#30: 5 Key Perspectives to Pursue a More Fulfilling Career


When we’re honest with ourselves about the thought that we want to change our career, it can be an anxiety-inducing realization. For many of us, we assume this translates into some hard-to-stomach material changes: a big drop in salary, moving back home, not having much to offer in terms of professional achievements at social events, and having to start over again.

This agony can be powerful...even immobilizing.

But it doesn’t have to be. And, in today’s episode of Bullshift, we’re diving into 5 key insights or perspectives to help you pursue more fulfilling work.


Imagine someone who's 40. They’ve already established themselves in a career as a teacher, having gone to grad school for additional specializations, and logged some intense hours writing lesson plans. Throughout the years, they’ve enjoyed watching their former students flourish into adulthood. And they’ve invested so much of themselves throughout it all, often using their own money to help kids pay for school supplies and even lunch.

But now they’ve started to think of changing careers, perhaps toward becoming a yoga teacher or wellness manager. It might mean another round of school, which at 40, just adds to the list of commitments.

As time goes on, the idea of further study somewhat fades against the backdrop of a whole working life, while the consequences of not having undertaken that career change grow ever larger. It’s a paradox. Some call it the job investment trap. This helps explain why so many people mistakenly turn away from making changes: it’s because the present looms large and the long, long future, which will in fact constitute by far the greatest part of our lives, doesn't carry data to counter this tendency. The mere months or years of training time is quite short in comparison with what lies between now and when we leave the workforce altogether.

We need to weigh our investment now...not against our most recent experiences, but in light of a more accurate picture of our entire life. We need to believe in something that's so hard to really trust in the reality of our own future decades of life. And then we need to dare to turn our mid-career slump into our mid-career jump toward greater fulfillment.

But the idea that work is fulfilling, rather than just necessary, is a recent invention. We live in a largely prosperous world, where we expect money in exchange for our labor. We also expect meaning and satisfaction.

It's a big ask. And this helps to explain why so many of us have career crises...usually on Sunday evenings. As we enter midlife, or what’s considered the prime of our lives, many of us are nudged to pursue more fulfilling work. Achieving success just isn’t the sole marker of our satisfaction.

So if you’re ready to pursue more fulfilling work, what’s next? Here are five useful perspectives:

First: Accept that your career confusion is perfectly normal.

In the pre-industrial world, there were roughly 2000 different trades out there. These days, there are estimated to be half a million different options. The result? We can become so anxious about making the wrong choice, we end up making no choice at all.

Psychologists call this The Paradox of Choice. It’s a sort of paralysis that stems from too many options. We need to acknowledge and remember that confusion is natural. And that fear is entirely normal. Yes, acknowledge and remember these...AND still, proceed with our plans.

Second: Know yourself.

I know, I know...this sounds so trite. And, yet, it’s relevant for so many of us...and not just in relation to our careers. Knowing what we want to do doesn't appear spontaneously. It’s not like knowing you’re craving some fresh fruit on a hot summer day. Most of us don't have a calling that’s easily discernible. We don't hear a commanding godlike voice directing us to accountancy or engineering. That isn't to say we don't have tastes or inclinations--we just don't know them clearly enough. And that can be a really challenging position to be in because not having a plan basically puts us at the mercy of those who do have one.

And when we’re busy following the agendas of others, that leaves little room for our interests. So we might catch glimpses, little hints of our tastes.

But we still need to learn to pick up on their sounds.

So where do we start? First up: set aside money concerns for a bit because financial panic too often kills all dialogue with our more authentic, passionate self. This often devolves into being too logical or analytical about everything you've ever enjoyed doing or making. The science of flow is really telling here because it’s the intersection of your interests--which could be everything from building a treehouse to sorting your summer clothes--that creates distinct possibilities. And, by the way, the weirder and more offbeat the list of intersections, the better in the long run. Again, there’s a science and process to this that’s really intriguing and compelling.

Third: Think a lot.

Let’s use the example of buying a car here. It might take a couple of days, maybe even weeks, to choose a new car. For me, my little Mazda 3 hatchback died at 185,000 miles and it’s since taken me a couple of weeks to test drive new options so I can make a decision. And I’m not even a “car person.”

So, applying this level of discernment to your career fulfillment means that it could take a year or more of consistent, daily reflection to identify a career or a calling that suits you.

We tend to feel guilty about this...imagining we're being self-indulgent. Far from it.

We may need to empty every weekend for months, just sort out the biggest conundrum of our lives...to make sure we don't continue to spend the rest of our lives trapped in a job unwittingly chosen for us by our unknowing 16-year-old selves. I laugh thinking back to when I was 16--I wanted to own a resort spa AND a Dairy Queen. I was more spot-on than I realized, though, because I’m working toward owning a retreat center...and my first job out of college was in corporate marketing for Haagen-Dazs.

Regardless of your ice cream dreams, you’ll need to be properly generous about the amount of time you’ll need to give this. And, yet, you’ll need the scaffolding to keep with it. This leads me to my next point...

Fourth: Try something.

It's tempting to imagine we'll be able to work out the shape of the workplace and identify our truest aspirations simply through the process of reflection. But we need data, and we can only understand ourselves and others by colliding with the real world. In this process, getting to know our own natures. We need to take small, malleable steps to gather information...could be by shadowing, interning, or volunteering, for example. It’s not always about turning in our resignation on a Friday. We can investigate our futures through side exploration.

Think about it: every successful business is at heart, an attempt to solve someone else's problem. And the bigger and more urgent the problem, the greater the opportunity to flex your entrepreneurial muscles. Consider an average day, and everything in it that might make someone unhappy--from losing your car keys to needing to get food to arguing yet again with your partner. Each of these is a business opportunity waiting to be exploited. It's a chance for us to serve, which is what work really is. It's easy to imagine that everything's been done and tried. But this is utter nonsense. We're unhappy enough for our world to have many more centuries of invention and creativity to address it.

Fifth: Be courageous.

Look, there are so many bad self-help books out there that it can be tempting to dismiss this piece of advice as another trope. But if we’re talking about fulfillment, as distinct from success, the difference is often the courage to give it a go with your interests...to imagine yourself in a new role. A lack of courage is often at heart a misunderstanding of the way the world works. It's an internalized feudalism, which imagines that only certain people (and never you), have the preordained right to certain things. This simply isn't true. So much more is possible than we might think. So much more powerful than our moments of timidity and doubt. That's the start of the path we won't regret on our deathbeds, which is sort of the ultimate criteria, isn’t it?

Okay, so now you’ve got an understanding of these five principles--normalize confusion, know yourself, think a lot, try something, and be courageous. What’s next?



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#31: Bullshifting the 3 Biggest Blocks to Your Fulfillment

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#29: On Your Potential Legacy