Jo Green | Career coach | Sydney

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Learning lessons from our career change history

“Insanity is doing the same thing over and over again and expecting a different result.”

While the quote belongs to a longish list of things Albert Einstein didn’t actually say – he could have done. It captures the spirit of enquiry and experimentation at the heart of successful science and so much else – including career change.

Why, despite great intentions and plans, do we often swap one unsatisfying job for another just like it?

You love digital marketing, but you’re stuck in a spin cycle of soul-sucking sales jobs. You land one lucrative corporate job after another, but you hanker after the fun and fulfilment you found in a six-month stint in a three-person start up.

What stops us from learning from our career change history so we can avoid reliving it?

Sometimes it’s the pain. We can’t face thinking about a job that made us miserable and damaged our sense of self.

Sometimes it’s the euphoria. We’re elated by our escape and ready to run headlong into our rosy future.

Either way, we just want to put the past behind us. And yet, we don’t.

If you’re struggling to make a genuine career change, maybe it’s time for a forensic look at what you loved and loathed about your professional ‘exes.’

Think about:

  • what each job involved

  • how you related to colleagues and clients

  • where did you ‘fit’ within differing workplace cultures.

Try these five tips for unmasking your inner career change saboteurs.

Review what motivated you

Which past positions and the people and values inspired you? Which ones drained and depressed you?

Did you work your heart out for a manager who acknowledged and celebrated everyone’s success, never forgot a birthday, and suggested you work from home when your child was sick? Perhaps, acknowledgement, strong teamwork, and flexibility top your ‘energisers’ list.

Did you tear your hair out over infuriating delays that blew out your deadlines and blocked satisfying outcomes? Maybe complex processes and long chains of command drive you to distraction.

Did being an ace at organising entire projects keep you busy but bore you witless? Were you stuck using too many of your most renowned skills and too few of your best-loved but less applauded ones?

Getting insight into what moves and motivates you at work is the traditional starting point for navigating career change.

So is evaluating how you move between jobs.

Look at how you make your moves

Does ‘fear of the career unknown’ condemn you to relive your professional past?

Change is exciting and liberating. It’s also downright scary and an open invitation to our inner demons to strut their confidence-shattering stuff.

It can be tough to act outside of your job-seeking ‘norms’ when your mental doomsayers (and maybe your significant humans) are sounding dire warnings. Where you see exciting new possibilities, they see potential career chaos.

Answer two indispensable career change questions

Answer ‘yes’ to either of the following questions, and it’s likely that your methods, not your motives, stop you from learning from history.

Do you stay until misery overwhelms you, then ‘cut and run’ from a job you hate?

Do you rely first and foremost on your established networks for inspiration and support to find a new direction?

As fallible fear-prone humans, we’re equally prone to act rashly out of desperation and to fall back on what we know.

When it comes to career change, both these behaviours can trap you into settling for more of the same.

Grow your ‘working identity’

Unshackling yourself from unloved bits of your work history means shifting your ‘working identity.’ Read Professor Herminia Ibarra on ‘How to Stay Stuck in the Wrong Career’ for some thought-provoking advice on how to do this.

Try taking an ‘act first reflect later’ approach to seeking out ‘new’ career options. Use common sense, courage, and a spirit of adventure in roughly equal measures. Think side projects, new networks, and a host of other clever contrary-sounding options likely to lead to places you may never have imagined but may well enjoy.

Nudge yourself gently out of your comfort zone by switching your decision-making from ‘autopilot’ to ‘manual.’ Think about how often you routinely choose your favourite pizza then wish you’d ordered your partner’s delectable alternative.

Be real about the good, great and ugly

Finally, or possibly firstly, if we are talking skilfully managed expectations, remind yourself that history rarely reflects a complete account of events. Blood, sweat, and setbacks don’t often receive their rightful airspace. This is likely to be true of your work history.

All jobs are a mix of what Michael Bungay Stanier describes as bad, good, and great work. Try using the tools in Stanier’s book ‘Do great work’ to assess:

  • how your past positions measure up

  • how you can up your ‘great work’ quotient in current and future roles

History can teach us heaps about our triumphs and our tribulations at work. An honest look at yours will highlight where you were more or less accountable for both these things.

Your career history can also highlight where and how you’ve outgrown work you once loved.

Absorb the lessons in your career change history, and you’ll be less likely to be doomed to repeat it.

Need help to unpack your career change history? Book a chat.


By Jo Green, Career Change Coach

I know what it feels like to be lost in your career. I also know that when you find what you love, heart and soul, your life changes. I work every day with people who are reshaping their current careers, starting new enterprises or searching for a new direction. Basically I help people who don’t like their job to figure out what to do instead!

As a Careershifters and Firework Advanced Certified Coach and experienced career changer myself, I can help you figure out what fulfilling work looks like for you.

Drop me a note to organise a free 20 minute consultation to chat about your career change and how coaching could help.


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