An Executive’s Guide To A Successful Career Transition

Irene McConnell
4 min read

August 1, 2022

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Is it time for a career transition?

It would be very symbolic of you to reinvigorate your career – just as the nation reinvigorates its culture, economy and freedoms.

If you were considering a career transition before the pandemic but were impeded by lockdowns, the need to set up WFH arrangements and homeschooling, I understand.

The plate is only so big.

But if you’re ready to put the idea of a career change back on the agenda, let me give you some unorthodox tips that will help you make the right decisions.

By the way, you can use our executive resume service to ensure your executive resume conveys details that will help you navigate your career transition.

1. Know Your Strengths.

The #1 cause of job dissatisfaction is insufficient competence. In other words, most people don’t like their jobs because they’re not very good at doing them.

Yes, I hear you – there are exceptions. Some people are unhappy in their careers because their boss is making them miserable, or because their job is intrinsically boring.

My (libertarian) push-back to these arguments would be that it’s still a matter of choice. The boss may be toxic and the job boring, but it’s still your choice to keep the job. But let’s not get distracted; that’s an argument for another day.

Your brain is built around a very simple dopamine-centred reward pathway, which gives you a rush when you achieve a big result or complete a difficult task.

  • No result, no dopamine hit.
  • No motivation to do more work.
  • Cue complaining & procrastinating.
  • Enter downward career spiral.

Certain members of society (usually, the ones who like to cover up their existential drudgery of rudderless existence with a veil of enthusiasm for “work/life balance”) like to tell you that “cruisy” jobs are the key to happiness and enjoyment, and that you don’t need to excel at work.

Just get a job, mate. Any job that will pay the bills. And they’re right – for a short time.

Then the hollowness and emptiness of it all set in. Because you’re not good at your job, you begin to watch the clock. When said clock hits “5”, you walk out of your “cruisy” office job feeling more tired than a 19th-century coal miner.

“Know thyself”, said some famous dead guy.

What he didn’t say is – use that knowledge to play to your strengths. In other words, put yourself in a position where you can leverage your innate strengths to be good – very, very good – at your next job.

  • Don’t like talking to people? Don’t apply for sales jobs.
  • Don’t like to be interrupted? Don’t apply for jobs at large corporates.
  • Like risk? Apply for a job at a startup.
  • Like to be creative? See the point above about corporates.
  • Love process and procedure? Apply for a job in government or the military or the police.

You get my drift.

2. Push Your Boundaries.

Once you’ve aligned your next job to your strengths, prevent a scenario where you get too good.

Sounds counter-intuitive? Let me explain.

Being good at your job is dangerous. It leads to an unhealthy ego and complacency. Those, in turn, lead to a lack of challenge, lack of growth, boredom, irrelevance, and – finally – resentment.

The solution? Put mechanisms in place that will move the threshold of competence just within your reach.

If you’re an entrepreneur, this process will happen automatically because, as your company grows, you’ll face an endless barrage of new challenges that you’re not yet equipped to deal with. You’ll get humbled every day.

But if you’re working for someone, you must be responsible for putting yourself into those situations.

How? Two simple steps.

First, choose a company with a results-oriented growth culture. Do not join a company that is just treading water, or is in constant “BAU” mode.

Good people at those companies would have long gone (or are in the process of leaving, hence the vacancy you’re applying for), and you’ll find yourself surrounded by bored, lazy seat-warmers.

You are the sum of 5 people closest to you, said another (likely dead) guy – and this certainly includes your colleagues.

Second, choose a boss who will champion your growth.

Remember – job interviews are just as much an opportunity for you to interview your potential boss as it is the reverse.

This doesn’t mean working for an abusive tool who enjoys berating people. But it does mean working for someone who:

  • has high standards
  • will hold you to account
  • will coach you to be a better person
  • you respect, and
  • you fear a little

Work for someone who is not afraid to tell you hard truths that benefit you in the long term, regardless of whether they hurt you in the short term.

3. Distance Yourself From Radical Activists.

We’re living through a major rethink of what it means to be a leader and an employee.

Leaders are searching for new ways to eradicate discrimination from our organisations. Companies are rolling out strategies that will help benefit our planet, as well as their bottom line.

Unfortunately, these movements often get hijacked by individuals more concerned about capturing moral high ground through oversimplification of complex issues than they are about the well-being of minorities or the planet.

These people exist in every organisation, at every level.

Avoid these people. More importantly, in the context of a career transition, avoid organisations that these people have infected.

Easier said than done, I know.

This is where pre-emptive research comes in. Recon, as we used to call it in the military.

Research the organisation you’re about to join. Go beyond just browsing their website and PR propaganda. Use LinkedIn to speak with at least 3 current and (importantly) 3 past employees from that organisation.

Find out why they’re still there and, if they’re not, why they left.

If you join an organisation and find yourself in a face-off with a wannabe activist, don’t get drawn into debates about any of the issues they purport to care about.

They are not capable of, or interested in, having logical debates that lead to deeper insights.

They’re simple ideologues, usually driven by resentments and cravings for attention – and they’ll use any opportunity to catch you in “gotchas” and double binds.

This is, of course, unless you’re a cool-headed, experienced debater with a reflexive ability to spot – and point out – cognitive biases and logical fallacies. If that’s you, by all means, all the power to you 🙂



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