The Alice in Wonderland Guide to Career Planning

There’s a wonderful moment in Alice in Wonderland when Alice asks the Cheshire Cat for directions.

In this moment, in the middle of this psychedelic journey through tiny doors, over-sized chessboards, and impatient rabbits, Lewis Carroll struck on a rather clever approach to career planning.


‘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 only you walk long enough’

It’s common career advice to focus on the destination: The job title we’ve always wanted; the salary level we’ll be satisfied with; the seniority we crave. And of course a level of importance that we can broadcast loud and proud to the rest of the world through posts, tweets, and news feeds.

The problem with focussing on a particular job title when planning your career is that things change. Companies restructure, industries collapse, and robots take control. And you change. The unpredictable predictably happens, new family members come and go, things that were priorities get quickly replaced.

The problem with focussing on salary is that we’ll never be happy with what we’ve got. One of the many studies by Daniel Kahneman and Angus Deaton found that £50,000 is the point at which income and happiness stops correlating. In the same vein, the brilliant Jonathan Haidt, in his book ‘The Happiness Hypothesis’, also shows that many workers would rather earn less and be the highest paid member of their team, than earn more and be the lowest paid, largely due our perception of success being shaped by the people we’re closest to every day.

The problem with focussing on fame and importance is that it can be fickle, a fleeting moment build on unsteady foundations, a replacement for time spent creating and building things for real.


So I agree with the Cat’s advice to Alice. It’s the journey that’s important, not the destination. If you get on the right path, and enjoy being on that path the whole time you’re on it, you’re sure to end up somewhere you’ll enjoy being.

Sebastian Coe seems to agree:

‘Throughout my athletics career, the overall goal was always to be a better athlete than I was at that moment – whether next week, next month, or next year. The improvement was the goal. The medal was simply the ultimate reward for achieving that goal.’

So how do you make sure you’re on the right path? In the paraphrased words of Aeschylus – and about a million other quotable people since – you have to take the time to really understand yourself.

The better you understand yourself, the better your next role will fit you. In particular, you need to know four things: what you’re good at; what you want to develop; what you enjoy; and what you want to try:


Good at

As Dan Pink shows in his book ‘Drive’, we all seek to have a level of competence in our careers – alongside autonomy, and relatedness. Having a role that we feel confident and secure in is vital for our happiness and sense of self-esteem, and being good at something also means we’re more likely to achieve things we can be proud of, helping to create a sense of worth and meaning in what we do.

Develop on

Just being good at something isn’t enough, though. Without some form of learning or challenge, jobs can become pretty boring, pretty quickly, an over-whelming sense of going through the motions and a yearning for something bigger and better to stretch your brain and give a sense of progress. Over time, these things you want to develop on become things you’re good at, continually refreshing and replaced by new areas to explore.


As with ‘Develop’, having new things to try helps to keep an element of variety in our lives. It might be working in another country, running a team, writing blogs or appearing on TV. The only way to know if you’ll like these things – and want them to be part of your future – is to try them. If you do, that’s one more thing on the ‘enjoy’ list. If not, it can quietly exit stage right, leaving your brain with one less thing to wonder about.


Doing something you actually like doing is often forgotten in many career advice sessions, with the focus drawing back to salary levels and impressive private medical cover. We spend a lot of time at work, often more than we should, and so should make sure it’s something that gets us out of bed in the morning. Not every role will have everything you enjoy in it, but knowing what these are lets you make a conscious choice to fulfil that need elsewhere, such as volunteering to be a student mentor, or coaching your child’s football team.


Knowing the answers to these four questions gives you a flexible pathway, a bit like a bowling alley with the buffers up. It doesn’t matter if you go a little bit to the left or the right, but if each step you take has these four things in it, then you can be sure you’re going to be moving in the right direction.

If you’re not sure what the answers might be, ask other people – Peter Thomson’s ‘50 cups of coffee‘ is a great guiding principle. And if you’re not sure whether you really are good at something, then Oliver Burkeman’s opinion that ‘Everyone is totally just winging it‘ is a great comforting thought.

As long as you keep going in the right direction, you’re sure to end up somewhere you like eventually – and the journey there would have been fun, too…

I really hope you enjoyed this article. If you did, I’d love you to subscribe to my blog at to get new thoughts sent to you on an infrequent basis, and find me on twitter @johnJsills.

Career Advice links I’d recommend:

3 Thoughts

  1. Reblogged this on youmustnotmissny and commented:
    …The only way to know if you’ll like these things – and want them to be part of your future – is to try them. If you do, that’s one more thing on the ‘enjoy’ list. If not, it can quietly exit stage right, leaving your brain with one less thing to wonder about…

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