I'm writing about something different today! This'll be interesting. I'd love feedback on what you think about this topic. I won't write regularly on this, but for an occasional random article? I hope everyone is comfortable with me straying away from my core business occasionally. This one ended up on the long side too. I got a bit carried away. It was fun to write!

Tech layoffs are in the news everywhere. I've complained about them on LinkedIn, more than once, and talked to past co-workers about them.

I have always gotten questions about how to interview better, or get promoted, or move into management. But what am I asked the most often? Particularly lately with these layoffs?

  • "How do you come up with your ideas?"
  • "What do you use to send your newsletter?"
  • "How do you find new subscribers?"
  • "What would it take to start my own coaching / newsletter business?"

I understand the curiosity. Having worked at a 9-5 job for my entire career, the idea of leaving work and doing a newsletter or coaching for a career was a completely foreign concept.

Every time someone asks me where I work, and I say "I work for myself", people's eyes light up. A dozen rapid fire questions, since I think everyone loves the idea of having themselves as a boss.

There are thousands of fluff articles in the world explaining how to be a creator or influencer, how to do clickbait marketing, or SEO.

There are very few tactical and practical guides out there to get started on the move from 9-5 employee to independent newsletter author / coach.

I decided I should make one.

Who are you, and why do you think you know this stuff?

I spent years at a variety of companies (mostly Amazon) as a senior tech leader.

Around 1.5 years ago, I left my CTO position at Bezos Academy, and decided that I'd pursue my writing hobby. A newsletter felt like a good place to start.

Fast-forward 1.5 years, and I'm making a (growing) decent income from my newsletter (some articles here will describe the results at some level of detail). Not Amazon Director income, but a healthy amount of money. I've additionally been doing hourly coaching, which has augmented the money I'm making. Considering I'm not trying to maximize my income, it feels like things are going well.

I'm also the type of person who tests things, and doesn't believe everything I read. This means that I have some practical results from interesting experiments to back up my recommendations.

Great! Can anyone do this?

Probably no. I think there are three major ingredients to doing what I'm doing.

  1. Writing skill

You need to be a decent writer to write for a living. This feels like an obvious conclusion, but I've read some aspiring newsletters which suggest that poor writers do try to become newsletter authors.

It's not just about your ability to string together sentences. It's about your ability to organize information (see how I'm using headlines somewhat logically?), and present that information in a way that's easy to read.

How can you build this skill? I don't know. Lots of practice. Lots of feedback. Probably genetics.

If you're poor at writing, you could certainly consider making short/long form videos, audio content, etc. Writing is not the only way to succeed.

2. Valuable work experience

I've seen (many) coaches on LinkedIn with 2 years of work experience, and then they become career coaches or newsletter authors.

Without serious work experience, it's entirely possible that you can provide value to people by being a sounding board. Perhaps you are brilliant, and you're able to provide logical recommendations without practical experience. I just think the chances are low.

Being successful as a business content creator usually requires that you had success in the space you're talking about. People will listen to your management advice if you've managed a lot. People will listen to your interviewing advice if you've interviewed a lot.

How can you build this experience? Well, that one is obvious. Get a job. Make a startup. Invest the work.

I think being a business content creator is really like collecting dividends from the investments of your career. If you've invested a lot of time into something, you can collect those dividends by creating content on them.

3. Savings or other means to support yourself

You won't make money immediately, and if you're ever successful, your income will take time to ramp up. You need to have a very long runway (or very, very, very minimal expenses) to make this work.

What are the components to doing this successfully?

I'll break this down into the following list:

  1. Topic - A relatively specific topic that you have competency with.
  2. Tools - Tools for the newsletter, coaching, and social media.
  3. Writing content - Regular content generated for your newsletter.
  4. Marketing content - Shorter regular content for social media marketing.
  5. Coaching approach - How to approach your coaching relationships, if you're going to pursue coaching.

I'll walk through the above sections and give concrete advice on how to proceed.

What am I not covering in this guide?

  1. Taxes. If you're in the US, you'll need to pay taxes on your income. Read about paying quarterly taxes. It doesn't seem too hard.
  2. Things I forget. It's possible I forgot to talk about something. Like when you go on vacation, and forget your toothbrush. I hope whatever I forgot isn't too important.

What's your topic?

This isn't just a topic for your newsletter. It's the topic for your social media and coaching as well. Your customers need to know what you represent as your personal brand.

Large enough

This topic needs to resonate with a large enough set of customers to provide an income. So if you write a newsletter for rare frog collecting, it might be interesting, but your target addressable market (TAM) is awfully small.

I write on leadership, career advice, management, and interviewing at tech companies. It's a broad topic with a large audience.

Specific enough

Your topic has to be specific because unless you're super famous like Tim Ferriss, you can't write about everything. Why?

  • Because people follow famous people to hear whatever they have to say.
  • Because people follow normal people to hear about the topic that person is an expert on.

The topics I write on are probably too broad. If I wanted to be more successful, I would likely narrow down my focus to just interviewing, or just management, or just tech company career advice. I'm pretty sure most customers are only interested in a subset of my topics, which makes it less likely that they'll want to stay subscribed. That's ok. Just letting you all know that I'm not optimized here.

Valuable enough

This is a super tough one! What are some of the highest revenue newsletters? Investing newsletters. Why? Because if I'm investing $500k of my money, I wouldn't blink if someone said I needed to pay them $350 per month for good tips.

Many people write newsletters on horror fiction, restaurant reviews in their city, or local political events. Perhaps they're interesting to read. Perhaps I'd subscribe for free. But are any of those topics worth a recurring subscription to me? Can I attribute any value to that sub? The only reason I'd pay recurring money is if they're incredibly better written than any free source out there.

The topics I write on all have the potential to either get you a job at a big tech company, or make you more successful (leading to a promotion, not getting fired, etc). This is the one area where I have a huge advantage over many newsletters. Tech industry leadership is highly valuable. I completely believe that the monthly fee I charge is pennies compared to the potential value received.

What tools should you use?

This is the part we all have fun with. Who doesn't love researching new tools to play with?

Try not to build a hobby of tool researching. What you need to do is find good enough tools, and then start the hard slog of writing regularly. I'll walk through the tools I use, and you can decide if that's good enough for you to start.

This post is for paying subscribers only

Sign up now and upgrade your account to read the post and get access to the full library of posts for paying subscribers only.

Sign up now Already have an account? Sign in