Embracing the void: lessons about pain, confusion, and guidance from a later mentor

My early 20’s were chaotic. I studied abroad in Hong Kong, then dropped out of school, traveled until my money ran out, and started volunteering and working on an international development project in South Africa.

When I came home, I was lost. My days were spent sleeping in my parent’s basement, drinking Jack Daniels, and playing Guitar Hero with my brother. In two fast years, I went from being a student, to a traveler, to an international developer, to a burnout.

I was broken.

People seemed to expect that after so much adventure I would be confident in my next steps and ready to make something of myself. Heck, I expected that of myself.

And yet, I couldn’t. I didn’t understand myself or the world I lived in.

Right around this time, I started meeting T* for lunch once a week or so. T* was a psychology professor and an experienced international volunteer with the Red Cross. He was one of those people who seemed to live in the crosshairs of wisdom, compassion, and action.

One day, after listening to me wrestle with everything, he said something that forever changed my life. He said, “It’s ok to not be ok. It’s ok to be broken. Not only is this a normal ebb and flow of life, it can lead to greater insight, clarity, joy, and direction.”

He explained that there are times when the best thing you can do is to step away from the world. Doing so may feel chaotic and reckless but it allows you to reflect on your past experiences. More importantly, it gives you the space to step into a truer, more mature, more integrated version of yourself.

He explained that in developmental psychology, these phases are called moratoriums. Though moratoriums tend to be associated with adolescents, T* believed that the people who live in mental, emotional, and spiritual integrity will likely go through multiple moratoriums in their lives.

In effect, he said, “Look, if you need a bit of time to crash in your parent’s basement, drink, and play Guitar Hero, so be it. Use that time to gently process and reflect on everything that you’ve experienced. It’s been a lot. Be curious about your past. Be brave enough to let go of the imagined futures that no longer feel right. You’ll need to pop out of this eventually, but in the interim, realize that time away from the world – painful and confusing as it is – will help you develop.”

And holy shit was T* right. With time, I moved to Montreal, worked on new projects in Uganda, and started working in leadership development. All of that was born from learning to be cool with stepping away from the world for a bit. It allowed me to find – and eventually trust – a newer, more mature version of myself. A year ago, when I realized I needed to change careers, I went through the same process of stepping away from the world. And once again, it helped me reconnect and find clarity.

T* passed earlier this year. His insight has forever transformed my life. For that, I am more grateful than I can easily express. Thank you, T*.

PS: On saying goodbye while you still can…

Unfortunately, T* was the second mentor I lost this year. In April I wrote about the passing of P* and what I learned from him.

P* was in his 80’s. Without warning he was moved into hospice where he died a few short days later. While he was alive I used to think, “I should let P* know how he affected me,” but I never did. I kept putting it off to some undefined tomorrow and then suddenly, there were no tomorrows left.

When I learned that T* had fallen ill, one of the first things I did was write a letter thanking him for his guidance and letting him know that I still feel – and cherish – his influence. To my delight, he responded. It made saying goodbye a bit easier.

Life, strangely, is both fragile and enduring. Learn from my mistake. If there’s someone who may be close to the end of their life, and you would like to reach out one last time, do it now. There may be fewer tomorrows than you think.

On the beauty of setting boundaries and drowning out the world

Mexico, Sept 2019, during my first solo trip in 4.5 years: I didn’t think that eating a taco could feel like a divine experience – I mean, most of the time I barely even notice what I’m eating – but right now, this taco is making me believe in God.

And no, I’m not high. It’s just that for the first time in ages, I’m rested, relaxed, and focused on what’s right in front of me.  

The past four years have been a whirlwind. I abandoned projects that weren’t working, sought projects that will, and created fairly stable inner wellness (here and here). Though there were certainly some hard parts where life felt relentless, mostly, it seemed like the time slid through my fingers. I haven’t come to a full stop until… now. And good lord is it nice.

***

When we try to take care of ourselves, we generally think in terms of adding more to our plate. Exercise. Meditation. Salads (blah). Date nights. Massages. Time management software. Whatever. And that makes sense. In many instances, we need to add stuff to our plates. It also fits culturally: we live in a world obsessed with doing and taking action.

For years, when I thought of self care, I thought in terms of doing. The catch is, doing more inevitably creates further complexity and often complication.  I recently realized that there is another approach to self-care that can unlock new levels of happiness, contentment, productivity, and creativity. Specifically, it’s learning what not to do and what to remove from your life. In this article, we’ll cover three approaches to improving your life by doing less.

1: Strategically block out the world

Have you ever been so stressed that you’ve forgotten what it’s like to be at ease? Though I didn’t realize it until I was in Mexico, that’s exactly what happened to me. While it’s tempting to point at a busy schedule as the main culprit, that’s not exactly it.

In fact, the real problem is much less complicated: it’s my damn phone.

If some acquaintance from way back when happens to have my number, he can make my phone vibrate – without my permission – from a million miles away. In doing so he’s killing my focus and inspiring a mini existential crisis as I debate, “Do I respond now? Later? Never? Maybe now because my attention is already broken. But also, maybe later – I don’t want to get into a text conversation. I’ll schedule a reminder. Also, why in the world is he contacting me? Wait. Do I even want to talk to him? AHHHHHHH!!!!!!!!!!”

There’s also the more mundane occurrence of someone I know and love texting something non-urgent that I quickly reply to, and before I know it, 20 minutes have vanished into the ether.

Of course, the problem isn’t the phone itself. It’s how we respond to it. Though we live in a world that pretends that multitasking is possible and fun, it’s not. Studies are very clear: we’re happier and more productive when we’re focused on one thing at a time. This is especially true if our phones are out of sight. 

The trick is to get cool with shutting the world out. With intent, I’m responding to texts, emails, and calls more slowly. I want the people in my life to understand that unless it’s truly urgent, I’m not able to drop what I’m doing. This isn’t easy for me. As a people pleaser, I feel an almost moral obligation to respond ASAP, but I’m working on it and it’s making my life better. For me, this is especially important – and difficult – in the relationships that aren’t as balanced as they should be. In some cases I’m learning to just delete or ignore the emails, voicemails, and texts that just aren’t worth my time.

2: Set boundaries with yourself

I’ve developed a stupid habit. I’ve been watching Lucifer and simultaneously playing with my phone, checking email, and skimming the news. The end result: what should have been relaxing is actually mildly stressful and horribly unproductive. This, of course, is just one example of dozens that show  I’m failing to set good boundaries with myself.

Fortunately, the solution is equally obvious: protect time just for yourself. Go for a walk. Garden. Journal. Nap. Read. Watch Lucifer (without checking your email). The activity is less important than the time dedicated to rejuvenation and big picture thinking. And of course, keep your phone off and leave your computer at home. This is time just for you.

More on setting boundaries here.

3) Every now and then, do nothing

Doing nothing can be scary. We tell ourselves that we hate boredom without realizing that boredom is a defense against the moment. We fear that if we examine our mind we may not like ourselves all that much.

But allowing boredom can be an enchanting experience. When you turn the volume down on the rest of the world, the simplest things, like eating a taco, can become borderline divine. With luck, you might notice your demons are less powerful when you surrender into the moment.

I realize that doing nothing is such an alien concept that some people will need instructions:

  1. Make a cup of tea and grab a piece of chocolate (or pour a whiskey and get a sandwich, whatever).
  2. Turn your phone and computer off.
  3. Hide somewhere beautiful where people won’t find you (or lock the doors and make the space you’re in beautiful).
  4. Now slowly, drink your beverage and eat your snack. If a brilliant idea strikes you, write it on the back of a napkin.
  5. That’s it. After an hour or two, you can resume your normal life of doing.

If you’re anything like me, your mind will go nuts at first. Then it gets bored. Then, it finally becomes enchanted. Somehow, you become a bit more equipped for it all.

Hat tip to Pico Iyer’s book, “The Art of Stillness

When the world won’t stop beating you down

Earlier this year: It was already an impossible week. After 60 hours at work and school, I needed to hop on a red-eye to attend another funeral.

To make matters worse, A*, my then girlfriend, and I had a stormy sort of love. Before leaving for the funeral, I made a reservation for us at a little Japanese place hidden away at the foot of the Rockies.

The pressure of it all overwhelmed me. I longed to connect with A* but knew we couldn’t always pull it off. I doubted my ability to continue meeting the demands of work, school, teacher training, and life. Quietly, I feared that I wouldn’t be able to offer my friend the love and support I wanted to at the funeral.

As A* waited outside to pick me up, I paused to try something a meditation teacher suggested. I was skeptical, but also desperate, so I took a slow, deep breath, placed my hands lightly over my heart, and whispered, “This is hard for you.” Without expecting it, some of the pressure, stress, and fear that seemed to define this chapter melted away. Moments later I realized something simple. This must be hard for A* too. And for my friend who lost his mother. Amidst the isolation of enduring more pressure than I’m cut out to handle, I quietly felt connected to myself and the people I loved.

***

It’s inevitable that every now and then, you’ll get torn apart by the world. For many, our natural reaction is to fight through the pain, grit our teeth, drown it out, or deny it. And while I understand the tendency, I fear that these approaches are little more than covert forms of self-denial.

Though it can be harder than running from the weight of the world, I suspect that the most skillful way to deal with being broken is to hold yourself with a sense of care and compassion. After all, this is almost certainly the way you would tend to a friend who’s feeling beaten down.

When you pause to acknowledge, “This is hard for me,” with sympathy and grace, two things seem to happen. First, you stop fighting against reality, and instead, embrace it. This is a position of true power and courage. Second, you seem to drift back to becoming a bit more whole and at ease.

I know that claiming that compassion and vulnerability is a truer path to strength, healing, and power sounds like a contradiction. I don’t want you to take my word for it. Instead, next time you notice that life is more difficult than it should be, pause, close your eyes, take a few deep breaths, place your hands over your heart1, and allow a momentary sense of grace and compassion to wash over you. Perhaps whisper, “This is hard for you,” and see what happens. You might also spend time cuddling with your puppy, choosing to cancel a meeting, dedicating a few minutes to coloring, or whatever. The point is to extend a bit of gentleness and compassion to yourself amidst the storm. You may notice that you too deserve the same care that you so willingly give to others. You may sense that granting yourself a bit of affection restores your ability to face a world that refuses to let you live in peace.

A mental model to boost happiness and productivity

“I understand there’s a guy inside me who wants to lay in bed, smoke weed all day, and watch cartoons and old movies. My whole life is a series of stratagems to avoid and outwit that guy.” – Anthony Bourdain

These days I’m constantly under the gun. I’m working six-day weeks, and at least once a week, my first meeting starts at 7:00am and my last wraps at 8:30pm. It’s nuts. And while I don’t love living this way, it makes sense for now. It allows me to efficiently get the credentials I need for my next project while also serving as a consultant. That said, I’ll shift down to a sustainable pace as soon as I can.  

Recently, I’ve found myself leaning on one productivity trick more than any other. I ask myself, “What’s the kindest thing I can do for future Jason?” When I say future, I don’t mean the Jason of 2029, or even 2020. I mean the  20 minutes from now Jason, or tomorrow’s Jason, or maybe the two weeks from now Jason (at most).

It’s inevitable that we will deal with an endless amount of mid-level bullshit. Laundry, ironing, dishes, meaningless assignments, difficult conversations, other people’s stupidity/requests, stress from never  having quite as much money as we want, etc. It’s seductive to ignore that stuff until it becomes urgent. While it sort of works, procrastination creates a crappy quality of life. The time you spend relaxing is ruined with guilt and the awareness of unfulfilled responsibility, while the time you spend working is defined by urgency and mild self-loathing.

So these days, when I’m tempted to leave the dishes in the sink, check reddit or facebook, or put grad school off until tomorrow, I pause and ask, “How would future Jason feel about that?”

The answer is always some version of, “Ya. He doesn’t love that. If I just get the work done now, future Jason can chill.”

Don’t get me wrong. I’m not advocating giving up all of your free time in favor of deadening productivity. Just the opposite. Since dealing with bullshit is inevitable, it usually makes sense to just address it now, and in doing so, you’re investing in a better near-term future.

I’m also not suggesting that you never rest. Again, it’s the opposite. I’m suggesting that you learn to be kind to the person you’ll be five minutes or five days from now. Sometimes that means joyfully sleeping in, smoking a joint and watching cartoons, or going on a camping trip with your significant other. If it’s been a minute since you’ve actually enjoyed the moment, then you’re overdue. In many cases meaningful rest and play renders you more effective in the future.

As you start to invest in your future self, you’re likely to discover an obscure truth: the hard part of unpleasant work is rarely the work itself. It’s the anticipation and resistance that suck. It’s the transition from doing nothing to being productive that tends to be the hard part.

The end result  is pretty cool. Without meaning to, you may find yourself ahead of even the most demanding schedules. This will leave you with time to sink into life without being plagued by guilt. Every now and then you may even find yourself skillfully reveling in the eye of the storm.    

Harnessing the fires of anger

Earlier this month during a meditation class, the teacher asked, “What’s holding you back from living with a more open heart?”

The answer popped lucidly into my mind, as though it were sitting just beneath the surface waiting for someone to ask.

The unexpected answer was as clear as it was uncomfortable: anger.

To say I was surprised is an understatement. I thought to myself, “I’m a sensitive dude. I meditate, journal, and try to do no harm. Anger? Really? WTF?”

As much as I wanted to deny the existence of anger in my life, I could tell that I was onto something. Like it or not, it was time to face the anger I had been ignoring and carrying around for a while. I also had to figure out what the fuck to do with it.

Over the following days, I started addressing the repressed anger I noticed in myself.  Though difficult, digging through my past few months, even years, was so valuable in identifying where it was coming from. Along the way, I became happier, lighter, more energetic, more playful, and more creative.

In this article, we’re going to talk about one of the trickiest topics in the emotional realm: anger. We’ll discuss why anger can be so difficult to identify and ways to work with it.

The misplaced taboo against anger

In case you need a reminder, you are the apex predator. As humans, we have been able to tame and shape our environment in a way that no other animal could even dream of.

Doing so would have been impossible without the capacity for anger and violence. If we were content we would never bother changing the world. If we were discontent but had no ability to channel anger and violence, then we wouldn’t have succeeded in shaping it.

Anger, like any emotion, is a normal part of the human experience.

What’s abnormal about anger – and the reason it caught me off guard – is that it’s an emotion we tend to bury instead of deal with. We’re never taught how to work with it. And unlike  joy, disgust, or a few other emotions, working with anger demands nuance and skill. Most people just ignore it until they can’t anymore, letting it build up until explosion. But of course, explosion is frowned upon, so for many of us, the anger gets redirected to random outlets, like bad drivers cutting us off, the people we love, or ourselves. To hedge against outbursts, many of us numb ourselves or disconnect. All of this creates the illusion of having no anger and encloses us with self-denial, preventing us from fully stepping into our lives, relationships, and power.

The nuance that makes the difference: no singular feeling owns you

In addition to the tendency to suppress anger, we avoid it because most of us hold incomplete understandings of how our emotions work.

We tend to believe that the borders that define our emotional lives are crisp and have straight edges. In reality, most of us experience a complicated array of emotions in any given moment.

Imagine that you’re on a diet and getting good results. You’re also kind of hungry. Then, a friend who doesn’t know you’re on a diet offers you a piece of chocolate cake. How do you feel? Virtually all of us will experience the following:

  • Desire for the cake
  • Desire to say no to the cake
  • Frustration with your friend for tempting you
  • Anger that you’re tempted – after all, you’ve been dieting awhile
  • Frustration with yourself for being frustrated with your friend who didn’t know any better
  • Understanding that your friend wasn’t trying to frustrate you

It’s important to understand that our emotional lives don’t always have clean edges. They’re swirling, variable, contradictory, complicated, and fleeting. Instead of avoiding anger, our best bet is to identify it without identifying with it. One of our biggest fears about acknowledging our anger is that the anger will define us. As long as we work with it skillfully, it won’t. In other words, it’s our job to understand that we have room to work with anger, without being controlled by it.

Identifying anger

The first step is to learn to identify the anger seething within you. And I want to be clear about something: the question isn’t “Am I harboring anger?” but “What am I harboring anger about?” Trust me – it’s there.

To say you don’t have any anger is like saying that there’s nothing you love or nothing you’re afraid of – it’s absurd. But again, as a society, we’ve made embracing anger taboo, so many of us have become so disconnected from it that we deny its very existence.

When we picture anger, we often picture roaring fires. A driver cuts us off and we lean on the horn, and/or flip the bird. Someone jostles us on the street and we feel the heat and tension rising in our body. Someone betrays or pisses us off and we feel the urge to punch them in the face and verbally tear them to shreds.

This type of anger is obvious. It so thoroughly takes us over that we can’t help but lean into it. We physically shake ourselves off, punch the wall, scream, rant, or vent, and a little while later, it’s gone. Because we can’t help but deal with this type of anger, it’s often short lived.

What surprised me was that the anger I was feeling wasn’t the easily identified, roaring fire I’m used to. Instead, it was much closer to a bed of embers – hot, dangerous, quiet, easy to miss, and capable of burning for a surprisingly long time and starting a much larger fire.

So, how do you find the anger you’re unaware of?

First, you have to make a commitment to being honest with yourself. Because anger is so commonly suppressed, we often tell ourselves that it’s not really there and that we don’t deal with it. If you want to get further in touch with yourself, you’re going to have to strip away the lies, and shine a bright light on your life.

Sometimes, we don’t want to even touch our anger because it feels violent or dangerous. More often we’re ashamed of the things we’re angry about.

After you’ve decided to be uncomfortably honest with yourself, the next step is simple. Close your eyes, spend a few moments centering, and then ask, “What am I angry about that I haven’t let myself feel?”

Keep in mind that the answers may be deeply uncomfortable. A short and very incomplete list of examples:

  • You can secretly empathize with people and decisions you find morally repulsive
  • You dislike some of the people you’re tasked with loving
  • You hate or are disgusted with yourself
  • You’re mad at people for dying
  • You’re harboring intense amounts of fear and inadequacy
  • You’re incredibly frustrated with many of the ideas, people, values, and circumstances that define your life
  • You resent your friends because their lives seem better than yours
  • You hate your job and hate yourself for working in it
  • …etc.

Again, the trick is to acknowledge the source without falling into the trap of letting it define you.

You’ll notice that once you allow yourself to feel one or two things you’re mad about, many more will waterfall out. That’s good. We want that. We want to be as in touch with ourselves as we can.

Again, nuance matters. Just because these feelings are coming up, doesn’t mean that they own you or that they’re entirely true. You’re an adult. You can hold space for conflicting feelings. You can dislike your friends and family while also caring about them with enough warmth to melt the world. You can feel disgust at a rival’s morals and ethics while also empathizing with them. You can find parts of yourself that you’re totally ashamed of, and still feel love, compassion, and optimism about who you are.

Strategies to process anger

The last step in working with anger is learning to process it in a way that’s healthy and constructive. I’m not talking about venting (that’s healthy but often not enough) or complaining (I’m not convinced there’s any benefit to complaining for its own sake). Instead, I’m talking about strategically letting the anger move through you so that you can release it.

Personally, I’ve started keeping a list of the different things that piss me off, and then, every few weeks, sitting down to process it. I call it the anger list. Here are four ways of processing it:

1) Journal like you’re channeling the devil himself. This is often my first move. Turn on some angry music (I like System of a Down’s album, “Toxicity”) and write about every little thing that pisses you off. Feel free to write things so cruel, vile, and nasty that you feel the need to text your friend saying, “Hey, if something happens to me, break into my apartment and destroy every journal and laptop I’ve ever used.”

Again, you don’t need to believe everything you write, and just because you write it doesn’t mean it’s true. Don’t worry about that stuff. Instead, just let it out.

2) Tell the world to fuck off. Another effective way of processing anger is to play what I call the “Fuck everything” game. The game is simple: you spend time simply saying aloud, “Fuck you,” to everything you need to. A good round should go on for a little while, and could start like this:

  • Fuck you J* for being way richer than I am.
  • Fuck you B* for dying. I can’t believe you left me like that. I miss you.
  • Fuck the Spring for being bright and beautiful when all I feel is darkness and gloom.
  • Fuck myself for waiting for so damn long to address my needs.
  • Fuck my friends for living all over the country instead of living here.
  • Fuck this stupid neighborhood for being filled with people who think it’s appropriate to stop me on the street and babble at me when I’d much rather be left alone.
  • Fuck K* for being such a stupid boss. I can’t believe how poorly you handle this stupid fucking team and all of the projets we have to work on. I can’t believe we have to report to you you stupid &^%$.
  • …Etc.

3) Rage. Like many emotions, anger can be held in the body.1 To fully process it, we need to get into our body and express it. There are a lot of ways of doing this. A few include:

  • Doing something physically demanding – a series of all out sprints, hitting the gym and lifting as heavy as you can, going on a long ass hike, etc.
  • Doing something that simulates violence – throwing big stones with all your force into a lake, axe throwing, pounding a punching bag, etc.
  • Throwing a controlled and passionate temper tantrum – punch your pillows, cry, tear at your hair, smash shit with a bat, jump, stomp, and scream, etc. This is especially fun if you blare fast angry music.

4) Chanel it into art. Take all the shit that you’re angry about, and then use that energy to draw, paint, sculpt or compose a piece of art that reflects how you feel – the more horrible the better. Or, alternatively create a beautiful depiction of the things that are pissing you off, and then destroy it. Or both.

Of course, this list isn’t exhaustive nor do these exercises need to exist in isolation from one another. The goal, really, is to confront whatever you’re dealing with and let it out in a controlled and effective way. If you’re drawn to other strategies, use those.

==

After you’ve worked through some of your stored anger, give yourself a bit of space to let everything sink in and return to normal. Go for a walk by yourself without your phone for a bit. As time goes on, you’ll notice that you feel lighter and that life flows through you with a bit more joy and ease than it used to.

Finding your path part 2: 7 questions to help you on your way

I’ve spent a lot of time trying to figure out how to create a life worth living. This included learning to love myself, meditation, therapy, and a lot of time and money wasted on personal development and coaches.

My most recent step has been learning to find meaningful direction with my career path. For most of my professional life, I’ve been modestly successful, but also sort of miserable.

2019 has been very, very different. As it turns out, finding your path is one of the ultimate life hacks for happiness and productivity. There’s still plenty of frustration – as a student and an intern, a huge amount of my time is dedicated to pedantic busy work. And since I’m still consulting and training to be a meditation teacher, my spare time and energy is truly scarce. Despite the demands, I’ve found myself waking up happy, playful, and with tons of energy and space.

This is the second article in a three part series. In the first article we covered the subtle signs of being successful, but off the path. In this article, we’ll discuss different questions to help you find find your path. In the third article, we’ll discuss how to summon the courage needed to take the first steps.

A FEW NOTES ON PURPOSE AND PASSION

I’m not sure that I believe that people have purposes, per se. What I do believe is that if we find something good enough, and dedicate ourselves to it, that we can create amazing lives for ourselves. What does this mean when it comes to finding your path? It means that you can take some of the pressure off of yourself. Instead of getting it exactly right, I suspect that all you need to do is come close enough.

Right now, it’s trendy to try to turn passions into jobs. In fact, it’s so trendy that I’ve met people who feel guilty for having a normal job, and not one that they’re disgustingly in love with.

As we’ve discussed, I think that turning your passion into a career is misguided, unnecessary, and at times, destructive. A far better move is to find something that you like well enough, and move forward from there.

7 QUESTIONS TO HELP YOU FIND YOUR PATH

Finding your path is an art, not a science. The following 7 questions helped me find my path, and I hope that a few of them help you too.

1) Do you secretly know what you want to do? In many cases, we know exactly what we want to do, but we hide it from ourselves because we’re afraid. If you’re in this position, for now, just work to own your dreams. We’ll talk about bringing them to life in the next article.

2) Did you used to know what you wanted to do? I know that sounds like a strange question, but it was a valuable one for me. As a teen I knew I wanted to be a psychologist. I was (and still am) amazed that some people understand the mind so well that they can help it heal. But then I got distracted. I quit my psych major in college because my peers were too crazy, then I traveled, then I got involved with international development, and then got sucked into the business world. For a decade or so, I lost myself.  

As you find yourself searching it’s worth pausing every now and then to ask, “What did my teenage self want to do?” She may have been more on the mark than you ever imagined.

3) Is there space in your life for new possibilities and ideas to emerge? Trying to find the right path can be a deceptively difficult project. If you don’t dedicate time to reflection and experimentation, you may never succeed. Most of us stay pretty busy these days, and when we aren’t busy, we fill the space with distraction.

If you want to get clarity about yourself, one of the best moves is to spend time doing less. I wrote about my experience doing less last year. Not only did it lead to the happiest part of 2018, it also helped me get clear on what it is I want to do when I grow up.

4) What are some weird paths that you could fall in love with? It’s tempting to try to get your life to fit neatly within the lines. For some, it’s totally possible. Others, like me, need to go way outside the lines in order to find something that feels meaningful and worth doing.

Are there seemingly disparate skill sets that you can combine to create something unique? Or can you wrestle with something and get it to serve you? I know this sounds a bit abstract, so I’ll explain how it played out in my career.

I love writing, psychology, speaking, business, working for myself, and serving the least fortunate. If my work didn’t include most of those attributes, I would feel like I was leaving valuable parts of myself behind.

So my plan is to open a high-end mental health spa that includes psychology, meditation, and cutting-edge interventions. Then I’ll use the profits to fund a mental health center for those who can’t afford services. Along the way, I’ll continue to blog and give the occasional speech. Does this fit neatly inside the lines? Not at all. Will it work? I’m not sure. Does it feel right? Absolutely.

5) What do the people in your life think you should do? Sometimes, other people have good insight into what might make you happy. My dad was the first to point out that I would likely be unhappy if I were a full time executive (a path I seriously considered). My guy friends from college and high school encouraged me to become a therapist. In both instances, people close to me had a clearer idea of what might make me happy than I did. Asking people for suggestions can prove fruitful.

But this is not a fool proof strategy and can potentially cloud your vision. The trick is to ask for other people’s opinions, but not take them too seriously. When someone makes a recommendation, spend a bit of time considering it and trying it on for size, but don’t take it as gospel.

6) What do fortune tellers and personality tests suggest you do? Don’t get me wrong. I don’t believe in fortune tellers or personality assessments (and yes, that includes the MBTI, Strengths Finder, Enneagram, and whatever other silly assessment is currently en vogue). I mean, it would be lovely if figuring ourselves out were as simple as taking a multiple choice test, but of course, little in life is truly so simple.

That said, you can use career and personality inventories as well as fortune tellers to get the creative juices flowing. Maybe you’ve only been thinking about white-collar jobs when a fortune teller (or whatever) suggests that you’re destined to work as a police officer. Suddenly, you start imagining yourself as a cop. While that isn’t quite right, it opens a whole new realm of possibilities including: firefighter, barber, construction manager, bike mechanic, etc. Doing this can shine light in unsearched corners of possibility.

7) Have you actually tried your dreams on for size? Big decisions often feel like an all or nothing proposition. We either stay in our dead end jobs, or we burn it all to the ground to become a tortured writer.

While this approach can work, it’s needlessly reckless. Instead, try your dreams out before you commit to them. If you want to be a writer, force yourself to write for an hour or two every evening to see what it’s like. If you want to start some sort of business, work on it during the nights and weekends until it’s generating enough income to support you before you quit your job. If you’re thinking of becoming a hospital chaplain (which I was) take a few days off to shadow one and see if you like it.

Note: It’s possible that your job is taking up so much space in your life that you can’t dream while you’re still in it. In that case, consider building an off ramp. Spend time saving money and then quit, or get a job that doesn’t demand as much of you. Yes, this requires making sacrifices and can take a lot of time. But doing this will give you the platform you need to really dream and pursue something that is a better fit.

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It took me several years and about a dozen false starts to find my path (seriously). I think the important part is finding work that is an honest reflection of how you want to live and what you value. That includes working at Burger King or some other place that you’re apathetic about in order to support the rest of your life. I hope that the strategies above help you find the next few steps on your path. They’ve been invaluable to me.

PS: One thing to keep in mind while you’re searching

There are literally billions of people out there who don’t have the luxury of considering how they want to spend their time. Any job that helps avoid hunger and exposure to the elements feels like a gift from God. I think this is worth considering for two reasons. First, it gives some perspective to our own struggles. Yes, the problem of existential and professional unrest is a problem, but it’s an amazing one. Second, I think it offers a bit of insight into finding a path that you’ll love. My experience is that we all tend to be a bit happier when we use at least a small part of our lives, to improve those of others.

The secrets we don’t share: lessons about pain and belonging from a late mentor

My inner circle isn’t huge – a dozen people give or take. They all seem smarter and more put together than I am. They found careers, got married, bought houses, etc. Me? I returned to school in my 30’s, still rent an apartment, and seem to have a restless soul.

There are periods of my life defined by pain, fear, disappointment, confusion, isolation, and feeling lost at sea. When I look at my friends, I sometimes mistake their lives as being devoid of those particular demons. It makes me feel like there’s a chasm between us. Their lives seem perfect. Mine, on a good day, is a work in progress.

Though hard to see, the truth is far from my surface-level perceptions. All of us go through dark and difficult periods. When I think carefully about my inner circle, I am reminded that in the past few months:

  • One lost his mother in a freak accident. A few years prior he lost his Dad.
  • Another friend’s mother was just moved into hospice.
  • Two suffered miscarriages.
  • One built a business only to watch it crumble. Now he’s struggling to support his family.
  • Another told me that he’s in the grips of addiction and may lose his marriage and family.

Personally, I just lost a mentor. Years before I became a speaker he asked me to give a speech. Years before I started meditating he talked to me about spirituality. He constantly saw a better version of me and helped me grow into it. When I found out he was on his deathbed, I sent a letter, but I’ll never know if he read it.

All of this reminds me of one of the most isolating and deceptive aspects of being a human: we notice how nice other people’s lives are while failing to notice their pain. Through omission, misperception, and failed communication, the pain of existence gets hidden away. It makes us feel like there’s something wrong with us, like we’re somehow doomed to struggle while everyone else flourishes. On bad days, it prevents us from showing up when we’re most needed.

All of this points to a simple truth about the human experience: even the best lives will be dealt seemingly inordinate amounts of pain and injustice.

I sometimes find myself asking, “What the fuck do I do with this information? How do I deal with the fact that to be alive guarantees more pain than we think we can handle? How do we make any of this shit worth it?”

While I don’t have a complete answer, I do know where to begin:

  • Hold the people you love just a bit tighter
  • Be kind and gentle to yourself
  • Call just to say hi (it’s been many years since M* took his life and I still wish I called him more)
  • Relish the good times when you can
  • Notice the striving humanity in other’s eyes
  • Reach out when the world breaks you
  • Let others lean on you when the world breaks them
  • Open your heart just a bit more
  • Sleep in every now and then
  • When you meet your edge, soften

Through it all try to remember a simple lesson from my late mentor: we belong to one another. Keeping that in soft focus makes this all a bit better.

Finding your path part 1: what it’s like to miss the mark

I’ve struggled to find my path in life. Prior to starting this blog, I moved from Washington, DC, to Colorado. I also stopped touring as a speaker, despite unexpected success and a 13 year career in the field. While writing this blog, I opened and quickly closed a leadership coaching practice, opened and continue to run a consultancy for speakers, raised capital for a business I decided not to pursue, took on a bunch of side projects, and finally, returned to school.

It’s been a long, strange, and difficult ride, and for the first time ever I feel like I’m on a true path as I work to become a therapist and meditation teacher. It’s reasonable for readers to ask, “Well, how does Jason know that? He’s had a decent number of false starts.” On one hand, I know that I’m on the right path – I haven’t felt this way before. But a far better answer is that as a writer and sometimes speaker, I work in public. I’ll prove it to you as you watch from afar.

This article is the first in a two part series. In it, we’ll discuss a phenomena that a lot of people fall victim to, including myself: being successful, but off your path. We’ll also talk about how to identify some of the subtle signs of missing the mark. In the next article, we’ll discuss practical steps that you can take to help find your path and start moving down it.

Two friends who got it right

Though many of my friends are successful, it’s C* and W* whose work I admire the most.1 Despite not knowing one another well, their paths are shockingly similar. Both became elementary school teachers after finishing undergrad in 2008.

After a few years in the classroom, C* was promoted to Vice Principal of his school. The following year he accepted a Principal position at a struggling school in his community. C* was tasked with turning the school around while concurrently completing his doctorate. He improved the school so dramatically that other districts routinely contact him for advice.

W*, after a few years in the classroom, co-founded one of the nation’s leading public charter schools. He was recently promoted to CEO where he is tasked with overseeing the school’s effectiveness and expansion.

Three signs you may be missing the mark

For years, C* and W* were complete enigmas to me. Like many people, I was obsessed with efficiency, success, status, leadership, influence, etc. C* and W* barely paid attention to that stuff, yet they were happier, more successful, more effective, and much less burnt out than I was. This of course, is the difference between being on your path and missing the mark.

Looking back, I realize that I missed a few critical warning signs that should have let me know I was on the wrong path. Unfortunately, catching these signs is trickier than it seems. In many success-oriented communities, they’re par for the course. If you’re in one of those communities, you kinda have to become a fish out of water, and it’s hard to understand what’s going on. A few of the most glaring signs that your heart is no longer in it:

1) You’re always on the precipice of being burnt out. Even when I had plenty of time to myself, I felt exhausted. This was in part because of the subtle but omnipresent sense of dread resting just below the surface. The truth is, I didn’t want to go through the falderal of doing the work I was doing. This is in sharp contrast to C* and W* who, despite working harder than I ever did, rarely burnt themselves out. To them, work was enlivening.

2) You’re spending a lot of time with self-help, personal/professional development, self-care  or motivation. C* and W* didn’t waste time with self-help, personal/professional development, or motivation because they didn’t need to. Since I was out of integrity, I needed a ton of resources just to keep myself going. In many cases, an obsession with motivation, efficiency, self-help, personal development, acknowledgement, self-care, etc. is an artifact of being on the wrong path. Of course, there’s a time and place for all of these things, particularly when you’re going against the grain to better the quality of your life.  But if personal development and its satellites are dominating large parts of your time and attention for extended periods, it’s a pretty clear sign that something is wrong.

A related indicator is being deeply driven by money, status, fame, and other forms of accolades. If you’re routinely seeking or in need of external validation, then there’s a very good chance that something has gone awry. One of my close friends is a book marketing consultant. When clients tell him that they want their book to become a best seller featured on Oprah, he responds by saying, “Ok, we can try to make that happen, but therapy is going to be a lot cheaper.”

3) In theory, you should be happy, but you’re not. While it seems like my success should have made me happy (and I certainly expected it to), it didn’t. Instead it inspired something a bit closer to self-loathing. Yes, I could find happiness elsewhere (and I often did), but doing so required work. C* and W* were entirely different. Though their success wasn’t nearly as flashy as mine and though they worked harder than I did, they were much, much happier.

Note: feeling like you should be happy, but not being happy, or enduring prolonged periods of apathy, ennui, or unhappiness can be symptoms of depression and other forms of inner unrest. As always, if you feel like you’ve been struggling with your mental health, I urge you to turn to a qualified mental health provider.

What do C* and W* understand that the rest of us don’t?

People immersed in entrepreneurship, leadership, thought leadership, sales, social media, and personal development, tend to believe that success is something that must be aimed for in order to achieve. This makes sense. The process of making sales calls, building funnels, cranking out content, split testing, engaging in humiliating levels of self-promotion, failure, rejection, chasing money and status, writing copy, covertly trying to impress your peers, etc. is so inherently meaningless that we need external motivation just to get out of bed. And again, I get it. I spent most of my professional life with these burdens.

To further complicate the matter, whenever we’re motivated by external validation, enough is never enough. At the beginning you’ll be excited just to have a client. Then you’ll be excited when a client pays for your flights. Then you’ll want first class flights. Then you’ll feel inferior for not flying private. I know that sounds crazy, but trust me.

C* and W* understand something that is lost on many people. They have figured out that if you take the time to do good work that you care about, especially in service of others, all that’s left is to consistently show up and do your best. For them, their stunning success and influence was never a target they cared much about; instead it’s an artifact of doing work that they find intrinsically meaningful. As far as I can tell, true success always works like that.