want to redefine success on your own terms, I help accomplished professionals navigate transitions with clarity and confidence.