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How plans and checklists have shaped my career (and life).

Hands up the planners! Ah, how I love a plan and how twitchy I get when they get messed with. I am perpetually curious that most of my clients show up identifying as planners. They love being in control and the very idea of not having a plan – a checklist - is alien. I identify! Much of my work on me, has been unlearning my need, yes need, for a plan and my desire to control the little things, oh so much!


This week I want to share my experience of being a planner – how this influenced my career and life journey for better and for worse and what I have learnt to better embrace and crucially, let go of.



My planning goes back as far as I can remember, and I created my checklist from it. It became my map and informed all the decisions in my life. I started in life ticking off the checklist I had created unknowingly for myself; a checklist influenced by those around me, by the world telling and showing me what was expected, and by my built-in drive to achieve and please. I’m not knocking the list – it got me through school, through university and into a large successful, respected organisation and profession. My checklist continued to serve me well as it took me on to secure my first company car, to buy my first flat on my own, and to go and find the partner I ultimately married. It was all on the list, see?


I think if the list had continued to deliver, my life would have taken a very different course. But the list fell over when I couldn’t check off the next ‘thing’. In fact, it came to rather an abrupt and rude halt, and I was left bewildered looking up and blinking into a what next space, without the map that I had been staring down into for the majority of my life. I ran out of boxes to tick.



This was the part I was unprepared for. As a lifelong planner, a cruncher of options and risk mitigation (ok avoidance), I was woefully lacking in the skill of winging it, the skill of going with the flow, the skill of experimenting, of just seeing, of trying, of accepting, of ultimately being ok to fail. It’s so incredibly painful to fail when you aren’t practiced in it. It’s so difficult not to get it mixed up with the very essence of who we are, and if we end up there, we have the real risk of feeling shame; and that’s a big one to sort out.


My biggest learning to date around plans, has been dispelling my own myth about forever. My checklist was a forever checklist – it spanned a lifetime, and I wrote it when I was a child. I now know, through sharing this over the years, that I am not alone in this. So many of us believe we must have this forever plan, and then to make it more impossible – the plan needs to be this one thing. Purpose – you should know what you want to do, who you want to be, and you should go and do it, and you should stick to it. Not knowing is not acceptable.


Well, I think that is just plain wrong. I’ll let you into a poorly kept secret - I don’t know what I want to do. Truly I don’t. But here’s what I can tell you. I love who I am now. I love what I do and what I get to try. I have a direction of travel and I have some plans – and I am seeing how that goes. I am deeply grateful for the people in my life. I have ambition, there are things I want to achieve. There are things I have got very wrong; I will undoubtedly get things wrong again (hopefully different things!). There isn’t one thing for me, or at least I haven’t found it if there is, so I am not doing one thing; I am doing lots of things, being lots of things. And I love the variety (spot the value), I love the freedom (spot the value), I love the creativity (guess what?) and I love the collaboration (you get the gist)…


Scrapping about for the answer, for our one purpose can be corrosive, we can feel such grief if we can’t find it. What if there isn’t one answer? Can we contemplate not just one way, one path- can we acknowledge and accept that we don’t know?



When we compile our plans and checklists, I wonder how many of us do so with an understanding of purpose, of the why behind them. My why didn’t stand up to great scrutiny in the end – it went something along the lines of – because that’s what people do, it’s what I think is expected of me, I assume it will make me happy and I want to be successful. And sure, for a time it coincided with satisfaction and contentment, and then I think it just didn’t deliver anymore. Plans and checklists will always be useful… they are tools and as such they bring value to the right situation. But if, like me, your plan is a little too rigid, you may find yourself, like me, one day looking up from that plan that perhaps is no longer delivering for you and finding yourself in lonely unfamiliar territory.


If there is one thing my experience and my story could offer – it would be that I see so many of us clinging to a plan that we have outgrown. And because it was a great plan at some point for us, we are terrified of putting it down. The fear for me was that if I changed my plan, it must mean that I had got something (everything?) wrong thus far. That I was abandoning something, that I was failing something. It isn’t true, my plan served me incredibly well. Personal contentment in my relationships and a professional education second to none, now fuelling my own business. Challenge one therefore was putting the list aside. Challenge two has been accepting that I don’t have anything so detailed to replace it with and leaning into the fear that I feel with that.



I leave you with my reflections on plans and checklists:


  • They serve a purpose – comfort, familiarity, goals, targets, achievement … action

  • They get risky when you draw one up to represent a whole career or life

  • They get scary when you don’t revisit them regularly

  • They start to not serve when you blindly follow them, ticking away, ignoring the changing world around you, and the changing you

  • You miss a lot of opportunities if your nose is only in your plan, all those open doors you walk past because you don’t see them

  • Write them in pencil, not pen, and embrace the mess as you cross out, rewrite again and again

  • Leave spaces for all the things you don’t know yet

  • Accept that sometimes binning it is the next checkpoint, it’s done its job


If you are curious about how I can work with you , you can speak to me directly, you can book a free initial 30 minute coaching session with me here and there's no hassling from me if it's a no thanks after that.

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