When I was in school, I disliked writing. The topics of school papers were boring. Fiction writing felt forced. I was motivated to get it done as quickly as possible. Thankfully I've always typed quickly, which was a huge advantage in getting papers done on schedule. However, once I graduated, things changed.

Writing at my own motivation felt different. I enjoyed writing papers at Amazon. I enjoyed writing long rambling emails to my family about hikes I went on. It turns out that your personal excitement about topics can be hidden by a public education. Ouch.

While working at Amazon, I ended up writing some popular articles. I found I really loved the process of writing for the public. I decided that when I did end up taking a break from a corporate job, I should consider doing a newsletter. When I decided to leave Bezos Academy, I thought that was a good time to take that step.

When I started this newsletter, I spent some time researching how often people write, and how their paid and free memberships work. For better or worse, I dislike pondering decisions for a long time. I always have. This usually worked well at work, since making decisions quickly at Amazon is preferred ("Bias for action"). Occasionally I'd be seen as rash, but that's a fine tradeoff on average.

Rather than delay my newsletter start, I decided I would write two articles a week. Monday and Thursday. Writing two articles a week was a reasonable amount of work for me, and was a good volume to read. I offered a paid membership, with no benefits at first, simply an offer that people could support me. That worked fine, and I'm thankful to the great people who paid for memberships.

After I had enough paid memberships, I felt like I should do something different, so I changed my Thursday newsletters to be paid. Now I had one free, and one paid article a week. This was a pretty simple solution. I like simple solutions. It also gave a benefit to those paid members who were complimenting me with their subscriptions.

I didn't spend much time thinking about the types of content to include on paid versus free. I just continued to write articles. The articles I wrote for Thursday ended up paid, and the articles I wrote for Monday were free. No differentiation between the content; if you supported me, you could read twice as much. I've done that for the past three months the newsletter has been running.

Always be learning and changing

I've never been satisfied operating a business, I like to build and iterate. While I've been writing my articles, I've also been researching how others write, and how they handle their paid memberships.

What I wasn't satisfied with was this concept of more. If you're paying for more on something which was free, you're then paying an infinite amount more for the additional units than you paid for the first unit. Perhaps as if a restaurant offered one free glass of water, but the second glass of water costs money. I'd probably just drink my first glass for free, and then move on. Not the perfect analogy, but you get my point. Articles aren't quite the same, as the second glass of water is a different type of water than the first, but it's still yet more educational content.

In the three months I've been writing, over five thousand readers have subscribed to read my weekly free articles. This is a vote of confidence for my content that I appreciate. I'm thankful that many of those readers have also paid for memberships. It's awesome to have that type of support. I want to differentiate my paid content from my free content. I want to feel as if I'm sending something other than more to those who have supported my work.

I feel more connected with my paid members. You're often the ones who reply to my newsletters by commenting or asking questions. When I write a particularly attractive article, I see a number of you subscribe in response. I wanted to feel more connected when I was writing my content for paid members.

Hello reader! It's just like you're sitting across from me.

Education vs openness

Here's what I'm going to try. My normal articles are aimed at being educational. I write on topics I'm confident about. I communicate what I know, and my goal is that they are usually actionable for readers. I'm confident in my method of running one-on-one meetings, and I can communicate that with authority.

My intention for my paid articles going forward is to be open with my thoughts. I want these paid articles to not be authoritative, but instead I will try to be more open regarding what I'm thinking about, and how I arrived where I arrived. It may be less authoritative, but hopefully you'll know me a bit better.

It's going to be a challenge, because sharing a thought process feels to me like being vulnerable. It's easier to share from a position of strength and factual information. It's more stressful to share my opinions and thought process. It also tends to lend itself to more rambling articles rather than an organized "how to" article. Regardless, I'm going to try it out.

I'll ask you to please let me know what you think, as it's important to get feedback when you're trying something new.

My daughter complained yesterday that I was going to be unavailable today for a few hours while I was doing my writing. I explained that most adults have to be gone all day long. This surprised her. I asked if she could remember when I used to be gone all day. She only vaguely remembered. She's seven, and 2020 was a long year in a child's lifespan. So for this article, I was thinking about my position of being able to write newsletters rather than going to work. How I got to that position, and what it means to me.