What if your most challenging career moment becomes your most defining?

I recently watched a video on LinkedIn featuring Dolly Parton where she was asked what her biggest mistake had been.

Her answer really made me stop and reflect.

She said she didn't look at her life in terms of mistakes, but as a series of events. Sometimes, the things that might look like our biggest mistakes can turn out to be our biggest blessings.

It got me thinking about leadership and about my own career. Those moments when, as a leader, I had to stop, reassess and make a different choice.

What if we looked at our careers in the same way?

What if some of the experiences that feel like mistakes or failures at the time are actually the most defining moments in our careers?

Moments that build our learning, our resilience and our self-awareness.

Moments that shape who we are as leaders, moments that help us become more authentic, and encourage us to take ownership of what happens next or to choose a different path.

These moments can come in many forms:

  • The promotion that didn't happen.

  • An organisation or working environment that doesn’t align with your values.

  • A decision we made that didn't work out.

  • Being overlooked for a role or project we felt was right for us.

  • Being pushed outside our comfort zone into something we aren't sure we're ready for.

When you're in the middle of it

Thinking about the challenging times in my own career, one thing stands out.

When you're actually living through these moments, they rarely feel defining. They can feel like some of the worst moments in your career.

Often, we can't see the wood for the trees. We can't see a way forward. We can feel that we've failed.

And sometimes we lose a little of ourselves along the way. Our confidence takes a knock, or we realise we're no longer quite aligned with the organisation or environment we're working in.

But perhaps this is where the defining moment begins.

Because at some point, there is a choice about which road we take next.

One road says:

“I give up. What's the point?”

The other asks:

“What can I learn from this?”

“What is this situation telling me?”

“What can I control?”

“How do I move forward from here?”

For me, that is where ownership comes in.

We may not have been able to control what happened, but we can begin to take control of what happens next.

And sometimes taking back control doesn't mean having all the answers. It simply means making the next choice.

So where does coaching come into this?

When you can't see the wood for the trees, it can be incredibly difficult to work out the answer on your own.

This is where coaching can support you.

Coaching gives you a safe, non-judgemental space to pause and ask:

  • What next?

  • What is right for me?

  • What can I learn from this situation?

  • What do I want in the longer term?

  • And what is the one action I can take now that will start moving me towards that?

Sometimes it is not about having the whole plan.

It is about gaining enough clarity and confidence to take the first step.

Hindsight is a wonderful thing

One thing I always encourage my clients to do is continually reflect.

Because often, it is only six months or a year further down the road that we can look back and recognise what a particular experience created for us.

What felt like failure at the time may have prompted us to change direction.

What felt like rejection may have made us question what we really wanted.

What felt like being pushed outside our comfort zone may have shown us that we were capable of much more than we thought.

The defining moment isn't always the event itself. Sometimes, it's what we choose to do next.

And perhaps the next time something doesn't go to plan, instead of immediately asking:

“Where did I go wrong?”

We could also ask:

“What might this be here to teach me?”

 

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