Rolling a boulder over a hill

MountainHere’s my thesis: building a life of freedom and autonomy is like rolling a heavy boulder over an inverted parabolic hill while the villagers gather around laughing at you. That obviously sounds crazy but do bear with me as I meander towards the point!

I’ll start with a couple of observations.

Observation 1

First, life is usually hard in some way. You can have a large influence over exactly what specific challenges you’ll come up against, but there isn’t a magic way of making life easy. Learning to accept this fact was probably the single biggest personal development leap I ever made.

For example, if you had 10 million pounds, assuming you made reasonably sensible decisions, you’d be set for life (financially) but it wouldn’t ‘complete’ you. There would be no chorus of singing angels or sense of permanent fulfillment. Maybe you wouldn’t be able to think of what to do next. Perhaps you’d attract a load of shallow, money-grabbing friends who only wanted you for your wealth. Who knows? The grass would not be as green as you think it would.

In my experience, there will always be a new difficulty to contend with when the one that currently holds your attention has been squashed. This persistent dissatisfaction is part of what is commonly referred to as ‘the human condition’. It’s what drives us to make things better. It’s why the scientific, technological and economic advances of the last 10,000 years have happened.

Observation 2

My next observation is that anything which is worth having is worth working hard (and sometimes suffering) for. This is a cliche but it’s really important to illustrate the main point of this article.

Some examples from my experience:

  • I would not have had an 11 year long relationship with my wife without many hundreds of arguments, disagreements, debates and compromises.
  • I wouldn’t have the career which has played such a big part in my quest for freedom without forgoing a lot of income and free time for several years in my 20s whilst I got my degree and built my skills.
  • I’m a healthy weight and in reasonably good shape, but in order to keep myself that way, I get up really early in the morning and go to the gym. I park my car far enough away from the office that it forces me to walk 2.5 miles every time I go to work. Most of the time, if other people are handing out sugary snacks, I politely decline. Forming these habits took effort and self-control.

Now put those two things together: life is inevitably hard and you need to work hard to get anything that’s worth having. Remember those observations for later.

OK. Now I’m going to talk about boulders.

Meet Steve

Spare a thought for this guy, let’s call him Steve (forgive my non-existent artistic skills).


Steve has decided that life is shit on Side A of the hill. He’s pretty sure that things would be a lot more pleasant if he was on Side B. Unfortunately, he has to take the boulder with him (don’t ask me why – that’s just the way it is). There’s absolutely no way he can get to Side B without getting the boulder there too.

Now, Steve has a choice to make. Is it worth his effort to roll the boulder over the hill? Would the pain be worth it? Would it not just be even worse than the perpetual shitness he has come to expect inhabiting Side A?

I think that to answer that question in full, it’s useful to divide his gargantuan task into phases.

Phase 1- Starting

Phase1At the very beginning of the task, Steve really feels like the universe is against him. The boulder is heavy and standing completely still. Not only must he get it moving, but he also needs to immediately start fighting gravity and the friction between the boulder and the ground as he pushes the giant body up the steepest part of the slope. Steve’s not had much practice at pushing the boulder yet so his technique is inefficient. He keeps making mistakes and the boulder occasionally rolls back down the hill a little bit.

This is the hardest thing Steve has ever done and he is starting to regret the amount of pain he’s subjecting himself to. Is Side B really all that great? Sure, Side A has been slowly destroying his soul but perhaps this pain is even worse! Maybe he should just resign to living (and eventually dying) on Side A.

People have gathered at the foot of the hill on Side A and they’re laughing at Steve. They’re incredulous. What a loser. Why would he do this to himself? Steve could make the pain  stop immediately by just letting the big rock roll back down to its original resting place. After all, none of the people in the crowd are stupid enough to be messing around trying to change things.

Most people give in during Phase 1 of this type of challenge. But what if Steve won’t give in?

Phase 2 – Building Momentum and Skill

Phase2After a while, Steve figures out a better technique for pushing the boulder. He’s managed to keep it moving at a fairly steady pace for a while. With every step he takes, the slope becomes shallower. Gravity is still his enemy but it has nothing like the same effect as it did when he started.

Steve feels like he’s making some progress. Don’t get me wrong, he’s really tired but he feels like he might be able to achieve his goal if he can just persist. Whereas when he started he was genuinely unsure whether or not he was physically capable of the task at hand, now he knows that it’s really just a question of his own willpower.

The crowd at the foot of the hill are now divided. There are still plenty of naysayers but a few of them have realised that it’s not completely out of the question that Steve will succeed.

Phase 3 – The Brow Of The Hill

Phase3As Steve nears the summit, he starts to feel distinctly satisfied.

The boulder is rolling at quite a rate and he’s really improved his skill in pushing it. If he could have started the task with his current level of skill, the earlier phases would have been much simpler.

Steve’s nearly at the point where gravity will become his ally. He knows that if he gives the boulder enough of a push over the top, he can rely on gravity and the momentum he’s already built to get the boulder to its destination.

The most vocal members of the gathered mob have started to talk about something else (they want to distract their friends from the fact that Steve is probably going to prove them wrong). A couple of them have been watching Steve’s technique and taking notes. They surreptitiously slip back to their garages to get their own boulders.

Phase 4 – Momentum + Skill + Gravity

Phase4Now Steve is really flying. Even if he stopped pushing completely, the boulder’s momentum and gravity would get it a reasonable way down towards Side B. Steve can afford to just push occasionally and rest for the remainder of the time. When he pushes, he does so skillfully and efficiently. A small push has a massive effect.

The naysayers are out of Steve’s earshot. They’ve moved on to criticising the few breakaway members of the original group of mockers who are now trying to follow in Steve’s footsteps.

Steve’s task is all but complete. He feels totally vindicated in his choice to endure the pain of the earlier phases to get into what he knew all along was a better situation.

The Villagers

Steve was right and the naysayers got it wrong. However, they can be forgiven.

In my experience, many (most?) people have the following qualities

  • They are conformists. They are unable/afraid to think independently.
  • They are good at following recipes but bad at properly weighing costs against benefits.
  • They are bad at deferring gratification.

The villagers made a very common mistake. Members of the heckling mob focussed on the difficulty of Phase 1 and had no foresight for Phase 4 (or being on Side B). If Steve’s original calculation had been

Which is worse – staying on Side A or remaining perpetually in Phase 1 of the boulder rolling task?

then obviously he would be well advised to stay on Side A. However, it wasn’t. In fact, Steve was considering reality to be something like this:

Remaining on Side A has a high cost because I’m miserable. The first bit of the journey to Side B has an even higher cost than staying where I am. However, averaged out over time, the cost of enduring the journey to Side B is more than outweighed by the cost of staying on Side A. Side B also has benefits which I could never even have dreamt of on Side A.

Steve was able to think for himself, ignore the ‘common wisdom’/heckling and properly perform a cost-benefit analysis.

Back to reality

I think that the analogy is pretty thin so I’m sure you can relate my story about Steve and the boulder to the process of building a life of freedom without me filling in too many blanks.

When I was in the early phases of my transition towards a life of greater freedom and autonomy, I sometimes got into bed after a full day at the office followed by a 4 hour stint of client work and wondered why the fuck I was doing this to myself.

The boulder was heavy. The hill was really steep. I hadn’t even pushed into profitability yet. I was shit at marketing. I was a professional engineer who refused to pay £4 for a sandwich at lunchtime. People actually laughed at me. The collective opinion was that I was crazy.

But I knew that eventually gravity and momentum would take over if I just kept pushing.

Fast forward a few years to now. My professional skills and cash stash are my momentum. My network, entrepreneurial skills and investment income are my gravity. If I knew at the start what I know now, I’d have built the life that I wanted much quicker. But I didn’t know – so I had to stumble around whilst I learned to push the boulder.

Remember, life is never easy

Which brings me back to my earlier observations. You don’t have a choice whether life is going to be hard or not – it just will be, in some way or another. Sticking to a situation with which you’re familiar to avoid trying something brave is hard. It’s a long, grinding monotonous kind of hard rather than a short, sharp poke in the eye, but it’s hard nonetheless. Staying in the 9-5 you hate because you think that getting out will be too hard is a logical mistake. It’s hard to live a life of misery.

Be Steve. Pick the right kind of hard.

See the start of your journey out of the rat race in its true light. You will have to summon superhuman strength to get the boulder moving up the biggest hill you’ve ever seen. If you’re starting with no savings, have debt, or a low income or loads of kids, your boulder might be bigger and your hill might be steeper than mine was.

But please, please respect the one single, finite life that you have and start the change soon. Stumble around incompetently whilst you learn (maybe even get some help), feel like a fool when you get it wrong, but whatever you do, ignore the villagers!


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[Image “Cartoon Character Hamster Exercise” courtesy of saphatthachat at]

6 thoughts on “Rolling a boulder over a hill

  1. Great analogy, Love it!

    Ignore the villagers! Be Steve! 🙂

    I think I accepted reality around the age of 30 and knuckled down to some hard work to get a few promotions at work. The boulder was large in those days! But I’m glad I did that before we decided to have a kid. I guess I’m in stage 2 still but things already a seem a lot easier. Looking forward to reaching the brow of the hill in a few years time.

    1. Cheers TFS.

      Steve will be making another appearance in the not too distant future so watch this space.

      My leap was pretty much parallel to what David Cain described in An Interview With The Man. Instead of the evil ‘them’ versus the oppressed ‘us’ I started thinking win-win. My boulder became a lot easier to move once it was possible to meet The Man on equal terms (by having a reasonable stash and other income sources).

      You’re crazy. You’re in stage 3 and you’re a little bit of freelancing experience away from stage 4! Feel free to disagree.

      Thanks for the comment.

  2. Resonates well with me, I love the analogy and this is inspiring. I’m probably getting close to the top of the hill, I’m at a point where I would actually have to fight back for the boulder to not get to side B now. Just wishing it was getting there a bit faster 🙂

    1. Thanks Stockbeard!

      It depends on what your hill is I suppose. If it’s total FI, it will be many years before I get anywhere near the top. I just cheated and changed which hill to push the boulder over from ‘financially free forever’ to ‘I get to do what I want most of the time anyway (and will still be wealthy eventually)’.

      Looking at it like that, it sounds like, in my world, you’re already free now (if you want to be). On the other hand, you’re so close to ‘proper’ FI that you might as well carry on pushing.

  3. Hi Andy,

    Love the analogy, as well as the drawings – dont put yourself down, your artistic talents are still far better than mine 🙂
    You are spot on though, the first part and getting the inertia is always the hardest, and so many people give up. I’ve seen it said before, but us humans are not naturally geared to think 5 or 10 or more years ahead, so just focus on Phase 1. I do however think that if you enjoy the challenge when you setup your own business (I did, although I am working for The Man again), then it really doesnt feel like hard work, it feels great fun (or maybe I am really just rather odd…)
    Looking forward to reading the rest of the blog and catching up – Ill be cheering for Steve throughout 🙂
    London Rob

    1. Cheers Rob.

      I don’t think I’m going to include ‘professional artist’ in my big list of possible side-hustles! 🙂

      I get what you mean about loving the process of setting up your business. I enjoy turning ‘nothing’ into ‘something’ as it’s really rewarding.

      However, there’s a big difference between my approach to being creative with the aim of making money and me being creative because I enjoy it. My freelancing/business ventures do give me a lot of satisfaction, but to a great degree, they are a means to an end: giving me lots of free time to do the other things I enjoy (e.g. creativity with no financial incentives).

      I hope you enjoy the rest of the blog. Thanks for dropping by.

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