A few years ago I realised that I’d got myself into the most almighty rut.

I was single. My social life revolved around the same small group of friends. We did the same thing every week, more or less. Went to the same places. Had the same conversations. Probably had the same thoughts.

The formula had served us well for a number of years, so why change it?
Why? Because I was BORED!

I wanted to meet new people. Do new things. Have new thoughts. Maybe get a new relationship. Have holidays in different places.

I yearned for change. But I also didn’t want to abandon my friends. These were good people. I still liked them. They accepted me for me.

But the reality was - they were holding me back.

Something had to change.

Word of the Week: Comfort

Nice word, comfort.

We all want it. It implies something warm and familiar and safe.

But comfort, would you believe, has a dark side too.

Comfort is the place where ambition goes to die.

Nobody wakes up one morning and decides to abandon their dreams. More often, they gradually exchange challenge for comfort. They spend time with people who reassure them that their current situation is perfectly fine. Their frustrations become jokes. Their disappointments become personality traits.

And before they know it, ten years have passed.

Cliché of the Week: “Your friends accept you for who you are.”

Which goes a long way towards why they’re your friends. But should they?

The modern world worships acceptance. We are constantly told to accept ourselves exactly as we are. ‘You do you!’ as the muppet influencers say.

Yet every meaningful achievement begins with rejecting something about your current situation.

You don’t lose weight because you accepted your fitness.

You don’t change careers because you accepted your work.

You don’t improve your relationships because you accepted how you communicate.

The best influences in your life don’t simply accept you. They challenge you.

They ask difficult questions. They expect more from you. They make excuses harder to believe.

Question of the Week: ‘Are My Friends Holding Me Back?’

As always, let’s run it through the Long Truth Method and put some helpful definitions onto this statement.

1. The Short Truth

My friends are holding me back.

OK, that might be how it feels. But you’ve made some big assumptions there.

Let’s start off by finding out what it is they’re holding you back from.

And having done so, let’s try to find out whether they are, in fact, the cause of you being held back.

And if they are, let’s consider just what you can do about it.

2. The Structural Truth

OK, so they’re holding you back. Holding you back from what?

• More money?

• A better relationship?

• Starting a business?

• Writing a book?

If you can’t define the destination, you can’t identify the obstacle. You need to be way more specific about what you wish was different in your life. Then you can look again at the role your friends might be playing in (unintentionally) keeping you back from that target. If, indeed, they really are.

3. The Personal Truth

The reality is, your friends don’t control your choices.

You choose who you spend time with. You choose what advice you listen to. Ultimately, you choose whether to stay where you are - or change.

And this is the crucial bit.

4. The Long Truth

Most friendships are not malicious. Your friends aren’t secretly plotting your failure. But people do naturally protect the status quo.

How many times did a so-called good friend plant negative thoughts about your new partner, claiming to be ‘just looking out for you’? Only later, on reflection, did you suspect that all along there wasn’t really a problem. They just didn’t want to be the one left on the shelf, without a drinking mate to hang out with.

Most people have what we call Tall Poppy Syndrome. They don’t want to see their contemporaries thrive - in a career, a relationship, or just life in general - if it means they get left behind. So they snip away at the growing friend. Plant seeds of doubt. Question if it’s the right choice. They reinforce the status quo option, in the hope of keeping you back to stay at their level.

Because let’s face it, what happens if you do change? That forces them to think about changing too. That’s uncomfortable. So they may discourage your risks, mock your ambitions, or remind you to “be realistic.”

5. The Long Solution

Stop assuming that your friends are always your best source of advice. Especially where change is concerned.

Start asking whether your friendships are helping you become the person you want to be.

You don’t necessarily need new friends. But you may need different conversations. Different expectations. Different standards.

And perhaps less time seeking approval or endorsement from people who have no intention of following the path you’re trying to walk.

Final Thought

One of the great anomalies of modern life is that we should carefully choose our careers, our partners, our homes and our investments—but never question our friendships.

Why not?

Choose accordingly, my friend!

Leave a comment

Most people don’t hate their jobs.

Not hate in the sense that they’d like to burn the place down, sitting in the car park, laughing manically.

What they hate is talking and thinking about their jobs.

They hate Monday mornings. Endless meetings. Performance reviews. They hate it when some wanker in HR says the word “journey” and doesn’t go anywhere.

They hate all that. But not enough to do anything about it.

Instead, they spend years trapped in a strange no-man’s-land between misery and comfort. Too unhappy to enjoy it. Too comfortable to change it.

Welcome to modern work.

Subscribe now

Word of the Week: Potential

Potential is one of the most dangerous words in the English language.

It’s probably the most positive-sounding word we can use that doesn’t involve actually accomplishing anything.

It sounds hopeful. It’s the sound of success waiting to happen. It’s that feeling of expectation when you get a penalty in the last minute of the game, just before your striker fires it over the bar and into the car park.

A frightening number of people spend their entire lives living on potential.

Potential is all about ‘One day.’ The promotion they’ll go for. The business they’ll start. Eventually. When the time is right.

Potential is just procrastination waving a motivational quote.

Cliché of the Week: “Better the devil you know.”

This phrase has ruined more lives than actual devils.

People say it whenever they’re scared of change.

Bad relationship? Better the devil you know.

Terrible boss? Better the devil you know.

Soul-destroying job? Better the devil you know.

The cliché quietly assumes the purpose of life is avoiding risk rather than creating something worthwhile.

It’s the surest way we know to die disappointed.

Question of the Week

Why am I stuck in an unfulfilling job?

Let’s put it through the Long Truth Method.

1. Short Truth

“My job is unfulfilling.”

Fair enough. But that’s a description, not an explanation.

Saying your job is unfulfilling is like saying your car won’t start.

You’ve identified the symptom. Not the cause.

2. Structural Truth

What exactly is wrong with it?

• The pay?

• The people?

• The work itself?

• The lack of challenge?

• The lack of meaning?

• The lack of progress?

Most people throw all these problems into one giant bucket labelled “my job”.

Then they wonder why they can’t fix it.

If your definition is vague, your solution will be vague.

And vague solutions produce exactly what you’d expect.

Nothing.

3. Personal Truth

Here’s the part everyone loves.

(Just kidding. Nobody likes this part.)

What are you doing to keep yourself stuck?

Not your boss.

Not the economy.

Not the government.

You.

If you take a Long Truth 1:1 session, I’m asking you to check all of these things:

• Have you stopped applying?

• Maybe you’ve convinced yourself you’re too old.

• Maybe you’ve convinced yourself you’re too young.

• Are you waiting until you feel more confident? (When do you expect that to happen?)

• Maybe you’re waiting for certainty.

• Maybe you’re waiting for permission.

The world is full of people waiting for a green light that never arrives.

4. Long Truth

Most people aren’t trapped by their jobs. They’re trapped by their identities.

You’ve spent ten years becoming “the accountant.” Or “the manager.” Or “the teacher.”

Or “the guy who’s worked here forever.”

Then one day you realise you’ve become loyal to a version of yourself you don’t even like.

Changing careers isn’t scary because of the work. It’s scary because it threatens the story you’ve built around who you are.

5. Long Solution

Forget finding your passion. Most passion advice is rubbish.

People don’t usually discover passion. They develop it.

The better question is:

What are you curious enough about to explore further?

What are you interested enough in to spend a Saturday learning more about?

What problem are you willing to struggle with?

Then do something embarrassingly small.

One conversation. One application. One hour. One experiment.

Not because it will change your life. Because it proves you’re still capable of changing direction.

That’s the muscle most people lose first.

Final Thought

The modern workplace has mastered a remarkable trick.

It convinces intelligent adults that spending forty years doing something they don’t enjoy is perfectly normal.

People call it stability. Or security. Or being realistic.

Sometimes it’s those things.

Mostly it’s just surrender.

And on that cheerful note - see you next time!

Leave a comment

One of the strangest things about money is that the amount itself doesn’t really matter. There’s no magic income number guaranteed to satisfy everyone. People on low incomes can feel financially secure, whilst people on six figures but addicted to spending will always feel cash-strapped. We tend to assume that money problems are caused by a lack of money, but it’s simply not the case.

The uncomfortable truth is that most of us just don’t know what “enough” looks like.

We know what “more” looks like. We know what “better” looks like. We know what other people have. But we rarely stop to define the point at which we’d actually be satisfied. Without that definition, you’re set to earn more every year - and still feel permanently behind.

Word of the Week: “Enough”

“Enough” is one of the most important words in the English language, and one of the least examined.

Think about how much time people spend pursuing success, money, recognition or possessions. Now think about how rarely they stop and ask themselves a simple question: how much is enough?

For many people, enough is always somewhere in the future. They tell themselves they’ll relax when they reach a certain salary, buy a certain house or hit a certain milestone. Then they get there, move the goalposts, and start the chase all over again.

The problem isn’t ambition. The problem is that without a definition of enough, every achievement feels temporary. No matter how much progress you make, the finish line remains just out of reach.

The Long Truth question is this: if you don’t know what enough looks like, how will you ever know when you’ve arrived?

Cliché of the Week: “Money can’t buy happiness.”

Really? If certainly would be nice to test that sometime!

Money can clearly buy things that make life easier. Comfort, convenience, freedom and security for a start. Who in their right mind would choose financial stress over financial stability?

But if money is certain to get you satisfaction, why do miserable rich people exist?

Satisfaction depends on comparison. If your sense of success comes from having more than the people around you, you’ll always be vulnerable to somebody with a bigger house, a newer car or a more impressive lifestyle. There will always be somebody ahead.

If the money feels enough, happiness will be possible in that part of your life. But what about the million of other ways you can be unhappy? Money doesn’t touch those.

Question of the Week: Who would I be trying to impress if nobody could see my life?

Imagine nobody knew what car you drove. Nobody knew where you went on holiday. Nobody saw your clothes, your house, your social media posts or your job title.

How many of your financial decisions would stay exactly the same?

Most of us like to think we’re completely independent thinkers, but human beings are social creatures. We take our cues from the people around us. We compare. We imitate. We compete. We signal.

There’s nothing unusual about that. The interesting question is whether we’re aware of it.

Many purchases are not really about the thing being purchased. They’re about belonging, status, identity or approval. The money leaves your bank account, but the thing you’re actually buying is often emotional rather than practical.

Spending more than you need to in order to impress others is a mug’s game. Yet so many people fall into that trap.

The Long Truth Method

Short Truth

“I’m spending money to keep up with my friends.”

Structural Truth

The first thing to notice is the phrase itself.

What exactly does “keeping up” mean? Keeping up financially? Socially?Professionally? Lifestyle-wise?

More importantly, who decided that keeping up was necessary in the first place?

The phrase contains a hidden assumption: that life is a race and your friends are the competition. Before solving the problem, it’s worth questioning whether that assumption is true.

Personal Truth

It’s easy to blame external pressure, but the harder question is what role we are playing ourselves.

What are we getting from the spending?

Perhaps it creates a sense of belonging. Or maybe it prevents feelings of embarrassment. Does it help us feel successful or accepted? Perhaps it protects us from feeling left behind.

The spending may look like a money problem on the surface, but the reward is often emotional rather than financial.

Long Truth

Most people do not spend money simply to acquire things.

They spend to acquire feelings.

The feeling of being included. Or being successful. Or being admired. Or simply not being the odd one out.

The problem is that these feelings are temporary. A purchase can create a momentary sense of status or belonging, but it rarely lasts. Soon there is another meal out, another holiday, another upgrade, another opportunity to compare yourself with someone else.

What looks like a spending problem is often a comparison problem.

Long Solution

Instead of asking how to keep up with your friends, ask a different question: what kind of life am I actually trying to build?

The answer may have very little to do with what your friends are doing.

Define what enough means for you. Define what success means for you. Define what financial security means for you.

Once those definitions become clear, many spending decisions become easier. You stop asking whether a purchase helps you keep up, and start asking whether it helps you move towards the life you’ve chosen.

The two questions often lead to very different answers.

Final Thought

One of the most expensive assumptions people make is that everybody else is paying close attention to their lives.

Most people aren’t.

They’re too busy worrying about their own finances, their own careers and their own insecurities.

That means a surprising amount of spending is performed for an audience that isn’t really watching.

The Long Truth isn’t that you’ll never have enough money.

It’s that you’ll never feel like you have enough money until you’ve decided what enough actually means.

Ever noticed how some arguments seem to come back like a bad sequel?

You think you’ve dealt with them. You think you’ve won them. You might even think you’ve resolved them. Then three weeks later, there they are again, sitting on your sofa and helping themselves to your biscuits.

The problem is often not that the argument hasn’t been solved. It’s that it hasn’t been defined properly.

This week’s theme is simple: Define your argument better.

Word of the Week

Definition

A definition tells us what something is. But it also tells us what it isn’t. That’s why definitions matter so much.

Take the word success.

Is success making lots of money? Having freedom? Being respected? Having time for your family? Doing something you enjoy? Not having to answer emails at 11pm?

There’s no one correct answer.

But if you don’t know which definition you’re working with, you can spend years chasing someone else’s version.

The same thing happens with words like ambition, freedom, respect, happiness, failure, confidence and love.

Big abstract words. Small definitions.

“You don’t have any ambition!” usually means, “You don’t have the same ambitions as me.” It’s not fair, and it won’t do.

Take the time to agree on the definitions and maybe the argument never happens.

Cliché of the Week

“Let’s agree to disagree.”

Sometimes it feels like the only way to end a cyclical argument that’s spiralled out of control.

But it’s really just the coward’s way out. That argument is now parked, waiting to re-emerge at the earliest opportunity.

How about let’s not agree to disagree? How about let’s agree to think about this and come back to it when we’ve got a clear head and a bit of perspective?

Cliches are empty expressions. Placeholders where original thought should be.

If you must say ‘let’s agree to disagree’, at least inject some honesty into it and say, “Let’s agree to disagree for now, like the big, uninformed procrastinators we are. We’ll do better with this next time.”

Question of the Week

What problem am I actually trying to solve?

Probably one of the most useful questions I know. Because your first stab at defining a problem is often just the headline.

A business owner says:

“I need more customers.”

Maybe. Or maybe they need better pricing. Or better retention. Or a better product.

Or fewer customers who never pay on time.

A student says:

“I’m bad at exams.”

Perhaps. Or are they just bad at revision. Or planning. Or sleep.

Or good at messing about on TikTok when they should be working.

The first description of a problem is often like clickbait. Catchy. But incomplete.

The Long Truth starts when we get specific. And honest.

The Long Truth Method

Short Truth

“Why do we keep having the same argument about money?”

Structural Truth

What exactly does “money” mean? Define it better.

Income? Spending? Saving? Financial risk? Control? Security?

Different people often use the same word while talking about completely different things.

Look at the context of the argument. What sparked it? That’s your definition of money for now.

Personal Truth

What part of this problem am I contributing to?

• Am I making assumptions?

• Am I avoiding difficult conversations?

• Am I expressing frustration instead of explaining my concerns?

• Have I clearly explained what I actually want?

Long Truth

The argument may not be about money at all.

One partner may be worried about security. The other may want freedom.

One may feel ignored. The other may feel controlled.

The visible argument concerns spending, but the underlying disagreement concerns values, priorities and expectations.

The word “money” becomes shorthand for a much larger conversation.

Long Solution

Stop debating the symptom. Define the problem more accurately.

Instead of:

“We keep arguing about money.”

Try:

“We’re struggling to agree on how much financial risk we’re comfortable taking.”

Or:

“We have different ideas about what financial security means.”

Or:

“We’re arguing about who should make major financial decisions.”

The more precisely the problem is defined, the easier it becomes to solve.

Final Thought

Most people spend a lot of time trying to win arguments.

The Long Truth asks a different question:

Have you defined the argument properly in the first place?

Because when the definition improves, the solution often gets a lot closer.

And sometimes the argument you thought you were having turns out not to be the argument at all.

See you next week.

Leave a comment

Every week I’ll give you a word, a cliché, and a question. I’ll also apply the Long Truth Method to a real-life problem.

Relationships, money, workplace and career, self-improvement.

Five minutes a week.

Enter your email below to register for FREE. Cancel at any time.

I can’t promise it’ll change your life, but it probably will.