Last week, I went to my first business mastermind.

I’ve written a two part series to share what I learned. Today’s the personal stuff—a 5 minute read about life and business.

Quick overview

I joined Olly Richard's 12-month mastermind.

10 education entrepreneurs (£150k-£1.5m/year) meet every few months to get feedback on our plans and problems.

Olly asked us to prepare one big question—mine was structuring an offer.

But during dinner the night before, Olly asked a killer question (he usually does!):

“What do you want your life & business to look like in 5 years?”

I woke at 2am with my mind racing.

I didn’t need to talk about an offer. I needed to think deeper—strategy, not tactics.

So here’s what I (tiredly) presented instead:

Where my business is

It’s almost 5 years since I started writing and 3.5 years since making my first dollar.

The results:

• $1,202,948.89 total revenue
• 92% from products (2 big products and a library of smaller ones)
• 80% margins

In a month, I’ll release my third product, Productize Your Knowledge, sharing how to package your expertise into a high-leverage asset.

This would complete my original ‘plan’ of 3 quality assets.

I had a clear vision of what was next.

…Until recently.

A change in plan

I’m here to write. I love it. Every second is a genuine joy and in my completely unbiased opinion, it is the best skill in the world.

Kieran Drew @ItsKieranDrew If someone offered me $10,000,000 but I could never write again, the first thing I’d write is a ‘no thank you’ letter. 7:0 PM • May 20, 2025 2 Retweets 95 Likes Read 62 replies

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My dream is to write books.

I’ve got the runway and marketing ability to give it a good go now. My plan was to go full George R R Martin, 10 hours of writing a day.

No calls, no distractions.

So I was surprised when I said the next 7 words:

“I want to work closer with people.”

Previously, I’ve enjoyed having a calendar emptier than a LinkedIn influencer’s brain.

But this year, I took on two 1-1 clients for a 12 month mentorship, and 7 group coaching clients.

I worried I’d hate the commitment.

But I’ve loved it. Live teaching is fun. And I get to solve a range of problems for people I consider friends.

My writing has been much better as a result.

I’ve realised I need to be in the arena—kicking ass with you. Not on the sidelines with a quill up my arse.

So the question I asked:

How can I build a business where I spend most of my time writing and creating content, with an offer that’s streamlined so I can support & serve my fans?

Because right now, I feel spread thinner than my rapidly receding hair.

I know some people thrive on chaos, but I crave simplicity.

The options

The great part about presenting is that you see your business from an outside perspective.

We discussed two options (and stumbled across a critical blindspot).

Option 1: Create a coaching program

This was the bulk of the chat. I could:

• Run a cohort
• Relaunch the 1-1
• Run a group coaching program

And make this my ‘primary offer’.

I don’t want a community. I’m an introvert so I prefer intimate contact (in my business, I’m not getting any in my personal life 🙂 ).

But as we spoke, several people highlighted an option I didn’t consider:

Option 2: You’re there

I don’t have a money target. If I can pay my bills, travel the world, create content, and write books: I’m a happy man (understandably).

The group asked:

Why don’t you?

In July, I’ll have 3 great products. I have clients I’m working with already. What happens if you take a swing at just go for the book—promoting what you’ve built and accepting slower business growth?

And then I felt it:

Fear.

Fear of not making enough, fear of falling behind, (fear of getting what you want?)

My reply exposed a blindspot.

The fallacy of ‘complete’

I stumbled through some answers and said that ‘once my high ticket was streamlined’ I could focus on the dream.

Olly called me out.

He said that I say this stuff often (he’s spent almost 2 years as my coach/therapist).

And he’s right.

I’m always chasing the horizon. Always waiting for permission.

I say stuff like:

Once I’ve finished this product, I’ll go hard on the book.

Once I’ve made enough money, I can focus on writing with more meaning.

The irony?

There is no ‘once’.

I heard Joe Hudson discuss this with Ali Abdaal recently. This language implies faulty wiring:

You believe you are not OK until you hit an imaginary, and constantly moving, milestone.

Which is f**ked up, because I’m living dentist-Kieran’s wet dream right now.

The problem?

Success becomes a chase, not a journey. A struggle, not a joy.

But you perform at your best when you feel at your best.

This only happens when you give yourself permission to go for it, without fear.

So here’s what I agreed with the group:

After Productize Your Knowledge, I’ll increase my book writing time from (pretty much) zero to at least 3 hours a day.

That window becomes sacred—untouchable.

Then I’ll take some time to figure out how I can serve you best.

Because you don’t need to rush from decision to decision. Speed is sexy, but only if you run in the right direction.

Our next mastermind is in September, I’ll have at least the first draft of Digital Freedom done.

Regardless, I know my overall strategy:

1. Do interesting things and share everything I learn
2. Overdeliver at every opportunity (I’m starting YouTube in July and plan on giving away as much as I can—really excited)
3. Write the books I wish existed
4. Enjoy myself along the way

It feels good, it feels exciting, it feels right.

Hope these musings of a madman help. Kieran

P.S.

Would love to hear your thoughts.

If anything struck you, or you have any idea/resources I might find useful, please fire away.

Would highly recommend jumping on Olly Richard’s newsletter. He’s a wealth of knowledge for people in our space.

See you on Saturday for part 2.