Getting out of a rut part 2: overcoming the hidden fear and self-sabotage that’s holding you back

Note: this is the second installment in a two-part series on getting out of a rut. The first part, which can be found here, is on emotional spring-cleaning.

One subtle characteristic of being in a rut is that we become self-obsessed. We ruminate over the past and where we went wrong. We scornfully replay all of the mediocre decisions that left us feeling hopeless and strung out. We get taken over by anger at ourselves and others for the ways we feel wronged. The self-obsession artificially amplifies any stress, anxiety, or depression we’re already dealing with. We begin to define ourselves by it.

How many times have we all told ourselves that we won’t waste the day, only to waste the entire. fucking. day. As though that weren’t bad enough, we’ll most likely feel bad about that decision, doubling down on the self-resentment.

But do you see the vortex we’ve created here? All of your attention is on yourself, and since you’re not feeling well right now, you’re magnifying the bad stuff.

There is a weird evolutionary logic to this type of behavior. Obsessing over our mistakes is protective. It keeps you firmly planted in your rut and prevents you from exposing yourself to the potential perils of the world again.

Generally, we approach getting out with a combination of discipline and new behaviors. We tell ourselves that we’ll spend time learning to play ukulele, hitting the gym, going to improv classes, saying “yes” more often, taking a trip, etc. And while I like all of these moves for their own merit, they fail to cut through the trance of self-obsession. Instead, they act as healthy distractions.

A far better move is to shift your attention away from yourself and toward others. Volunteering is one amazing way to do this. Find a cause that you care about, and dedicate some of your time and attention to it each week. In this troubled world, there is always a cause in need of volunteers. To name just a few:

  • Walking and caring for animals at local shelters
  • Helping the homeless meet their material and existential needs at missions, kitchens, and shelters
  • Stocking and amassing supplies for food pantries
  • Working on political campaigns to help shape your communities (this is a big one for me right now)
  • Getting involved with community development projects in struggling areas locally and globally
  • Championing environmental issues
  • Assisting the elderly and infirm with the day-to-day chores of living
  • Teaching, tutoring, or participating in after-school programs
  • Spending time as a big brother or big sister to an at risk youth in your town

A lot of people get stuck in the rut. Again, I get it. Ruts start to feel so familiar that staying in them is easier than breaking them. If you can, scrape together just enough energy to spend an hour or two each week working to improve the lives of others. Doing so, zenfully, will improve your life and help you get out of the rut.

If you don’t know where to start, consider volunteering at an animal shelter. You’ll meet other cool people and be surrounded by the unbounded love and playfulness of cute animals. And seriously, it’s hard not to feel charmed when a puppy wants to play or a kitten curls up in your lap.

Getting out of a rut part 1: emotional spring-cleaning

Summer, 2018, during a brutal silent meditation retreat: It’s been two days since I’ve had significant human contact. Worse still, my thoughts are dominating me. There’s no corner of my mind that isn’t overrun by fears about work, love, loss, the past, the future, and… everything. I’ve given up attempting to sit still, and I decide to go for a walk in the forest.  

It doesn’t help.

Out of quasi desperation, I try something new. Instead of trying to fight against the difficult thoughts and feelings, I accept them. I accept that – at least for now – my mind is a mess.

When I stop fighting against myself, things change. My mind slows down a bit and I feel more present. For the first time, I’m able to take in the forest.

As I sit with the conflicting experiences of being dominated by my mind, and stunned by the natural beauty, something surprising happens: I feel months of existential weight leave my body.

Though I hadn’t realized it, I was being owned and defined by my recent past and clinging to it’s darkness. Now, seemingly without intention or effort, its grip is loosening. I’m coming back to myself. I’ve forgotten what it feels like to be light like this.


As many readers know, the first three quarters of 2018 kicked my ass. Deaths, breakups, lawsuits, professional missteps – the whole thing. It left me feeling weak and exposed to the elements. In truth, a lot of it was my fault. I drifted out of integrity and suffered the consequences.

As anyone who’s gone through a difficult time knows, the darkness has a quiet seduction to it. Friends shower us with care and attention, giving us an easy excuse to mope around and watch TV. As our motivation tanks, being down and out starts to feel familiar and almost comfortable. What should have been a week or two of pain turns into months of shit.

The trick is to dust yourself off, put the darkness behind you, and come back to yourself. For some, this seems to happen automatically. For others, like me, it helps to go through an emotional decluttering process and address any lingering anger or tension. Think of it as spring-cleaning for the heart and mind.

In this article, the first of a two part series, we’ll cover different techniques to help you complete your past and create optimal conditions for letting go. Concurrently, you’ll free up mental and emotional space for you to grow into the new – often better – version of yourself

Begin by holding time for yourself

When life sucks, one of the first things to go is our connection to ourselves. The loss of connection is subtle; we often feel connected because we’re mesmerized by the darkness, but to focus on the darkness is to lose sight of the rest of the world. And I promise you that there are plenty of beautiful things remaining in your life.

Begin the process of emotional spring-cleaning by holding space for yourself. Personally, I went to my favorite coffee shop and spent an hour or two journaling each day for two weeks. I’d grab a drink, sit down with a journal and pen, and process whatever was on my mind. A few times a week, I also went for long walks at night without my phone.

While these sessions may begin dark, they will allow you to shine light on what happened. Along the way, you’ll notice plenty of great things about yourself and your life that you likely missed. Allowing space for yourself burns off some of the negative energy that’s been following you around.

Understand that you may need white space in your life

Depending on the intensity of the shit you’re recovering from, you may notice that it’s changed you. I’m the type of guy who rushes head first into the future. While this makes my life exciting and fast paced, it’s little more than a thinly veiled defense mechanism. Rushing into the future prevents me from dwelling in the moment and addressing any lingering difficulties. Inevitably, the stuff I ignore catches up to me.

A far better approach is to move slow, rest, become reacquainted with yourself, and allow time for dreaming again. Erik Erikson, a psychologist, referred to this as a moratorium and considered it an integral part of maturing. In fact, future be damned – work to build a present that you fall in love with.

As dreams begin to capture you, talk through a few of your ideas with friends. Imagine how different futures would make you feel before you start work on them. Eventually your next real dream will start to capture you. For now though, just try to get comfortable with the in-between.

Reinforce the foundations

How’s your self-care? If your life is anything like mine, self-care tends to atrophy when life gets hard. If that’s happened, take some time now to reinforce the foundations. Clean up your sleep, diet and exercise. Reconnect with your friends. If there are books, albums or works of art that have influenced you, revisit them. If you have spiritual, religious or psychological practice that slipped through your fingers, now is a good time to pick them back up.

While you’re at it, consider taking care of all that personal maintenance stuff you’ve been putting off too: cleaning your home, balancing your accounts, getting a physical, going to the dentist, etc. The day after I got back from the retreat I went to the dentist for the first time in too long. Yeah. I was being a glutton for punishment that week. That said, there was a silver lining: no cavities!

Happiness can often be found in eliminating the stuff that drags you down. Take a bit of time to consider removing things from your life that no longer serve you. This can include moving, getting rid of an office you don’t use, making basic repairs, selling or donating stuff that’s been cluttering your space, etc.

If there are any hard conversations you still need to have, now is the time

To get back into integrity, I needed to have sticky conversations with a bunch of people (lucky me) including: business partners, a client and an ex. None of them were pleasant; all of them were 100% worth it.

As you work to complete your past, you should also be leaning into any pending difficult conversations. These can include asserting yourself more thoroughly, apologizing, asking for an apology, fixing a mistake, correcting a deception, or expressing appreciation. Though hard conversations suck to get through, having them will make rebuilding yourself far easier. You’ll no longer be weighed down by the feeling of needing to fix things with some of the people in your life.

Depending on the situation you can write an email, place a call, or talk face to face. Personally I’m a face-to-face guy when at all possible, but you do you.

More on handling difficult conversations here.

Thank the people who helped you through

My friends spent countless hours letting me lean on them and talking me through career moves, broken hearts, business decisions and other mini-dramas.  As a thank you (and as a way of letting go of the past) I bought a bunch of correspondence cards and wrote notes to the people who helped me.

I’ve always hated writing thank you cards, but this was surprisingly joyful. It was nice to slow down and acknowledge the difference my friends made for me. I hope the cards were as delightful to receive as they were to write.

If you’re working to complete the past for yourself, I urge you to express gratitude and appreciation for the people who have supported you. If you only take one practice from this article, make it this one.

Finally do something nice for yourself

Skillfully handling dark phases of life is like being forged by fire. All at once everything is beautiful and painful, chaotic and controlled, creative and destructive.

When the world beats you down, it’s important to become a champion for yourself. While there are all sorts of sophisticated ways of doing this, I’m a fan of a simple approach: do something nice for you. Schedule a massage or a spa day. Take a trip. Spend a long weekend with your best friend. Get yourself a gift or a chocolate cake. Skip work and spend the afternoon sailing. You deserve it.



Eight ways to improve your people skills

Modernity is filled with false gods. How many of us have chased – and even achieved – success, only to find that it didn’t fill the void we hoped it would? How many times have we felt even more isolated after getting exactly what we thought we wanted? Of course, success isn’t the only false god. It’s money, casual sex, strict diets, better looks, hobbies, pets, meditation, juice cleanses, spirituality, a raise, a promotion, a new city, and a million other things.

Sure, these false gods can make an important difference in our lives, but at the end of the day, they rarely provide the relief and happiness we thought they would.

But you know what does pay off? Good relationships with a few people you love. Though it’s not nearly as glitzy as a penthouse apartment or an IPO, deep connections create happiness and joy in a way that little else does.

The sad part is that most of us are quietly struggling to form and maintain strong relationships. The good news is that relationships are a learnable skill. In this article we’ll cover eight of the skills that have improved my relationships with friends, family, girlfriends, business partners, and more. Hopefully they’ll improve yours too.

And if you’re at the stage where you’re just starting to build your group of friends, check out this article first.

1) Saying, “Thank you” instead of, “Sorry” when you make a small and innocent mistake. This was one of those small changes that made a huge difference for me. Like many people, I used to apologize at the drop of a hat, even if the issue was trivial and unintentional.

Today when someone lets me know that I’ve behaved differently than they’d like me to, I’ll often thank them instead of apologizing.

For example, a client recently said, “Hey man, you can be more direct when you’re giving me feedback. I’m not that fragile.” My instinct was to say, “Oh my God, I’m so sorry – you’re right. I won’t beat around the bush anymore.” Instead, I said, “Thanks for letting me know. I’ll be more direct next time.”

Shifting from “Sorry” to “Thank you” can have a surprising impact on your relationships and sense of self. Doing so gives people permission to let you know how you’re affecting them, which allows for greater connection. It also avoids the clunky dynamic of falling in and out of the good graces of the people you care about. By saying thank you, you also reaffirm that it’s ok to make mistakes and release yourself from insane levels of perfection.

Keep in mind that this is not an excuse to avoid apologizing when you’ve done something wrong. While you’ll have to figure out for yourself what warrants an apology and what doesn’t, I use a few guidelines. If I’ve dropped the ball, hurt someone, made a severe mistake, or if it seems like the other person just needs an apology, I’ll almost always apologize. I do this even when the issue was accidental or felt insignificant on my end. In this case, getting back to fluidity matters more to me than figuring out whether or not it’s reasonable to apologize.

2) Ask for comfort during times of darkness and distress. Of all skills on this list, it’s this one that’s made the biggest difference in my life. Since I was a child, I’ve wrestled with life’s problems on my own. I was  afraid to reveal that I was flawed and imperfect.

When I was really dark, I’d pretend like everything was ok while trying to avoid contact with other people. On the rare occasions when I did talk about my feelings, I simply recited facts about myself while walling off emotionally. I was never really being authentic or letting people in.

Emotionally isolating myself only amplified the already sharp pain I was experiencing. It also prevented me from forming stronger relationships because I never gave myself to others.

A few years ago, I tried something different. Instead of secluding myself when I was feeling low, I picked up the phone and called a friend. As I dialed his number, my hand literally shook. Instead of dismissing the pain, I told him about it. For the first time ever, I let someone in while I was messy and chaotic. Though it was scary as shit, it really helped me get through a difficult time.

If you’re afraid of letting people see you when you’re scared, weak, confused or depressed then you’re a perfect candidate to try opening yourself to loved ones. Next time you’re feeling bad, call a friend and explain what’s going on. Better yet, ask if you could spend some time together. If that’s too much, start by emailing or texting them and then working up to a phone call or hang out.

3) Realize that with some people you’ll want to set boundaries; with others you’ll want to tear walls down. Both setting boundaries and offering vulnerability are essential skills when it comes to forming healthy relationships. They’re also a bit contradictory.

Boundaries allow us to protect ourselves and prevent people from getting closer than we want them to. Vulnerability allows us to be seen for who we are and form deeper connections.

The trick is to understand when to use each technique. When there’s someone you want to keep out, set a boundary. When there’s someone you want to get closer to, offer vulnerability.

Make sure that the people you’re letting in treat you well and reciprocate by letting you in too. With the people you’d rather keep at arms distance, feel free to gently decline their invitations, cut conversations short, or withhold personal information at your discretion.

4) Saying, “Hey, I may be totally off base, but it feels like there’s something important on your mind. What’s up?” Have you ever felt like there was something that someone wanted to share, but for whatever reason, wasn’t? Or have you ever felt like there was a deeper issue at play that just wasn’t coming up in the conversation? If so, ask about it.

For me, asking this question has led to shocking revelations and depths of conversation. This year alone people have told me that they’re pregnant, leaving their partner, quitting their job, grieving a loved one, and many other things, simply because I trusted my intuition and asked.

5) Initiating hard conversations. I used to avoid hard conversations at all costs. I figured that engaging in them would jeopardize the relationship and make whoever I was speaking to dislike me.

I’ve since done a 180. I now believe that hard conversations are one of the best paths to deeper connection and intimacy. In failing to speak our truth, we are subtly lying about who we are and building walls when we should be tearing them down.

Today, when I’m upset, insecure, or confused about something, I’ll talk to the other person about it. While this is rarely easy, it’s consistently worth it.

The trick is to own your perspective and feelings, rather than make accusations. So instead of “You’re an asshole for calling me fat,” it’s “I doubt that this was your intention, but when you called me fat it really hurt.”

Keep in mind that there is a time and place for everything. You don’t need to rush into hard conversations, and it often makes sense to wait until it’s a good (enough) time for you and the other person to sit down and work things through.

Generally, when we think of hard conversations, we think of telling someone how they’ve hurt us. However, that’s not the only direction we should be thinking about. We should also lean into the conversations about how we’ve hurt or disappointed people. This includes both apologizing for the pain we know we’ve caused, as well as proactively asking, “Hey, have I done something that upset you?” when someone seems frustrated with us.

More on handling hard convos here.

6) Trust your inner circle’s consensus when you’re blurry. Once or twice a year there will be an issue that I can’t wrap my head (or heart) around. In these cases, I’ll turn to three or four friends who have a lot of experience with the issue I’m facing. I’ll explain what’s going on individually, and ask them what they would do if they were in my shoes and why.

If they all come to the same conclusion, I’ll take their advice. If there is no consensus, then I’ll understand that my problem is intrinsically murky and that there may never be a “right” answer.

One important note here: if you struggle with a specific area of life and your friends don’t, chances are that their advice will be difficult for you to follow. In these instances, following their advice (if you can) will likely reap huge rewards.

7) When someone is upset with you, work to understand their perspective emotionally and rationally. When I’m fighting with someone my default thought is, “Man, this person sure is a jackass. I’ll straighten them out.” This does nothing productive. It only widens the chasm between myself and the other. While this may not matter if the other person is someone I don’t care about, it sucks when it’s someone I do.

Instead of doubling down on the fight, I’ll work to understand why the other person is so upset. This generally begins by listening and asking questions (which, at least for me, is deceptively difficult during an argument). Then I try to imagine how I’ve made this person feel. If you realize that you’ve done more damage than you intended to, or that you really were in the wrong, consider offering an apology.

I won’t lie, empathy in this context feels borderline impossible most of the time, but it’s also worth it. Confronting the issue head on repairs the distance between you and the other person, and fosters understanding. It may also inspire the other person to extend more empathy to you as well.

By the way, this doesn’t need to be a thought exercise. When you feel like you’ve begun to understand someone but you’re not sure, ask. Say, “Hey I imagine that you’re feeling x, y, and z – is that right?”

8) Accept that it’s ok for relationships to experience friction from time to time. So much of this list is dedicated to forming deeper relationships with other people. This however does not mean that all of your relationships will be – or even should be – placid 24/7. As a recovering people pleaser, I used to hate it when there was conflict between myself someone else. While I still don’t like it, I’ve realized that friction is inevitable, especially in intimate relationships. It’s ok for people to be upset with one another from time to time. In fact, far more important than never fighting with the people you love is noticing that you come back to one another. That is one of the true markers of love.

It’s ok to not be ok from time to time

Right now life feels particularly unstable. Long time readers know that I endured a decent amount of turbulence this year, and to the best of my ability, I used it as an invitation to build a better life.

As I write, I’m raising capital for my next business1 and exploring a new relationship. I’ve also started curating my personal and professional circles with more intention.

While it’s easy to look from the outside and think, “Damn, what an exciting time for Jason!” I assure you it doesn’t feel that way.

It feels more like, “Fuck. What in the world am I doing? I’m going to blow all my savings and social capital on this new business which will probably fail, and the icing on the cake? I’m liable to get my heart ripped out of my chest along the way. I have no idea how I got here or what I’m doing, but I think I’ve fallen behind. Worse still, I can’t tell if I’m moving forward, backwards, or if I’m just on a hamster wheel. Maybe I should move to Nova Scotia and work on a fishing boat or something. How am I like this at 32? I thought I’d have my shit together by now.”

Yeah. That’s about right.

In moments like this, where I feel overwhelmed, my mind drifts to my friend’s lives. They all seem so put together, happy, successful, and better equipped to deal with life than I am. I wonder what it would be like to trade lives.

Of course, feeling that other people’s lives are free from the pain and chaos of existence is nothing more than a fickle illusion. Like it or not, suffering and strife are components of the human condition. When you pay attention, it becomes obvious that we all deal with heartache, frustrations about work and money, and a generic sort of blah and boredom from time to time.

But there’s something subtle at play here, too. This particular sense of being lost at sea comes along with living more vividly and courageously than most people dare. It’s a sort of existential tax on the bold. It would be possible for all of us to settle for something less – and maybe one day we will – but today’s not that day.

Along the way, we have to accept a hidden part of the human experience – one that’s a bit easier to drown out than discuss. Specifically: sometimes life just sorta sucks. More than that, sometimes it’s really fucking hard to be a human.

And I’m not just referring to the obviously difficult things like death, disappointment, the current political climate, illness, and deceit.

I’m talking about the things that more easily blend into the day, like:

  • Never quite being able to stick to a budget (or diet, exercise routine, or sleep schedule)
  • Needing to deal with people you’d rather not
  • Spending time every single day doing the dishes (is it just me, or does it feel like life is defined by doing the dishes?)
  • Wrestling with the mind-numbing bullshit of spending more time at work than with your friends, family, and lover combined
  • Accepting that the people who love you the most will accidentally hurt you every now and then (and that you’ll accidentally hurt them, too)
  • Perpetually feeling tossed between abundance and scarcity, confidence and insecurity, connection and abandonment, getting it together and falling apart, etc.
  • And a quiet, unidentifiable longing for something more

For the most part we just skate over these nuisances. Heck, there are huge chunks of life where we barely notice any of them (except for the dishes – I hate the dishes).

But every now and then, we get hit with the perfect storm and start to get weighed down. It’s a passing phase, of course, but it feels chaotic and endless to get through.

When this happens, it’s tempting to fight against it, or attempt the emotional jiu-jitsu of searching for shards of beauty amidst the chaos. Neither has ever worked for me. Instead, I think it’s best to just accept what’s happening, lean on your friends, throw on your favorite record2 and remind yourself that this too shall pass.

I know that marketing, personal development, and your nauseatingly positive friend, Jeff, all make it seem like there’s something wrong with you if you aren’t happy 24/7. But I don’t buy it.

I don’t think it’s human to be happy all the time. People who claim they are probably don’t understand the concept. I think it’s human to be lazy, joyful, confused, messy, charming, gross, ambitious, generous, capable, bored, happy, awkward, smooth, fulfilled and a million other discordant things – sometimes all in a day.

The important part is to try to live close enough to your potential,3 while accepting that you’ll still have to deal with the suckiness of it all.

So know this: it’s ok to not be ok every now and then. In fact, it’s perfectly normal

And if you’re starting to get buried by it all, reach out to a friend or professional. Because one thing I know: we don’t get through this on our own. We’re designed to lean on one another. While it doesn’t make the ennui go away exactly, it does defang it a bit. And if things are going great for you right now, call one of your friends to check in and see how she’s doing.

The art of suffering: how to use pain to improve your life

March 2018, Botanical Gardens, Denver, CO: C* has always been generous, kind, and loving. Two years ago, I did something very hurtful to him. I’ve never apologized, and we’ve never talked about it, even though I feel its weight every time we hang out. It’s not that I don’t want to apologize; I’m just afraid.  

We’re walking around the gardens talking about life, when I turn to him and say, “You know, I’ve been trying to find the courage to say this for a while. A few years ago I was a huge dick to you, and I’m so sorry. You didn’t deserve that. It was reckless, unloving, and totally unfair. Again I’m so sorry.”

C*, looked at me, gave me a hug and said, “I forgive you.”

Apologizing to C* was one of the hardest things I’ve done this year. It forced me to confront myself and own the repercussions of my actions. In any given moment with C*, I found it easier to  pretend nothing happened, even though the guilt and shame was always there, quietly eating away at me.

I’m so glad that I endured the awkwardness of apologizing; it cleared the air and paved the way for a closer friendship.


One of life’s most obvious truth’s is also one of its least discussed: pain and suffering are entirely inevitable.

It’s unfortunate that we don’t discuss this from day one because the way you approach dealing with pain dramatically shapes your life. Approach it correctly and you can create an abundance of joy, connection, and stability. Approach it incorrectly – which most of us do – and huge chunks of your life will remain dampened and unlived.

We’re going to take pain and suffering head on in this article (fun, right?!?). We’ll talk about why the intuitive approaches are flawed. We’ll also discuss two unusual techniques that can allow you to live a more engaged, vivid life.

The common approaches to pain and suffering, and what’s wrong with them

Because we never really talk about how to deal with pain, most of us use ineffective strategies for coping. The two most common strategies are:

1) Pretending like you don’t have any pain at all. The people who use this approach talk about, “just having a good time,” “staying busy” and “getting after it” (whatever that means). They drink a bit too much, over commit themselves, don’t sleep enough, and rarely, if ever, engage in any sort of meaningful introspection or silence. By staying busy and distracted they eliminate the potential to deal with their pain. If you offer them support or compassion when they are going through something difficult, they’ll often bristle and say “Yeah, it’s not really a big deal.”

While they appear to be living the good life, it’s total bullshit. What they’re really doing is distracting themselves. By failing to acknowledge the pain in their lives (either past, or present), they’re blunting their potential for joy, awareness, and connection.

2) Pretending that your pain and suffering defines you. Some people share insanely personal stories about their past traumas before the appetizers have even arrived. They seek attention by complaining, worrying, being exhausted, and “looking after” others. They spend a disproportionate amount of time dealing with anxiety, and often use their anxiety as an excuse to lie to and manipulate the people around them.

Though these people are sometimes captivating – we  want to help them and mistakenly feel honored by their trust – they’re also draining as hell. More than that, the obsession with their own pain prevents them from healing and connecting with others. Like the people who pretend to feel no pain at all, they fail to engage with the depth of the human experience.

While it’s tempting to either ignore pain or let it own you, there are far better ways to work with it. Specifically, using it strategically to improve your life, and using it as a guide towards healing.

Using strategic suffering to improve your life

In most cases, getting from where you are right now to where you want to be in the future requires leaving your comfort zone.

In order to repair the distance between C* and myself I had to endure a few minutes of shame and vulnerability as I apologized. But the pay off for those five minutes was huge. Not only did I feel a weight lifted from my shoulders, I also got closer to someone I love.

In most cases, any sort of action that will move your life forward requires a relatively small amount of discomfort in exchange for a large amount of growth, for example:

The good part is that in most cases, you’ll only need to endure a few minutes of discomfort in order to reap long term rewards. For example, asking for a raise is nerve-racking as hell. However, the conversation really only takes a few minutes, and if it goes well, you’ll enjoy a fatter paycheck for the rest of your time at the company. If you’re really having trouble taking action, break whatever you’re working on into smaller steps.

If you’re attempting to raise money for a new business, begin by figuring out how much money you’ll need. Then make a list of friends who have experience raising capital. Then schedule calls with them to get their advice. And so on.

There is a trap here. Some people end up believing that leaving their comfort zone is intrinsically valuable. This is why we see people walking on hot coals at personal development seminars, guys trying to talk to every pretty woman they see, and people arbitrarily going skydiving. That stuff is useless because it provides almost no long-term value or growth. More than that, it will needlessly spike your anxiety and drain your inner resources with nothing to show for it.  

Being in your comfort zone is awesome, and I would argue, fairly healthy and nurturing. The trick is to only leave it when there’s good reason for doing so, and otherwise just enjoy the heck out of your life in the moment.

Using pain as a guide for improving your life

I recently injured the rotator cuff in my left shoulder. It was painful as hell. To heal, I scheduled an appointment with a physical therapist and stuck to the protocol he laid out. Today, my shoulder is 90% better.

We all understand that recurrent physical pain is an indicator of something wrong in our bodies. We correctly interpret the pain as a sign that we need to modify our behavior. Strangely, we fail to understand this about emotional pain. We tend to try to suppress, compartmentalize, or ignore our emotional pain, hoping that it will magically go away. Usually, it doesn’t, and it  instead weaves itself into our lives, subtly defining how we experience the present moment.

What we should really do is approach emotional pain the same way we approach physical pain. Once we notice it, we should treat it as an indicator that our inner lives need a bit of maintenance.

  • Lonely? Call a friend.
  • Chronically lonely? Build a social life.
  • Depressed or struggling to get over a long-term problem? Talk to a professional (this worked amazingly well for me).
  • Unsatisfied at work? Start looking for a new job or ask for a promotion.
  • Anxious all the time? Figure out what is causing the anxiety and work to fix it.
  • Stressed about money? Put together a budget, earn more, or change your lifestyle.
  • Worried you were a jerk to your friend two years ago? Take him to the botanical gardens and apologize.
  • …You get the idea.

By allowing pain to guide you towards healing and improvement, you’ll be able to dramatically advance your life.

The trick is to figure out how to use the pain to serve you, instead of letting it own you. In learning to work with your pain instead of denying it or allowing it to define you, you’ll unlock new potentials for joy, growth, healing, and abundance.

Putting yourself back together: guidance for when life collapses

Earlier this year: Going a day without crying feels like an accomplishment. Over the past few weeks, I’ve watched many things I cherish fall apart:

  • I found out that one of my projects was in copyright violation and had to deal with a bunch of lawyers to sort everything out.
  • A business partner of several years left the team and has become an aggressive competitor.
  • A family friend passed away from brain cancer.
  • Without warning or explanation, L*, my now ex-girlfriend, left me.

  • Two old friends did something extremely hurtful, leaving me feeling betrayed and abandoned when I needed them most.

  • The icing on the cake? Somewhere along the line I injured my rotator cuff. Full recovery will take months.1

With so many difficult things happening all at once, it feels like there is nowhere for my mind or heart to turn to that isn’t overrun with pain.


Early April, 2018: For the first time in months, I’m feeling good again. Without thinking about it, I started dancing around the apartment while I was getting ready for the day. My thoughts are no longer dominated by pain and loss, instead, they’re busy creating a present and future that I can easily fall in love with.

I’ve realized that before things started to crumble, large parts of my life fell out of alignment. In other words, I had more agency and responsibility for the bad things that happened to me than I initially understood. In a way, they were a blessing. As I rebuild, I’m working to integrate the lessons from earlier this year.


One of the stranger parts of the human experience is that life occasionally collapses, often without any obvious warning or cause. When this happens the pain and confusion seem almost too much.

Stranger still is that this type of collapse is deceptively common. Many of the people you admire have endured similar shit storms. Still, they were able to reassemble their lives and create something even better – and you’ll be able to do the same.

In this article, we’ll discuss what to do when it feels like your life is falling apart. We’ll examine how to deal with the darkness and how to re-assemble yourself in a way that is gentle, compassionate, and healing. Our goal is to shepherd ourselves through the collapse and use it to improve the overall arc of our lives.

First and foremost, let your friends love the shit out of you


The best thing I did during my collapse was leaning on my close friends. For a few weeks, I became legit needy. I called people and poured my heart out without really asking how they were doing. I wrote long emails trying to understand what the fuck was happening. I let other people cook, pick up the tab, take me to the movies,2 and help with chores.

More importantly, I let them see me as I was: scared, confused, weak, defeated, and soaked in tears. I trusted them to hold me when I couldn’t support myself. Though exceptionally healing, doing this required more vulnerability than anything I’ve done.

Keep in mind that not all of your friends will be able to offer the skilled, open-armed embrace that you deserve. Be thoughtful in who you open up to. The ideal is someone who will allow you to be just as you are. They won’t tell you to cheer up or remind you that other people have it worse. They wont turn away because your vulnerability makes them uncomfortable. They’ll turn towards you and do everything they can to make you feel loved, supported, and seen.

And remember: you don’t need to tell everyone everything. Only open up to the people you feel comfortable with.

Surrender to the pain

During periods of extreme difficulty, almost everyone’s instinct is to flee from pain. We distract ourselves with the usual suspects (work, sex, drugs, alcohol, television, Internet, video games, food, etc.). We strive to compartmentalize, deny, reframe, and power through. I certainly don’t fault anyone for any of these behaviors. Dealing with intense pain often feels impossible.

Unfortunately, if your goal is to heal, then you’re going to have to face the pain, and you might as well do it sooner rather than later.

Instead of working to ignore or deny the discomfort, I urge you to feel it. All of it. Cry. Wail. Feel crippling sadness. Scream. Beat the shit out of your pillows. Whatever.

A really important caveat: if things get really bad, or if the darkness feels like it’s too much to bear, or if you’re thinking of hurting yourself, please call someone. Whether you need to call a friend, therapist, or crisis line, reach out to get the love and support you need. While it’s important to experience your feelings, it’s also important to let the light in.

But also, invite distraction and relief

At the risk of seeming to contradict myself, it’s important to give yourself breaks too. The goal is to face the pain, but not let it become so overwhelming that it crushes you. Consider spending time doing some of the following:

  • Seeing friends
  • Resting (this is really, really important right now)
  • Watching TV or movies (I really loved Westworld)
  • Reading (I’ve included a few recommendations in the PS)
  • Traveling to see loved ones
  • Exercising
  • Cooking
  • Playing with puppies and kittens
  • Talking on the phone
  • Redecorating your apartment (I got an awesome salt lamp and finally hung stuff on my walls)
  • Going to comedy shows
  • Taking a class
  • Doing nothing much at all, including not working through the pain

Yes, it’s likely that you’ll be a wreck during some of this stuff. That’s ok. I got a text that made me choke up in the middle of my coworking space one day. While that’s not exactly my definition of fun, it’s also true to where I was: capable of holding parts of my life together while still very raw and unsteady.

The goal is to strike a balance between facing your pain and seeking relief. There’s no formula here. Some days you’ll be able to function almost normally. Other days, you’ll be so destroyed that returning an email is too much. That’s ok.

Practice compassionate self-care

Many people don’t pay much attention to their relationship with themselves, especially during difficult times. While self-care is always important, it’s essential during times of crisis. The goal is to treat yourself exactly how you would want your best friend to treat herself if she were in your shoes. Here are few tips to help get you through this phase of life. Focus on the ideas that seem most beneficial.

1) Accept that your inner life is going to be more chaotic than normal. Adjust accordingly. For a while, expect that your memory will be shoddy and that your inner life will be turbulent.

Your only real responsibility here is to let yourself off the hook. Be gentle with yourself. It’s fine if you fall behind, cancel meetings, or struggle to hit your normal standards for the next few weeks. If you’re able, let other people know that you haven’t been feeling well and ask for understanding if you’re more scattered than normal.

2) Enlist the help of a psychotherapist. There is no benefit to dealing with more pain than is necessary, and a skilled therapist can dramatically speed up your healing. They often have advice and insights that friends, mentors, and coaches don’t. Get more information on finding a good therapist here.

3) Keep a healthy (enough) diet. Drink a lot of water too, because even at the best of times, many of us are dehydrated. Personally, I leaned heavily on greens powders, rehydration salts, and Huel (Huel is one of those weird nutritionally complete food things)3 to make sure that I was staying healthy enough.

To be clear, I also ate a lot of pizza, cake, and candy. In it’s own way, that stuff helps too.

4) Consider staying sober. As I mentioned before, it’s better to work through your pain than to run from it. Though virtually everyone will offer to buy you a drink, consider staying sober – or at least mostly sober – as you heal. Sobriety will speed up the processes of rebuilding your life. It will also prevent adding a killer hangover to an already shitty day.

Personally, when my friends offered me a drink, I got used to saying, “I know this sounds crazy, but I try to stay sober while dealing with pain. Any chance I can take you up on it when I’m feeling better?”

5) Do gentle exercise. It helps to move around. A bit of yoga, a quick jog, a few pushups, or even just a walk around the block will do the trick. Bonus points if you get some fresh air and sunlight. When you’re ready, you can incorporate something more vigorous into your routine, but for now, consider any type of movement a win.

6) Give yourself little treats to brighten your day! This can be a massage, a candy bar, a new cologne, time in a flotation tank, a new book, whatever, just make sure to spoil yourself a bit. The goal is to add a bit of light – or at least distraction – to the darkness. This is especially important if you feel like you don’t deserve to be spoiled. You do, damn it!

7) Journal. Whether you’re on your computer or using pen and paper, spend at least a few minutes writing about your thoughts and feelings every couple days. Choose the journaling approach that works best for you – for me, it’s stream of consciousness. Another effective technique is to ask open-ended questions in your journal and then write out whatever answers come to you in the moment. When you stumble upon a valuable insight, underline it so you can come back to it later.

8) Dedicate extra time to silence, nature, religion, or spirituality. Engage in whatever form of connection to the universe makes the most sense to you. Personally, I like silence, meditation, and nature. Other people like reading religious texts, speaking to spiritual mentors, or attending groups and services. Whatever it is that helps you feel connected to something greater than yourself, engage with it.

9) Though I wanted to strangle my friends when they told me this, it’s worth remembering that this too shall pass. One of the worst parts of dealing with darkness is that it feels like there will never be light at the end of the tunnel.

The simple truth is that you will get through this. If this is the first time you’ve dealt with extreme difficulty, think about your friends who have endured hardship and how they persevered and fell  back in love with life. If it’s not your first time dealing with hardship, lean on your past as inarguable evidence for your own ability to persevere. You can handle this. I promise.

10) When you lose a job, or endure a breakup or falling out, the mind plays a cruel trick: it obsesses over the great things that were lost. Counterbalance this by making a list of all the shitty things that will no longer bother you. If you were just fired, make a list of all the things about your old job that you hated. If you’re recovering from a breakup or falling out, make a list of all the things you disliked about your partner/relationship.

When your mind starts obsessing over the good things you’ll never have again, read through your list(s). For easy access, I kept mine on my phone. I was delighted by how effective it was to create and review lists of the BS I never need to deal with again.  

Ask yourself: is there any way that your collapse could go on to improve your life?


When the world falls apart feeling victimized is inevitable. You can’t help but ask, “Why me?” or “When will this all stop?” or “What the fuck did I ever do to deserve this?” I certainly asked all of these questions.

As you slowly work to accept your new reality, it’s also important to ask, “Is there any chance that this may end up serving me and making my life better? Is there anything for me to learn from this collapse? Did I have any agency over what just happened?”

Sometimes life falls apart and it has nothing to do with you. A death, a freak accident, a lay-off, illness, and many other things can be functions of circumstance. Besides learning to embrace the innate impermanence of everything, there may not be a lot to learn here.

However, some forms of pain and collapse offer valuable life lessons. If you suspect that you had even a bit of agency in your life falling apart, it’s important to mine these experiences for wisdom. I don’t mean searching for silver linings, reframing your thinking, or anything like that. I mean working to seek the hidden lessons beneath the pain and using them to build a better life. This is done through deep introspection, either on your own, or with the help of someone you trust. The goal is simple: navigate the chaos in a way that will be healing and serve you in the long run.

In retrospect, I realize that many of the spheres of my life drifted out of alignment, which ultimately caused a lot of my pain.

Finally, start building a new, better version of your life

The last step is to pull your life back together. Be gentle and give yourself plenty of time here. The pain you endured transforms you. You may seem subtly unfamiliar to yourself. That’s ok. With time, the important parts will click back into place. This is an excellent time to make other changes you’ve been considering, like being healthier, improving your social life, or looking for a new job. You can use the lingering pain to guide you. If you’re feeling lonely, invest in your social life; if you’re feeling strained financially, re-evaluate your budget or job.

I started by making two lists. One for everything I needed to do in my personal life, and another for everything I needed to do in my professional life. From there, I was able to sequence and group different activities and tackle them one by one. I’m still slowly working through those lists. Other people like to find an accountability buddy, create a vision board or set goals to aspire to. Those can all work well too.

Regardless of how you go about it, your goal is simple: create a gentle path forward that will allow you to step back into your life as a better version of yourself.                                                                                                                                                                                     

PS: A few books for troubled times

Here are some of my favorite books for when life collapses:

When Things Fall Apart” by Pema Chodron. Chodron is my go to author for navigating life’s turbulence. Her insight is just insanely comforting. Start with “When Things Fall Apart” and if you like that, move on to “Take the Leap.”

The Self-Compassion Skills Workbook” by Tim Desmond. I was skeptical when someone suggested this book to me. Most of what I’ve read about self-compassion is hokey and more aspirational than actionable. This book, to my delight, is different. Desmond is a student of the legendary meditation teacher, Thich Naht Hanh. He’s also a psychotherapist. “The Self-Compassion Skills Workbook” does a beautiful job of teaching readers to be gentle with themselves, especially during difficult times. Along the way, it will help you speed up your recovery and deepen your insight.

Love Yourself Like Your Life Depends on It” by Kamal Ravikant. This is the book that put self-love on my radar. Though I no longer use Ravikant’s techniques, I still find myself turning to this book for motivation and reassurance that things do get better.

How to Fix a Broken Heart by Guy Winch. This short, actionable book offers an illuminating explanation of why dealing with breakups is so difficult. It also offers instructions on recovering from them. Winch’s TED Talk by the same name is also excellent.

Getting Past Your Breakup” by Susan J Elliott. If you’ve just gone through a breakup, this book is for you. While the introductory chapters are worth skimming, the real value is found in Elliott’s relationship inventory. The inventory is filled with great questions and exercises designed to help you learn from the past, heal, find closure, and move on.

Harry Potter! I read books 4, 5, and 6 while my life was falling apart. It was enchanting to revisit these staples of my childhood. The books also managed to pull me straight into the world of Harry Potter, which offered a lovely distraction.


Permission to dream small

In my current phase of life, I find myself searching for next steps and trying to stay open to new possibilities. When I mention this to people, many urge me to “dream big,” or something along those lines. I realize that “dreaming big” means different things to different people. To me and my circle of 30-somethings, it often means a demanding career filled with status, money, influence, travel, pressure, tight deadlines, and accolades. They envision a high-risk, high-reward type of endeavor. While I understand that they’re trying to be encouraging, I really wish they wouldn’t be so quick to steer me toward workaholism.

We’ve been taught to worship ambition and feel shame for “playing small.” When we think about our jobs and our life strategy, many of us can’t help but factor in a decision’s high or low status.  Contentment seems to take a back seat to glitz.

In truth, I find more joy in the quiet moments than the flashy ones. I’m happier when my life isn’t overrun with meetings, deadlines, and stress. The blank space gives me room to live.

As I dream about what comes next, I can’t help but be excited by the small things. I think it would be amazing to have a simple life with people I love, a job or business that meaningfully helps a handful of people, and the training1 required to make responsible decisions for them.

Though we’ve all heard stories of famous people insisting that they succeeded because they took risks and shot for the stars, I don’t buy it. Luck seems to play a larger role than the ultra-successful care to admit. To further obscure reality, we never hear from the countless people who dreamt big, took a risk, and failed. For them, dreaming big turned out to be a horrible life strategy.

When I look at the small group of 30-somethings in my life who have made a meaningful impact in our world, none of them started off by dreaming big. Instead, they found something they cared about and dedicated themselves to it. Because they consistently put out high quality work, people started calling on them to lead, and they accumulated true influence.

So instead of asking myself, “How can I affect a million people’s lives with my next project?” I ask myself, “How can I affect 30 people’s lives? What do I love so much that I’d be happy to suffer for it, even if no one notices?” For the first time ever, I’m giving myself permission to dream small.


How to avoid burnout, beat stress, and find calm amidst the storm (a guide for when life gets crazy)

“Every search begins with beginner’s luck. And every search ends with the victors being severely tested.” – Paulo Coelho in the Alchemist

Jan 29th, 2018: Finally, the professional speaker’s training that I’ve worked on for years is live and ready for students. Unfortunately, the rollout has been more turbulent than I could have imagined.

Over the past two weeks:

  • A partner quit the project because he’s starting a business that will compete directly with mine.
  • The designer I hired left the project because her husband is suffering from serious health issues.
  • Sales are way below where I want them to be.
  • I’ve been hit with a cease and desist because the title of the training uses language owned by a competitor. Meeting the demands of the cease and desist (which my lawyer tells me I need to do quickly) will require reworking the marketing and technology behind the training.
  • And the cherry on top? Things in my personal life that I have no control over (like the health of loved ones) are going haywire too.  

I should be completely broken, but I’m not. I’m driving to a friend’s house to grab dinner and chill for a bit. I feel playful and happy. Stressed too, of course, but not nearly as much as anyone – myself included – would expect.


I’m tempted to tell you that I was able to remain calm during the darkest hours of the storm, because I’m the modern day Fonzie, but obviously, I’m not. I knew that the beginning of 2018 was going to be extremely stressful and demanding, so I decided to try a lot of new stress management techniques. My goal was not merely to keep my head above water, but to enjoy the process. To my delight (and surprise), I succeeded.

There were eight strategies that worked remarkably well.

1) Set reasonable expectations for everyone – yourself included. In the past, when life got chaotic, I responded by increasing my workload while maintaining all of my other commitments.

This, though common, is a near perfect formula for burnout.

With this most recent whirlwind, I did something different. I told everyone in my life that I’m going to be temporarily less available than normal as I deal with an increased workload. (This is one of the reasons I didn’t publish a single article in January.)

Of the dozens of people I spoke to, only one struggled with this decision. Me.

I still wanted to hold on to the idea that I can maintain my normal life regardless of the increased demands on my attention. Unfortunately, I have a long history of burning myself out, so I knew that unless I changed my behavior and attitude, I would burn out again.

By adjusting people’s expectations of my availability, I was able to avoid the burnout that typically plagues me. Now that my life has settled down again, I’ve spent the past week reconnecting with friends and clients and all of them understood – and supported – my decision.

2) Fortify the foundations. Usually when life gets chaotic, the first behaviors to change are the very ones that keep us sane. We tell ourselves that it’s ok to skip the gym if we need to squeeze in a few more hours of work, or that if we’re too tired to cook, we can grab takeout on the way home.

I get it. I’ve done that a million times. The problem is that sacrificing self-care only exacerbates stress.

This time, I went in the exact opposite direction. Since I knew the demands on my time and attention were going to spike, I scheduled time for meditation, exercise, sleep, and social events into my calendar. This forced me to schedule work around the stuff that keeps me happy and grounded, not vice versa.

To further fortify the foundations, I temporarily quit caffeine (it makes me anxious) and stocked up on healthy food.

3) Stop pushing through walls and learn to respect your limits. For most of my life, I kept working until I was exhausted. I learned to push through walls, a skill prized by many self-described “top performers” and “Type A’s.” The problem with pushing through walls is that it’s almost never worth it. Even if you accomplish a bit more than you would have, your future productivity will suffer. More importantly, your present and future happiness, stability, and vitality will suffer too.

Choosing to push beyond your limits is a form of neglect. Learning to rest before you’re tired is a form of self-respect.

Now, when I feel myself starting to approach the wall, I rest. Instead of opening my email, I catch up on Game of Thrones. Instead of working for one more sale, I go for a walk without my phone. Instead of taking a meeting that’s unlikely to produce anything of value, I call a friend.

At first, respecting my limits felt wrong. It made me feel guilty and like I was a slacker. Today, resting before I’m tired is one of my most cherished habits. It’s left me with a steady reserve of energy, calm, happiness, and focus. It’s also armed with me a far greater work capacity, though that’s not really the point.

4) Transition before resting. This is a trick that I learned from a CrossFit coach. She emphasized transitioning between movements before resting. In other words if you have to do several rounds of pull-ups and squats she suggests finishing the pull-ups and immediately switching to squats – even just one – before taking a break. This works, because, while the upper body is exhausted from the pull-ups, the lower body can still get a few squats in before coming anywhere near needing to stop.

Not only is this a brilliant move in CrossFit, it also works well outside the gym.

Today, before I take a break, I try to create a little bit of inertia on whatever I’ll be focusing on when I return. This way I’m both refreshed and focused when I get back, making work less stressful.

5) Lean on your people like your life depends on it. The most chaotic moment in the last two weeks came shortly after receiving a cease and desist about a trademark violation. Sales were already below where I wanted them to be, and fixing the violation was complicated.

It’s easy in moments like this to collapse under the pressure of it all, but in retrospect, it was one of the best parts of the entire process. It led to my feeling extremely loved and cared for by my friends.

Over the past year, I’ve gotten in the habit of reaching out to loved ones when I need help or comfort from other people.1 Before that, I used to hide away from the world until I felt better, not allowing anyone to see me when I was feeling distressed. I feared that asking for help was both needy and a sign of inadequacy.

So, when the shit hit the fan, I called, texted, and emailed my friends. I told them what was happening and that I could really use their support. Wow, did they come through.

One loaned me his car. Another offered to fix the technology so it was in compliance; someone else connected me with a specialized lawyer who could help navigate the situation. Yet another brought me dinner, and a bunch of friends checked in to see how I was doing.

The end result? During the most demanding moment of the whirlwind, I felt light, playful, safe, and capable. More than that, everything ended up being fine. I fixed the copyright violation and sales ended up exceeding industry averages. But here’s the important part: the success was only possible because of the people supporting me. Without them, I would have collapsed.

6) When possible, just bypass the stress. Stress is amplified by anticipation and overanalysis. There are two tricks to avoiding these tendencies which will allow you to bypass huge amounts of stress.

First, figure out what issue is causing the most stress. Once that’s clear, start working on that problem now. If you continuously put it off (which most of us do), you’re  forcing yourself to live with much more stress than necessary.

Ignoring problems tends to make them worse. They command mental and emotional resources and will continue to plague you until you address them. By acting on the stressors in real time, you eliminate their ability to linger and fester.

Second, only spend time analyzing the stuff that needs it (and most things don’t). In many cases, analysis is just a hidden form of procrastination. All you need to do is ask yourself, “If I make the wrong decision here, will it be hard to undo it?” and “Will there be serious repercussions if I get this decision wrong?” If the answer to these questions is no, then there’s no need to spend much time contemplating. Just take action.

7) Indulge in Do Nothing Days. This is a tip that two of my friends have advocated for years. A Do Nothing Day is exactly what you think it is. You spend the entire day lounging around and intentionally avoiding stress. You binge watch Netflix, order delivery, read magazines, play video games, and take naps. If something has the potential to spike your stress levels, avoid it.

Waking up the next morning after a Do Nothing Day feels like getting back from a beach vacation. It’s revitalizing.

Knowing that I was going to be under more pressure than normal, I scheduled several Do Nothing Days. They were bright lights at the end of the tunnel and ensured that I rested before burning out.

8) Ask, “What is the kindest decision I make for myself right now?” I learned this from a meditation teacher. It’s simple. When you find yourself facing a difficult decision, ask, “What is the kindest decision that I can make for myself right now?”

Keep in mind that the kindest thing is not always the easiest and is often a moving target. Sometimes it’s getting up early to get work done before your first meeting. Other times it’s cancelling the meeting, telling your boss your work will be late, and sleeping in.

By asking, “What’s the kindest thing I can do for me?” you’ll start to make decisions that gracefully walk the line of being efficient and compassionate.