The biggest mistake people make when determining a second career in their 40s and 50s

It’s confession time. I made this mistake. (I know, imagine).

Ten years ago, I was hankering after a second career. While I’d built up years of knowledge, skills and experience in my field, I dreamed of a making a real change.

I’d spend hours visualising a lifestyle and career that afforded me more time, more freedom and more personal fulfilment.

I imagined living in the countryside or on the coast, working for myself and doing a creative job with meaning and purpose, whatever that might be.

As it became harder to reconcile my dream with my reality (I lived in the city, worked for a global organisation and did a job that didn’t scream purpose at me), I knew it was time to start planning my second act.

And so I did what pretty much everyone does.

As I tried to figure out my ideal second career and how I might make money from it, I started with my CV.

Sensible decision, right?


Bear with me here, I know this probably seems surprising.

While it might belie logic, this is why it was a bad idea.

My CV pigeonholed me as a “communications person”.

Those pages of copy documenting my skills and experience formed parameters that boxed me in.

They presented a tunnel vision of the options available to me, and at best helped me generate ideas that were only one or two steps removed from my current position.

It meant that I started looking at communications roles in different cities, which is where the majority of those jobs were based, and I also considered becoming a freelancer in the field.

Not only did these ideas leave me utterly cold (read freezing), they didn’t deliver on the most important criteria of all.

They didn’t cater for the lifestyle factors that had fuelled my increasing desire for a change in the first place.

One way or another, each idea lacked time, freedom, personal fulfilment or a combination of all three.

Which left me feeling demotivated and like a fulfilling change was impossible to achieve.

What I didn’t know then was that by trying to determine a new path through the lens of my résumé, I was unwittingly curtailing my options and actively courting compromise.

So here’s the eye-opener.

Starting with your CV doesn’t help you make a real change.

It doesn’t steer you to towards a better work/life balance or a genuine sense of purpose, which is what those in their 40s and 50s most often crave.

Instead, the most effective place to begin is with a deeper dive into not just what you’ve done, but who you are.

Taking the time for some intentional self-reflection can make all the difference.

What I’m talking about here is the kind of self-contemplation that feels like fun. Where you dig deep to uncover what truly drives, motivates and interests you, and explore your most feel-good talents.

This is the opportunity to make a change that ultimately delivers the life you dream of.

It should feel playful, exciting and inspiring, and most importantly of all, deeply personal to you.

So where to start?

Well, in my experience there are four foundational areas that combine to shape the right ideal career and life path.

Those areas are your personal values, strengths, passions and skills.

To help kick-start your own process of self-reflection, have a go at answering these questions. Take some time to really mull over your responses, to see what they tell you.

  • What are your values? Which principles underpin the way you need to live and work in order to be happy?
  • What are you passionate about? What activities or topics absorb you so that you lose time when you’re engaged in them?
  • What are your strengths? What are you naturally talented at? What do people always tell you you’re good at?
  • What are your skills? Which of your skills do you enjoy using the most?

I can promise you one thing. Your answers to these questions will provide a much better foundation for decision making than your CV.

They will also help direct your thinking without trapping you in a single line of focus based on your field experience.

So in the words of the wonderful Mary Oliver, what is it you plan to do with your one wild and precious life?

P.S. If you’d like some structured help with your self-reflection, which leads you to a clear answer on your ideal second career, check out my Work Wonderland and IDENTIFY programmes.

It will lead you, in a fun way, to uncover the personal gems that will form the foundation for your next career chapter.  

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