Try Harder or Walk Away
Notes on Staying or Leaving
Deep Life Notes | Staying or Leaving
It can be brave to push through, and it can be brave to quit. The trick is knowing whether you are giving up too soon or recognising a better fit.
“Of one thing I am sure, you are no artist. You started too late.”
So said the art-dealer boss, who had deemed his employee’s paintings to be unworthy of being displayed for sale. It was a theme the man had heard many times before. He had been a student, an art dealer, a teacher, and a prospective pastor. He’d failed at all, despite promising starts.
At thirty-two years of age, the man enrolled in an art school alongside students a decade younger, but lasted only a few weeks. Before he left, he entered the class drawing competition. The judges advised him to join the beginner’s class with ten-year-olds. In a letter to his brother, his anguish was palpable.
“A man doesn’t always know himself what he could do, but he feels by instinct, I’m good for something, even so! … I know that I could be a quite different man! … There’s something within me, so what is it!”
The man was a hard worker, but his interests changed like the seasons. He became consumed with one thing, failed, then moved to the next. Only in the last four years of his life, from ages 33 to 37, did he settle on his unique style. And there his creativity exploded, creating the masterpieces we know today, like Sunflowers and The Starry Night.
Searching for your “match quality”
Vincent Van Gogh is a perfect example of an individual’s search for what economists call “match quality”—the degree of fit between the work you do and who you are. That feeling of being closer to the place where you properly belong.
Van Gogh tested options with intensity, learned quickly whether they fit or not, then moved to something else. He repeated this pattern until he zigzagged his way to an artistic place no-one had ever ventured, and where he alone excelled. His style was spontaneous. Failure and new directions set him free.
Today, it’s never felt more important in our careers to be somewhere we belong. Somewhere we feel useful, stretched, and closer to the work that fits us. Finding our own match quality.
One way we get closer to match quality is through different experiences across a career. It often surprises us how capable we are of significant changes to our lives and careers. Closing one door to open another.
Yet, we’re reminded that winners never quit.
The trouble with a never quit mentality
Grit is popular. It’s what winners have. If you lack the courage to stick with something and see it through, you’ve failed. That’s a common message today. There is a well-known quote by Winston Churchill often used in motivational messages: “Never give in, never, never, never, never.” But that quote isn’t complete. Churchill continued, “except to convictions of honour and good sense.” That part of the quote is rarely added.
Passion and grit have an important place, of course. We shouldn’t give up when something is difficult. That perseverance through difficult times can be an advantage and help us reach places we would otherwise never reach. This is resilience, but resilience is nuanced. It’s perseverance with a purpose. If the goal or outcome no longer makes sense or has changed, it may be better to quit or shift direction. Resilience requires us to continually reevaluate our position based on new information we receive.
It can be brave to push through, and it can be brave to quit. Quitting is a decision, not a character trait or flaw. Sometimes it means letting go of an opportunity that is no longer really there. Changing direction can move us closer to a better fit.
Nintendo quit the playing card business to focus on making video games and consoles. Roger Federer quit his dream of being a professional football player to focus on tennis.
The trick is to stay attuned to whether switching is simply a failure of perseverance, or astute recognition that better matches are available based on your abilities and interests.
Try harder or walk away.
One way to make that distinction is to question some of the beliefs we inherit about work, passion, and perseverance.
Don’t follow your passion and other dysfunctional beliefs
In his 2021 TED Talk, Bill Burnett from the Stanford Life Design Lab dispelled what he called dysfunctional beliefs: myths that prevented people from designing the life they want.
Dysfunctional belief #1: Follow your passion. Most people don’t know what their passion is and there isn’t a lot of good evidence that matching the content of your work to a pre-existing interest is a major driver of satisfaction in that job. Many people who love their careers didn’t follow their passion. They followed the goal of being passionate about their work, experimenting, trying different things, building mastery, autonomy, and impact.
Dysfunctional belief #2: It’s too late. There’s no such thing as being late to a good life. We can start wherever we are. The more useful questions are often smaller and more testable: what could I explore next, and how might I begin? Every experience you’ve had up to now has been valuable, even negative ones.
Dysfunctional belief #3: Be the best possible version of you. This implies best is a single thing, and that life is linear. There are many versions of you that can play out. We are each made up of many possibilities and we grow and evolve and blossom and discover new things all the time. Our identities can change.
The work of Brent W. Roberts, a psychologist and specialist in personality development, supports Burnett’s argument.
Roberts’ research illustrates we are all works in progress and that our personality traits change over time. The most significant changes in personality traits often take place between 18 years of age and our late 20s. So, if an individual tries to specialise in something during these years, or have notions of following a passion or dream because that’s what everyone tells them to do, it’s much harder because they are trying to predict match quality for a person who doesn’t yet exist.
We learn who we are by living, and not before
David Epstein’s 2019 book, Range: How Generalists Triumph in a Specialised World, makes a case for breadth over specialisation, that people who think broadly and embrace diverse experiences in life will increasingly get more from it.
Epstein highlights the work of Herminia Ibarra, Professor of Organisational Behaviour at London Business School. Ibarra’s research support this idea that we learn who we are only by living, and not before.
“We maximise match quality throughout life by sampling activities, social groups, contexts, jobs, careers, and then reflecting and adjusting our personal narratives. And repeat.”
This goes against common advice like follow your passion and don’t give up on your dreams, where someone just needs a clear picture of what they want and then go after it. Instead, Ibarra recommends “First act, then think.” We discover possibilities by doing: trying new activities, building new networks, finding new role models, and embracing chance encounters. Testing, learning, and adjusting.
Ibarra sums it up: “I know who I am when I see what I do.”
I can relate based on my experiences. In my 16 years working for Dell Technologies, I’ve had eight different roles. An average of a new job every two years. And it was a chance encounter in London in 2011 that led me to move from the U.K. to the UAE, beginning a new chapter of my life.
I’ve sampled a lot of different experiences, including operating a restaurant, advising a not-for-profit arts group, launching a website on how to live a deeper life, and being a running coach and ambassador for ASICS.
All these experiences have helped me get closer to the fit between the work I do and who I am.
Getting closer to fit
If match quality is discovered through living, then a few things seem worth considering.
Know what cannot be changed. Some problems are really just circumstances. They may be frustrating, unfair, or inconvenient, but if they cannot be changed, they are not the best place to spend our limited energy.
Let the future have more than one shape. It can help to imagine different versions of the years ahead: where you might live, what kind of work might suit you, what kind of people you want around you, and what kind of life would feel worth building.
Test things in the real world. Conversations, small experiments, side projects, courses, volunteering, and new environments can all provide useful information. The most helpful insights often come through action, not endless thinking. Some things will pull you closer. Others will tell you what to leave behind.
Keep building useful skills. Skills create options. They give you more room to move, more evidence about what fits, and more pull when a better direction begins to appear.
We all progress at different rates
A satisfying life is a collection of experiences, adventures, memories, and a few failures that teach us important lessons. They strengthen us, help us understand ourselves better, and provide valuable insights on what we can do next.
People progress at different rates. Whatever stage you’re at, there is usually something useful to notice or do. Sometimes we need to persevere. Sometimes we need to abandon previous goals and change direction entirely.
If Van Gogh hadn’t failed repeatedly, quit consistently, yet persevered in his journey to find his place, the world today would have one less vase of sunflowers and one less starry night.
And it would be a poorer place for it.
Pass It On
If this note was worth your time, it may be worth someone else’s.
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