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How to do vocation honestly

A model to find your Work, not simply something that fits your skills and temperament

2023 is in full swing. ‘Tis the season of big audacious goals. 

Either you’re reading 52 books this year or you’re falling behind. Either you’re building a $5m, one-person company or posting a thread a week or hitting 50% revenue growth or closing a Series B. Whatever it is, you either have a target, and you’re organizing yourself to hit that target, or you’re doing it all wrong. 

It’s compelling, this model of driving yourself toward the future. It hits on something deep within us, this feeling that we’re not good enough, that something is inexorably wrong with us and we need to achieve SOMEthing to make ourselves feel ok and complete. 

It’s compelling. But it’s wrong. 

No matter how high we reach, attaining things, accomplishing things doesn’t satisfy for long. Eventually we all learn that success, on its own, is empty. Life, and work, is about more than success. It’s about purpose and meaning. It’s about vocation.

“Discovering vocation does not mean scrambling toward some prize just beyond my reach but accepting the treasure of true self I already possess. Vocation does not come from a voice out there calling me to be something I am not. It comes from a voice in here calling me to be the person I was born to be.” – Thomas Merton

Vocation is the part of you, deep down underneath all the layers of conditioning and protective patterns, that knows why you’re here on this Earth. What Work you’re meant to do. 

Those engaged in vocation understand that Work, in its most meaningful sense, is not actually about fixing anything. It’s about expressing themselves. It’s about being fully here during your one lifetime, and showing your love for the world, and for life itself, through your efforts. 

Only through engaging with vocation can we do our best Work, and only through vocation can our work truly satisfy. 

The problem is that it is impossible to “find” your vocation. No amount of critical thinking or applied problem solving will lead you there. To engage with your vocation, you must look inward, and develop a relationship with that part of yourself.  

As the world force feeds you content telling you you must plan BIG DEAL ACHIEVEMENTS in 2023, it seems useful to me to have at least one model describing how to throw all that aside and finally engage with the Work you’re here to do. For those of us who are aiming higher than just success.  

If this resonates, I invite you to make 2023 the year you consciously begin to develop relationship with your vocation.  

Here’s how: 

A model for how to consciously engage with your vocation, instead of chasing the next shiny thing (to be used only by those who are really certain that the next shiny thing isn’t the answer, because that’s certainly an easier path) 

“I think it would be well, and proper, and obedient, and pure, to grasp your one necessity and not let it go, to dangle from it limp wherever it takes you.” ― Annie Dillard 

Part I


The first part of engaging with your vocation is to shift the way you think about the process, from finding your vocation, to developing a relationship with your vocation. Everything else flows from this framing. 

So how do you develop a relationship with a part of you that is often quite shy (understandably so after being ignored most of your adult life)? You slow down. You quiet down. And you listen. Meditation, walking alone in the woods, formal retreat. Even an afternoon by yourself without your phone. There are many structures to create this space, but create it you must.

You can ask yourself direct questions like: “what is the work I’m here on this Earth to do?” or “Who have I always been all my life before I got caught up in being successful?” I even sometimes have clients write their own eulogies to gain context on what is truly important to them. But the important part of the space you create is to use it as an opportunity to listen, not as an obligation to figure something out. The ego can see prompts like these as an opportunity to solve a problem, and that’s not what we’re after. We’re after something deeper.

After a time, in one of those quiet moments (you may need to create space more than once), you’ll hear what I can best describe as a “longing.” That’s it. That’s as clear as it gets. Not a bumper sticker. Not a phrase or an arrow or a billboard. A longing. A sense – vague, but clear – that indicates direction. The direction might be an act – something like “write” (my first engagement with vocation) – or it might be a problem – “founder mental health” – or a project – “write a book” – or a passion – “basketball.” But like pornography, you’ll know it when you see it. 

A good indication that you’re onto something is if the longing carries with it not a small amount of fear, for it requires a good deal of fear to keep us away from the Work we’re meant to do. 

You might be asking now – how long do I need to create space? When will I have an answer?  I know because I just caught myself asking that question. The answer is that we’re creating a relationship, not checking a box. How long will I need to be in relationship? Kind of an offensive question, really. The relationship itself is the point. 

There’s another reason why there is no answer to how long it takes: you don’t have only one vocation. The work you are meant to do now may not be the same work you’re meant to do in five years, or a month, and that’s ok. If you’ve read this far my guess is you’re engaged in the work of evolving as a human being, and because you evolve, so does your vocation. As Gandhi said, “I am committed to the truth, not consistency.” 

So part one of the model is to build space into your life to be with the deeper parts of yourself. To reflect, to think, to simply listen. And part one never ends. If you’re interested in doing the Work you’re meant to do, you must be in relationship with your vocation. Like any relationship, either you’re in it, or you’re not. 

Part II

And then there’s part two. Once you’ve created regular space to support your relationship with your vocation, and once you’ve heard the call, you must follow it. No matter how vague it is, no matter how little sense it makes, you must trust it. You must have faith that your deeply held desires are worth expressing, you must have faith in your hard won abilities to express them, and you must be willing to turn away from the things you’re taught to want – the safety and security of your job, your company, or building a financial wall against future uncertainty – to engage with your vocation. 

Following the call does not necessarily mean quitting your job to become a writer or a teacher (although it might eventually mean that). Because of our conditioning to target big things in the future, it can seem here too that we need to target some radical change to make progress. But while those types of radical changes surely do happen, think of them as home plate. You’ll eventually get there, but it’s enough at first to simply take a step toward first base. And then another.

“The test of meaning is not a cognitive decision, so one should not suddenly quit this present life for any quixotic mission. Meaning is found, over the long haul, through the feeling of rightness within.” – James Hollis

So for example, if the sense you get is simply “write,” as I did early on, then that’s what there is to do. Write. Now. Today. And tomorrow. If your sense is you need to solve the climate crisis, then how can you get started today? Make a call? Do some research? Great. Don’t ask questions, just do it now. What you’ll find, if you do this honestly, is that by the time you get to first base, you start to have a sense of where to go to find second. Your relationship to vocation strengthens and begins to leverage more of the gifts and skills you have developed over your lifetime. And in this way, “write” might become “write a book.” Thus does “solve the climate crisis” become “start a web3 solar company.”

“Trust the process.” – Daryl Morey

“But where is it all going?” I can hear some of you asking. Again, relationship. You wouldn’t start your first interaction with a potential partner by quizzing them on lifelong marriageability, would you? You’d start by simply taking them to dinner. Same thing here. If you’re engaged in vocation honestly, you’ll never know where it’s all going. It’s enough to do the work you’re called to do, as well as you can do it, and trust that the rest will figure itself out.

“If the path before you is clear, you’re probably on someone else’s.” – Carl Jung

Why most people are not yet ready to engage in vocation

One more thing. Most people are not yet ready to do this work, because most people are still looking to their work to fix something that feels broken inside them. And if you’re still trying to fix yourself through your efforts, vocation is yet another compelling achievement that will be proven empty in the end. 

Engaging in vocation will not fix you. Because you are not broken.  

It can take a lifetime to learn that. But if you have done the work to learn to love yourself, truly, deeply, and just as you are, then vocation is the most pure expression of that love. 

“Work is love made visible” – Khalil Gibran

The new year has begun full of energy, full of hope. People will tell you that if you’re not aiming to do something impressive this year, you’re doing it wrong. 

But how about this for a big, audacious goal: get to know yourself. Grow to love yourself. Because if you love yourself, truly, deeply, and just as you are, vocation is simply the expression of that love. 

And loving ourselves, having a relationship with our deepest longings, and then being brave enough to express those longings, using all the skills we’ve acquired, into a world that sorely needs it, is really the biggest, most audacious goal we can have in this life.


Things I read this week:

One: The lifelong power of close relationships (WSJ)

Harvard has been studying happiness with a single group of hundreds of people over 80 years. And they've found out some remarkably consistent shit about what makes human beings happy.

What about you? Have you found similar? 
LINK >>
Related Link >> 

Two: How tech could commission a new art renaissance (Twitter)

The Renaissance was a notable cultural era not because of good marble or new paint. But because a bunch of newly-rich Florentine wool merchants started commissioning art out of spite. This thread is an awesome history lesson and a call to arms.
LINK >>


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