Photo by Tyler Farmer on Unsplash

A funny thing happened on the way to the Enlightenment. More access to published material led, over a few brief centuries, to a revolution of social and cultural forces.

All of which contributed to the vocation myth: You should know what you’re going to do for the rest of your life early in life.

When it comes to individual freedom this is great news. For the first time in human history, you could follow “who you truly are” and pursue fulfillment.

Who wants to be a baker or a cobbler or a farmer just because it’s what your ancestors have done for a few generations? The main time it’s comforting to have a prescribed role is when opportunities and choices are scarce.

Choices are no longer scarce. Opportunity is a different story.

For the vast majority of humans populating the planet, we are faced with a literal existential crisis: We must do something remunerative and fulfilling. If we don’t, we are destined to anxiety and an endless list of what-ifs.

It doesn’t help that the “paradox of choice” and our propensity to negativity bias is a real thing. You are more likely to be distressed about what you choose not to do than what you choose to do.

How does this cultural expectation get embedded in our minds in the first place? Who should we listen to and who should we tune out? When is self-help harmful? What does luck have to do with anything? And how do you know when to stick with something and be strategically patient, or just jump into the great wide open?

I don’t know, but I have some ideas.

The Great Pie In The Sky Lie

Today, all you have to do is educate yourself, dream a big dream, work hard, and eventually, you’ll find what you were born to do. While all this idealism is well and good, we are immediately confronted with what you might call “gravity” problems.

Bill Burnett and Dave Evans, founders of Life Design Studios, introduced this idea in Design Your Life: How to Build a Well-Lived, Joyful Life. Gravity problems are unchangeable and fixed realities. Just like gravity, the problems exist like a law of nature.

They are fixed and the only way to handle them is to accept the situation for what it is or reframe the way you think about it.

That is because there is this thing with our systems. Most, perhaps all of them, are flawed. The systems don’t achieve the ideals of a just society. Not everyone has access to the same quality of education. The truth is also that there simply isn’t an endless source of opportunities.

But that’s not the message the modern world promises. We are told we have limitless potential to succeed. We are told there isn’t scarcity. The pie is ever-expanding. The more economic activity, the bigger the pie. A slice for everyone who contributes and competes.

How many self-help books tell us that with a good use of our time and very little money all that’s really required is the will to follow through and a positive attitude? Just look to the high platform achievers on Twitter and find all the New York Times bestsellers and Medium bloggers telling you how you too can become a success like them.

This story we collectively believe — that merit finds its reward — is not going to come true for all of us even if we follow all the directions on the back of the box. There is a reason these people are in positions of prestige and power: It’s not there for everyone.

In fact, only very few will succeed.

Where does this leave the rest of us who were dreaming big dreams? How do we go about the rest of our lives realizing at some point we missed the bus? If you failed to realize an earlier version of yourself, you are the rule, not the exception. To make things worse, as the story goes, it is your fault you failed.

Others Are Unreliable And You Still Need Them

In the months leading up to graduation from Baylor University as an English Major, I had no idea what I wanted to do or what I should do. There wasn’t any clear path like there is for some professions. At the same time, I was only just getting comfortable in Waco, Texas. I had transferred there for my junior year.

I had a girlfriend. On top of everything else, it had taken me a long time to become a serious student. Now that I finally realized learning was a privilege, and that the life of a student was really wonderful, I had to stop and enter the great unknown of the “workforce”?

My dad was a minister and my mom was a middle school English teacher. I had no professional connections. I wanted to be a writer but had absolutely no idea how to go about it. Email and the internet were only emerging. There was nothing close to a Medium.

When I learned that a brand new seminary was being founded, I figured why not apply? One of the things I wanted most to learn in the process of deciding whether or not to go to seminary was the same question I wanted to learn once I began seminary:

How do you know what you are supposed to do?

Other ways this was put through texts and assignments and lectures and batteries of personality tests was: What is your calling? What is God’s will for your life? and so forth.

Ultimately of course there was no answer, no clear answer anyway. Everyone wants that “burning bush” experience (or many say they do), in which Moses was told what he was to do.

Or like Augustine who went through a definitive career change. As he tells it, he went for a walk one day in Milan and heard a child singing a beautiful song that he didn’t recognize. The song’s chorus was “pick it up, pick it up.”

Although he was a pagan professor of literature at the time, Augustine took the words as a command from God. He was to pick up the Bible, and read the first words he set his eyes on. The message told him to change his life. Clear orders from above.

During my first year in seminary, I found particularly one “answer” especially irritating. You can know what you’re supposed to do (or God’s call for your life) from what others tell you. That wasn’t the transcendent message I was hoping for.

There are lots of reasons not to do what others tell us. One gigantic reason is that many people — even (or especially) those who are close to us — have agendas for us.

They want to see us become something for how it would reflect on them, or possibly what they could get out of it. Not that it’s always so Machiavellian. Probably as often as not, it’s unconscious.

Also, people know as much about you from what you reveal and how you represent yourself as by what they observe you doing. In other words, through your own lack of self-knowledge you may misrepresent yourself authentically.

The point is, few people “know” us so well as to be reliable guides on how to choose incredibly important things like what we are going to do with our lives.

Frederick Buechner wrote one of the most widely quoted formulations of vocation (at least among contemporary Christians):

“The place God calls you to is the place where your deep gladness and the world’s deep hunger meet.”

Between that statement and Joseph Campbell’s even more famous, “Follow your bliss,” for a little while I thought I had begun to figure it out.

But what does Buechner mean by “deep gladness”? Does he mean desire? Does he mean contentment? Does he mean the kind of joy that can be present even in the midst of suffering? And what does Campbell mean by bliss? Does he mean passion? Does he mean contentment? And what is the difference?

And how does this apply to the accountant, the executive, the banana farmer, the insurance salesman, or the bicycle seat manufacturer? In other words, theoretical formulations are fine and dandy, but some of us need specifics.

With all of that said, both the philosophical and psychological traditions make it clear that you are not going to ideate your way to self-knowledge or merely feel your way to desire or bliss.

Developing an integrated self-knowledge does not happen “in a vacuum” as they say. There are no perfectly reliable guides, and others (and how we represent ourselves to them) will have to do. But here’s the kicker: You must choose loyalty to yourself over others’ expectations.

A Case Study In Desire and Luck

Besides how others contribute, finding your desire may also require a different theological construct: blind dumb luck. We can call it serendipity or blundering or wayfinding, but luck plays a part in how our stories unfold. How could it not?

Let’s put one scenario this way: You go to graduate school with very little concept of what you’re interested in. You write an essay on a subject that you also know next to nothing about. Your professor enters it into a contest without telling you, and it wins.

You get invited to an international conference with giants in the field. This experience brings you important connections and continues to spark your curiosity. You become a prestigious professor teaching a subject you love, and the rest is history.

You did the work. You knew next to nothing, but your curiosity turned into motivation, which you pursued. You did so well you now teach it. There was luck and hard work. There were many different points where the story could have gone sideways.

You might not have entered the right class in the first place. You might have chosen a different curiosity, which didn’t lead to opportunities.

The most obvious one is that your professor might have seen a good essay and given it an A, but certainly not submitted the essay on your behalf, and so forth.

I actually had a similar situation in which I wrote an essay trying to argue as rationally as possible for the existence of God. I had a professor submit it to the Acton Institute. They liked it and offered me a free scholarship to join them at a conference.

I was given their course materials and attended workshops and panel discussions. There were opportunities to pursue, but there was one problem: I didn’t subscribe to their worldview.

I had no interest in pursuing their agenda further. I did learn about myself and what I valued (and didn’t) through the process, but it didn’t bring about a grand and fulfilling series of career opportunities either.

Find Your Root System

The platitudes you might expect from these ideas are: (1) Try things out, (2) Be willing to fail (fast), (3) Find a mentor, etc. While true, they don’t bring us depth.

They don’t come from a place of lived experience, of authenticity, of being wounded in that very place where we have failed to find our thing or a clear sense of who we are supposed to be.

We want the hot takes because we crave answers. We are desperate to hear if we follow the numbered dots we’ll sketch the perfect life pattern.

It’s not pleasant to hear there aren’t easy answers, but that’s closer to the truth. We resist the discomfort of self-evaluation for the same reason people resist annual physical checkups: We fear what we might find.

Takeaway #1:

In the final analysis, because it is so hard to observe ourselves, we must rely on the observations of others.

Takeaway #2:

To fix a problem you have to first admit that the problem exists and that you have the power to do something about it. Hold yourself accountable, recognize the issue, understand that you play a role in it.

As Burnett says, “You can’t solve a problem you aren’t willing to admit you have.”

Takeaway #3:

Jack Nicklaus famously said, “The more I practice, the luckier I get.” Certainly being willing to try things and “fail fast” as they say, does lead to increased chances of finding fulfillment in your career.

At the same time, realizing that luck does play a role can help you have more perspective and modesty about your accomplishments when they come.

It can also help you have compassion for yourself when your initial early dreams don’t manifest the way you thought they would when you started out.

Cultivating the ability to deal with obstacles and challenges in a healthy way is the foundation of mental toughness. It requires discipline and mindfulness. This skill requires inner action. It requires reframing your thoughts and seeing things from a perspective other than your own.

With all of that said, you are more than your job. You are a human being, not a human doing. You find your purpose by surrendering into the person you already are. How can you know who that is without getting to know yourself a little better?