The saying “Choose a job you love, and you will never have to work a day in your life” has been (incorrectly) attributed to a variety of people over the years. But regardless of who originally coined the phrase, it has become something of a North Star for folks looking to build a better, more enjoyable life.

The trouble with such sayings is that they leave a lot of important details unsaid; which is the price we pay for concision.

Yes, because we spend a great deal of our time working, it makes sense to carefully choose your career path so that you spend that large percentage of your life focused on things you don’t hate. But the unspoken reality of this advisory is that simply choosing a path doesn’t necessarily help us traverse it successfully. It’s possible to discover and cultivate a passion, only to find ourselves unequal to the task of making it central to our lives and maintaining its position there.

Maybe we lack the proper knowledge or the requisite skills or connections. Maybe we don’t have the willpower and dogged perseverance necessary to wade through the inevitable, troublesome, victoryless moments in pursuit of growth. Maybe we simply haven’t accumulated enough perspective to accurately differentiate between different flavors of challenges and goals and accomplishments and difficulties.

I love the hell out of what I do for a living, today. My lifestyle is made up of a unique, cobbled-together combination of projects and frameworks and lifestyle choices that work splendidly well for me and what I want out of life.

That said, this lifestyle was decades in the making. Before I started my first business, I worked many, many jobs, none of which was ideal, many of which were abysmal in various ways. But those experiences, working those jobs, helped me prepare, to train, for when I eventually made the leap.

The same is true of the early businesses I started: they weren’t ideal, but they helped me acquire new skills, experiences, and perspective, all of which fed into what I do, today.

This kind of training is possibly unnecessary. I can imagine circumstances in which someone would emerge from the womb, perfectly primed and ready for their optimal career trajectory and lifestyle path.

But I would argue that in most cases, facing the non-ideal and persevering despite it is what sets us up for success when we eventually discover the things that make us happy.

There are aspects of my life, still, that are incredibly uncomfortable, both physically and psychologically. There are also tasks I would prefer not to do, people I would prefer not to interact with, and skills I have to tediously practice if I want to keep this whole, weird career-contraption afloat.

I didn’t learn to grit my teeth and make it work by doing only things I love. I didn’t learn to tolerate ideas I find repellant and come up with ways to consistently complete work I don’t particularly enjoy by focusing all of my time and attention on my passions.

On the contrary: those positive lifestyle attributes—my passions, the work I love—emerged because I learned to get things done regardless of my feelings about those things. Working very hard, completing tasks that were only mildly rewarding (at best) allowed me to build a life in which I mostly do things I enjoy.

I’m not arguing in favor of worthless work and bullshit jobs, but I am saying that we have the power to reframe seemingly worthless, agonizingly boring, or tedious tasks as training for what comes next.

Each moment spent doing anything at all is potentially valuable, if we’re able to find the lessons in that moment.

Sometimes those lessons will teach us practical skills, sometimes they’ll help us better know ourselves and what we would like to pursue in the future—either by introducing us to something we love, or by introducing us to something we hate.

In some cases these situations will help us recognize our own durability, our stamina, our sticktoitiveness. These personal attributes can easily go unnoticed or unhoned if we only ever do work we love and chase goals that are life-defining.

It’s worth investing the time required to figure out who you are, what you want out of life, and how best to achieve those outcomes.

But the moments leading up to such pivots needn’t be wasted or decried as worthless. These periods in our lives can serve as runways, helping us build up the energy and momentum required to take off—to change everything for the better.

This shift in perspective may not make the path leading toward a more you-shaped lifestyle any easier to traverse, but it could help strengthen and prepare you to take those next steps.

This essay was originally published in my newsletter.

Recent Posts

  • Simmer or Sear
  • Some Final 2023 Thoughts
  • Taking Time
  • Instrumental Flute Era
  • Rearviews