Cheshire cat

What can “Alice in Wonderland” teach us about cybersecurity careers.

Would you tell me, please, which way I ought to go from here?”
“That depends a good deal on where you want to get to,” said the Cat.
“I don’t much care where—” said Alice.
“Then it doesn’t matter which way you go,” said the Cat.
“—so long as I get somewhere,” Alice added as an explanation.
“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”

(L. Carrol – Alice’s Adventures in Wonderland)

Whenever someone asks me for advice on how to get into cybersecurity, this is the scene that comes to mind.

The Cheshire Cat was one of my favourite characters growing up, who would have thought that in my career I would find myself grinning at many cyber-loving Alices looking for direction?

This is normally how I respond to that:

1) If you know which role in cyber you want, research the requirements and start working through them to attain a good number of those skills and make yourself employable.

2) If you don’t very much care about which route in cyber you pick at the moment, then it doesn’t matter which way you go. You will end up somewhere if you stick at it long enough. Then you will either know and you will change for the role you want (back to point 1) or you will realise you went in the right direction after all!

This also applies to already practicing cybersecurity professionals looking for a career change.

Sometimes we feel we need a change but don’t have a complete vision of what it entails yet. This can also be because we are exhausted so we don’t care in which direction we go as long as it is away from here.

It is ok to not have a clear direction, there is value in exploring and testing. There is value in taking time to reflect. One could argue there is also value in ending up in the wrong place and learning more about what we don’t want.

In this goals oriented culture it feels scary to not have a goal. What we forget is that we always have a goal as humans. That fundamental goal is more of a feeling goal. We aim to be content, free of worry, inspired, involved, serene, happy.

As my clients know well, this is where I start from whenever they tell me they don’t know where they want to go: “how do you want to feel when you get there?”.

If I have to be completely honest, also when they have a clear goal in mind (“I want to be a CISO”; “I want to work for FAANG”) I always check whether that goal is in line with the way they want to feel and the way they want to live.

Because if achieving your goal doesn’t make you happy, then what’s the point, right?


Are you experiencing similar doubts? Feel free to book a free 30 minutes coaching consultation with me and let’s find that way forward.