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.

Why I turned comments off

As the blog grows, managing comments has become more difficult than it’s worth, so I’ve decided to turn the comments section off. It’s not that there are so many comments that I can’t keep up, it’s that they take up time, focus, and energy that would be better dedicated to other projects (like working on new articles).

While keeping comments open may be good for SEO and social proof, it’s not good for my sanity. So, as an act of self-care, I’ve decided to turn them off.

Does this mean I no longer want to hear from you and other readers? Absolutely not.

Connecting with readers as well as trading stories and ideas is one of the most meaningful parts of this blog. I want you to reach out and let me know how I’m doing. The best way to do this is by subscribing to the blog here. You can also reach me through the contact form here.

2017 personal review: lessons, losses, and victories

I almost don’t know how to describe 2017. Over the course of the past year, I:

  • Was threatened with my first ever lawsuit (it scared the shit out of me when it happened, but now it feels strangely validating)
  • Closed my life coaching practice (I realized that virtually all of my clients would be better served by skilled therapists)
  • Changed the business model of my consulting practice to run by referral only
  • Built an amazing relationship with L*
  • Neglected, for the second year in a row, to hang anything in my apartment besides a giant whiteboard

But more than anything, 2017 was a year of personal growth. I learned more about life, relationships, and work than I expected. This article covers the most important lessons I learned this year. It also discusses the biggest mistakes and victories along the way. And if you’d like to compare this article to my 2016 recap, you can find it here.

The four most important lessons I learned this year

1) Rest before you’re tired. Like so many others, I thought that working to (or beyond) the point of exhaustion was no big deal. In fact, I thought that it was one of the best ways to get ahead. In reality, it’s neither. Exhaustion and burnout are glaring signs of personal neglect.

I’ve had a lifelong struggle with energy management, and it all came to a breaking point this summer. After eight weeks of being wildly overcommitted, I broke. For weeks after, I felt hollow, burnt out, and lifeless. Not only that, but it destroyed my ability to be present and caring with other people, jeopardizing my relationship with L*.

Though this wasn’t the first time I burnt myself out, it was the first time that I took the problem seriously and the time to find a solution. The fix? Learning to rest before you’re tired.

Unfortunately, resting before you’re tired goes against the grain for many people. We’re often encouraged to ignore our limits. For people like me, learning to rest before you’re tired can feel similar to giving up.

Preemptive rest is a daily practice of choosing not to push through the wall. It’s about learning to respect your limits (and yourself). This means strategically skipping events, occasionally cancelling plans, and pushing back deadlines as needed. It means choosing not to respond to unnecessary emails and invitations. It means doing less.

At first glance, it may seem like resting before you’re tired will make you less effective. For me, that hasn’t been the case, and I actually feel more productive. I’m also much happier and healthier.

2) There are skills that help romantic relationships flourish. I’m not sure how I came to this conclusion, but I used to think that healthy romantic relationships should require little to no effort. My logic was that if I didn’t effortlessly click with someone 98% of the time, then we are wrong for each other…

Holy shit was I being an idiot. I was neglecting a bunch of realities like:

  • Communication is an extremely imperfect and difficult art
  • Everyone has demons (both known and unknown) manipulating their behavior
  • Sometimes people just don’t quite link up for a bit

As it turns out though, being in a healthy romantic relationship – like almost everything worth pursuing – benefits from a bit of effort, thought, care, experimentation, and nurturing.

Earlier this year, L* and I kept getting into the same stupid fight over and over again (about what? I don’t think either of us could honestly tell you). Eventually, we figured out that if we wanted to improve our relationship, we needed to try new approaches to connecting.

We experimented with a bunch of ideas and skills to see if they moved the needle at all. There were two that stood out.

The first is scheduling time for our individual lives. This allows us to pursue friendships and activities in addition to the things we share within our relationship. It enables us to return to one another with new stories, ideas, and energy that wouldn’t have entered our lives otherwise. It also gives us a chance to miss one another.

The second is periodically “checking in” with each other. Check-ins are dedicated time for going over what’s happening in our lives as individuals and within the relationship. The goal of a check-in is to create space for thoughtful and loving openness, vulnerability, and collaboration. These are times dedicated to deepening our connection with curiosity and compassion instead of severing it with defensiveness or aggression.

During check-ins, one partner listens and asks questions while the other talks. After the first partner is done we switch rolls.

At the individual level we discuss work, stress, social lives, dreams, and anything else that’s affecting us. On the relationship level, we discuss what’s going well and what needs improvement. We also attempt to tackle any of the issues we may have been avoiding.

The results of the check-ins have been stunning. I’ve learned new things about L*, and we’ve been able to ward off tension before it became significant.

3) Want to improve pretty much every sphere of your life? Prioritize your mental health. My mental health was better in 2017 than ever before. I was happier, calmer, and more effective. I had more fun and dealt with less anxiety than ever before. Corny as it may sound, I often found myself thinking, “Holy shit life is good right now.”

I also got better at asking for comfort and dealing with difficult emotions. In the past, I used to ignore unpleasant feelings.  

I write about this all the time, so I’ll be brief: taking good care of your mental health is one of the most important – and bountiful – things you could ever do. The best recommendation I can make is to find a licensed mental health professional and work with her (more on how to do this, here).

4) Carry money for the homeless. Earlier this year my friend Z* mentioned that he always carries a few $1 bills to give to beggars. I started doing this too, and loved it.

It’s really simple. As needed, I get a bunch of $1 bills and give them to the people who ask for spare change. When I can, I pause and chat with the person I’m giving the money to. I keep the ones in a specific compartment of my wallet so that I don’t accidentally spend them.

If you can afford to do this, I urge you to do it. Not only does it help people in need, it’s also a constant reminder that you have more than enough.1017

Where I messed up

Of course, 2017 wasn’t a flawless year. I made plenty of mistakes. These stand out:

I ignored my intuition. Doing so cost my business partners $160,000. Oops. I was the lead partner on two different projects. In one case I decided to fire one of our most profitable clients (he was exceptionally unpleasant to work with). In another, I decided to fire one of the partners (he was lying to us). Unfortunately for my sanity, these two problems came to a head at the exact same time, and I fired both the client and the partner on the same day. Yeah… that was a long afternoon.

While I’m glad that I addressed these problems head on, they could have been prevented if I trusted my gut a bit more. In both cases I had a hunch that something wouldn’t work out with these people.

I gave very incomplete advice in the article on people pleasing. In this article I advocated putting your needs above other people’s 99% of the time. In doing so, I missed something embarrassingly obvious: focusing exclusively on your needs will put you on the fast path to isolation.

Since publishing the article I’ve realized a simple truth: forming deep relationships requires give and take between individuals. I’ve realized that there are plenty of good reasons to put other people’s needs ahead of your own, especially if they are people you love or want to get closer to.

Don’t get me wrong: I think it’s important that you prioritize your needs, especially your need for sustained self-care. However, with loved ones, I think it’s also important to consider their needs, and periodically put theirs first. Just make sure that they are willing to do the same for you. If you want a guideline, it’s this: default to focusing on your needs, but be open to prioritizing the needs of others, too, especially if there’s a good reason.

If you’re spending a lot of time with people who are unwilling to help you meet your needs and preferences, then I’d urge you to slowly phase that relationship out of your life (unless their children).

I missed the timeline for releasing my course on pro speaking. Again. This time by about 10 months. For the past three years I’ve been working behind the scenes on a course to help professional speakers build their businesses.

My plan was to release the course in March of 2017. However, as the release approached, I realized that with a bit more effort, I could make the course exponentially more effective. So instead of releasing it, I refined it (again) and ran one more round of testing. The testing takes about six months to do correctly, and I’m thrilled to report that the tests went really, really well. The course will be released next month (eeep!). If you’d like updates, please hop on my mailing list.

What went well

The year-end review wouldn’t be complete without a quick look at what went well in 2017. While there were a lot of stand out moments and accomplishments, these are the most significant to me:

This blog grew by about 3x (and I owe it all to you)! In 2017 I published 24 articles, including this one, which was my first truly viral piece (I still get hate mail about it). Along the way, readership nearly tripled in size and I owe it all to you. Thank you. I can’t tell you how much I appreciate the fact that you take the time to read this stuff. It means more than I can express.

Men tend to grow more isolated as they get older. I worked hard to buck that trend. It’s normal for men’s social lives to shrivel up as they get older. While it’s tempting to dismiss this as no big deal, it’s actually a huge deal. Our relationships are one of the few things that make life worth living. They also directly correlate with (and arguably cause) things like happiness, success, health, contentment, and meaning.

So this year, I paid careful attention to my social life. I hosted professional events, guys nights, and a bunch of dinner parties for awesome people. I also started hosting monthly conference calls with my close guy friends from college who all live in different states. And of course, at the tail end of 2016 I met L* and had a blast spending 2017 with her (here’s to the next year of growth, adventure and koalas!).

For those of you who also want to double down on your social life, I wrote an article about how I built mine, here. For those of you who are interested in overcoming men’s isolation, I wrote two articles about that (here and here).

I ran a men’s retreat in February with Nick Notas. It was one of my favorite live events of all time. It was also one of only three live events I worked on in 2017. It was great to work alongside Nick, who is both a close friend and someone I admire. But more than that, it was an honor to help these men improve their lives. Nick and I spoke with them earlier this month, and they’ve all experienced dramatic growth. While Nick and I are certainly not responsible for all of their growth – they did a lot of work on their own – it was a true privilege to contribute to it. Thanks guys.

Saying no. Finally, I got in the habit of saying no more often than ever before. I declined requests to hop on the phone, grab a coffee, give free advice, and arbitrarily “connect,” like it was my job. This freed up huge amounts of time and sanity. It’s not that I don’t want to connect with these people – I do – it’s just that there are only so many hours in the day.

Finally, thank you

I know I’ve said this before, but once again, thank you. When I started this blog a few years ago I wasn’t entirely sure it would be worth reading. I know that seems like I’m making it up, but I’m not. I literally wrote about that doubt in my very first post.

It’s been a true pleasure writing for you this year. And to those of you who left comments or reached out, it’s been great getting to know you. It makes this work even more exciting and meaningful. Thank you.

Here’s to making 2018 the best year of our lives so far!

Staring the human condition straight in the eye

“Every morning I awake torn between a desire to save the world and an inclination to savor it. This makes it hard to plan the day. But if we forget to savor the world, what possible reason do we have for saving it? In a way, the savoring must come first.”

-E.B. White

***

If I had to capture the span of the emotional and spiritual existence in one moment, I think it would be this: holding someone you love while she passes away in your arms. That moment captures it all: love, loss, light, darkness, connection, isolation, cruelty, beauty, and so much more.

It reminds me that our lives and our world are both overwhelmingly beautiful and cruel.

Embedded within that realization is a quiet secret: it’s possible to adjust the dials of life. Doing that begins with learning to stare the beauty and the cruelty straight in the eye.

Connecting to the beauty

Your existence alone is a near miracle. Without effort, your heart rhythmically pumps blood, neurons fire, and countless internal systems function in harmony.

You were born with god-like powers of creation and destruction. Moment by moment you can work to improve your life and others’. We can create, destroy, and change in a way that no other creature can.

While you’re alive, you’re granted access to countless forms of joy and pleasure. On the simple end, you can savor a piece of candy, play with a puppy, listen to music, or watch a film.

On the profound end you can be swept away by the raw beauty of nature, mesmerized by the cosmos, and observe countless people acting selflessly. If you allow yourself, you can feel the love of your friends and family coursing through your body.1

With a bit of stillness you can find deep levels of connection between yourself and all other life forms. With a bit of openness and reflection, the reality of deep interconnection of life always seems to topple the illusion of autonomy and isolation.   

Embracing the cruelty

Of course, to only notice the beauty is to miss half the story.

Life was inflicted upon you, and with it came the promise that you and everyone you love will eventually pass away. Not only that, but virtually all of us will deal with various forms of trauma throughout our lives.

As you move through the stages of life, you’ll be forced to wrestle with a quiet truth: there is an inherent shittiness to the human experience that sometimes becomes all encompassing. Your boss annoys you, your bike gets stolen, you miss your flight, and your best friend forgets your birthday.

Through it all, finding contentment is deceptively difficult; we seem to have a nearly limitless capacity for being dissatisfied with our situation.

And the world we are forced to inhabit is filled with needless suffering in the form of starvation, violence, war, neglect, and poverty.

As we move through our lives, we hope that the fates and our loved ones will treat us with gentleness, understanding, and compassion, but sometimes they don’t. In fact, half the time we don’t even offer gentleness, compassion, and understanding to ourselves.

Living in a world that is both too beautiful and too cruel

How does one live in a world defined by overwhelming beauty and cruelty?

The common answer seems to involve numbness and willful ignorance, but that comes with a cost. Dialing down your ability to feel pain hinders your ability to experience beauty and love.

Fortunately, with a bit of practice we can learn to let the beauty overwhelm the cruelty.

Begin by cutting back on whatever you use to distract or numb yourself. This does not mean perfect sobriety, giving up sugar forever, never playing a video game, or anything like that. Instead, it means being thoughtful about the stuff you use to take the edge off. Engage them with moderation and intention. Consider giving up your vices for a few weeks to ensure that you’re the one in control.

Next, allow yourself to be weak, open, and vulnerable. Most of us have spent our lives trying to be as strong as we possibly can. All of the abuse, trauma, disappointment, heartache, and fear? Let it in.2

Allowing yourself to be weak will be one of the most difficult things you’ve ever done, but it will also be one of the most powerful and authentic. Remember you can be a warrior when you need to be.

As you embrace your weakness, you’ll start to notice the wounds you’ve been ignoring. Now you can begin to heal them. How? Start with whatever you’re drawn to. Go to a plant medicine ceremony, talk to a therapist, move to a new city, travel the world, visit a shaman, do breath work, meditate, journal, look at yourself in the mirror and say, “I love you,” go paleo, go vegan, go to church, try a 12-step program, become a dice person, whatever. Keep trying new things until you find something that works, and when you do, go as deep as you possibly can.

Stay open to new ideas. Many people have found healing and relief in unexpected places.

As you begin to heal, your final task is to make life a bit better for other people too. Do simple things like picking up a bit of trash, bigger things like dedicating your life to fighting oppression, and anything in between. This will allow you to cut through the illusion of separation and feel the deep levels of connection that bind us all.

Move through the world with gentleness and compassion towards yourself and others. Give when you can and ask for help when you need it. If you can mostly enjoy life and leave the world a little bit better off than you found it, I think it’s safe to say that you lived well.

Post script: on working with death

While I put death under the “cruelty” section of this article, I’m not 100% sure that was the right decision. If you’re willing to accept the simple reality that all of us will die and that tomorrow isn’t promised, something almost miraculous happens.

The shittiness of life melts away a bit. In it’s place you’ll start to notice the gentle urgency of beauty, love, kindness and connection asserting itself.

Instead of neglecting opportunities to be kind and loving to yourself and others, you’ll embrace them. Instead of pulling yet another all nighter for yet another meaningless project, you’ll curl up in bed with your lover. Instead of allowing someone’s anger and anxiety to infect you, you’ll let it roll off your shoulders, opting to call a friend and shoot the bull. Instead of worrying about money, you’ll know that money will never make you as happy and content as the people you love do.

Wrapped within the unavoidable reality of death, you can find a surprising amount of beauty and connection.

 

How to make friends as an adult: a guide to finding and connecting with people you love

New Year’s Eve, 2015, Denver, CO, 11:50 pm: I feel lonely. Though New Year’s Eve is one of the biggest party nights of the year, I was only invited to one small event. I joined J* and A* for dinner, but they dropped me off at my apartment before midnight.

Instead of spending the last moments of 2015 with friends, I’m alone. I have nothing better to do, so, I decide to end 2015 and start 2016 in silent meditation.

When I open my eyes, I make a simple promise to myself: in 2016, I’ll build a great social life. My goal is to have plenty of options for New Years Eve 2016.

***

While you’re in school, making friends is easy. In the real world… not so much. Life often puts thousands of miles between ourselves and the people we love most. I am a perfect example of this – none of my family or close friends from college live in Denver, and only one of my friends from high school lives here. With only one exception, all of my old friends are a plane ride away.

On top of that, life gets cluttered with paying bills, running errands, commuting, building careers, and all the other necessary evils of adult life. It leaves little time for making and deepening new relationships. It becomes easier to heat up a frozen pizza and watch Bojack Horseman than to see if that person you’d like to hangout with wants to grab a beer.

As a result many people feel lonelier than they ever expected they’d be. They find themselves drinking, watching TV, and “staying busy” to distract from the glaring isolation. Heck, I’ve been there.

To further complicate the matter, most people don’t really know how to go about making friends, especially after college. You’d think that after all these years, we’d know how to do it, but many of us don’t. Men especially seem to prefer the pain of isolation to risking the raw vulnerability required for true friendship.

When I say “friend,” I don’t mean someone you call just to shoot the shit with (though that’s important too). What I mean is someone you respect and admire and someone who feels the same way about you. Someone you can open up to and trust. Someone who will help you wipe away the tears when the world rips you apart and celebrate with you when you’re on top of it all.

In this article, we’re going to discuss how to make friends at three different levels. First, we’ll discuss how to find people that you have the potential to click with. Second, you’ll learn how to create communities of people you love. Finally, we’ll talk about how to form deep relationships with a select few.

Along the way, I’ll share tips for overcoming social anxiety, being gentle with yourself, and letting the best parts of yourself shine through.

Part 1: finding and connecting with people you adore

The vast majority of the people on this planet are people you won’t want to be friends with. In fact, finding those you actually like is kind of like mining for gold.

The good news is that you can speed the process up. The trick is to create and attend social events where you’re likely to collide with great people. In most cases, if you enjoy the event, there’s a good chance that it will be filled with people you’ll get along with.

A few ideas to get you started:

  • If you work remotely or for yourself, join a coworking space. I’ve met a handful of good friends in coworking spaces.
  • Take a multi-week class that interests you (think cooking, dance, improv, acting, sword fighting, etc.).
  • Participate in group fitness classes like yoga, CrossFit, spinning, boxing, or a running club.
  • Join a rec sports league like Ultimate Frisbee, volleyball, soccer, flag football, bocce, etc.
  • Work for a company that hires great people. One of my close friends closed his small business because it was too isolating and joined a startup. He is so much happier.
  • Attend meetup groups that interest you.
  • Volunteer for a cause or political campaign that matters to you.
  • Go to religious or spiritual services that speak to you.
  • Join a book, knitting, or game club.
  • Start a slow but steady campaign to convince your friends to move to you. I know this idea sounds insane, but I’ve had surprising success… hi S*, hi M* – I’m so glad you’re in Denver!
  • Move into a group house – you can find houses looking for roommates on Craigslist as well as other sites and apps. If you take the time to find a house that’s a good fit for you, this can be a fast track to jump-starting or rebooting your social life.

The goal is to hang out with people  you are likely to get along with. Of course, just showing up isn’t enough on it’s own. You also have to interact, at least a bit. If you’re shy or introverted (like me), you don’t need to leap out of your comfort zone every time you leave the house.

Instead, start off by consistently showing up. In many cases some of the more outgoing members of the group will come up and start talking to you.

If that doesn’t happen or if you want to be proactive, initiate conversations. I tend to go with, “Hi – I’ve seen you around a few times but don’t think we’ve met – I’m Jason.” After that I’ll generally ask a question related to the context we’ve met in. For example, “How long have you been doing CrossFit?” if we meet at the gym, or “What line of work are you in?” if we meet at a coworking space.

If you’re like most people and have trouble remembering names or details, take quick notes on the people you meet. Scribble down their name, what they look like, and what you guys talked about. If you want to get fancy, write down the important things that are happening in their lives and ask about them next time your paths cross.

Part 2: create a community

With a bit of luck, getting involved in one or more of the activities above will allow you to join an existing community. If so, terrific! You can skip this step. If not, read on.

If you find yourself in the situation of knowing a lot of people but still feeling lonely, it’s almost certainly due to a lack of community.

Almost everyone is longing for community, so forming one tends to be easier than expected. By being proactive, you put yourself in the amazing position of being the linchpin for a group of people you enjoy, which will make your social life explode with activity.

Begin organizing and attending events and inviting the people you’ve met to come with you. A quick text, email, or facebook message a few days before the event, followed by a confirmation a few hours before will do the trick.

If you’re going to host an event on your own and are worried that no one will attend, here’s a trick I lean on all the time. Before you invite the whole group, confirm the event with one or two people who you really like and encourage them to invite people too. This way, in the unlikely event that everyone else declines your invitation, you’ll still have a few people to hang out with.  

Here are some of my favorite group activities:

  • Organize a lunch where you introduce all of your professional contacts to one another. Bonus points if you put a bit of thought into the guest list and invite people who are likely to get along or do business together.
  • Invite your friends to attend a sports game (if your city has a rugby team, go check them out – it’s surprisingly fun and inexpensive).
  • Host a dinner party at your apartment. If the idea of cooking for a group intimidates you, try ordering in, asking a friend to help, or making it a potluck.
  • Teach something you love. If there is something you love doing – let’s say salsa dancing for example – start teaching other people how to do it. You can do this in a professional capacity by offering lessons or informally by inviting your friends over and teaching them the basics before you all go out dancing.
  • If you drink, invite people to a wine, beer, or whiskey tasting. You can find a bar that offers this, or tell everyone to bring their favorite bottle to share with the group.
  • Invite friends to happy hour.
  • Organize a brunch.
  • Go to trivia night.
  • Go to karaoke night.
  • Host board game nights (lately I’ve been winning big at Settlers of Catan, but getting my ass handed to me at Coup and Ticket to Ride).
  • If your town has any quirky or seasonal events happening, organize a group to go check them out (think axe throwing, go karts, cultural festivals, cool exhibits, haunted houses, etc).

Of course, organizing events comes with risk: it’s basically guaranteed that some people will decline your invitation. When this happens, it’s hard not to feel at least a bit rejected. Many people let their fear of rejection prevent them from ever extending an invitation. Bad idea. It’s far better to deal with minor rejection than to be lonely and isolated. Besides, rejection is usually far less personal than it feels.1

Part 3: forming deep relationships

The real goal isn’t just to have people to hang out with; it’s also to find a few people you can form deep relationships with.

For many, true intimacy is both intimidating and elusive.  Fortunately, it’s a learnable skill. There are two components here. First, you must allow yourself to be open and vulnerable. Second, you have to create space for people to be open and vulnerable around you.

Component 1: opening yourself up

Most people struggle to open up and be vulnerable around other people. In fact, many people struggle to admit their weaknesses and vulnerabilities even to themselves. And yet, opening up is the only true path towards deep, fulfilling relationships.

Begin by sharing how you’re actually doing in the moment and letting your guard down. Feeling depressed? Secretly afraid that your hard work will amount to nothing? Lonely? Excited because you got a raise? Feeling really powerful and synced up? Let the other person know. Over time, share more and more of yourself. Yes, doing this will usually feel risky. That’s the point.

As you develop intimacy, the goal isn’t to recite facts about yourself while secretly remaining guarded. The goal is to allow all of yourself to be seen, even though it’s pretty much guaranteed that parts of the real you feel messy, complicated, afraid, and unattractive.

Of course, deep relationships can’t just be about you, they also have to be about the other person, too…

Component 2: creating space for the other person to open up

The other part of intimacy is genuinely caring about the other person and making sure they know it. For most, this is often easier said than done.

Fortunately, there are a few tricks to this:

  • Stop playing it safe and ask questions that you actually care about. All that complicated and taboo stuff in life like death, sex, politics, drugs, religion, and philosophy? They make amazing conversation topics. Lately I’ve been asking people, “What do you think happens when we die?” and “What’s going on in your spiritual / religious life right now?” When you do this, be generous with your attention and spend more time listening than talking. You should always be willing to answer any question that you ask.
  • When someone tells you something that seems important follow-up about it later on. Is your new friend perpetually bothered by her lazy coworker? Ask her how the situation is going next time you see her. Solving her problem, offering insight, or being clever isn’t the point – the point is to let them know you care.
  • Remember that true friendship is a gradual process. Intimacy is (usually) created over the course of many encounters with the other person, each leading to a deeper and deeper relationship. You really don’t need to share your greatest insecurities and fears on day one. Instead, pave the way so that on day 1000, you’re filled with appreciation for that person’s role in your life.
  • Don’t judge. We are all filled with contradictions, laziness, flaws, traumas, quirks, and other unappealing attributes. If someone opens up to you enough to let you see them, don’t judge her. Doing so will prevent her from opening up in the future. Instead, respond with curiosity, comfort, or compassion and by opening up yourself.

As you start to form deeper and deeper relationships, it’s important to remember one final thing: not everyone is capable of, or willing to, form real relationships. When you meet someone like this, you have a few options. You can maintain a surface level relationship. You can gently let the person go. Or you can love the shit out of them exactly as they are, which – with a bit of luck – may be the exact thing they need to melt the walls around their heart.

Postscript 1: If you’re really struggling…

If you’re really struggling with intimacy or loneliness or just can’t seem to get your social life off the ground, get help. If it’s a matter of needing a few new skills, a bit of encouragement, and some accountability, hire a coach. If you sense that the issue is deeper find a good therapist.

Postscript 2: how I met my girlfriend (or, one year later…)

New Years Eve, 2016, Denver, CO, 11:50 pm: I can’t believe it. Just a few minutes ago there were 30 people in my studio apartment. Now we’re all at dance club about to ring in the new year. This is amazing.

Last year, it was my goal to be able to have better plans for New Years Eve 2016, than I did for New Years Eve 2015. I’ve succeeded beyond my wildest expectations. Instead of just attending someone else’s party, I threw my own. Not only that, but this really amazing woman, L*, came to the party too. Her energy bowled me over. I hope I can get to know her better in 2017…