How sending a newsletter to 9 people launched my career

So many writers and artists I speak to strive to do their work full-time — to be able to spend their days on their craft and developing an audience around it.

I was considering the moment when everything changed for me… when it became possible for me to work full-time on my own, to spend my days doing creative work that I love.

It all started by sending an email newsletter to nine people. If I hadn’t done that, I likely wouldn’t be where I am today.

Today, I want to tell you that story and reflect on how the moment that everything has — or will — change for you.

In 2005, I worked in a gray cube at an office of a large media company. In fact, I felt like I had won the lottery, I had been given a “double cube!” Instead of 8-10 hours per day being spent in 5′ x 5′ confined space, I could spend it in a 5′ x 10′ confined space!

This was before the days of social media, when it was still controversial to consider how the internet would change publishing. The concept of self-publishing was still perceived as vanity publishing — something to be looked down upon, an exercise in ego-fulfillment.

I worked with a lot of writers, and the company’s focus was still squarely on the value of print. Sure, they had websites and digital strategies, but few saw it as a viable future.

As I read article after article about the way that publishing will change because of the internet, I decided I wanted to share some of my thoughts around it with my colleagues.

I asked my boss if I could send a small email newsletter to nine of my friends in the company, and explained the focus on the content. She approved it, which was a pretty exciting milestone. Communications in the company were tightly controlled, and she was in charge of the formal company newsletter. It felt like a big step that she would approve a (dramatically) smaller one, run entirely by me.

That Friday I sent out the first newsletter to those nine people. It turns out, I would send an email newsletter every single Friday for the next 14 years as well.

One of the nine people I emailed was a lawyer for our company. He replied back that he thought I should send it to our CEO, and that he would appreciate it. I resisted. Emailing the CEO seemed like the type of thing that a guy sitting in a gray cube didn’t do. Too often, in corporate culture, you don’t raise your hand in order to stand out, you simply try to fit in.

My friend gave me an ultimatum: if I didn’t email it to the CEO, he would.

My cube was near all of the executive offices, and this was the chain of events:

  1. I asked my boss permission to forward the newsletter to the CEO. She approved.
  2. I forwarded the first newsletter to the CEO saying that it was suggested I forward it to him, and that he may appreciate it.
  3. A few minutes later, I saw the CEO walk out of his office, past my cube, and into my bosses office. He shut the door.
  4. Five minutes later he went back to his office.
  5. 30 seconds later, my phone rang, and my boss called me into her office.
  6. When I arrived, she asked me to close the door and sit down.

At this point, I was 100% convinced that I was about to be fired. Why? Not only because I had spoken up within a corporation, but because the topic I was writing about (how digital media will effect writers and print media) represented a huge threat to the company’s core business model, and to many of its employees.

This is the type of thing that would threaten the bonuses and stature of every executive. That still confounded the entire sales operation. That editors eschewed.

Who was I to stoke these flames? What my boss said next still astounds me:

“The CEO would like to forward your email to the entire company, suggesting that everyone subscribe.”

That instantly boosted my subscriber base to well more than 9 people. Over the years, my subscriber list grew within the company, and more and more, I began sharing my own thoughts about how digital media, blogging, and social media was changing opportunities for writers and other creative professionals.

Within the company, I became well-known. I had advocates, but I’m also well aware that I had detractors; those who did not like what I had to say, and were not supportive of my ability to share so easily within the company.

I knew that many executives received the newsletter — people whose bonuses were tied to print revenue, and who constantly had to reassure their employees that print revenue will continue to grow. I clearly remember telling my wife in that era, “One Friday I’m going to click “send” on this newsletter, and I’m going to get fired. Some executive will get offended, argue that my newsletter is hurting the company, and I will lose my job.” I wasn’t trying to be dramatic, I genuinely felt this would happen.

To my surprise, it didn’t. In fact, when the company was disbanded in 2010, with the pieces being sold off or closed, I was one of the last remaining corporate employees.

Even though we had months of warning, I never looked for another job. I had decided I wanted to try my hand at starting my own company when this job ended. That’s when I started WeGrowMedia.

Because of my email newsletter, I got a few clients right away. My business quickly developed a firm foundation because I had created an authentic way to share my voice, and connect with my audience via the newsletter, and the blog that accompanied it.

Marketing expert Seth Godin talks a lot about not waiting to “be picked” by others. He encourages you to “choose yourself.”

When I consider any lessons to take from my moment that everything changed, I consider his wisdom. There is no doubt that my lawyer friend, my boss, and the CEO all had a hand in these things happening. With their (generous) actions, I got lucky.

But what I did with that luck is also something that matters.

I didn’t just send a newsletter once a month, missing months when distracted. I have sent a weekly email newsletter (and posted weekly to my blog) every week for more than 14 years. I have shown up to my writing and to connecting with my readers.

Since that time, I have created hundreds of newsletters and blogs for writers, and trained thousands of individuals how to do it themselves.

If you have long considered starting your own email newsletter and blog, or if you want to improve one that you already have, then consider joining my Blogging & Email Newsletters for Writers program. Here I walk you through the exact steps to take, I provide direct feedback to you each week of the program, and I give you all the tools you need.

This isn’t a course where you drown alone in information. I guide you with personalized recommendations and answers to your questions. This is a collaboration.

More information and registration for Blogging & Email Newsletters for Writers can be found here.

Each week, I talk to successful writers and artists, and I often consider the moment where things changed for them. For me, it was in sending that newsletter to 9 people.

For your own work, I would encourage you to consider:

  • Will you wait to be picked?
  • Will you squander a lucky hand?
  • What is your creative shift — the moment where everything changes for you and your creative goals?