Motivation, Personal Development, Travel

How to Begin Engaging with Yourself

In my Flourish post I briefly mentioned the way we excuse ourselves from doing difficult things, how we rationalise that next beer, or one more episode, or continuing on somebody else’s pursuit of happiness. Often this is just because we haven’t paused for a moment to consider what might be the best course of action for our lives or the lives of other people around us. Why do we give up? Why don’t we legitimately question the direction of our lives? Our brains fight against us because they don’t want to be uncomfortable – and when we work long enough on anything (a project, a job, ourselves) there are bound to be significant periods of discomfort. That, combined with the default mode that we’ve been programmed into by society not to question and simply to follow the norms, has an astounding effect. It is not concerned with our flourishing, with whether or not the direction we are going in life is actually what’s best for us, it’s simply concerned with our consumption. In this article I want to go deeper into how to move past the excuses and expectations of our brains and society and do real life better. How do we learn to observe ourselves honestly so we can ignore the million excuses and actually do the things that matter? And why is it even important?

Here’s the point where a lot of people stop reading or begin to skim. Thanks to the brief attention spans produced by long term internet use, you might be struggling with the desire to check some messages, or your newest notification. To try and mitigate this, for your sake, I’m going to introduce something I call Engagement Exercises to this and future posts. The first exercise is this – if you are really serious about gaining some control over yourself and your future, just for the time it will take to read this piece through, close/minimise/silence/destroy any possible distraction. I recommend continuing now rather than putting reading this off to another moment, and I also recommend the following: consider if you actually want to try redevelop yourself. If so, tell yourself now that you will read to the end of this article and do the Engagement Exercises (they are easy, get a notebook or start a document). If not, don’t worry, read as much or as little as you want – but consider if the excuses you are giving are actually well founded (an example of a bad excuse is having to get up to find pen and paper, or you don’t feel like it now but you’ll do it later – realise those excuses are foundationless rationalisations).

What do you expect?

The first step is to define the normalised life things in terms specific to you, the person reading this. Any expectations you hold of yourself, they are most likely the expectations of others, internalised over the course of your life. They float around in your subconscious and pretend to be your own voice. They are the dictates of your society, your parents, your friends, the media, and any other external influence. For a lot of people reading this, it may be the expectation to own a house, or be a doctor, or make good money, or go through some graduate career stream and end up with a job in consulting, or management, or public service, or be beautiful, or have lots of friends, or Instagram followers, or whatever it is.

I’m not saying any of those things are bad, what I would like you to consider is that many of the desires you have are not your own, they don’t represent you, and in the end they won’t make you happy. Moreso, the expectations that come along with those desires are what often end up hurting you in the long term. Usually there will be associated baggage, like a fear of failure, high standards, self punishment, an insatiable desire for novelty, and a continual journey up to the next rung of the ladder. The expectations force you to view life as a climb to the next goal, rather than a walk on a scenic path. If you can take a look at your own life right now, a long and meaningful evaluation, and you notice that you are constantly striving for the next thing for the sake of it being the next rung on the ladder (ie because you think it will make you happy), rather than having its own intrinsic worth, please read this article as deeply as possible and consider its message in terms of your own life.

Here’s the second Engagement Exercise: write down the three biggest expectations you have for yourself and try figure out where they come from and how you think they will make you happy (this might take a while and include things like “to be excellent”, “to never fail” , or “for everyone to like me”). Now, try to accept that they might not make you happy, in fact they probably won’t, and that instead your expectation to achieve them will make you unhappy – particularly when you inevitably don’t.

You chameleon, you!

So what’s the answer to all this pressure to get things or become something and then be happy about it? What are the things you can do to respond to the spiral of Sansara (the birth, death, rebirth cycle to which life is bound)? The expectations come from your environment. Look at humans all over the world at every point in time – we adapt. We exist in the worlds we are born into, we fit. Even if we feel like we don’t fit, we fit way better than we think. Humans, on a macro scale, in terms of our ability to become the people who surround us, we are all basically the same. We conform to our families, our cultures, and their associated expectations. So, the big question is, why can’t we choose our environments? Why can’t we construct the expectations we have for ourselves to be broader, more open to change and more prepared to face anything sent by life? Well, I think we can. We can put ourselves in situations which force us to learn, which surprise us because of how we respond, and which help us develop wisdom.

Over time we become attached to ideas of the self, “I am a generous person” or, “I’m a person who works hard” or, “I’m a person who has anxiety in response to x”. Whatever ideas we have about ourselves, they are less fixed than you might believe. I’m not going to go into the nonexistence of the self right now, but the basic idea is that we create notions of who we are, not based on who we actually are, but based on the collection of experiences we accumulate in life and our responses to those experiences. So, here’s the obvious answer. Change the experiences and reactions and the responses will change.

In this piece I’m just going to focus on the experiences part, stay posted for some work on the reactions part later.

To make yourself, make your home

If you give yourself a handful of experiences that are inconsistent with those you have had up to this point, you’re going to surprise yourself. You’re going to learn a heck of a lot more about who you might (and might not) be than had you simply continued your normal life. Like I said, the more varied experiences you can have, the wider array of situations you can experience, the more you will learn about how you react to life, and who you actually are. If you have been in the same place, doing similar things, with similar goals, for more than a couple of years, you might start to think that you are the person living that life. You aren’t. You are much more adaptive than that and all you need to do is prove it by going somewhere else and doing something else.

Engagement Exercise three, write down three things you could try that could take you out of the zone of comfort. Any things, big or small. How could you make those things a priority in your life?

Reading through this article and nodding your head is a much easier task than it is to actually do anything, obviously. To actually break the molds of your existing life you need to commit. Not a huge commitment, just one that means you are actually going to consider your place in this world, and the fact that you can build a little nook for yourself in that place. Do you want to learn more about yourself? Do you want to develop mastery over yourself? If it’s a yes, then out loud tell yourself: “I want to learn more about myself. I want to develop mastery over myself.” Great! Just FYI, it’s going to be painful.

We have established that if you can change your environment, learn new patterns and shift your expectations and experiences, you will adapt to them and thus better understand yourself (and hopefully people in general), but what are some ways to do it? There are a lot of options, and here are my favorites and why:

Writing a Reflective Journal:

This is by far the easiest change you can make. It’s also a prerequisite to learning more about yourself. You cannot begin to become something different unless you have observed and understand yourself, at least a little bit. This one is the only mandatory suggestion in this list because of how necessary and potent it is for personal growth. This journal can contain anything you want in it – but once you write about your day, try go back and reflect on what you wrote, what you were feeling and why, and write on that too. After some time, if you write for long enough, you realise some deep and powerful things about yourself, you’ll find yourself writing about your entire life up to that point, you’ll find yourself making visions and plans for the future. You can start one right now, be it digital or physical, and do your engagement exercises in it. The Journal becomes a physical reflection of your mind that you can see and interact with. The act of doing your engagement exercises in the journal behaves like a device that will help your brain to commit to doing some real self reflection – try it out and see for yourself!

Long term solo travel:

I can’t recommend this enough – seriously, most of the other ways to shake yourself out of a pattern of life I’ve written below can be done during travel and are more likely to happen during travel. You realise that the identity you developed in the life you were leading just a month before was not actually you, and neither is the identity you create when travelling. The freedom shocks you – perhaps you do things you never thought you could or would, that you never even considered before (both positive and negative). So many crazy and new opportunities will offer themselves to you if you are open to them. Tell me your excuses and I’ll say this: has someone like you done long term solo travel before and been fine? Yes. Did they become a more interesting person? Probably. No excuse is good enough – you don’t need a lot of money, your commitments back home will wait, and of course it’s safe just don’t be dumb! You. Should. Long. Term. Travel.

New Challenges:

These can be in any form and really encompass every other option I’m giving, but the reason I’m including them is this: challenges that directly go against the grain of who you think you are force you to grow. You’re not who you think you are – but the only way to figure that out is to prove it by doing crazy stuff. Look, the challenges don’t need to be huge they just need to create some friction. They need to make you uncomfortable and teach you that you are MORE. And that you can do more than you or anyone around you ever expected. Hate running? Sign up for a 10km (or a marathon) and start training. Have issues with your food touching? Be a Freegan for a week (check out TrashWiki for worldwide dumpster maps). Talk too much? Take a vow of silence. Always getting the newest product? Don’t buy anything for one month. Believe you are an honest person? Try to lie as much as possible, or actually observe how much you lie every day. Whatever the challenge to yourself is in life, have something on the go to push yourself.

Vipassana courses:

Challenge level: super tough. These things are painful and so, so worth it for everyone who can push through As long as you realise it’s temporary, it’s fine. 10 days of 10 hours a day of meditation, no speaking, and both physical and mental agony. It changed me so much for the better, and it will hopefully change you too. They are donation based (so you don’t have to pay anything if you don’t want to), and all over the world, (check out To me the format of these courses and what they teach represents such useful skills and a kind of bootcamp that should exist for so many other things. Do one if you can, maybe while travelling. Warning: if you are very mentally unstable at the moment talk to someone who runs the courses for their advice before doing the course straight away.

Joining communities and meeting new people:

So many communities exist around you with people who are really different to you in really cool ways. We become more like the people we spend time with, so spend time with a lot of different, interesting people and you will become more like them in many interesting ways. Bowling, community gardens, hand-crafts, poetry, improv, whatever. The key is to go to something and stick to it for enough time to really begin to understand the people, even (especially) if you don’t like it or feel like you don’t fit in with them.

Consuming varied and positive media of your choice:

We are constantly absorbing information in the world and so much of it is filled with judgement, expectations and consumerism. Not only that but we often don’t even get to choose what we see. Avoid the media that will make you a more judgemental or consumption oriented person and begin to look for the kinds of things that can change you as a person for the better. There are a lot of great books, YouTube channels and podcasts out there that will have a positive impact on how you see the world – check out my recommendations post coming soon.

Additionally, you could set out large portions of time where you don’t consume any digital media – a digital Sabbath. This might be for 3 hours a week or it might be a portion of every day – whatever you choose, being disconnected from the web – if even for a little while – is really important to focusing more on real life.

Action Therapies:

This is an idea that has been around for a while. They are forms of exposure therapy that teach you through repeated experience not to be afraid of something or to realise something about yourself or society. For example, the idea of trying to get rejected at least once a day. Repeatedly asking strangers for strange requests with the hope of getting rejected short circuits the fear of rejection we all have by creating the paradoxical situation where it is an experience you are looking for. Over time and with practise your brain learns that rejection is a natural part of life, and that it should not impact your sense of self worth or your ability to try request things of people. There are many forms of these you could do, Vipassana is one of them. If you have an anxiety or fear, think about how you might gradually expose yourself to it (in a safe environment) to reduce its effect. Here’s the original Rejection Therapy guy.

Move to a noticeably different place:

The premise is simple: every environment you know is associated with particular feelings you have. If you have been in a house and were depressed in that house then you might associate the mental state of depression with the house. Changing your living space gives you the opportunity to associate the feelings you want with a new location, one unsullied by previous experience. It could be in a new city or country or it could be up the road – the more different the greater the opportunity you have to change your associations. If you want less of a big change you could move around your furniture, wear new clothes, or paint your house – these will have an effect but obviously one much smaller than something bigger. Warning: if you don’t change your behaviour then the old associations will move with you.

There you go – heaps of ways to start changing your thinking for the better – here’s an exercise to help crystallise the changes.

Engagement Exercise – choose two of the above options and brainstorm things you could do. For example: think of country you would like to visit and search for opportunities in that country – you’ll be amazed by all the cool and cheap stuff you can do (eg/ Volunteering in Bolivia walking pumas and jaguars through the jungle).


There’s a lot of pressure around the post-University or school period to actually get a job, and start a real life doing real world work things. If that’s calling you then heck yeah go for it, but if that’s just an expectation, if it’s just the next rung, maybe consider travelling, or looking for something that will really challenge your perceptions. My biggest recommendation would be to start with a Vipassana course at (it’s free, and will really stretch you) and then go from there.

I’m also going to be providing you with some suggestions for great books to read and videos to watch, as well as an article on learning new skills and creating the right environments to help you change – keep an eye out for them. For now, if you want some great beginner travel advice, check out Vagabonding by Rolf Potts – if anything will convince you to go on a journey, I think it’s this beautiful mix of accessible philosophy and guide book. Plus, if you’ve never read On The Road by Jack Kerouac I can highly recommend it for glorifying dirty, pickup truck travel. Click the titles to buy them and support Flourisch!

If the next step in your life is going to stretch you, if it’s going to be painful and force you to grow, do that. If the next step is the expected, comfortable and recommended option – question it heavily. We don’t need more people in this world that follow the rules, although if that’s you then we love you too. What we need is loving compassion, drive to change, and flourishing. I know that can be you, and so the final Engagement Exercise is to simply think to yourself – “what can I do to break my mold?” And if you can’t think of anything, try some creative Google searches or writing something down.

There are a lot of ways that you can flourish, and a lot of things I can tell you about that will help you on the path. I’d love it if you joined me on my search to honestly work on trying to be more open, and learn new things. By the way, I love you heaps – remember to be friends with yourself and believe in yourself the way I believe in you. Please consider subscribing for updates about when new articles come out so you can keep going on this journey with me – just put in your email address in the column on the right.

All my love and metta,

Josh Mason

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