A Love Letter To Failing Upward (1 Viewer)


Apr 15, 2019
North Wales
calvin hobbes.jpg

Failing upward is simply the concept of failing by mainstream standards and yet achieving more fulfilling outcomes in the long run. Often this is connected to a feeling of unlocking opportunities you didn’t even know existed.

Power – Failing to take every opportunity to lead from the front

Due to the unfair distribution of power in society in the hands of very few, the good any one person could strive to achieve is immense, because one can imagine wielding the kind of power those at the top currently have to do good. But this power is denied the many.

So, like how a figure like Bernie Sanders could have harnessed the position of presidency to do lots of good, how he did educate the masses on the positives of socialised government institutions and, if he’d gotten into power, mobilise a grassroots movement to demonstrate and strike to push through bills.

And most importantly power can be a mirage. It’s the carrot dangled in front just beyond our reach. We need to create opportunities for ourselves, to achieve great acts of good on our own, like the personal heroism of people flying to Syria to fight Islamic Fascism or organising edible gardens in low-income neighbourhoods.

As well, even though we may cherish those opportunites to do great deeds today, counter-intuitively, the goal should be to move to a world where grand feats of good deeds aren’t necessary or possible. So that more people get a chance to strive to do good.

So a move to devolve government power to a multi-party system through preferential voting, to… Some local government positions being elected by sortition, to… The majority of society being so content with worker-co-ops and syndicalist unions that we transition from representative democracy to direct democracy. So, a chamber of ministers to federated spokes councils.

Time – Failing to rush to achieve a bunch of outcomes without fully considering the value.

With the ever expanding knowledge each new generation is able to harness, the hard material outcomes of our goals in life will always be out performed better or faster than before.

So, while some people fret about failing against others, which makes them feel their life is not worth living, you, by failing to set strict goals for yourself and instead giving a leg up to those around you, can just observe everyone acting around you, contemplate your time and place in history and experience a peace of mind knowing you’re part of the fabric of everything.

We were nothing before we were born and we’ll be nothing again after we’re dead. The zoomed out size of the universe and length of time we aren’t around for overwhelms the blip of time we are here. This not-self follows us like a shadow throughout our life, like a chalk outline on the pavement, with every less able iteration of ourselves in between, refracted along a scale and merging back into the universe with other people’s similar layers.

A philosophical denial is just a view, a theory… it does not get one actually to examine all/ the things that one really does identify with… as ‘self’ or ‘I’, / This examination, in a calm meditative context, is what the not-self teaching aims at. It is not so much a thing to be thought about as to be done.

Finally allow ideas to percolate to the surface, don’t rush to nail down what an experience meant to you for time in perpetuity.

Authenticity – Failing to modify your behaviour to be more comprehensible

It can be annoying or hurtful for others to presume they know everything about you, but rather than assert their wrongness and make them defensive, you can acknowledge it as a common human failing and find nice creative ways to hold a mirror up to what life experiences they’ve had that lead them to jump to that conclusion.

One way is a kind of playful authenticity, telling a lie about a lie, to get back closer to the truth. So don’t outright challenge the idea, but don’t live up to it either, in fact live down to it. Playfully undermine the idea by failing to live up to the glamour of what it would mean to be that person, then find a way of revealing that it was a misunderstanding all along, so they needn’t worry about it applying to you.

The Middle Way – Failing to achieve short term gratification

Take satisfaction in starting a project with the tools at your disposal in which you have no idea whether it’ll ever be valuable to others, just that you learnt something new and that you really enjoyed the process.

There’s a quote I really like from the Tao Te Ching which explains how we can harness our higher inner character through acting with a conscious awareness about the way the universe works:

The way of heaven is like the bending of a bow.
The high is lowered, and the low is raised.
If the string is too long, it is shortened;
If there is not enough, it is made longer.

The way of heaven is to take from those who have too much
and give to those who do not have enough.
Man’s way is different.
He takes from those who do not have enough
to give to those who already have too much.

Knowledge – Failing to keep track of every piece of information

It’s great to live with people who are observant of clues as to your mindset and can offer suggestions to help you or give you the room to learn from your own mistakes where the consequences aren’t dramatic.

It’s less useful to try and acquire every piece of gossip about a person and come into interactions with funny presumptions about who they are and why they act the way they do.

Meaning – Failing to live up to expectations

Through having an accurate accounting of some of the worst possible outcomes at any moment and having a healthy way of coming to terms with that, we can truly decide if the road we want to be on us is as much ‘our choice’ as anything can be.

Compassionate comedy for the wholesomeness of peoples mistakes is one really great way of feeling comfortable in your own skin. In being able to laugh at ourselves, we can feel freer to experiment and enjoy a culture with more complex forms of expression being understood.

Vulnerability – Failing to avoid pain

Love is the feeling that you almost had no other choice than pursuing the road you’re on. It’s both a scary feeling for opening yourself up to pain and a wonderful feeling for realising a passionate interest you may not have even been aware you had. Embrace it.
Click here to buy the Anarchist's Guide to Travel!

Deleted member 28239

I closed my account
Wonderful write up, thank you for sharing. It articulates a lot of vague thoughts I've been having lately, trying to figure out the best to live in a failing state. Having "goals", like what the culture encourages, feels kinda silly right now. I've been trying to make peace with accepting a more observer-type role. Like watching things burn with a cup of a tea and knowing new growth will come after, even if I don't get to see it. And planting seeds where I can.


Jan 24, 2017
South Central Iowa
That was absolutely fantastic, thank you for sharing your thoughts and insights.

You may not be interested, but this certainly seems like great material for a book. I'm really impressed and there's a lot to unpack and think about there!



Oct 17, 2020
Lost In The World
Thought provoking and beautifully written. Thank you for your insight. I hope you don't mind if I share some of my reflections on your observations.


Power - A small minority have access to true power and influence. Due to personal and logistical limits, sharing those benefits with others is a challenge.

Both are often illusory. Artificial comparisons of whose wallet is bigger. Who knows who. Meaningful kindness without impact. Impactful kindness without meaning.

This is fine. Every bit matters. Selflessness is precious when the world is founded in selfishness.

Time – the rich have money but no time to enjoy it while the destitute have the opposite problem. Balance is a the key. Both as individuals and a society. Outcome without value means nothing at all.

The marathon engine of bureaucratic efficiency and technological development leans towards the former. And we reap the obvious benefits of modern society. But take it too far, and the reality of personal happiness is replaced with a meaningless warped parody. All that’s left is the pursuit of the next high.

Comparison is toxic by nature. We are a blink in the vastness of eternity. But we have meaning. Our meaning, given to ourselves. Bestowed upon us by others. Shared with friends and family.

Authenticity – conformity is a convenience for both you and others. By no means is it a requirement for function. The truth can be discovered through empathy and understanding. Not an easy task by any means. To see past unforgivable differences and grow something new from commonalities is costly. Painful even. But as ever, it is the only path for true growth.

Vulnerability – love is pain. The acceptance that some things in life are worth hurting for. That despite everything, it was worth it to you then and there.


Wise Sage
Nov 15, 2012
with accepting a more observer-type role. Like watching things burn with a cup of a tea and knowing new growth will come after, even if I don't get to see it. And planting seeds where I can.
This idea was huge for me in being sane more often; and less depressed/anxious on the regular.
I've always referred to myself as Jane Goodall in regards to my engagement with the world. The world can be fucked up and evil. When I was invested in humanity it always resulted in me feeling like shit. All the eastern philosophies have detachment as a tent pole toward being happy. Help where you can, let everything else roll without concern.

Comparison is toxic by nature.
This is brilliant.
We are a blink in the vastness of eternity. But we have meaning. Our meaning, given to ourselves. Bestowed upon us by others. Shared with friends and family.

Another idea that has always helped me when I am feeling blue; Universal totality?
Aint much matter that much when I consider the 5 billion? year timeline.

Vulnerability – love is pain. The acceptance that some things in life are worth hurting for. That despite everything, it was worth it to you then and there.

Love is pain bc there are so few people that can admit the impermanance of it, platonic or romantic. We need it to last forever instead of, from the start, saying "maybe I can have a good 3 or 4 year run with this person and just enjoy it". We get sad when person isnt in our life any longer.

Love is something I've never been able to quite understand.
Most of us won't admit that we "love" someone because of the way they make us feel, rather than out of admiration and appreciation for who one is. That takes years and forever.
A fisherman will say he loves fish. Then why the fuck you hunt and kill them?
It's not the fish he loves, it's the way the fish makes him feel.
This seems to be true for most of what I have seen an experienced with love.

Anyhow, I enjoyed reading everyone's thoughts.

Users who are viewing this thread

About us

  • Squat the Planet is the world's largest social network for misfit travelers. Join our community of do-it-yourself nomads and learn how to explore the world by any means necessary.

    More Info

Support StP!

Donations go towards paying our monthly server fees, adding new features to the website, and occasionally putting a burrito in Matt's mouth.

Total amount

Monthly Goals

  1. Paying the Bills
    $0.00 of $50.00
    The first $50 in donations go towards paying our monthly server fees and adding new features to the website. Once this goal is reached, we'll see about feeding Matt that burrito.
  2. Buy Matt a Beer
    $0.00 of $75.00
    Now that we have the bills paid for this month, let's give Matt a hearty thank you by buying him a drink for all the hard work he's done for StP. Hopefully this will help keep him from going insane after a long day of squishing website bugs.
  3. Feed Matt a Burrito
    $0.00 of $100.00
    Now that the bills are paid and Matt has a beer in his hand, how about showing him your love by rewarding all his hard work with a big fat burrito to put in his mouth. This will keep him alive while programming new features for the website.
  4. Finance the Shopping Cart
    $0.00 of $200.00
    Now that the bills are paid and Matt is fed, perhaps it's time to start planning for those twilight years under the bridge... if only he had that golden shopping cart all the oogles are bragging about these days.