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The Single Most Important Lesson I Learned After 9 Years as an Online Writer | RP 107

PLUS: Why you should make your entire life tax-deductible

Welcome to Rox’s Picks where I share productivity tips and business tactics to grow your online writing business — without spending $100k on an MBA.

Hey friends!

I’m back from Portugal 🇵🇹 — that’s my last planned trip of the year. I’m excited to settle back into my Toronto routine of writing, working out, and reading for the rest of the year.

The last newsletter about how I balance leisure and work struck a chord. I hear you. We want to work hard, do meaningful work… Without compromising on travelling or time with loved ones.

This is one reason why I began writing online in 2014. I wanted to leverage the Internet to achieve the financial, time, and location freedom to live the lifestyle I want.

This week, I’m continuing to dig into that. I’m sharing one of the biggest lessons I learned since I began this journey in 2014.

Here’s your 10-minute MBA for the week:

The Single Most Important Lesson I’ve Learned (After 9 Years As An Online Writer)

Not all lessons are created equal.

Some lessons are small. Little signposts to remind us of what truly matters.

But other lessons are large. Lighthouses that fundamentally change the course of our entire lives.

Over the past 9 years I've been an online writer for others and now, for myself, this lesson is one of those lighthouses:

Be a sell out

Sure, readers might unsubscribe. "Real" writers might call you a hack.

But here's why you should anyway:

Sales are a signal of valuable writing

One of the best gauges of the value of work is customer validation. Think about the writers you enjoy reading:

  • Doesn't it feel satisfying when Packy McCormick's essays answer your questions as soon as they come up?

  • Don't you feel understood to read Ramit Sethi's emails that speak to the exact problem you face?

  • Isn't it engrossing to learn new, mind-blowing ideas in an easily digestible format from Tim Urban?

… And they all “sold out”:

  • Packy started an investment fund and makes at least 6-figures from selling sponsorships to his newsletter.

  • Ramit built a 30+ person, multimillion dollar online education business from his writing.

  • From my estimates, Tim makes at least $40k per month or over $500k per year from his 2k+ Patreon subscribers.

“Sold out" is a signal for very valuable writing

Writers tend to be neurotic creatures. We don't even have to shill a product per se to feel like a sell out.

  • Paying attention to engagement metrics

  • Marketing our work

  • Promoting ourselves on Twitter

… already makes some of us feel slimy. And guilty that we’re no longer focused on The Art.

I say screw that.

If you're serious about building a writing business, becoming a full-time creator, and publishing valuable content, then…

  • Paying attention to what people engage and resonate with

  • Offering products and services

  • Learning to sell and selling out

… Are all good things.

I mean, isn't the "Sold Out" sign one of the best clues of a successful business?

Selling out lets you continue to bring value to the world

All your favourite online writers sold out because they published work people found valuable.

If your writing is so valuable that people are willing to pay for it, then you owe it to the rest of us to keep writing.

If financial constraints stop you from writing, then you’re doing the world a disservice.

In other words, building a business that let you keep writing is a service to the world.

😉 You're welcome

A selection of interesting links & fun recommendations.

That’s all for this week

Stay strong, stay kind, stay human.

Have a great weekend!

Till next week,

— roxine