The Alice in Wonderland guide to career planning

There’s a wonderful moment in Alice in Wonderland, when Alice asks the Cheshire Cat which way she should go next. And in this moment, whether he planned it or not, Lewis Carroll struck on a rather clever approach to career planning…


For many of us, it’s common to focus on the destination. The job title we’ve always wanted, the salary level we’ll be satisfied with, the seniority we crave, accompanied by a level of importance that we can broadcast loud and proud to the rest of the world through timelines, pulses, and news feeds. This focus remains despite the increasing behavioural evidence suggesting that these things really don’t make us that happy at all, such as this study by Daniel Kahneman and Angus Deaton that found £50,000 as the point at which income and happiness stops correlating.

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 the problem with focussing on salary is that we’ll never be happy with what we’ve got. As Jonathan Haidt reveals in  ‘The Happiness Hypothesis’, 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.

It’s the journey that’s more important, not the destination – if you get on the right path, then a great destination will appear eventually. 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? Take the time to understand yourself.

The better you understand yourself, the better your next role will fit you. That means considered self-study, spending time to observe what you do and how you do it. 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.


Just being good at something isn’t enough, though. As my doppelgänger Kevin Spacey once said, ‘With every job you should have something to learn’. 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.


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.


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.


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.

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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