3 Hard-earned Lessons From 17 Years Of Grit

Hey Guys, today’s episode is 3 lessons (hard earned lessons because I had to pay the price myself). 3 lessons on how to transform the way you approach your goals.

Expect to learn:

Why we avoid the fundamental that actually work Cal Newport’s theory of mono-tasking Accelerating success through failure

Hope you enjoy.

The Lowest Hanging Fruit

The biggest lesson you need to hear is one you’ve already thought about, accepted, had the aha moment about, deeply connected with it, had it click - and then moved on to thinking about sexier shinier objects.

Chris Williamson had this realisation that he’d already found the secret to removing the current obstacle, and he simply forgot it.

There’s a couple of sub-reasons why this happens:

• Thinking about something tricks the brain into thinking we’re doing something about it. Knowledge doesn’t mean action. In fact, I was just listening to Arthur Books -Harvard happiness researcher - PhD - writing about happiness and not putting them into practice. Practice is the art of putting knowledge to work.
• The more complex ideas have all the sex appeal.
• Because they’re novel more people talk about them as a way to say something different.
• Because your brain is in goal-seeking behaviour mode our minds are attuned to pick out relevant information that might be useful, and because we’ve heard all the usual stuff we hear the tail end distribution of conceivable valuable information. The recency bias tilts us towards remembering more recent information that’s usually easier to do and less effective.

The cycle usually goes like this: person A has a problem, that problem causes pain and person A goes out to find a solution to solve the problem. They go and speak to a wise old elder or find a book or course to start educating them on the subject. Then they find a book like the 7 habits of highly effective people, or even more basic a book on time management that teaches you 80% of the basic frameworks and skills of being productive like time-blocking. Then, spend the next decade having general declarative knowledge on how to solve their problem without applying the specific fundamentals consistently, with a volume that would be unreasonable to not see success from it.

We need novelty. It’s one of the basic human needs. But wouldn’t it be better to find it somewhere on top of applying the boring basics that work? You can play with the basics while still consistently applying them.

Because Play is one of the most potent sources of motivation. It burns clean and kicks you into having an effortless edge. That’s Jim Dethmer idea of motivational fuel. He talks about play, which is really another way of saying intrinsic motivation.

But play requires rules.

Just like creativity, play feeds off of constraints that put you in flow state.

So -

What are the basic inputs to solve your problem?

If you’re not sure - You can put them into an AI chat, read 5 articles and get a good pulse check.

The prioritise that.

I heard Jonny and Yousef from Propane Fitness riff on this topic and it really stuck with me. Results that take a long time require systems that you can set and forget.

A good system has a decade worth of mileage. You pay a price every time you switch contexts, just like you pay an attention cost when you switch tasks.

One of them said that if they had just stuck with a good training programme INSTEAD of switching back and forth between sexy specialisations - they would be way stronger than they are.

The lesson is this: you’ll get more out of choosing one way to achieve your goal. A mediocre plan executed perfectly is better than a perfect plan executed with mediocracy.

People can spend a decade trying to figure out the perfect 12 month goal, and wonder why 10 years later they only have 1 years worth of growth.

Cal Newport (and Chris Beardsley) on mono-tasking

You can’t wait for the result of achieving complementary goals so you try to work on them simultaneously.

But you can’t do that well. Or, at least I can’t

I have an email from my first mentor dated 2015 that warned me against this exact lesson. He said, look, the way you get good at something is you decide on the one skill you want the most right now, and dedicate time to it until its done. You can’t chase 2 rabbits. Pick one, chase it down, put a bow on it, and then chase the next.

Cal Newport gets mathematical about the problem in his book Deep Work, and he lays it out on a podcast episode, I’ll try and put it in the show notes.

The most compelling argument Cal has for working on fewer goals at the same time is the idea that putting in deep work towards a single goal for 6 months produces better and faster overall results that working on 6 goals at the same time for the same 3 years of total progress. Even though the time commitment is the same, you can’t focus on any one goal sufficiently enough to get compounded gains in efficiency or insight.

Now you can apply that on any time scale. Instead of getting 6 things done over a day, get 1 thing done each day for 6 days, focus on a thing a week for 6 weeks. And so on.

Story from WebDev

Then, if that wasn’t enough, I was reading in the WebDev sub-reddit the other day, and this guy is telling a story about the number of 10X developers he’s met in his career.

Now a 10X developer is someone who puts out 10 times the value of any other developer on the team. And he said he’d met no more than 7-8 10X developers in his career. And then he went to google and he met a guy who was doing a bunch of crazy technical tasks at different level of abstractions to increase the performance of the app from garbage collection, to caching, then back up to the UI component lifecycle and the CDN. And the guy said that after he’d met this guy none of the other developers he’d met were 10X and this guy was the only one.

But the lesson there is you can become incredibly skilled to the point where your productivity is 10 times the average by focusing on 1 project at a time where you can learn a new skill or new context for existing skills.

This is where you run in to problems and I’ve ran into these problems.

You’re so excited by where you want to go, and its easy to write down 2 to 3 projects that will help you to get there faster. You think that by giving them all a slot on the calendar you’ll get 3 times the amount of progress.

But the problem with shortcuts is they never truly get you there.

I realised and I’m still trying to remind myself that when I’m looking for a shortcut I set the wrong markers for success. Shitty conditions. And what I mean by that is I’ll focus on the results that are easiest to tick off on a to do list but not do the work that is required to get the stated outcome of the goal. It’s sneaky

And this becomes the main problem. The problem of being busy achieving nothing. Now here’s where I do some philosophical judo:

Fear will keep you from committing. Not committing will prevent you from embracing the fear and learning from failing forward.

It might be the case, and definitely not for everyone, but if you look back and realise you’ve had lots of different goals and you haven’t made significant progress then see if this lands with you:

The goal was always to become so busy doing nothing that you wouldn’t ever have the time to face the real challenge.

Said differently, the goals you’re working on are working perfectly, which is to prevent you from taking the call to your life’s adventure.

If that even remotely hits, I highly recommend you read or listen to The Courage to be Disliked. I read it in 2020 and I came away with a completely new perspective on why people (including myself) behave the way they do, and Adlerian Psychology which is the philosophy at the core of the book continues to be an incredibly useful tool to reflect on my own habits and actions.

So, Let’s bring this home

Not committing to your real goal will stop you from moving your life forward in exactly where you want it most. And ironically, we often struggle to move forward in the places we most want to because of how important it is - and so, because its so important it has weight, and because it has weight we move slower, with more hesitation, and procrastinate more often.

Tackling big goals head on invite the possibility of failure, and that can be hard to manage, so we place our attention somewhere else.

James Clear talks about this in his book too - the important goals become intimidating and lead to procrastination, perfectionism, or analysis paralysis - and ultimately reduce your chances of achieving the very thing you want most.

I can resonate for sure.

Which brings us back to commitment and fear.

Failing at the right projects makes you more likely to succeed, not less likely.

The process of Learning is all failure.

You’re trying something for the first time, you’re realising your current mental model is wrong, and then you find out you’re working on the wrong things because you didn’t know what you didn’t know.

I hope to be way more capable than I am now. Which means I need to learn a great deal. And because learning is all failure, I need to learn to LOVE to fail.

And actually, not working on your most important goal is also failing - its directional failure.

I’m inviting you to have a better association with failure. The people you and I want to be like, the people who have achieved similar goals to what you want?

They failed faster than everyone else, because they learnt what the needed to - in the timeframe they set.

And once you achieved your goal, 1) nobody really cares, 2) they only see the outcome, and 3) anyone who doubted you along the way were short term right but ultimately wrong.

How do you overcome the fear of starting, how do you keep it light enough to Play, and how do you make a commitment to the ONE thing?

I’ll tell you what I’ve learned: and it’s a 2 step process -

• Use the fear of regret. Regret can be a loaded term. I define regret as feedback that reorients you towards your core values. If you’re procrastinating replace the weight of your important goal with the weight of not living up to your potential.
• It works because it’s simple psychology of how our brain works - the pain of moving forward is greater than the pain of the uncomfortable comfort of NOW. You’ve got to ask yourself what’s more painful about your current chapter than the pain of moving towards the next.
• And step 2 is knowing that the pain doesn’t last forever. We assume that how we feel when we start something difficult is indicative of how we’ll feel for the entire process. It’s just not true. Making the first step is the hardest and before you know it you’re walking downhill. And then, it will start to feel easy - your confidence increases, you move the goal posts, and you go through another first step, and the cycle continues.

Last thought on this one. The best experiences in my life have been a direct consequence of “negative feelings”. So why would I shy away from them?

It’s funny. I’m recording this on the same day as running my first obstacle course race. 6 miles, 30 obstacles, and I was stupid enough to sign up for the elite squadron, which was the first like 30 people to start the race because they all wanted to set a personal record. Then there’s me. So, when I got there this morning.. I was a little jittery, the goosebumps were up, I could feel the nerves in my stomach. But, I finished the race on cloud 9. I was buzzing.

I’ve come to know, fear is the physical sensation we experience as a result of our amygdala being activated. Our brains are prehistoric. This is just a feature of our minds in the face of the unknown. And its so strong because its part of our alert system to a potential danger. But, in combination with our pre-frontal cortex and modern agentic lifestyles, fear is more a signal of personal growth.

Getting to the outcome. Voluntarily approaching the unlived but simulated path between where you are and where you want to be. Becoming your potential. Having the best year of your life. Fear is the marker of success. So, why think of fear as anything to avoid anyway?

Perhaps fear is the best measure of your progress.

--- OK.

When I was first making my notes for this episode I had 10 or so ideas, but these 3 linked together nicely. So if you liked this style of episode, let me know, maybe we can record a part 2 and 3.

As I get deeper into my 30’s I’m finding I think more and more about reinvention and change, and what lessons I keep learning over and over.

The fundamentals done exceptionally well trump the new shiny tactic. Are you consistently applying the basic inputs that lead to the output e.g. the lowest hanging fruit. Hormozi says being professional means never NOT doing the basics well. When you eliminate alternatives, what’s left is focus for the most essential actions and projects. So instead of trying to move multiple projects forward and getting buried by the administrative and cognitive overhead, chase goals singularly until completion. Don’t be directionally wrong by working perfectly on that which doesn’t matter. And when you notice hesitation and procrastination setting in, remember that failing on the right things makes you more likely to succeed - not less.

I want to end this episode by breaking the 4th wall a bit. I’ve “failed” at starting a podcast. I broke every single rule in this episode. I majored in the minors. I was doing multiple projects at the same time. And because I’ve been such a big fan of podcasts my whole adult life, the significance of starting my own got the better of me. But, here I am. Still failing forwards.

You can too.