Your real dream job is potentially much simpler than you dare to admit

The surprise of the real dream job

In my line of work, I have the privilege to often meet with incredibly capable and successful executives and have deep and meaningful conversations with them. Not surprisingly, my first weeks of 2024? have been marked by many such interactions and,? without having intentionally triggered it, I’ve realize that most of them have naturally gravitated towards the theme of the real dream job. You might be thinking that probably the dream jobs I’m referring to are big roles in the corporate world, C-suite positions, etc. Not really. To my surprise (and probably also to yours), the dream jobs my recent conversations landed on were rather simple, mundane ones. One of my conversation partners would love to be the guy he saw mowing the lawn of the hotel he was staying at; the other one dreamed of picking olives in a farm in Italy; another one wanted to be a taxi driver; one wished to be a receptionist, and the list goes on in that direction… Interestingly, what surprised me even more than the words I was hearing in my conversation was the energy that I felt as the executives described their real dreams. There was something rather special in the air: their faces were relaxed, there was a contagiously positive tone in their voices, there was an adventure-like atmosphere in their narrative. It all felt lighter and more inviting than the other parts of our conversations. I wondered how come those highly talented and accomplished executives actually dreamed, deep inside, of a much simpler life, some even contemplating that this would be a much better next move for them versus accepting a promotion or a change into a bigger executive role.

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The holiday-blues effect

My first hunch is that, at least partially, the philosophical tone of my conversations might have a time-bound year-end effect: after a busy year, we go into our well-deserved festive season breaks and find ourselves with rare mind-space for self-reflection, unexpectedly bumping into some uncomfortable existential questions that our regular busyness numbs us from. Restarting into the hamster wheel after having paused for reflection and restoration is always a tough task, and in the middle of holiday blues I think many of us feel a little confused for a few weeks, contemplating whether that treadmill is what we want, or whether we’d rather just go back to holidays again, or yet maybe try to come up with something in between - like a much simpler job? Is that perhaps the real dream?

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Complexity Fatigue

I also wonder whether the real job = simple-life dream has to do with the fatigue, especially in corporate executives, of dealing with constant complexity and ambiguity. In a never-black-or-white environment, most leaders high up in organizations really spend a lot of energy navigating a bit in the dark, having to make decisions in the face of ambiguity and not being able to clearly see the results of their actions, the direct impact of their work. “I’d love to just work a full day in my garden, then look back and see the tidy grass and the neat flowers that I’ve produced with my own effort” - someone told me in a lunch conversation. It makes me think there’s probably also something in that simple-job dream about a craving for freedom, control and autonomy - something top executives, in reality, have extremely little of despite their fancy titles and hierarchical positions.

Midlife reflections

A third and maybe also very relevant factor impacting the unexpected direction of my conversations is that I spoke mostly with successful executives in their late 40’s and early 50’s, at a life stage where their family structures might be changing, their physical energy most likely starts fading away a little bit, and where they have already conquered (or are not far from conquering) whatever for they define as financial independence. Possibly, all these liberating factors are beautiful fuel for dreaming about a simpler life and the real dream job.

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Settling for the roads most travelled

One curious observation about my conversations was that, after they took that adventurous off-piste tour into the dreamland of a simpler job, they seemed to organically gravitated towards a kind of grown-up self-talk. In this chapter of our conversations, the executives and I made sure we painted those alternative lives as silly and improbable, and our talk migrated (without exception) into a rationalization exercise where we listed all reasons why we could not take the leap right away. Yes, I admit that sometimes there were concrete real-life limitations which indeed were practical and hard-to-remove barriers to living the dream, but honestly I felt we were more kind of solving for accommodations than looking for real solutions, we were justifying our stuckness and feeling a little bit sorry and mortified for ourselves instead of being courageous and giving our dreams the attention and nourishment they deserved. And of course, we were also humanly settling for a comfortable outcome so we could finish our conversation on a high and without having to do something about it.

My early-2024 conversations have triggered in me the realization that, specially within the world of corporate executives, there seems to be a point in the trajectory where we actually have more agency than we dare to admit over what we do with our lives. Our struggle is to find the courage to take the leap, we are scared by the idea of separating from the herd, turning our phantasies into plans and making them happen - and we are also terrified by the possibility of failing and embarrassing ourselves in that process. We therefore end up playing safe and settle for the roads most travelled.

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Liberating possibilities

There is hope, though. In my own professional journey and in my work as an Executive Coach, I have often seen that transitioning into a happier place is possible - sometimes it doesn’t even require a drastic change.

Often a good first move is simply to give that dreamer-voice inside of us some acknowledgement, and to allow it to be heard and taken seriously. Then, sharing the dream with someone we trust and who will not judge us for it might be a nice next step - I often find that it's only when I talk to someone who won't judge me, that I end up really listening to myself - and that of course helps me connect the dots of my own reflection and associations.

Once the dream becomes a little bit clearer, formulating small experiments and talking to people who have taken similar moves is often a good way to start dipping your toes into the water before diving in - as my father says, "learning from your own mistakes is a sign of intelligence, but learning from other people’s mistakes is the real genius”. This experimentation process may lead to concluding that what is needed is perhaps not even a huge leap but rather just a few tweaks or upgrades to your current job or to the way you live your role. (Last year, for example, I experimented with taking my workload down to 90% and using the remaining 10% as additional holidays - I’ve learned a lot through that!).

Still, if the big leap is however the thing you want and need to go for, then planning practical things some years in advance (such as financial retirement planning, location planning, etc) might be a necessary enabler. I’ve recently spoken to a top executive who is retiring at the age of 60 and she told me her retirement plan, mutually agreed and executed with her life partner, actually started more than 10 years ago. For big leaps it is indeed sometimes necessary to break the transition plan down into smaller, more palatable pieces, and work on each one of them little by little, like we are trained to do in large corporate projects.

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Whatever January reflections may have been on your mind, the good news it that there is also a growing body of useful advice out there about navigating professional or life transitions, especially in midlife. My favourite ones come from Herminia Ibarra (author of the book Working Identities), Bill Perkins (Die with Zero - a real masterpiece) and Bill Burnett and Dave Evans (Designing your Life). More recently I’ve also heard many good things about Dr. Arthur Brooks ' book From Strength to Strength, which I haven’t yet read but have just ordered.

Good luck navigating the rest of 2024 and - for what it’s worth - the next holidays are just around the corner!

Has this article resonated with you? Share it around and feel free to reach out if you’d like to have a deeper conversation about your own real dream job.