The Last Unexamined Realm

If I asked you to name the realm of life on which we spend nearly a third of our time, the one so much of our happiness depends upon -- the one we navigate every day, over the course of decades -- what would you answer?

Is it relationships?

Physical health?






No, the realm is work: navigating our jobs and our careers.

Compared to our parents’ generation, we tend to change jobs often these days. And when we do, the process of finding a new job -- something more meaningful, better paid, what have you -- is hard and stressful. It takes a lot of time, and involves a lot of risk, ambiguity and unknown.

Despite that, most of us are pretty cavalier about navigating these career moves. I’ve come to see the cycle as: we graduate into adulthood -- from high school, or university, or the school of hard knocks -- we enter the working world, and follow three stages:

  • the initial surprise stage that we have to navigate a career; that there is even a game to be played here
  • followed by the stunned realization as to how ill-equipped we are to play that game, and how painful and stressful it can be
  • which invariably leads to the third stage: a sort of resigned, cavalier acceptance over the years that the game just has to be hard:  “I’m always gonna suck at it, so I’ll just slog it out whenever I have to.”

So, we wing it. We make little conscious effort to improve. And by doing that, we leave our jobs --  huge determinants of our overall happiness and success -- to chance.

But this is work we’re talking about, folks! Work.

Work, where we spend more than half our waking hours in a week. An area of our lives from which we derive such immense amounts of pride, meaning and self-worth. With all sorts of knock-on effects for who we are, our quality of life, our relationships outside of work.

In fact, I believe there is no other realm on which we spend so much of our time, and from which derive so much meaning -- there is nothing else we navigate every day of our lives over the course of decades -- but fail to invest in getting better at.

By contrast, exercise, nutrition, relationships, all get so much effort, discussion and intent. Even sleep is now (rightly) talked about and optimized to-the-hilt.

But, when it comes to navigating our careers, rather than trying to improve, we continue to accept the downsides of being mediocre as just the way things are. We hope for the best.

That is crayyyy-zee to me. 🤯  Wrong, and illogical and wildly inefficient. The thought of so many millions of people treating something so important with resigned haunts me. Haley Jo Osment saw dead people. Me?

But what really does me in, what crushes my tiny, talent heart, is that this stuff is doable. It’s learnable. And getting even slightly better at it, early on in our careers, can have such an outsized impact on our lives and happiness.

But let’s look at what I mean when I say:

  • “We change jobs a lot these days”
  • What that process of changing jobs actually entails and why it’s hard-if-not-exhausting
  • The idea that you can get better at this stuff

I’ve worked in recruiting and talent for a while, and think a lot about work and career. But I’ve actually never stopped to ask how many jobs I might have in the course of my career. How many do you think you’ll have over the course of yours?

Let’s add some quick (and easy, I promise!) math to things: say you start working at age 20 and retire at 60 -- that’s about 40 years of work. Unless you win the lotto, we’re talking about many decades of work. Now let's assume an average of...five years in a job? That feels generous and rare these days, but if we use that average, that means eight job changes. If we make the average time in a job four years, it goes up to 10 job changes.

Think about that number for a second. Really try and internalize what that means, both for the length of the career game you’re playing, and how often you’ll need to figure out a next job.

Now let’s get specific about what’s involved when we go about exploring a new job. And remember, we estimated we’d go through about 8-10 job searches. Most of those searches will be time-consuming, stressful processes involving these steps:

  • Continually asking where we’re at in our current job, and whether it’s right for us or not
  • “Job searching” in some way, shape or form -- directly applying to new jobs, networking, reacting to opportunities that come to you, etc.
  • Interviewing for jobs
  • Negotiating things like salary, start date, etc
  • Making the decision to accept an opportunity or turn it down
  • Offboarding and saying goodbye to the organization you’re working for

How many of these steps can you do well? How many can you make less painful, and actually use to your advantage?

The bottom line is that these job processes are intense, and messy. Oh, and rinse and repeat, by the way, because the dirty little secret of this game is that it NEVER. ENDS.

But despair not, faithful reader, for there is good news! A lot LOT of it, in fact:

  • You can absolutely learn how to get better at the game. It is so not rocket science.
  • Just like other important realms of life: if you approach it as something you can improve at, work to get better, and apply thought and intention -- you will improve!  As you do, the return on your effort will be huge.
  • As you get better, the impact of your learning will compound in amazing ways.

Which then begs the question: do you want to learn to play the game?

A game you’re going to need to play for decades; a game that will directly impact the quality of your life; a game that you can improve at, whose rewards are potentially life-changing.

Next time around I’ll write more about the components of the game, how they compound, and how you can start to get better.

“Either you play the game or let the game play you.

- J. Cole

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