Ever since I went full-time in my ghostwriting business this past summer, I’ve had a lot of conversations about how that happened. People have been very interested in the mechanics of my transition from a college professor to a full-time writer.

They’ve asked me questions like:

• How do you make a full-time living as a ghostwriter?
• How long did it take you to build up your business?
• When did you find time to build your business?

Those who have been following me for a while knew this transition had been coming for a while. But to many others, this seemed like it came out of nowhere.

Just the other day, someone commented that “It must be awesome to be living your dream … I wish I could do that.” Yes, it’s awesome to be in charge of my own schedule and income. However, that person’s comment seemed to be a way to suggest that I basically got lucky.

As a result, I thought I’d take this opportunity to share the journey of how all this actually happened. It has definitely not been an “overnight success.” In fact, it’s been a long, long time in the making.

After I share my story, I’ll share a few practical tips if you’re on the same journey (WARNING: Long post ahead!).

It Began with Blogging

My business journey began sometime around 2010 or 2011 when I started blogging. I had no idea what I was doing, other than having the impulse to write. I had always wanted to be a writer, but the only opportunities I knew about were submitting articles to magazines or trying to find a publisher for a book. Then when blogging came along, I saw it as an opportunity to sharpen my writing skills and maybe help a few people.

For a few years, I wrote on a semi-consistent basis about teaching, faith, family, spirituality, worship, and whatever else came to mind. There was no rhyme or reason other than just getting my thoughts out there.

Around the same time, I began to follow a few people who gave me a vision for what a writing-based business could look like. There were five specific people I followed: Dan Miller, Joanna Penn, Jeff Goins, Michael Hyatt, and Kimanzi Constable. They each emphasized different topics and had their own unique way of writing. But each one impacted me in a huge way.

As I studied these amazing writers, I noticed they all had several things in common:

• They all wrote books.
• They all sent email newsletters.
• They all had courses or memberships you could purchase (as well as other digital products).
• They all wrote blog posts.
• All but one had a podcast where they either shared great content, interviewed leaders in their field, or both.
• They all frequently collaborated with other writers through podcasting and blogging.

Bit by bit, I saw that it was possible to build a business around writing. And with each passing month and year, I got more and more hungry to build a business around my writing. I didn’t want my life or schedule to be dictated by anyone else.

My First Books & Podcast

In 2014, I had been blogging for a while but decided to take things to the next level. I was a big fan of the Evernote productivity app, and had been teaching it to my college students for a while. Encouraged by all the online courses I was seeing from others, I created my own course on Evernote and promoted it to a few dozen people I knew. (I even got official permission from the Evernote people so I wouldn’t be sued, ha.)

A few people bought it, and I remember being so ecstatic that people had given me $47 each for a course! Let me tell you, when you get those first payments for something you created, it’s a huge rush!

Soon afterward, I took my course material and wrote a book on Evernote for pastors. It was published with a small Christian publisher, and was only an ebook, not print. I think less than 25 people bought it.

However, I was proud that I had at last written a book, which gave me the confidence to write my second book, The Artist’s Suitcase: 26 Essentials for the Creative Journey.

That was 2015, and around the same time, I started a blog and a podcast by the same name, “The Artist’s Suitcase.” I loved podcasting but it was a lot of work. I gave up on my show after only 37 episodes, but I kept on writing and blogging.

Negotiating for a New Teaching Role

Around that same time, I had been teaching music/worship ministry at my college for about ten years. I was totally burned out and needed to either change jobs or teach something different. So I used the negotiation skills I was learning from my side jobs to gradually work my way into a new role at my college.

Over the next couple of years, I transitioned completely out of the music area and into a newly-created role for me: Professor of Communication Arts (yes, I made up that title but the college let me keep it).

The way I figured it, I might as well be doing similar things in my day job as my side hustle. The things I was learning in my side job were so valuable that I wanted to teach them to students. One of the advantages of teaching at a small college is that you can work your way into a new role if you play your cards right. I will always be thankful to the college for being open to my crazy ideas for classes such as Faith & Film, The Art of Storytelling, Communication Technology for Ministry, and Writing for Publication!

This development also irritated some of the other professors. One of them remarked to me, “Why do you get to teach all the fun classes?” I responded, “Because I asked. You don’t have to settle for what the Academic Dean gives you. Be proactive and negotiate for what you want.”

That didn’t seem to sit too well with the professor, but it was all true. I was done just accepting what others wanted to throw me.

Dipping My Toe into Client Work

Back to the side gig. In 2016, I struck up a friendship Rye Taylor, a podcast producer. We connected on a site called 48days.net, which was a networking community and an early version of Dan Miller’s Eagles Community. He needed someone to write show notes for a client podcast he was producing. I agreed, and we worked on the show together until just a few months ago, when I handed it off to another writer.

Soon after getting the hang of writing podcast show notes, I started doing the same thing for a few other clients, and my business started to slowly grow over the next couple of years. I will always be grateful to Rye for giving me my first shot at client work! He was such a pleasure to work with that he forever set the standard of how I should treat anyone who works for me.

Then in 2017, I started podcasting again. At the time, I was focusing on the topic of creativity, so I started the “Born to Create” podcast. I was working on a book of the same title. I’m embarrassed to admit this now, but I worked on that book for 2-3 years and never finished it. I created 150 pages of raw material, ideas, character sketches and backstory, and outlines … but never actually wrote the book.

Yep, it’s easy to get stuck. Been there, done that, have the t-shirt.

Around the same time, I started writing for The Good Men Project, a website with several million visitors per month. Then after a short time, I became a lead editor. This meant I was not only recruiting new writers, but also editing and posting their material. The pay was abysmal, but the experience and connections were invaluable.

Despite some successes, the summer of 2019 was one giant frustration. I applied for several jobs with companies that needed writers or content consultants. A couple of those companies required extensive pre-interview work. I spent about 25 hours doing required work for one of them, made it to the top 50 out of 2,000 candidates, but didn’t get any further.

Later that summer, I connected with a potential client who was very interested in me helping her company implement a training program. The possibilities were huge–so huge, in fact, that if they accepted my proposal, I would be able to quit my teaching job and focus on that for the next year.

She asked for a detailed proposal, so I spent about 60 hours over the next two weeks putting together an amazing proposal. I did a bunch of research on her industry and put together an incredible proposal that included podcast production, a book, consulting, assessments, the whole shebang.

It was rejected immediately. Over text, no less.

To say I was discouraged and defeated is a huge understatement. Truth is, I was angry. And I stayed that way for two months.

I was still a college professor in my day job, so I started that school year in a very bad mood. I couldn’t get over the fact that 60 hours of proposal work had been flushed the drain.

Or was it really down the drain? Turns out, it wasn’t.

The Big 5: Deciding What I Really Wanted

That anger, that desire to succeed, is what fueled me to sit down one day in the Fall of 2019 to figure out what I really wanted. If I were going to design a business that was perfect for me, what would it look like?

I whittled it down to several criteria–what I called “The Big 5.” Whatever direction I went with a business, it had to include these 5 things:

• The ability to work from anywhere.
• The ability to set my own schedule.
• A focus on writing, which is my main marketable skill.
• The opportunity to make as much income as I wanted, not limited by someone else.
• The opportunity to spend time around highly successful business people and creative thinkers.

Around that same time, I enrolled in Ghostwriter School, a course created by Nick Pavlidis. Aha! Now I had found the business model that met all my criteria! Ghostwriting would allow me to set my own schedule, be geographically independent, earn as much as I wanted (over time), be writing-focused, and put me in touch with successful people.

So it really wasn’t until last year, 2020, when things finally started to coalesce into something that I knew could be a viable business. Once I got my first ghostwriting client, I knew it was going to work if I continued to work the system.

However, I had a conundrum: I did not want to focus exclusively on ghostwriting. I still wanted to create my own stuff and teach writing. So I decided that my business would have two parts: Inkwell Ghostwriting (which does client work), and The Daily Writer (which creates resources for writers). The Daily Writer includes books (three of my own coming within the next year), a membership community, and a podcast.

These are two distinct sides of my business, but there is a lot of overlap. What I learn in my client work, I then teach via The Daily Writer. And all the material I develop for The Daily Writer, I can then share with my clients as added bonuses if it fits with their project.

The 90% You Don’t See

When you see someone who has a successful business on some level, you may think you know their story. But a business is like an iceberg: what you see is only the top 10%. There is a whole lot of stuff, and a whole journey, that lies under the surface, unseen by most people.

When people see me from the outside, here is what they see:

• A guy who has a full-time business doing things he loves.

But here are the things most people didn’t see the last ten years:

• The late nights, early mornings, and weekends writing, recording, and editing podcast interviews and episodes.
• The hundreds of podcast show notes I wrote for clients in my spare time.
• The frustrations, dead ends, and discouragement that cropped up on a regular basis.
• All the courses I took, books and articles I read, and audiobooks and podcasts I have listened to in order to learn new skills and make myself more valuable (Not to mention the many thousands of dollars I spent doing those things.).
• All the weird, random, low-paying writing jobs I did for clients. Those jobs were not exciting, but I was grateful for the income, and they taught me valuable skills.
• All the times I have gone for hour-long walks, dictating content for articles, newsletters, or podcasts.
• Hundreds of phone calls and Zoom calls connecting with people.

When you talk about people who have a similar journey as mine, those things are not unusual. It takes a few years to get some skills under your belt and figure out your direction.

A Few Lessons

I’d love to close out this email with three observations if you’d like to turn your writing into a business.

FIRST: It is critical to get around the right people. You must spend time around those who have a similar vision for their life. These people need to be positive, encouraging, and helpful. The Daily Writer Community is a great place to find those people.

SECOND: You must keep learning and moving forward. Even when it feels like you’re not making a lot of progress. Keep trying new things, keep putting out content, keep creating. The moment you stand still and say, “I’m done learning,” is the day you might as well quit.

THIRD: I highly recommend starting a podcast. A podcast, for me, has been essential for meeting new people and creating opportunities. When you have conversations with awesome people, magic happens. I guarantee I would not have a full-time business today if I hadn’t been podcasting.

I know this has been a super-long episode, but I hope it has been helpful. I have made a lot of mistakes in my journey, but I honestly wouldn’t change anything because I have learned from each mistake–probably more so than from the successes.