The curse of moderate success

May, 2009: It was advice I didn’t want to hear. I was trying to start a business and busy dreaming of a comfortable life – one with a nice apartment, vacations in Costa Rica and an exotic sports car. J*, a trusted mentor, turned to me said, “You know Jason, if you do become successful, you can’t get too comfortable. Comfort is the enemy. A little is deceptively dangerous; a lot will stunt your growth. Someone who’s hungrier and more driven will overtake you. Comfort will kill your lust for life.”


One thing that no one mentions is that moderate amounts of success can – and probably will – sabotage you. It’ll hold you back more than the fear of failure ever could. This is especially true if initial success came quickly for you; the same success you fought so hard for risks stunting your growth. When I think about the ways I could derail my life, becoming too comfortable and too complacent tops the list. Here are the demons I look out for:

Earned laziness preventing me from working hard. In most cases, finding initial success requires endless rejection, false starts, loved ones trying to ground you, navigating an unruly marketplace, and your own inner critic doing her best to fuck your shit up.

But along with that sense of achievement that comes with beating the odds there’s often a subtle sense of earned entitlement. You’ve given everything you have to give, and you’re at the top of the game. It doesn’t feel like you should have to keep working, fighting, doubting, and risking it all anymore. It feels like you should be done, like you should already have the relationships, skills, reputation and knowledge to open any door.

Unfortunately, that’s not the case. What got you here won’t get you to your next destination. You’ll have to return to being a beginner, being humble, moving slowly and getting crappy results for months or years on end. You’ll be less successful than the people around you again. You’ll have to let go of the sense of being on top of the world in order to create the mental and emotional space you’ll need for even bigger battles.

You once told yourself that anything worth having doesn’t come easily. That allowed you to keep working and get to where you are now. For better or for worse, that still rings true.

The hidden fear of losing myself makes it easy to perpetually focus on something else. As you know, leveling up will require sacrificing a lot of what you’ve already built. I know from experience that it sucks. I spent nine years building my speaking practice. At the top of my game, I was one of the best in the market, but I scrapped it to build my consulting practice. It took me four years to build that business. Now, I’m scrapping that too, because my heart’s no longer in it. I kind of feel like I’m losing pieces myself as I sacrifice old projects to start new ones. It’s destabilizing and scary.

Yet the fact remains: you’re going to have to do the same damn thing. If you’ve identified yourself with your current success (and who hasn’t?), then it’s going to feel like you’re losing yourself as you grow into your next project. But creation can’t be untethered from destruction. That’s just the way it goes.

Perhaps even more frightening, you’re going to have to deal with rejection again, too. If you want to grow, you’ll have to jump right back into the fire. It’ll be painful, but it’s less painful than stagnation and frustration.

Of course, you’ll fight against this. You’ll tell yourself that since you’ve become successful, it’s unacceptable for you to put out anything besides perfect work. Obviously, this is nowhere near true. The only path forward is to do your best and polish up in real time. Don’t worry, if you’re dedicated enough, you’ll be fine.  

I’d love to be able to give you life hacks or something that would allow you to avoid facing these fears. But you and I both know that these are demons you’ll have to stare straight in the eye (and do your best not to blink). The good news is that you’re perfectly capable.

Comfort enables me to keep pushing off my next dream. When you first built your life, you may have felt fear and entitlement, but you mastered them. You had no other choice. You were hungry and that was enough to fire you forward. Now you’ve got enough time, money and status to keep you happy(ish). Where there was once a burning hunger that fired you forward, there’s now comfort – maybe even a sense of responsibility. If you really want to own your next great adventure, you’ll have to sacrifice the comfort that keeps you immobilized. I don’t mean that you need to give up your nice home, dinners out or your social life. What I mean is that you’ll have to notice the tension and resistance in your body that begs you not to start the new project. You’ll have to notice your mind sabotaging you with compelling arguments in favor of procrastination. And when you notice these things, you’ll have to fight against them again, and again, and again.

So, how do you overcome the curse of semi-success?

The good news is that the curse of comfort and semi-success is one that you can break. Here’s one way of doing it:

Take some time off. Like a month or two. Travel, learn an instrument, stay at home and rest, whatever. It doesn’t really matter what you do, you just need to remove yourself from your work and routine. This will help you regain your identity as a creator, a fighter, and a risk taker. It will allow time for your next dream to take residence in your heart. Perhaps most importantly, it will give you a moment to rest. The battle in front of you is real. You’ll win, of course, but you’ll probably have to leave it all on the field. Don’t worry. You’ve done this before, and you can do it again.

Allow new motivation to take over. In the past you were able to motivate yourself with raw hunger, but you can’t do that anymore. You’re too successful. You need to find something different to inspire yourself. Personally, I like to spend time imagining two different realities. First, I vividly imagine embracing my dream life. I try to generate feelings of excitement and gratitude for the life I want to create. Then, I try to imagine what would happen if I fail to act on my dreams. I try to generate feelings of fear, depression, and regret. The sharp contrast of my dream and nightmare makes it easier to take action.

Some people find it motivating to spell out their vision for themselves. If you’re one of those people, I highly recommend Cameron Harold’s book, “Vivid Vision.

Now return to the game. What did you do last time that enabled you to succeed? Did you apply to 117 jobs and move to Colorado? Did you do 50 cold calls a week? Did you go back to school even though you were a decade older than your classmates? Whatever you did, you needed courage and dedication. While the path may be different this time around, you’ll still need the same fuel. Your only job is to keep putting one foot in front of the other and refusing to accept failure. Depending on how you look at it, it’s as easy as that, or as complicated as that. The trick, as always, is to fall in love with the process.

PS: An entirely different solution to the curse of semi-success

There is a different approach to dealing with semi-success, and it’s one I’m a big fan of. Learn to be content with what you have. It’s already more than enough. What will your next big victory really do for you anyways? You don’t actually believe that more money1, more status, a bigger home, a hotter lover, or more fame will change anything for you, do you? Chances are they’ll just further fuck you up.

If you’re hunting success for the sake of validation, then you’ll never have enough. I’ve fallen into that trap dozens of times in my life. While falling in love with what you have may prove just as hard as becoming more successful, it’s almost guaranteed to be more satisfying and meaningful.

Sneaking up on happiness

August 2018: It’s been months since the last wild night with the boys, ambitious project at work, or whirlwind romance. Given that pretending to be a rock star is one of my favorite pastimes, this is a dramatic change of pace for me. I feel… boring.

And yet, despite the boredom, happiness keeps sneaking up and slapping me in the face. I notice it coming home from the gym, making dinner with a friend, going for a walk in the mountains, or working from a coffee shop on a Friday. After a year defined by just trying to keep my head above water, this is a very welcome change of pace.


I’m a bit reluctant to publish this article. Not because it’s controversial, but because it’s simple. In fact, the idea is so simple that I can sum it up in a sentence: you can significantly increase your happiness by removing the things that destabilize you and make you unhappy.

I realize that for many people, this is obvious. Still though, it took me nearly 33 years to understand it. Even still, it’s easier said than done; we often end up addicted to or identified with the things that make us unhappy. So, with that in mind, I’ll break down the process that I used to find stable happiness in hopes that it will serve you too.

Kill the bull in your china shop

Most of us have one or two things that create a disproportionate amount of chaos or unhappiness in our lives. It can be an unhealthy relationship, a lack of discipline, a dormant dream, a crappy job or boss, a lack of self-care or self-esteem, an addiction, the need to lose weight, unresolved trauma, or a million other things.

You may already know the biggest sources of your stress and unhappiness. If not, they tend to exhibit a few common traits: it’s the stuff that keeps you up at night, that you dread when you have to deal with it, that fill your body with tension, or that you spend the most time worrying and complaining about.

If you’re still struggling to pinpoint what’s sabotaging you, consider asking a few close friends if they have any idea about what’s going on. Keep in mind that you may not love what you hear. One of my best friends looked me right in the eye and said, “You love chaos man. You always have. You won’t really be happy or stable until you shake that.” Talk about bitter medicine, but also a true friend.  

Once you’ve identified the major roadblock(s), work to eliminate or fix them. I know that most self-help people will encourage you to make changes quickly, but I don’t buy it. I think there’s something to be said for moving slowly here. Besides, if you need to change something big, like your job, you may need to move slow if you want to do it responsibly.

For me, the biggest barrier to happiness was work. My heart was no longer in my consulting practice, and I needed to figure out what my next move was. Instead of blindly rushing towards the next shiny object, I spent a year experimenting with different options until I found the right move, and starting in January, I’ll begin a new career.1

And don’t feel like you need to go it alone either. When I was 30, I spent months in therapy removing some of the obstacles to happiness from my life. If you’re dealing with a particularly difficult problem, recruit support.

Return to stability by eliminating instability

Next, remove all of the things that reliably destabilize you.

For me, this included eliminating:

  • Caffeine (I love coffee more than life itself, but caffeine makes me jittery and destroys my sleep)2
  • Dating (there weren’t huge gaps between my last few girlfriends, and I could benefit from some time on my own)
  • Work drama (I cut my hours and services, and only took on home-run clients; this slashed my income but saved my sanity)  
  • Career change drama (I started telling people who offered unsolicited advice that I appreciated their intent but didn’t want to hear their opinions)

Of course, you may need to eliminate other things. A few areas to consider:

  • Video games
  • Alcohol, cannabis, and other drugs
  • Lying
  • Sugar
  • Casual or reckless sex
  • Excessive screen time (think: TV, internet, your phone, movies, etc.)
  • Extreme busyness
  • Constant travel
  • Pornography
  • Etc.

Don’t limit yourself to this list. If there’s something else you think you’d benefit from giving up, then try that.

Keep in mind that you don’t need to give these things up forever. Letting go of them for two or three months should help you find increased stability. After that you can decide for yourself whether or not you’d like to add them back in.

An uncomfortable note: if the idea of giving something up makes you anxious, then you should really explore that. Ask yourself why you’re so afraid of letting go. We often engage in mild (or serious) forms of addiction, anxiety and compulsive behavior as a protective measure to help us avoid deeper issues. The problem is those deeper issues will continue to sabotage us until we address them, and if we’re using addiction or anxiety as an unconscious avoidance technique, then we’re effectively shooting ourselves in the foot. Again, no need to do this on your own; if necessary, get the help you need.

Set boundaries

Setting boundaries is more of an art than a science. As far as I can tell, it boils down to this: when someone treats you differently than you’d like to be treated, let them know. If they continue treating you poorly, consider spending less time with them.

Keep in mind that you can – and should – set boundaries with yourself too. One personal example is that I try to only take unscheduled calls when I’m genuinely excited to chat with whoever is calling me. If I’m busy or just not in the mood, I let it go to voicemail and call them back some other time.

Will you or the people you care about be perfect at setting and respecting boundaries? Nope. We’re messy creatures guaranteed to make mistakes. The important part is letting people know when they’ve upset you and that they, in turn, strive to change their behavior. Of course, it’s on you to respect other people’s boundaries as well.

Fill the space with stuff you love

If you’ve followed along so far, there’s a good chance that eliminating things has left you with some free time. One option is to leave the space open and allow yourself to hang out in the grey for a while. That’s what I did. It took a bit of time to adjust, but now, I love it. I sleep, read, see friends, try to play ukulele, watch The Wire, and go for more walks. Of course, this won’t go on forever – I have a small project in October, and a huge one in January. But for now, I’m really cherishing the space.  

The other option is to dedicate some of your newfound time to things that you know make you happy. While there are countless ways of doing this, here’s some of the stuff that tends to work:

  • Engaging more with spirituality, religion, or nature
  • Creating art
  • Practicing meditation or gratitude
  • Spending time with friends and family
  • Exercising
  • Reading

Keep in mind that the goal isn’t to keep your life on hold forever. The goal is to build a solid foundation of happiness to operate from and slowly begin to add stuff. You may be pleasantly surprised to discover that you no longer crave the things that used to sabotage you or that they no longer have the destabilizing effect they once did.

PS: You may not recognize yourself at first – I didn’t

September 2018, after spending 5 minutes updating N* on what I’ve been up to lately: “…so that’s the gist of it man. I’ve been boring and happy. I don’t know that I have tons of stories to regale you with.”

N*: “Dude, what are you talking about? You just told me that in the past week you saw Nine Inch Nails, spent two nights in the mountains with friends, published a well-received article, and hit a grand slam for your client. Why do you think you’re boring?”


It was kind of surreal when N* held the mirror up for me. For the first time, I understood that I failed to recognize some of the quieter emotions. Most of 2018 was defined by feelings and experiences that burn brightly, like chaos, drama, and anxiety. Happiness, at least for me, is a bit different. It’s kind of like a warm breeze on an already perfect evening – if you don’t know what to look for, you may not even notice it.  

It may take a beat for your system to calm down enough to appreciate the more subtle experiences of life. Change always brings a bit of discomfort and if you’re used to instability, then your resting state may be one of heightened alertness.

That’s what happened to me. Without realizing it, I adopted a kind of always-on-guard stance in life. I needed to let go of the anxiety that kept me poised in order to let the waves of joy wash over me.

Using gratitude to shape your future

For years, thought leaders and pop-psychologists have been telling us that gratitude is the long lost secret to happiness, success, harmonious relationships, wild sex, financial abundance, world peace, and the perfect brownie recipe with crispy edges and gooey middles. There’s even a bunch of quasi-compelling science to support gratitude’s transformational power.

When I first started reading about these practices, I was totally seduced. For months, I started each day by writing five or ten things I was grateful for. I tried to tell myself that I was becoming happier and that success was right around the corner.

And of course… nothing much changed. I wrote gratitude off as one of the countless things that seemed like it should improve my life, but didn’t.

That is, until earlier this year when my friend Charlie taught me a simple gratitude practice.

1) Begin by sitting down and spending a bit of time thinking about the future you want to create for yourself.1

2) Once you have a clear picture of that future, try to foster feelings of gratitude and excitement for it.

3) Let those feelings wash over you for a little while.

4) That’s it. Open your eyes and move on with your life. I know it seems like it should be more complicated than that, but it isn’t.

I’ve been spending a minute or two each morning doing this exercise, and I love it. Has it allowed me to effortlessly manifest my dream life as if by magic? No.2 Has it at least made it so that I never have bad days anymore? Of course not. However, it has made a very real difference. So far, it has:

  • Helped me see my path. I tend to take the scenic route in life, just sort of cruising around without a clear destination. While there’s nothing wrong with that exactly, it makes getting to where you’re going sort of impossible. Thanks in part to this practice, I now have a very clear idea of where I want to go both personally and professionally. Though this might not seem like a big deal, it’s exciting for me. 
  • Shown me how to stay easily focused and motivated. Since I finally know where I’m going, it’s become much easier for me to agree to the right stuff and decline the wrong stuff. It’s also made avoiding procrastination far, far easier because I don’t struggle with motivation as much as I used to. 
  • Made me happier in the moment (and equipped me to shape a better future). A simple truth about the flow of time: the present is the only gateway to the future. In other words, if you want to improve your future you can only do so by improving your present. Spending a few minutes feeling excited and grateful for what’s to come gives me more energy and creativity in the moment. 
  • Helped me find a bit of magic in the mundane. Though technically this practice is future facing, I’ve also started to notice how amazing my present is. I’ve found myself delighted by simple things that I never used to notice like my bamboo plant, or the feel of the fresh summer air. Given that this has been an unusually demanding year, appreciating the little things has meant a lot to me.

PS: Two other gratitude practices I love

While the practice above is the only gratitude exercise that I do every day, there are two others that I really love and wanted to share.

1) The Five-Minute Journal. The Five-Minute Journal is a minimal and beautifully designed gratitude journal. It guides you to spend a few minutes each morning writing down three things you’re grateful for and three things that would make the day great. In the evening, you spend a few minutes reflecting on what went well and what could have been better. Simple. Fun. Effective.

2) Mailing thank you cards. Recently, I’ve been mailing thank you cards expressing appreciation for the roles certain people play in my life. Doing this brings me more joy than I expected. It also strengthens my relationships. I’d like to tell you that I’m disciplined and I do it every Friday or whatever, but that’s not the case. Instead, I leave a box of correspondence cards around my apartment, and write a note or two when I feel inspired.

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.