Why everyone should go on a retreat

Why everyone should go on a retreat: 3 simple steps to make it successful

Finally the actual post

Life is an amazing gift that we’re all given, and we owe it to ourselves to live our life to the fullest whatever that means for us. In order to live our lives to the fullest, we must live it mindfully and purposefully. Rarely does that happen without a little introspection. Some people are able to live their best life without thinking deeply about it. They’ve never had any second thoughts or doubts. That is amazing and wonderful. Life is a game we all get to play. If you are enjoying it and do not want to dig any deeper there is no obligation to do so. However, even if you think everything could not be going better, you’re still welcome to read on. You might still achieve a stronger feeling of being or wholeness in your life through seeking to understand yourself in a deeper way.

Life is an amazing gift, but we really only view it from the first person. Furthermore, we only really view life looking outward. We are social animals, constantly putting ourselves out to the world and showing what we need to of ourselves to get by. We exist in the different societal niches we have carved for ourselves, and we have to put on whatever mask fits us best for the world and situation. This is an incredible self-preservation technique that is likely as old as humans ourselves and probably predates our existence as a species. All this to say, we’re really good at trying to succeed in our niche regardless of how we really feel or what honest feelings we need to repress. We rarely express the many complexities of our personality, and for good reason. If you said everything that was on your mind constantly, people would think you were fucking insane. They’d probably be right. Every person’s inner thoughts, that they don’t voice to the world, protect them from coming off as mildly insane at best and fully institutionalizable at worst, but this hides and represses a significant part of our humanity. We are sacrificing part of who we are in order to preserve the whole.

Self-preservation is vital and one of the most important human instincts, but self-repression is at the root of a lot of our biggest regrets. Most people’s biggest regrets are of omission, not taking the chance or doing the thing, not commission, doing something wrong or failing. We as a species feel like we need to hide a little bit of our insanity to fit in and that isn’t objectively a bad thing. Being accepted is really important to your wellbeing and you shouldn’t start telling everyone on the street your deepest darkest secrets. Humans are social animals and we need to be accepted in society. However, after a lifetime of constant repression, we start to repress our inner feelings even from ourselves. There are dimensions of everyone’s personality that get shoved so deep down that the person doesn’t even realize they exist. The constancy and go-go nature of the world always with some mindless entertainment to fill the void never lets us reveal these parts of who we are to ourselves. People are afraid to sit alone in a room with just their thoughts for fear of what might come up. Fear that we would hear something from our inner voice, a voice that knows us at our deepest most fundamental level, that we don’t like. We wouldn’t reject it because what we hear in silence isn’t who we are. Rather it is so fundamentally us and so strongly repressed that letting it out of its cage scares us to death. People fear sitting alone in a room alone for even a few minutes without a phone to entertain themselves because they do not want to get to know themselves. We are so scared of what we might find out about the real us that we are better off doing the equivalent of putting our fingers in our ears and saying “lalala I cant hear you” to the internal voice that is calling us to be more authentic to ourselves. This is our reality and it is both terrifying and totally understandable.

Life is hard and the interconnectedness of a global world forces us to constantly showcase our best self. We have a society wide tragedy of the commons problem where everyone has to craft a narrative and be their best self. This prevents everyone from being their authentic self. This, on the surface, is not incredibly alarming to us. We are selecting for some great traits at the expense of repressing other not so great ones, as defined by the society and culture we live in. We all exist in multitudes, but some dimensions of our personality are more adapted than others, so we picked those as our main masks we wear. Not because these traits were more true to who we are, but because that is what society selects for. Some traits that we incorporate into the masks we wear every day aren’t even ours. We have likely adapted what we have innately or full scale copied some positive traits we saw in others. The upshot is we are living other people’s lives because we haven’t fully explored who we are at a deep level. We’re only really selecting for the traits that look the best to the outside world. We settle on some important attributes in our more impressionable younger days and then harden an identity around that. The rest rote memorization and habitual thoughts and actions. Living on autopilot is very easy and life is pretty hard. If you had to decide every day when to eat, where to go to the bathroom, and what to do for work, you would go insane and accomplish almost nothing. That’s just too many decisions to make during a regular day and have any sort of progress without a lot of habit. It is natural and positive that we develop routines and habits for what we do and who we are in the world, but a large part of our personality lays latent and untapped. This dimension needs to be explored because it is a part of us. These repressed parts are just as important as the sides that we show to the world. On a retreat, you don’t have to look outside. You don’t have to be someone. There are no models to copy, even if you wanted to. There is no benefit to trying to be someone you’re not. You are stepping out of society to take a dispassionate almost third person view of yourself and investigate your soul to explore the full expanse of your personality. The goal isn’t to leave having discovered any specific thing. The goal is to leave understanding yourself a little better. Hopefully this deeper understanding leads to a better happier life however, you define it.

As a slight aside, while what society selects for is very socially beneficial to copy, it has no inherent moral and ethical high ground. Morality is a function of the times and even in our current environment different cultures have vastly different views of morals and ethics. Some cultures value individuality while others value collective thought. Some cultures are anchored in religion while others are built on the separation of church and state. Just because society selects for certain traits that does not make them right or correct. Throughout history many people had thought they figured out the ideal way to live your life and almost all of those have been proven wrong at the societal conformity level. Nowadays we are just as apt to be wrong as people had been historically, so just because you are “well adapted” does not mean you are morally right. Furthermore the life “well adapted” to current societal dogma could run so counter to human nature it is actually destroying your happiness and ability to have a good life deep down. So just because you are picking the masks that work in you’re here and now, does not mean these are the right masks for you and trying on new ones may do you a world of good.

Another important part of a retreat is the physical environment you are in. We are constantly running and doing things. We don’t really get a chance to step back and think. Even if we do for, maybe we get five minutes or ten minutes of uninterrupted thought. In that short time, we can’t really explore ourselves that deeply. No meaningful relationship was formed 5 minutes at a time. Let alone the most important relationship we have. The one we bring everywhere we go. The relationship we have with ourselves. Some of us rarely even get those 5 minutes. We are constantly pumping information into our head eyes and ears. When was the last time you were in a public space like a grocery store or gym that didn’t have music. We constantly feel like we need to feed our brains. When we let them sit still for a second, we start to realize the deeper things there. These deeper things create emotions within us that we can’t fully explore. We struggle to ask those deeper questions through our inner thoughts, so we run from them. A retreat allows us to step outside of our body and life to explore ourselves, explore our lives, and explore the world and our place in it. People have some of their best ideas when they are forced to sit alone without any external expectations or stimulus. A common place this happens is in the shower. One of the last great refuges of solitude, shower thoughts can be some of our most insightful moments. Going on a retreat gives us days full of these shower thoughts. We get a better sense of that path we are on and can ask if it is the right path. We have the space to ask who are we and what life should we be living. Assuming you want to take a dive into the depths of your soul, if even for a couple days, how should you even look at going on a retreat?

I believe there are three steps you need to have a successful retreat. The one caveat is that a successful retreat could be done in two days or need months. Also, a successful retreat doesn’t solve all your problems, but it allows you to try to identify them, so you can take the steps to work on them. There are no silver bullets in life. Retreats provide an incredible amount of helpful perspective to inform the decisions and actions you take in your life, but any change must come from thoughtful purposeful actions.

So, what are the three steps? Step one cut a hole in a box. All kidding aside three steps are regroup, digest, and plan. There is no right way to go about these, but I would suggest putting away your phone, going to a place without any Internet, trying to be in nature and/or meditating and generally sitting still and not taking in any new information. We are constantly bombarded with new information, but you do not want to flood your head with new things because this will sit on top and block out the deeper thoughts that want to come up. The goal isn’t to change. The goal is to understand yourself better, so sit down and relax. The quiet allows you to realize what the deep down inner you, who may have been trying to talk with you for some time. However, it could not get a word in because of the screaming from your life constantly entering your head. Furthermore, the only person who knows what you want to here is you. It is almost counter intuitive that you need to try really hard at doing nothing. Give yourself the space and time to let those thoughts come from the depths of your head to the front of your brain. That comes with giving your mind space and allowing yourself to think. Create an environment of intentional boredom. Boredom creates the initial conditions for listening to yourself. Then you must actively listen. This comes through mindful awareness. It is probably best to write things down when they come up and constantly have a little notebook and pen with you because you never know when that insight will come up. For me, it often happens on hikes. When I am in nature listening to the forest, some thought peaks in from the back of my head. You do not want to hold these thoughts with you and have them monopolize your headspace. You want to give the full range of your perception time to show itself. Writing this down ensures that what you heard is not forgotten and allows you to clear your mind. Writing also allows you to explore your thinking at a deeper level and really dig into the topic on your mind and explore it in text fully right in front of you. Putting your thoughts down allows a different and deeper level of examination of your thoughts. Writing leaves no room for bad thinking and bad self-talk has no place to hide. Everything becomes some clear and real through the action of reverse compressing your simple thoughts into the boundaries of language. The goal is insight which can come anywhere anytime and we must set the table and invite insight into our minds and life.

Step one, the regroup. Life is fast and amazing and there’s so much going on all the time. We get in a routine and life happens to us. Things go great other things go horribly wrong, but there is so much constantly going on. We are constantly doing something. Going from work, to time with friends to TV and while you’re watching TV casual entertainment on social media or a game on your phone. We as a species have filled whatever “free time” we might have with everything under the sun but silence and rest. It is not like reading a book is much different. In essence, it is very similar experience because you’re blocking your natural thoughts from bubbling up. Were constantly going we are a species of constant progress. That instinct drove us from living in caves sitting around fires to the moon, but we have far surpassed the golden mean of optimal progress orientation to the determent of that progress we yearn for. We have so much to fill our time. Too much. The world is moving so fast and we want to move fast with it; we do not want to have any FOMO. It’s exciting. It’s fun to be on the treadmill of society, but when you get to your retreat you need to step off. The first thing you must do is catch your breath and regroup. Make sure you’re rested make sure you’re recovered. The anxious and busy mind breeds few authentic thoughts. You need to make sure your mind is in a place to receive yourself. If that requires you to sleep for an entire 24 hours, that successful first day. If you sleep for 48 hours, that is a successful first two days. You need to reset your mind and fully regroup from the constancy of life. Phones may be one of the best inventions of connection and knowledge democratization ever invented, but they are not made to bring solace. We are, at our core, an incredibly social species who need connection. Resisting these urges is a tall task and you need to create an environment conducive to vibrant internal conversation. You must put away your phone and limit your social interaction. You need to sit there with yourself long enough to wonder who you really are. The first step is just positioning yourself to receive what your body wants to tell you. If you were to leave having just accomplished a brief moment of connection with yourself, it is an incredibly successful retreat. Life is moving so fast and constantly punching you in the face. Shaking you every which way. Even just screwing your head on straight and facing the day with the wholeness of your being is success. Transcendence is a straight line with a non-linear path, but if you can regroup you can aim to digest.

Step two is to digest. This is when you really have to listen to your body and your mind. The body is a powerful thing that tells you so much about yourself if you can listen. The body is easier to listen to than the mind because we feel it so viscerally. Physical pain and emotion in the body is hard to ignore, but in our lives we have mastered suppressing it’s cues for our adaption. First, you will feel your body then you can start to face your mind. Listen to what thoughts are coming up and write them down. Insight can come and go with a passing thought or hit you like a ton of brick. You should constantly have a journal where you record whatever your inner monologue wants to voice. When it comes just say “oh, I did not realize that this happened to me” and record it. Some things maybe be known issues you had thought you processed months ago others might be novel. Maybe it’s a friend you hadn’t talked in a while and then realize you lost an important relationship. You were totally fine, but now that you’re stepping back, you realize how hard that is and how you haven’t filled that hole. Or you just left a job and you’ve started a new job. It’s going great but you realize that you’ve never settled on why you decided to leave and you’ve never really made peace with that decision. There is this nagging feeling that maybe you fucked up. Maybe something bad happened at work or in your life. It does not have to be a major thing. Major trauma is often pretty clear. Life is a series a momentary decisions and after a little quiet reflection you realize the accumulation of the mini decisions have created a version of you that you don’t recognize in the mirror. You’re just not as happy as you used to be. You’ve just gotten one percent less happy every day. These little steps are almost invisible but amount to a mountain of movement in your life. After even a month or two months compounding unhappiness at a one percent rate, you will be a miserable person. This is quiet spiraling. It has all happened so gradually, so until you take a step back and start to digest your feelings you don’t even realize you’re driving 100 mph bearing down a dead end. You can’t feel that in the moment. After a lot of the digesting though, you might say wow I am really here in my life? I thought I was somewhere else. I thought that I processed and I hadn’t processed these events. These past moments are still on my mind and weighing me down. When you can start to put words to feelings in your body, these feelings start to fade away. You rarely understand everything going wrong at once and some of these negative things could have happened last week or last year. It doesn’t really matter when they’ve happened. Digestion is facing what is really weighing on your mind and investigating those feelings deeply.

To digress from this road of misery and sorry, you will also realize the amazing things that have come into your life. We are a species wired to focus and solve problems, but life is often equal parts highs and lows. I would even argue there is a lot more amazing things in our life than horrible things. The stresses of our ancestors have been mitigated to mere after thoughts and our problems are no longer around survival and self preservation, but in how to direct the good life. We no longer wake up and have to fight the elements and search for food to survive every day. You must take time to bathe yourself in your success as well. You have gone from someone who could not even wipe your ass to a functioning member of society. The arc of our lives in no small feat and rarely do we have to sit back and celebrate out many accomplishment along the way. We have parties for milestones like marriage and graduation, but those last only a few hours. Rarely, can you sit back and smile about all the amazing relationships that have come into your world, all the random luck you have had that has vaulted you forward, and most importantly all the little kindnesses you have brought in this world that has made it a better place. There is a ton of vanity in self-indulgence of the past. We must recognize our accomplishments with a sense of humble pride because it allows us the realize the depths of our power and agency. The chances you took that scared you to death, but you still pursued. The trials that tested your resolve and formed you into a better person. When we sit back and listen to our body, we start to digest the glowing successes of our life, bask in our old glory, and dream of the great things to come. We get to look at the person we were 10 years ago or even 10 days ago and smile about how much we have grown. The world is driven by painful comparison, but rarely do we get to make the most important comparison. The one to who we used to be. Every day we have gotten out of bed and shook off the immaturity of youth and trials of our past to attempt to create a better life for ourselves with no guarantee of success. That’s pretty amazing and something to be immeasurably proud of. We deal with what we may be struggling to overcome and are reminded of how much we have accomplished. Through endurance we will conquer and continue to walk the golden road that is life. Recognizing all the good you have done allows you to tap into your immeasurable power to create more. Success compounds and listening to the positive things shows you the road ahead is paved with so much hope and promise.

Digestion is about simple processing of what comes up. You take stock of your successes and failures and accept them in order to grow and improve. You have a chance to listen to who you authentically are. Knowledge of these facts is incredibly powerful. Knowing not to touch the hot stove is as important and utilizing your skills as a chef to cook up the dishes of your life. Once you understand, you can integrate that into your life. Digestion is purposefully processing things in order to move forward a better and more authentic person to what your inner voice is telling you. You expose the inner contents of your mind and have a chance to face them. This does not mean that everything is fixed, but it means that you are at least aware of what’s going on and you can start to fix it. If you’re able to identify even one thing that’s weighing on your mind or lifting you up, your retreat has been a home run. There is so much that we do not realize about ourselves. Digestion allows us to stand up straighter and live with a more authentic smile. We don’t truly show ourselves in the world because we aren’t even fully aware of how we want to, who we are, and what is stopping us. Digestion allows us to hear what we really think about our lives and take stock. A slightly deeper understanding of ourselves is a resounding success. The next step in transcendence comes from good systems and purposeful action that we undertake.

Step three is to plan. How can you build better systems to tighten feedback loops on your life? Life will never be perfect and bad things will always happen. Life will likewise be filled with great things. The question is how do you live an integrated life to become a better person. Create the conditions in your mind to prepare it for the road ahead. When one of these events happens in real life, you want to be better able to process the whole situation. This comes from building thoughtful intentional systems of reflection with strong feedback loops that inform your life. Most importantly they must be easy to implement when you return to society. There are 3 major classes of changes we can focus on. Internal self talk and dialogue, physical actions you take in the real world, and overall direction on where you are going. First understand where you want to go then effecting real change in the mind and real world. The easiest way to implement changes is through physical systems that we build. These evolve into habits that we either create or destroy like going to the gym more or drinking less. If you’ve wanted to read more, one system you can build is that you set an alarm or calendar on your phone at a time you think it’s free every night. Then you try to open a book for 10 to 15 minutes, you can even time it as to not overdo it. Make a routine out of it and it becomes near instinctual. Tying what you want to do into existing rituals you already have can make them more natural and easier to stick to. Maybe you had brushed your teeth before bed. Now you can insert reading before that and stack your habits to build a new behavior in a familiar existing system. Physically putting a time on your calendar is key. You can never be over reminded of your commitments to yourself. Remember new habits are hard to build, but default behavior is incredibly easy. Make yourself an automaton in the areas you want. Systems do not create mindless living, but purposeful action. Other examples of good systems are screen time alerts on your phone or regular dinners with friends. Systems start with digesting who you are and where you want to go and then making a plan to get there. No one has ever sat down and written a book in a day, but almost everyone can write a sentence or a paragraph. The barriers to anything worth doing are high enough as is and paved with hard work and struggle. Without purposeful action and good systems, you’re fucking clueless. Build a map for the journey of your life. Chart your path and constantly keep checking that you’re following the path you set out. That does not mean your map will not change constantly, but without a map you’re screwed. You need to make a plan. You need to develop systems. Systems need to be clear and easy. Don’t expect yourself to read more because you want to. Systems are not built to be achievable on sunny days when everything is going well. Systems are the alarm at 5 am. Systems very clearly tell you who you want to be. Systems need to be resilient in the face of disorder and level up over time. Do not expect yourself to finish a book every week. Read a page every day. Some days if you enjoy that page read another. Getting started is the hardest part and lowering the barrier to entry for the life you want to live is the most important step in living that life. No one expects to go to the gym once and leave with a six pack. Set realistic expectations for your systems.

Anyone can build a successful system in a simple way. The attributes of a good system are universal. Clear goal, steps, and constraints with clear feedback loops. Create clear times that you can put on your calendar. You can set daily reminders and define the action you want to take. If you want to learn more, create a system around information collection. Reading is a great way to collect information, but what does reading mean? Does it mean page? Does it mean one paragraph? Set a realistic goal and be kind with yourself on execution. You can finish a 300 page book if you read one page a night for an entire year. While this might seem stupid, you have infinitely increased the number of books you read in a year through something as simple as reading a page. Now you have become a reader. This might prompt you to update your system and read 2 pages a night. Now you have doubled your output. Nobody likes to be forced to do things and trying to do something that is too difficult will lead you to quit. Gun to your head 99% of people could finish a 300 book in a weekend, but this is like going on vacation. You are just experiencing something not changing or integrating something into your life. The goal of simple systems is to change your life in a way big enough to be significant, but small enough to be repeatable and possible. There is nothing harder than starting. Once you get the ball rolling you can continue to make the same incremental changes. The jump from 0 to 1 is the hardest, but it enables the jump from 19 to 20 and it allows you to find your limit.

Systems need to have strong feedback loops. If you set out to run half a mile every day, eventually you realize that you can try to run a mile. At some point you hit a brick wall on the improvement curve where you break and experience diminishing returns. That could come at 5 miles or 50 and is based on the wider constraints of how the system fits in your life. Some people don’t have the time even run 5 miles let alone 50, so the system needs to be both feasible and actionable. The feedback you get from your body or life tells you when you have started to hit your ceiling. Sometimes that means changing other systems like eating healthier to give your body the right fuel to go farther. Other times it can be destroying a mental barrier or glass ceiling that exists only in your mind.

Most of reality is made of glass ceilings. The sub 4 minute mile was considered impossible for one person to achieve. Physically speaking humans can only run so fast, and there is a limit to how fast a mile time can be. 4 minutes is a round and perfect number, but it could have been the right time. For the first 250k years of human existence no one had run a 4-minute mile. People knew it was impossible until one day Roger Bannister ran a mile in 3:59.4. When glass ceilings break, they shatter. 46 days later John Landy ran a 3:58 breaking Bannister record. In the next 2 years, 8 more people ran a sub 4-minute mile. We perceive so many things as physically impossible, when in reality this perception is just a minor mental block. The objections to the story are clear. Training improved, diets improved, equipment improved, ect., but the reality is this was just a mental block. From 1933-1944 the world record mile time improved 8 seconds. From 1945-1954 the time had improved from 4:01.6 to 4:01.4. 4 years after breaking the 4-minute mark, the world record had declined another 8 seconds. It took 9 years to break this societal mental barrier and return to the normal rate of time improvement. If the most driven, athletically gifted people in the world can struggle with a glass ceiling for a decade, the average person can probably waste a lifetime with false perceptions across a range of their abilities.

Good systems attributes are universal, but the right systems and feedback loops for you rely on trial and error. A feedback loop of milliseconds could be the difference between a hi-frequency trader being incredibly successful or a complete failure. Likewise, checking your resting heart rate every second to see if your workout regime is working is neurotic and will likely lead to a higher heart rate driven by your incessant anxiety. Complex systems have a hierarchy that leads to different emergent phenomena. A good system has different feedback loops at different levels. If you want to become a more fit person, your daily feedback loop may be your alarm going off every morning and then on a weekly or monthly basis you may have a more holistic look at your health metrics to see if what you’re doing every day is beneficial or not. Desire to change does not change someone’s life. Everyone wants a better life. Purposeful action creates the life you want to lead. Systems create habits that make what you want to do easier. If you’re able to get to the place of system building after your retreat, you’ve had a 10 out of 10 retreat. You really cannot get better than that and now the hard work starts. How do you implement what you’ve learned about yourself to make your life more authentically you.

We all want to live lives that are authentic to us and that makes us genuinely happy. Through this simple three-step process and taking a couple days out of your life to truly listen to yourself you can take positive steps to improve your life. It’s not easy, takes time, and is frankly very uncomfortable trying to alter your life. Changing means saying goodbye to a part of you to welcome in a new version of yourself. Life is a process not a thing and the examined life required you to analyze who you are and who you want to be and take steps to close that gap while appreciating the ride. The journey 1,000,000 miles starts with a single step and taking even a day to take a step out of your life in order to improve yourself is an incredible cause and a valiant effort. Taking this step is an instant success. We cannot control this probabilistic world, but we can position ourselves well to take advantage of the chances that come our way. Retreats allow you to tune everything out and listen to your inner voice. You know what you want and all you need to do is give yourself the space and time to hear yourself clearly. This isn’t some lala high minded nonsense. Allow yourself to be bored allow yourself to think and be alert to what you say. You never know; it might change your life.