Planning for your second chapter in your 40s.

(Even if you think you don't have to.)

by Lisa Vermaak

Director of Operations | Huddle




(Even if you think you don’t have to.)


At the moment, most of us have only got the mental strength to imagine making it to the end of lockdown, never mind reimagining your life. And yet this is my challenge to you today.


If you can do one thing for yourself during this time perhaps it’s just this.


Give your Covid-weary self permission to dream about the future.

Allow the thoughts about your current situation to come to the forefront of your mind instead of letting them linger in the “too hard basket” at the back of your mind. Even if you don’t know what’s possible, allow yourself to imagine something is. Be real with yourself about the fact that at some point you may no longer be relevant in your current position. This doesn’t always mean you need to leave the industry you’re in, but it may mean reinventing yourself within that context. Don’t let yourself off the hook for another five years. Dreaming or allowing your mind to wander, opens it up to the possibilities. It also means you can write your own narrative.


In our parents’ day, they were not thinking about their careers in the same way we do. They would have sailed through their 40s and 50sat work because everyone knew you only had to make it to 60 or 65 and you’d retire or be retired. A second chapter or another career was not a thing. Whilst we Boomers are not in the league of the other Generations following us who according to McCrindle “will have 17 different employers and five separate careers during their lifetime”, we can expect to have at least two.


A couple of years ago I had a conversation with a friend and ex-colleague. She’s nine years younger than me and at the time we had this conversation she was in her early forties. She was the Managing Director of a medium sized business and expected to be doing that for some time to come. I had just made the decision to leave our shared industry in which I’d spent 30 years, to do something completely different. This kind of life change or thought process was not even on my friend’s radar but she did know she didn’t want to stay in that industry forever. She just didn’t think her early forties was the time she needed to worry about it.


So, being the good friend that I am, I made her worry about it. This is how the conversation went.


“Do you know which industry you’d like to move into?”

I think so.

“Will you need to retrain or gain some skills you don’t have now?”


How long do you think this process will take?

Maybe five years.

When do you think you’re going to make this change?

I’ll think about it after turning 50.

“So, you’d be 55 and looking for a new job in a new industry?”

I see what you’re saying…


The moral of this story is my clever and ‘never wait around for someone else to make things happen’ friend started networking with people in her desired industry and found out exactly what she’d need to do to enhance her already considerable transferable skills. She took another job in the same industry she was already in with less responsibility to give herself more time to focus on her new plan.  And voila – a little less than five years after that conversation she’s moved seamlessly from her first to her second chapter and I can assure you she’s got a third wind never mind a second one! She tells me now that this had been an invaluable conversation which made her confront something she never would have until it was very late in the day.

Oh yeah!


There are two ways to look at the second part of your life. Either wait for some imagined inevitability that dictates to you the way your life will look. Or my preferred approach which is to decide this is your moment to write your own narrative and design your own life. I know that sounds a little Byron Bay but just give it a go. Some of it involves career but a lot of it involves thinking about how you’d like your life to look five, ten or 20 years from now. You don’t have to choose between purpose, meaning and career in this next part of your life. You just have to be intentional about making it happen before something happens to you that you weren’t expecting. Allow yourself to think this can be something you choose rather be dependent on things you can’t control.


Another friend of mine resigned from his job at 46 because he felt like a change. He thought looking for a job at 46 was the same as looking for a job at 36. It isn’t and now he’s out there trying to find a job in the same industry which has younger, less expensive people competing with him. He has no real idea what he could do as a different career and no time to re-skill or even investigate it. The panic has set in because it needs to happen now because he has a mortgage, private school fees and all the other trappings of modern life to pay for. He no longer has the luxury of a job whilst he considers his options and as he told me, “I had no idea what it was like out here. I’m 46 and f&*%$#ed.”


Whilst the first story had a happy ending, this last story is more of a cautionary tale. Whether by choice or it’s thrust upon you, your mid-forties are the best time to be considering what to do with the rest of your life. Dreaming, planning and thinking about this earlier than you ever thought you’d have to means you get to make the choice about what it is and determine the time frame. It means you never have to feel like something will happen to you, but you’ve made a choice to make it happen for you.


And now that you’ve done more thinking and dreaming about the future than ever before during this future limiting period in our history, you may go back to desperately searching through the many streaming options available for something good to watch. That is something I definitely cannot help you with.

Happy dreaming!











Header image Photo by Ihor Malytskyi on Unsplash

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