Digital Freedom by Kieran Drew

🦷 The reason I quit dentistry to write

published17 days ago
7 min read

Welcome to this week’s Creator’s Corner. Your questions are my ammunition. So here’s what I’m firing at you today:

  1. How I’d build a newsletter business if I had to start again (without coaching)
  2. The 4 buckets of storytelling you need in your content
  3. Why I quit dentistry to write online

Let’s dive in.


Miranda Trevino asked:

I’ll start with the caveat that coaching and consulting are great entry points to the newsletter world.

If you want to write well, you need to understand who you write to. And there's no real substitute for live feedback.

But 1-1 work isn’t a prerequisite for a profitable newsletter.

So here’s what I’d do.

Financially, I’d let my current job fund my future business. Instead of chasing clients, I’d use that time to get good at what matters.

Writing and marketing.

A newsletter is a product. People might not pay money, but they pay with attention - and that's where the money is made. You need a magnetic message and compelling content.

You also need to decide who you serve.

A general audience requires scale to monetize. That means paid ads or a shit tonne of patience if organic.

But like they say, the riches are in the niches.

As an example, I could build a dentistry curation/news-style newsletter right now.

The industry writing is as dry as Ghandi’s flip-flop - so I’m sure I could build something pretty cool. But I wouldn't write to dental students. Hell no. They don't have money.

I’d create something for cosmetic dentists or practice owners.

If your list is small but high value, you can approach businesses that make big bucks from them. They'll happily pay more for advertising when their potential profit is huge.

When the money comes in, I'd quit my job.

But a quick point on that.

I see the advice that you should 'wait until your side hustle replaces your current income' before you quit.

Bad advice.

Why the hell would you stay on the boring ride when you've got the ticket to the theme park?

Cover your costs. Make sure the income is stable and your family is safe. Then bet on yourself.

Life's too short to 'wait' for a number on a screen.


Betty Van asked:

In my coaching program, I taught that you should focus on 3 buckets of storytelling.

  1. Your core topic
  2. Building an audience
  3. Your general life experience

There’s also a 4th bucket if you don't have much to say. Let's discuss those 3 first.

Your core topic is why people invest in you. These are your results, realizations, and current projects. For me, that’s about writing well and building my business.

Audience-building is for growth. If you’re building a following, a great way to speed up the result is to share it. I’m not suggesting you teach audience building once you've built an audience. We have enough of that malarkey as it is (guilty). But people will pay attention when you share your milestones and what building an audience means to you.

Your general life experiences put the person in personal branding. They let you share mindset advice without sounding like a braindead drone (Kieran chose violence today).

And if you struggle with all three?


Be a curious explorer. Deconstruct other people’s success. This way you build authority by association, giving you the perfect platform to springboard your brand.

Dickie Bush is a prime example.


Ohh Ok asked:

Dentistry has a lot of positives. But just because a career is good, doesn’t make it right for you. So let me explain what I enjoyed, what I didn’t, and why writing was worth starting again from scratch.

First, I loved helping people.

Most of my patients were in pain or hated their smile. Fixing that felt amazing.

I also met 20-30 people a day for almost 5 years. They generally don't like you when they walk in (except the occasional weird one who enjoys the dentist). That was a great forcing function to learn communication, sales, and relationship building.

But it was also stressful as hell.

There wasn’t a day I didn’t finish exhausted. That’s partly my fault due to the long hours I worked.

But it’s also the profession itself.

You’re hunched over a mouth all day (no bueno when your neck is held together by metal), your customers don’t want to be there, and there’s always the looming threat of litigation.

Ultimately, it’s not a bad job.

To some of my friends, it’s a great job.

But it wasn’t for me. The juice wasn’t worth the squeeze.

… Which is where writing comes in.

My girlfriend thinks I live a boring life, but I've never felt more energised by the daily repetition of crafting, teaching, and studying.

I hated the fact I didn't feel fulfilled at work.

I dreamt of a creative skill I could make my career. Plus I read all the time and that knowledge felt wasted as a dentist. I’m not gonna discuss Aristotle with a man bleeding profusely from their gums.

Even before I monetized, writing changed my life.

No habit will improve the way you think more than sharing ideas every day.

The fact I get paid for it now is just icing on the cake.

Like Seinfield once said, “your blessing in life is when you find the torture you’re comfortable with.”

Don’t settle until you’re obsessed.

On Friday

We’re going to take a look at my first monthly business breakdown.

You’ll see my revenue from February (I made a loss), audience growth (it’s down), and why both those points are irrelevant - it’s been my favourite month yet.

Keep writing your way to freedom,



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And if you've got a moment, I'd love to hear what you thought of this edition of Digital Freedom.

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