Some quickly find their calling—they find a career that engages, satisfies, and pays them. But for many of us, it’s not that simple. We end up drifting about, meandering down one path and then another, always wondering what it is we’re really meant to do.
After many years of having only a vague sense of career direction (and often grateful just to make ends meet), I pondered a series of questions and finally reached clarity about what I want to do.
But before sharing the questions I used, I want to point out that it’s perfectly fine—and often part of the process—to not be clear on what you want to do in life. Life is not a straight line from A to B, and sometimes you need to go through several transformations to gain the necessary context to find your calling.
During times when you’re unclear, the following advice may be helpful:
- Follow your curiosity, as Elizabeth Gilbert says. I’ve had several life junctions where I felt an overwhelming desire to study something, spend time with someone, change cities, or travel. Those whims often didn’t feel logical at the time, but pursuing them led to opportunities and insights that brought me further down my path.
- Put in the hard work to gain valuable skills. Cal Newport argues that ‘follow your passion’ is bad advice, and advises instead to “put in the hard work to master something rare and valuable, then deploy this leverage to steer your working life in directions that resonate.” His book So Good They Can’t Ignore You and the tl;dr blog post version are highly recommended.
Without further ado, here are the questions for finding your life’s calling:
1. If I died today, what would I be sad that I didn’t do?
Imagine you were to die tonight in your sleep. What are you most sad you didn’t get to do?
Another way to approach this: “If I were to die happy and satisfied, how would I have lived?”
2. What did I like doing when I was young?
Reflect on your childhood and see if any memories call to you.
I have a vivid memory of coating an elementary school worksheet in stripes of glitter crayon. I was worried that this act would be admonished, but I couldn’t resist making the drab worksheet more attractive. It turns out that this root desire to make ideas and information more alluring is my calling!
3. If I had all the money I needed, what would I do?
Often our sense of career is deeply intertwined with the obligation to make money. While of course our career must sustain us, this question can help us see past any money issues that may be skewing our perception.
4. What brings me satisfaction?
This question helps calibrate the previous one. If in the last question you pictured yourself laying in a pool sipping champagne, you’re unlikely to envision the same in this one.
Related questions: “What do I feel proud of?” or “What would I feel proud of?”
5. What do I do where I lose track of time?
Losing track of time lost in an activity happens when you are in a “flow state.” This state is often deeply satisfying and brings about our best work, so your answer to this question may indicate an activity to double-down on in your professional career.
6. Where do I gain energy, and where do I lose it?
Do you gain energy from working with people or working alone, or in a particular combination? What sort of challenges inspire and motivate you, and which drain your batteries? This question is posed to help you find a sustainable work situation.
7. Whose life am I jealous of?
I found this question after becoming green with envy upon hearing Tim Ferriss’s writing schedule. His schedule was something like waking up, taking a swim, doing writing, eating the same daily lunch, reviewing writing, and then meeting up for friends in the evening. I wanted that life so much—me against a blank canvas, every day—that I realized I should orient my career around that sort of “maker” schedule.
Related question: “What does a perfect Saturday look like?”
8. What am I good at?
Alternative questions: “What do friends ask me to do for them that I find easy?” and “What am I bad at?”
9. What are my “factions,” and what do they want?
This question is a way of finding a calling that encompasses all the different aspects of you.
I have three factions—aka inner drives—that are often in conflict with each other:
The caring faction that wants to save the world.
The artistic faction that wants to excel at creative expression.
The fearful faction that wants to be secure.
If I spend too much energy tending to any one or two factions, the omitted factions will start rebelling and demanding all of my energy.
Many times I’ve tried to go a path that only satisfies one of the three (e.g., a high-paying job for the fearful faction, or renouncing financial security to live a life of service), but inevitably I become unhappy because I haven’t fulfilled all of my drives.
10. What would I do if I could start over?
You might resist your calling because there’s a sizable gap between where you are now and where you would need to be to pursue that calling. Perhaps that’s a gap in skillset, knowledge, degree, network, funding, or identity. This question is a way to get around any resistance of the “but I don’t have X so…” or “but it’s too late to…” variety.
You may find as I did that the answers to these questions may not come all at once, but after many months of reflection.
What questions and processes have you found helpful? Please comment below!
1. Log off social media, turn off the news
Like laughter, fear is contagious. You can see this in birds where one of them starts acting nervous and a moment later the whole flock takes flight. For several weeks I went down the coronavirus news hole, and my emotions went right down with me. Then one day I shut my laptop and noticed the shining sun and swaying trees outside. In that moment, I decided that I was the one who would decide my experience of this time. While I still check the news and Twitter, I do my best to limit exposure.
2. Tune in, breathe, and feel
Soothe anxiety as you would a crying child: hold it, listen to it, be with it. To ritualize this emotional processing, each evening I take time to tune into my body, breathe, and feel through any emotions present. The book Deep Listening is a fantastic guide to this practice.
Troubled by circling thoughts? Try using the 4-7-8 breathing: inhale through the nose for 4, hold the breath for 7, breathe out the mouth for 8. The counting acts as a chew toy for the mind, while the breathing technique helps the nervous system switch out of fight-or-flight. To shift from shallow chest breathing to big belly breaths, tuck your chin and place one hand on the heart and one hand on the belly.
Another breathing practice I’ve found particularly useful is qi gong. It might feel silly to do at first, but I’ve never found anything that pacifies turbulent emotions so effectively. An easy way to start is this YouTube.
3. Be kind
If you’re living with others, go out of your way to do something nice for them. If you’re not, send friends and family thoughtful messages and reflect on the good times you’ve shared. Performing acts of kindness will help you as much as others.
4. Get going on your secret dream
Look! Everyone’s distracted and all your plans are canceled. Now’s the time to take up watercolor, learn to make ravioli, finish that David Foster Wallace novel, or whatever else you’ve been relegating to the forbidden land of someday. That someday is today—unless, of course, you are on 24/7 lockdown with kids. Then grab a beer and Netflix, you deserve it.
As the Stoics would say, the situation is as it is, but you still have a hand to play—even if it’s just choosing to consciously breathe through this time.
Is there another technique that you’ve found helpful? Please comment and share. We’re all in this together.
It started with a lingering sadness. My head was a lead balloon, my arms pinned by sandbag hands.
“I get it now,” I thought, recalling people’s tales of depression weighting them to the bed. Anxiety, my lifelong companion, looked productive by comparison. At least anxiety offered a nervous attentiveness I could use to fuel overwork. This depression seemed to not bear any gifts.
I made a pact with myself. Before losing myself completely to this void, I would fight. I would do everything everyone says to do to beat depression. I would get regular sleep. I would exercise. I would spend time with people instead of closing myself off. I would stop treating sugar and caffeine like major food groups.
And little by little, the depression lifted. But when I read Michael Pollan’s book, How to Change Your Mind, and how psychedelics help the brain find new routes instead of spinning the same faulty circuit, I decided to try it—if only for insurance against the void.
I did a quick Google search for legal psychedelic sessions. One of the first results was for a group psilocybin retreat in the Netherlands, a rare refuge where psilocybin truffles were legal, hosted by the UK Psychedelic Society. I wasn’t keen on tripping balls with a bunch of randos from the internet. I wanted an experience like Pollan had. He found an underground therapist who watched over him, 1:1, as he journeyed. But I was a millennial, too lazy to network and find one of these elusive practitioners. I filled out their short application.
Day one of the retreat arrived. In the first of many group check-ins, they asked how people came to be here. One by one, we recounted our tale. “I read Michael Pollan’s book. Then I searched on Google. Now I’m here,” said two people before me. I repeated the story, my identity as a unique snowflake melting.
According to the facilitator, the groups used to attract people seeking novel experiences. Now, with the changing perception of psychedelics, more and more people arrived in search of healing.
I came hoping to chill out, trip, and bounce, but the facilitators—beautiful bright beings you couldn’t help but like—had other plans. They coaxed us through one group exercise after another. The activities prodded us into dropping our defenses. We gazed into each other’s eyes and traded closely held secrets. Reluctantly, I engaged. There was something healing about being a part of a group of people sharing openly. I became less trapped in my own little story. Maybe I didn’t need psychedelics. Maybe I just needed a dose of humanity, a sense of belonging and sharing the truth of what living feels like.
But all this authentic relating was a bit intense. My mounting anxiety about the trip was slowly being outpaced by a desire to be left alone.
At last, it was time. We settled onto mats and were handed eyeshades and cups of honeyed ginger tea to pour over our shrooms. Almost immediately, swirling shapes appeared over my vision. My heart beat rapidly, a chunk of icy fear growing in my chest. Clinging onto reality, I downed what I perceived to be the minimum dose.
I donned the black silk eyeshades and shut out the room. Closing my eyes, a universe appeared. It was dark, but there existed… something. Swirls of colored smoke entwined around the edges, framing a stage. Scene after scene of never-ending strife unfolded on this stage. Scenes of galactic wars were followed by scenes of factory-farmed animals who never knew anything but a cruel and wretched existence. In one scene I clung to my boyfriend as bombs exploded in our city.
There was no escape. I had been mistaken about life. In the end, this eternity of suffering was all there was.
I was vaguely aware I was tripping, that this kaleidoscope of horrors would end sometime, and that I had the option to never ever do this again. That sounded nice.
The facilitators were there for us in case we should want help navigating troubled waters. They so sincerely wanted to help. But… what could they do to stop all reality from ultimately being endless strife and darkness without redemption? There was no help. I was quite certain that this was all that existed.
Then a thought sprang into my awarenss: “The only good in the world is that which we create.” This sentiment was a spark that pierced the darkness. There was still the darkness, but now also the kindness created by those who care. I saw that there was still time for me to join that group and use my life to make life better for others. Such precious grace! I recommitted my life to altruism.
The golden rays of the setting sun filled the room. We were coming down. The facilitators took us on a walk, which turned out to be less of a walk and more a herding of newborn kittens with stumbling legs and awe-filled eyes.
Overhead, a giant sky was streaked with voluminous spiraling purple-blue clouds so majestic they looked shaped by Zeus himself. Everything looked realer than real, like we had taken the offramp from Flatland. Does the sky usually look like this? How could I not have noticed before?
It was October and the start of fall. The leaves on the ground stretched the gamut of sunset hues. How could the leaves fall so perfectly, with each square foot of ground like a Monet? Again, I wondered how I could have walked this path before without noticing such immaculate beauty.
At the sharing circle that night, I learned that I had one of the more trying experiences of the group. Some people had full-blown mystical experiences—love and light, deep insights, whatever.
I tried to contain my envy.
I wasn’t sure what my trip taught me. Ok, I should be a better person and use my life to improve others’. But it still seemed horrible and dark. It seemed clearer what the retreat taught me: how to be. I realized I spent my life rushing out of the inadequate present to some perfect future that… probably didn’t exist.
The retreat was all about taking time to be. At a group activity, I would think: “Okay, this must be the end of this activity.” No. “Now this must be the end.” No. “Now this must be the end.” Nope. With nothing else to do, I started leaning into the moment instead of rushing to the next.
Centered in the moment, I breathed deeply, feeling through my emotions. To my surprise, I discovered a whole store of very old emotions stuck waiting to be felt. I breathed into the emotions of myself as an alarmed infant, screaming alone. Maybe in my never-ending rush for accomplishment and self-acceptance, I had never learned to just be a human, breathing and feeling. Now I sat breathing in the moment as it was, with all its wants and faults and hurts.
I realized my anxiety was nothing more than a mounting queue of unfelt emotions, and that if I took the time I could breathe through the debt of feeling, like patiently combing through tangled knots of hair.
There were too many aspects of my life that changed around this time to objectively tell what effect the retreat had on me. But depression, my original motivation for the trip, didn’t visit me again.
A year later, as I once more waded through autumn leaves, I realized what that trip had been about: it was all of my fears about the world. All of my fears were offered to me so I could confront and integrate them. From that perspective, the trip looked less like a nightmare and more like a very kind offering. Maybe the world wasn’t so dark after all.
Many thanks to the UK Psychedelic Society for facilitating the retreat. While these retreats may not be right for everyone, I felt the retreat helped me become more emotionally integrated and more capable of contributing positively towards society.
Book are categorized by nonfiction / fiction and then loosely organized from most to least recommended. Many of this year’s books were read to glean insights for my quest to get my life to a proper baseline of effectiveness; results from that initiative are in the two preceding posts.
The Uninhabitable Earth: Life After Warming – David Wallace-Wells
For most people, “climate change” conjures up mental images of cities underwater and warmer winters. Not a big deal—just don’t live anywhere coastal or hot, right?
Wrong. Wallace-Wells explains how climate change means problems that gravely impact everyone: massive food and water shortages, plagues, unbreathable air, and perpetual war.
Wallace-Wells’ beautiful writing makes the tragedies he foretells all the more visceral. You can get a good sense of the book from the article that originated it.
Guide to the Good Life – William B. Irvine
Guide to the Good Life is an approachable introductory guide to Stoicism. This book is replete with obvious-yet-remarkable gems like:
“We can either spend this moment wishing it could be different, or we can embrace this moment. If we habitually do the former, we will spend much of our life in a state of dissatisfaction; if we habitually do the latter, we will enjoy our life.”
The Stoics valued tranquility of spirit, and by looking through their eyes, I examined my life and saw how I routinely disturbed my tranquility with foolish thoughts and behaviors. Here’s an example of how Seneca watches for such foolish thoughts and corrects them:
At a banquet, Seneca was not seated in the place of honor he thought he deserved. Consequently, he spent the banquet angry at those who planned the seating and envious of those who had better seats than he did. His assessment of his behavior: “You lunatic, what difference does it make what part of the couch you put your weight on?”
Irvine views the Stoics as master psychologists. They prescribed, for example, negative visualization as a way to prevent hedonic adaptation. For instance, to help guard against the desire for a new phone, imagine your current phone being smashed to pieces. Or imagine being in a world without smartphones at all. Or imagine not having use of your hands and thus smartphones simply existing as a source of frustration. With daily negative visualization, it’s easier to stay appreciative of how much you have.
One of my favorite techniques in the book is only pursuing things you can control. For example, if you are playing tennis, instead of playing to win, your goal would be to play the best you can. You can’t control winning but you can control playing the best you can. And paradoxically, focusing on playing the best you can instead of winning is a better strategy for winning.
While time will tell how lasting the changes are, I felt that in reading this book I had at last found a compass for my life and was able to delineate which goals and behaviors are worth pursuing. I look forward to practicing the prescribed methods and further studying Stoicism as well as what seems to be its Eastern cousin, Buddhism.
Principles: Life & Work – Ray Dalio
I can see why so many people recommend this book: it is the distillation of a lifetime of unconventional yet effective wisdom. I was particularly inspired by how Dalio ran a wildly successful firm using radical honesty. As there’s too much to unpack in one read, I look forward to rereading it soon. This video is a great introduction:
A great book that inspired me to take more time without media. Recommended for anyone with a smartphone. Full review here.
Ultralearning – Scott Young
Scott Young is an overachiever. After graduating with a degree he didn’t care for, he did an experiment to learn MIT’s 4-year computer science curriculum in two years without taking classes. After that, he attempted to learn four languages in a year. Ultralearning is his strategy for aggressive, self-directed learning. I had a few takeaways about how to learn more effectively, but my biggest takeaway was inspiration to embark on my own ultralearning challenge.
Big Magic: Creative Living Beyond Fear – Elizabeth Gilbert
A beautiful book on creativity. I’m enamored by Gilbert’s enchanted view that ideas live in a realm of their own and come to Earth to find people to materialize them. Gilbert is an inspiring figure in that she has devoted her life to her writing without ever expecting it to pay her way. She worked various restaurant jobs to pay the bills while writing novel after novel, all of which came to no acclaim before her breakout Eat, Pray, Love. I believe most people with a creative calling will find something insightful in the book.
Better Than Before – Gretchen Rubin
This became one of my favorite books on habits, but I think more than any particular piece of advice in this, Rubin became a role model to me. Her personality is quite similar to mine, and so I came to think: “If Gretchen Rubin can do X, Y, and Z, why can’t I?” She became my inspiration to, e.g., wake up early and get more done.
Eat, Pray, Love – Elizabeth Gilbert
I wrote off this book because it was so mainstream and come on, there’s a movie version with Julia Roberts. But I got curious to read it because I loved Big Magic so much, and I’m glad I did. It’s a gorgeous story that I couldn’t put down. If you’re interested in spirituality, travel, and self-discovery, give it a try.
The Surrender Experiment – Michael A Singer
I became a Michael Singer fan when I read The Untethered Soul, one of the books I reread most often. This year I reread The Surrender Experiment after @bertstachios recommended it. While Singer wanted to live a quiet life of meditation, he decided to surrender to whatever was coming to him in life. This book recounts that tale and how that level of surrender transformed him.
The Obesity Code – Dr. Jason Fung
If you haven’t struggled with your weight, then congratulations! You have missed out on a world of suffering. Dr. Jason Fung dismantles the argument that “restrict calories and exercise more” is an effective weight loss strategy. Yes, calories play a factor, but humans are more complex than simple thermodynamic machines. If weight were as simple as “calories in, calories out,” then why do women gain fat during puberty and pregnancy when their caloric consumption doesn’t change? Hormones. In The Obesity Code, Fung discusses the hormonal factors that affect body composition. This was my second time reading this book and I got just as much out of it as the first time.
I Will Teach You to Be Rich – Ramit Sethi
This is still my favorite personal finance book. I read it again this year to get re-inspired about my savings goals, which worked. I made the change to put money into savings/investments and donations as soon as I receive it, which has been helpful. If you’re new to the world of personal finance, this is a great place to start.
What the Most Successful People Do Before Breakfast – Laura Vanderkam
Super short, fun read that profiles what different people do in their early mornings. I read it for inspiration about starting a habit to wake up at 6 am, and it did the trick.
Delay, Don’t Deny – Gin Stephens
This was the book that convinced me to give intermittent fasting a try. Stephens writes from a “here’s my story, here’s what worked for me” everyday person perspective. If you’re looking more for the science behind intermittent fasting, try another book.
The Fast Diet – Michael Mosley and Mimi Spencer
Apparently this was one of the first books to come out about intermittent fasting. The Fast Diet approach is to eat 500 calories or less two days per week. Apparently these days of calorie restriction mimic fasting. Seems reasonable, but I have yet to put it to the test.
Indistractable – Nir Eyal and Julie Li
In a very 2019 move, the author of Hooked, the bestselling book on how to get users hooked on products and apps, now writes a book on how to escape apps’ addictive distractions. I enjoyed reading it but not much stuck with me. If you haven’t read Deep Work yet, I would start with that.
Voss is a former international hostage negotiator for the FBI. He makes a compelling case for using his method to negotiate. His examples are dramatic and keep the book exciting, but I would have probably gotten more out of examples that were closer to my life.
Designing Your Life: How to Build a Well-Lived, Joyful Life – Bill Burnett and David Evans
This book would have been really helpful for me in high school when choosing a career path. I didn’t find it super helpful to my current life situation, but I still enjoyed reading the authors’ thoughtful approach. When it comes to life design, I found Stoicism to be more helpful.
Atomic Habits – James Clear
By the time I read Atomic Habits, I had read so many books on habit formation that I didn’t find Clear’s insights particularly helpful. I’d like to reread it down the road because I think it just wasn’t a match for where I was at the time.
The Happiness Equation – Neil Pasricha
Is “Want nothing + do anything = have everything” the formula for happiness? Not sure. This was fun to read but I didn’t find it had a lasting impact on me. This is why people wisely recommend reading classic books that have stood the test of time. I would have gotten more out of reading another volume on Stoicism.
Fiction / Poetry
The Way of Kings – Brandon Sanderson
This was a recommendation from a Twitter friend (thank you, @ModyVirag!) and is the first super-long book in a five-book series. I’m so glad I gave it a try; it’s the perfect fantasy escape with a tightly woven magical world, characters you fall in love with, and captivating storylines.
My favorite aspect of the book is the widely varying “spren,” elemental creatures that live in the Cognitive Realm and appear alongside phenomena like awe, creativity, honor, and rot.
I introduced this book to two people and they both loved it. I imagine Sanderson will someday be widely regarded as one of the masters of fantasy fiction.
Words of Radiance – Brandon Sanderson
This is the second book in the series and likewise recommended. I look forward to reading all of Sanderson’s work.
Bluets – Maggie Nelson
An inventive book of numbered short essays and poems about heartbreak centered around the author’s hypersensitive love for the color blue. I found the creative writing interesting but I stopped short with emotionally resonating with it, perhaps because I’ve never been exceedingly heartbroken (or felt much fondness for the color blue). Thank you to @joepetrowski for getting me out of my comfort zone with this recommendation.
A Discovery of Witches – Deborah Harkness
This book was bearable until the author had the characters act out her fantasies of drinking ridiculously expensive antique wines—then I gave up.
An ask for you, dear reader
Do you have any books to recommend, especially nonfiction and fantasy? Please let me know. Message me on Twitter or email alex @ this domain.