How to Live Life on First Principles

This post is about how to live the good life as an entrepreneur…

By using First Principles to decide how you spend your days.

But I’m going to start with a list of things that have gone wrong in my life recently.

Because – yes – Uncle Olly is also human, and s*** happens to me too.

Always has.

And I suspect it always will.

But I’ve worked hard to create a personal “operating system”, which helps to feel happy and fulfilled, no matter what’s going on around me.


If you sometimes feel unbalanced in your entrepreneurial life, I hope this will help in some way.


Tissues at the ready…

My 2024 So Far

Here’s a glimpse into my life recently:

  1. We had a major cashflow pinch at StoryLearning which was not fun (took my eye off the ball)
  2. The hedgerow outside my house collapsed, giving flat tyres to every car that passed (everyone blamed me)
  3. I received a personal tax demand that was 2X what I expected (I miscalculated)
  4. My best friend’s mother died of cancer, 3 months after being diagnosed (I didn’t even know)
  5. I need an operation on my shoulder (not major, but it’s general anaesthetic)
  6. I was hit by burnout after a period of intense work (lots of change on that front)
  7. My flying instructor needed major heart surgery and I haven’t flown for 6 months (she’s fine, luckily)
  8. The horses escaped and completely ripped up my lawn, just in time for spring (bastards)
  9. I was 4 weeks ahead of my publishing schedule here on the newsletter, and then lost it all (back to week-to-week)

That’s some of my 2024 so far.

Reason I’m telling you this is that I know I’m guilty of painting a rosy picture of life here in Hobbitshire.

It’s the influencer trap, I suppose.

And while it’s all true…

I, too, have to deal with s***.

Things Will Go Wrong

The truth is that s*** will happen in your life.

Big and small.

One day, a video refuses to upload to YouTube.

The next day, it’s cancer.

But it seems odd to me that we should call this “going wrong”.

It would be stranger to expect everything to always go right.

Anyway, there’s nothing inherently wrong with things “going wrong”. In fact, “wrong” is just meaning that we attach to events.

This can be difficult for entrepreneurs to accept, though, because our entire identities are wrapped up in the future. Our literal job description is “Create something that doesn’t exist yet!”

And let’s be real – if 90% of things don’t go wrong, you’re not doing your job properly.

If you’re counting calories, you’d have to be a robot to stick to it 365 days a year…

The day will come when you wake up tired and smash an entire kitchen full of waffles.

If you’re an entrepreneur, accepting that things go wrong is just part o’ the game.

But this can make you attached, which is unhealthy.

The truth is that stuff going wrong doesn’t matter.

Took me ages to learn this lesson.

But I’ve developed a way to deal with these emotions now. And it involves planning life from First Principles.

So that whatever mess may be unfolding in your business, you can develop a high tolerance for s***.

In fact, I might request that phrase be written on my tombstone:

“Here lies Olly Richards. Had a high tolerance for s***.”


Living Life from First Principles

Planning from First Principles means:

  • Understanding what The Good Life is for you
  • Planning around these principle
  • Bringing discipline to the plan
  • Being unattached to other stuff

In other words…

Get the big, important things right, everything else will take care of itself.

This is quite different from a to-do list.

If your week is always a big, long to-do list, you will live life with a permanent feeling of “never enough time!”

Instead, if you focus on protect the things that matter to you in life, you’ll always have a feeling of nourishment.

If the important things in your life are in order, it makes it a lot easier to ride out the ups and downs in your business.

What is The Good Life?

So what is The Good Life?

I’ll tell you what it means to me.

When I was younger, it used to be: “Do cool s***!”

Now, it’s much more about: “High quality of life day-to-day, with minimal exceptions!”

(That’s the rationale for flying business class, imho. It’s not about craving luxury, it’s about avoiding discomfort.)

Over years of experimentation, I’ve discovered there are certain practices that, if I do them, help me both:

  • be happy
  • avoid suffering

Here they are…


Things that make my life better, if I do them every single day.

  • journalling
  • meditation
  • exercise or walk
  • clean eating
  • 3 hours deep work
  • reading
  • dedicated family time


Things that make my life better if they are regularly in my life.

  • Family holidays (3-4 /yr)
  • Time with friends
  • Alone time
  • Daddy/daughter days (full days)
  • Be learning new things
  • “Me” planning time

I’ll explain a couple of these.

First, journalling.

I’ve noticed that if I journal every day for 15 minutes, it helps me get things off my chest, bring order to my thoughts, and feel less stressed.

Conversely, if I don’t journal, I notice unprocessed thoughts build up in my mind, which can lead to anxiety.

Whether or not I enjoy the act of journalling itself (I do, as it happens), I’ll do it because life is better when I do it.

So, I do it – every single day.


“Me” planning time.

Left unchecked, I’ll focus all my planning on business stuff, because it always feels urgent. This can mean that I neglect my own needs.

So, I’ve discovered that, every month or so, it’s good for me to carve out time to sit down and plan “me” stuff – alone time, days with my daughter, family holidays etc.

I don’t actually enjoy this planning very much – I’d much rather be working.

But I’ve learnt that if I don’t do it, my life eventually becomes unbalanced… all work, all the time.

So I do it.

It’s in the calendar.

Once a month on a Saturday morning.

First Principles Planning


Through trial and error, I’ve discovered that everything I mentioned above is vital.

When I do that stuff, life gets better.

When I don’t, life gets worse.

And that’s how I think about The Good Life today.

By keeping everything in balance, I find it easier to then relax and enjoy the things around me:

  • family
  • friends
  • nature
  • life

When I sit down to plan on a Sunday evening, the very first thing I do is look at the upcoming week and make sure these things are planned.

I literally enter them into my Google Calendar.

“06:30-06:45 – Journalling”


That happens before I even think about work.

Once all the important stuff is scheduled, then I’ll work through business stuff, plan that out, and fit it in whatever time’s left over.

Don’t have enough time to finish everything at work?

Who cares?

Like with everything else, as long as you’ve done the important stuff, nothing else really matters.

That’s why I have “3 hours deep work” in my daily practices list. It’s the simplest way of making sure I do good work (which I need in order to feel fulfilled).


When you plan from First Principles, it takes the pressure off.

You can have confidence you’re living your life well.

When your wider life is in alignment, work feels less critical.

It can help you detach your sense of self-worth from business outcomes.

It may also make you a better entrepreneur, because you’ll be a more balanced person.

Of course, to do all this, you have to have an idea of what The Good Life is in the first place.

And if you’re not sure…

What better time to start thinking about it?



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