This month, I crossed my 5th year as a writer.

I can’t find the exact day because I spent my first summer fumbling through attempts to get going.

But I can safely say this:

Deciding to write was the smartest decision of my life.

I’ve never worked harder or dealt with more doubt, fear, and uncertainty. But I’ve never learned more about life as a result.

And if I had to boil down my early success to one thing, it would be this:

Persistence.

Because you can overcome 99% of problems simply by refusing to stop.

So here are 5 lessons I’ve learned about playing the long game (the 5th is the most important and overlooked):

Lesson 1: Expectations are everything

When I started writing online, I devoured every podcast I could find from my favourite writers.

One truth became apparent:

There is no overnight success.

We live in a society of immediate gratification. But all good things take time, and the best things take even longer.

I knew I had a mountain to climb, especially considering I had no previous writing experience and didn’t want to write about dentistry.

So I made a pact:

I will expect results within 2 years, not 2 months.

For reference, it took me 13 months to attract 1,000 followers and 18 months to make one dollar.

The two year mark? My first $10k month.

Any project I start now, I apply the same rule. For example, I’m writing my first book. It’s tough now, but I know it’ll be 100x easier later.

If in doubt, zoom out.

Lesson 2: Change the rules to win the game

The hardest part about building online is a lack of response.

When you start creating content, no one reads.

When you launch your first offer, no one buys.

The worst thing you can do is let this stop you. It is a right of passage—the big bad boss from level 1 of the video game.

The only times I came close to quitting was when I cared too much about the result.

So I changed the rules, and based my success on three daily decisions:

• Did I commit to my craft ?
• Did I learn something new?
• Did I share a useful idea to help one person win?

You can’t control the outcome, but you can always control your output.

Lesson 3: Love the lows

The writing journey is hell. Don’t let anyone tell you otherwise. No skill challenges you more in so many domains.

I used to suffer from serious depressive slumps. I call these Writing Wobbles.

And initially, they would knock me for six.

I’d wonder what the hell I was doing waking up so early to write. Or working so hard to pursue a silly pipe dream.

The voice in my head would scream that I was wasting my time and should stick to my comfortable career.

And I would listen, letting it ruin my energy and enthuasiasm.

But with success, you can’t have the highs without the lows. They are part of the parcel, so you might as well learn to love them.

I still get Writing Wobbles today (pretty much any time I try something new).

But now I welcome them in like an old friend. They spur me on because I’m on the right path.

Like Marcus Aurelius once said, “what stands in the way becomes the way.”

Lesson 4: Stick your principles. Follow your curiosity.

The biggest challenge to success is rarely discussed, because no one wants to admit they have fallen victim to it:

Incentive drag.

Incentives are rewards or punishments that change your behaviour. And online, you will experience a constant jug of war between what you ‘should’ and ‘want’ to do.

• Social media demands you follow the algorithm.
• Business demands you try make as much money as you can.
• Marketing demands you rely on tricks and hacks to create change.

Trust me:

These are all honey traps. They might taste sweet, but the more you compromise your principles, the more you will hate yourself and your business.

And the more you become trapped with everyone else who followed the easy path.

Decide your principles and stick to them.

Don’t follow the crowd, follow your curiosity.

The path will be scarier. But fear will guide you somewhere beautiful if you have the courage to follow it.

Lesson 5: The secret to success is courage

The older I get, the more I realise focus is the ultimate game of life.

I don’t mean focus on the surface level, although that’s important. You can get more done with 2 hours of deep work than 8 hours of distraction.

I mean focus on a meta-level.

You can have everything you want. But the more you want, the less you get.

The mistake we make is spreading too thin, then beating the shit out ourselves to make success happen.

You know you fall into this trap if you are driven by guilt, fear, and shame.

(if you are unable to take a day off without feeling bad, you need to work less on your business and more on your mind).

The truth is we are all going to die someday. Yet we waste our short lives making stupid decisions then wonder why we’re never satisfied.

It’s because we are chasing growth for the wrong reasons.

To impress other people. To prove ourselves to our teachers, parents, and peers.

To finally ‘feel like enough’, without realising we were already enough in the first place.

I used to think the secret to a great life was discipline. But you only need to discipline yourself when you don’t trust yourself.

When you’re playing the wrong game for you.

Kieran Drew @ItsKieranDrew The best measure of intelligence is the courage to carve your own path. 1:33 PM • Jun 18, 2025 38 Retweets 299 Likes Read 92 replies

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True focus is about having the courage to carve your own path.

It’s about saying no when the crowd says yes.

It’s about finding work that feels like play and protecting it ruthlessly.

Not for money or fame or applause. But for the joy of the pursuit. For the creation of beauty. For a life of mastery and meaning.

This isn’t easy.

In fact, it’s the hardest thing you’ll do. Because we live in a sophisticated system that punishes the free.

A free mind has space to think, and thinking is dangerous.

So as you start to succeed, the temptation to ‘be a winner’ in society becomes more alluring.

Most people don’t end up free. They end up with prettier bars for their prison.

I’d hate to look back at my life and realise I made the same mistake.

Success is not how good you look. It’s how good you feel.

Play the game well, time is all we have.

Hope these ideas help you as much as they have me,

Kieran

P.S.

I still struggle daily with the tension between external and internal success.

But one thing I’ve found is the more I create, the more I come alive.

So I’ve decided to pursue books as my next iteration. It’s always been a dream, and I’m equal parts excited and terrified because books are one of the biggest tests of resisting short-term reward.

I’d love to write a book that has the potential to change someone’s life because many have changed my own.

So the first book I’m writing is Magnetic Writing.

It’s for you if you want to build a business on your terms, driven by your impact and ideas.

But to nail it, I need to hear from you Reader.

So would you mind filling out a brief questionnaire to let me know what you’d like to learn?

I’ll send you a free chapter once I’ve written it to a high standard.

I appreciate your attention:

​https://tally.so/r/3jAoBx​