How To Actually Enjoy A Career Switch

Think ‘discovery’ not ‘exhausting upheaval’

Robin Cartwright
Curious
7 min readFeb 10, 2024

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GORKON: I offer a toast. The undiscovered country: the future.
ALL: The undiscovered country.
SPOCK: Hamlet, act three, scene one.
GORKON: You have not experienced Shakespeare until you have read him in the original Klingon

Nicholas Meyer, Star Trek VI

I’ve been an executive coach for a few years. Before that I did the big old parachute jump: the career-switch late in professional life.

I now spend a great deal of time helping senior executives through these same career shifts. For some of them, the mental challenge of career upheaval is so overwhelming they often carry on in a role they either hate, or which bores them senseless. I can say this, boldly, because that’s exactly what I did when I was in their position.

2024: it’s rough out there

But, in 2024, we can forgive ourselves some resistance to change. The water looks far from inviting. Against a background of weak demand, challenging macro-economics, and ‘sticky’ inflation, the job market in 2024 ain’t looking pretty with job losses predicted in the first half of the year.

Senior executive may be tempted, or forced, to start exploring new avenues. And 22% of all employees are looking to change jobs in 2024 due to a lack of meaning in their work.

Meanwhile things are not much better at the beginning of careers: one in three graduates end up being ‘mismatched’ to the jobs they find after leaving university. These mismatched graduates face poorer prospects and lower earnings.

So, what is going wrong?

Transitions are an absolute b***h

One reason people fail to find their ‘calling’ is that transitions, at any stage in our career, can be downright hellish. A defining feature going into and through a transition is that the process can undermine our confidence and ability to project sure-footedness.

This is a strange, but entirely natural, by-product of ‘liminality’ the sense of being in between worlds, separated from an existing path, and not yet incorporated into another.

Our very identity feels threatened. Our sense of identity is inextricably entwined with our work. The longer we are in one profession or role, the greater our sense of self is associated with that role.

It’s like you’re swimming across a very wide lake. You start swimming, and you can still see the shore you started from. But then after a while you can no longer see it, yet you cannot see the shore you’re swimming to either. Suddenly, you’re just swimming, and feeling you have no guarantee you’ll reach any shore. Only if you just keep swimming, with ‘blind faith’ will you begin to see the oppostite shore.

So, in short, we face the toughest decision-making process at exactly the moment we are at our lowest ebb.

Hopson & Adams 1966

It is no wonder that organisational psychologists see career transition adjustment as akin to Kubler-Ross’ ‘grief cycle’. The emotional upheaval takes you through denial, anger, depression and acceptance, albeit within the confines of the employment trajectory, as shown in Hopson’s transition cycle above.

Risk aversion and self-sabotage

Add to this, we are programmed to be risk averse. As Nobel-prize winning psychologist Daniel Kahneman discovered we, as a species, ‘price’ downside risk higher than upside opportunity. So, we are designed to be oversensitive to the risk of a new career option.

It is no great surprise, therefore that there’s a tendency to engineer our own failure when job hunting. One example is the ‘wild card’ strategy…

  • Step 1: You find your job uninspiring, and plan to leave, involuntarily or voluntarily
  • Step 2: You look at other jobs in your segment or skillset, but you feel resentful towards the sector
  • Step 3: For the sheer hell of it you suddenly apply for something left-field
  • Step 4: You don’t even get an interview
  • Step 5: You lick your wounds and go back to step 1

Perhaps we’re expecting to fail with these left-field applications, so you don’t even try properly. Clinical Psychologist Ellen Hendriksen describes these as acts of self sabotage and attributes them, in part, to a need to find a scapegoat for our lack of success.

How to switch careers

There is a better way.

Step 1: Sense-making, re-building

First, we must create a safe, confidential space for ourselves, and be upfront and honest about what we want. We need to get underneath our own ‘cover story’: the narrative we all use as a front to hide our real truths. Many of us are fearful of even admitting we are considering moving on. 1:1 coaching is a good way to approach this. Coaches are trained to create a trusting relationship. They help us examine, openly, the reality of our situation, and most importantly how we are feeling about the future. This is at a point when we may be plagued by negative thoughts and coaches start to help rebuild our confidence in ourselves. We start with some baselining questions like: what are our financial requirements; what are our personal commitments?; how much breathing space do we have?

Step 2: Exploring New Possibilities: ‘what do we want to be when we grow up?’

Underneath the turbulence of the process, we need to take some time to explore our underlying motivations, and values. Schein neatly encapsulated our core professional values into eight ‘career anchors’.

Edgar Schein’s Career Anchors

Schein found that identifying how important each of these features were to individuals provided a ‘profile’ of their career needs. These remained relatively stable over time i.e. those who rated managing others as important to them continued to feel that way, whichever job they were doing.

Identifying these core anchors, away from role descriptions or specific industries, allows us to explore longed-for alternative directions in our career. There might be elements of our personality and capabilities that we have kept hidden for practical purposes and expediency of holding down our current career.

From this ‘anchor’ analysis we might develop a number of putative future paths, and we can score them against our career anchors’ scores. They are paths rather than jobs as they could be a combination of retraining, further study, contract work or regular roles.

Step 3: Personal Discovery

Having identified these paths of exploration, we then need to engage in a phase of discovery: where we undertake a structured process of desk research and informal chats with individuals from our own networks.

I find people often recoil a little when I mention this phase. They seem to think of this as ‘endless networking’ and ‘bothering people’. I thought this too when I embarked on my career switch seven years ago. “Why would they want to talk to me” I’d say to myself. But the truth is that pretty much everyone does this type of networking, and they are happy to help because they, themselves, needed, and will need, the same sort of help again in the future.

Add to this that our contacts will often feel flattered that we’ve asked for their help, and we’ll find very few ‘refusers’ when you ask for that coffee. The key questions to ask are:

  • What is your job/this field actually like to work in? What does it feel like? What are the challenges and what are the positives?
  • Would someone like me fit into this world? Where, do you think?
  • What would I need to learn to do these sorts of roles well?
  • Who else might you be able to suggest I talk to — would you mind introducing me?

These chats can take place over weeks, or months. You can do one a week, or several a day, depending on your time available. After each round of meetings, we should take time to reflect: what have we learned about the paths, about ourselves, and about the ‘fit’? How excited do we feel about each path?

Step 4: Campaigning

After the ‘discovery’ stage comes the ‘campaign’. Discovery can last a couple of months, or much longer. Once we have determined the path we want to follow, it’s time to start lobbying for the role we want.

This is not about applying for roles blind. Statistically we know execs are much more likely to find a role from networking than from ‘blind’ job applications. So there is an art to this process. Just as for the discovery phase, we should reach out to people we might know: people who work in the organisation, in a similar one, or have unique insight into the place. Again, many of us have real trepidation in approaching this. We feel foolish asking contacts for their time and advice. But we’re not trying to ‘cheat’ the system, we’re just trying to reduce the ‘unknowns’. This time around we’re asking similar questions, but with more about the actual tactics of the process: Who are the decision makers? What are they looking for? What will really make a difference for them?

So, transitions need not be this step into the abyss. With careful, considered research, planning, inquiry and most of all support, it can be a step in to the most exciting times of our lives. I know mine was.

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Robin Cartwright
Curious

Writer, coach, organisational psychologist. Recovering management consulting Partner. Trying to make the workplace human(e). Contact: ubikconnect.com