Connecting the dots of your career

No pets were harmed in the making of this post.

When I was little, I loved the dot-to-dot puzzles my mum bought me at the shops. In those early days, I would squint at the sea of dots and numbers and try to guess what they would reveal. The best ones kept me mystified, so I’d have to shrug, grab my Crayola crayon(Violet-blue or Denim were my favourites) and just find that first dot…and the next…and the next.

When I was a mere dot-to-dot rookie, I’d draw in big bold lines and sometimes I’d make a mistake, a glaring line in the wrong place that would need careful colouring out later. But if I was patient and careful, slowly the picture would reveal itself to me.

I loved that moment of revelation when I could see it-the picture emerging from the dots. As I became more of a “dot pro”, I could see the pattern or the picture quickly and easily, I was soon able to predict the flow of the picture rather than desperately searching the whole page for that next magic number, though sometimes I still tripped up.


A few months ago I was asked to speak to a room of professional women about my career. The woman who invited me said the audience would love to hear the strategies and skills I’d used to reach this award-winning phase, to get that magical MBE. I tried to sound confident and enthusiastic on the call, but as I hung up, I felt the panic rising.

The plan?! The strategy?!

I was 51 years old and I had just decided to make a big career change. I was starting “portfolio work” and still at the “early formation stage” (i.e., I was still “making shit up.”) I was finding this new chapter a real rollercoaster — 3 days a week loving it, 3 days hating it and 1 day panicking and telling myself I could always get a job at Pret a Manger because I was in there enough to know the routine.

I was 51 and still trying to figure out what I wanted to be when I grew up. Like most women, my sense of imposter syndrome always waiting eagerly in the wings and this event was putting it centre stage in my mind. What advice could I possibly give this group of talented professional women?!?

Many deep breaths (and a glass of lovely red wine)later, it seemed a little clearer. While it often felt crazy at the time as I looked back at it all, my career did make a bit of sense; and with a little understanding and storytelling (and another sip of wine) a picture did emerge that gave the vague appearance of a plan or strategy.

That was my “aha” moment — the realisation that for the vast majority of us, our careers are a giant, lifelong dot-to-dot puzzle. And that fact was okay.

Sometimes we can see a pattern emerge.

Sometimes we are just bloody grateful to get from 5 to 6 and pray that 7 is out there somewhere.

Sometimes we get it wrong and and go looking for 8 on the right hand side of the page, panicking until we realise that it is hiding on the left.

Or worse, we start drawing the line in the wrong direction and need to do some heavy post-colouring to clean that line up.

But it is our puzzle. No one else can tell us it is wrong. We get to step back to look for the pattern and grab more crayons to tie in those stray lines. Sometimes it just needs one more dot (or some careful colouring!) And we have to remember that we get to tell others the story of our puzzle. On our CV’s and in our interviews.

And if we can make sure the picture makes sense to us or get someone to work with us till we do, we can help others see it too. I can think of many of amazing people I’ve hired with less than traditional CVs once they helped me see what they’ve learned from their career and how my company is the best next step for both of us.

A month later, I sat precariously on one of those tall stools, wobbling a bit while I spoke to the women about my love of dot-to-dot puzzles. And I saw a room full of smiling, relieved women of every age and stage.

Like me, many were panicking that they didn’t have their rock solid 5 year plan, some were desperately trying to decide whether to quit or to stay and the majority were also still trying to figure out what they were going to be when (or if) they grew up. And all of us worried that we were somehow “getting it wrong.”

And it was a great time to take a breath and relax with all those women. And remind ourselves that we will tell the story of our careers, that we will explain our picture to others on our CV or in our interview interviews we sit in. And to have a sip of wine and pick up the bloody Crayon and figure out where 9 was.

I’ll be writing more about changing careers, choosing careers and figuring out how (or whether) to climb that ladder. If you need a speaker, a workshop or a coach to work with you in this area, please get in touch.

But for now, wherever you are in the puzzle, don’t worry about the picture, just worry about finding the next damn dot. There is no wrong way to do it and with careful colouring we can sort out the stray lines and missed dots.

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