10 years of WOBS: What I learned (Part 2)

My company WOBS continues successfully in 2025, ten years after I started it. Many things about what I do have changed, but others have remained constant. I thought it might be instructive to describe my journey as a freelance writer, editor, and ghostwriter.

Fundamental principles

When I started, I had a clear idea of what I wanted my experience as an independent consultant to be like. I’d had regular jobs at various companies for 33 years before this. While I was ignorant about what it would take to be successful as an independent, I had these fundamental principles in mind:

1. Don’t become swamped with work. It might seem contradictory to start a new business with a plan about not working too hard, but my career had been filled with stressful jobs for other people and I wanted to change that. My plan was to work about six hours a day and some time on weekends.
2. Do work for which I was extremely well qualified. This would include anything related to business writing and nonfiction books. My background also qualified me to write with expertise about technology, media, social media, marketing, statistics, and nutrition. Working on writing in these areas ensured that I’d be confident and do a solid and professional job.
3. Charge by the project, not by the hour. People who work quickly get paid more when they work by the project. Working by the hour rewards slow workers. I wanted to be a smart worker who was compensated for the value I created for clients, not a wage slave.
4. Get high compensation. When I was an analyst, I was billed out at more than $1,000 per hour. While I knew the work I was doing as a freelancer couldn’t support that rate, I still wanted to make a solid living.
5. Never grow the business. I specifically planned not to hire additional staff or freelancers and to do as much as possible myself. I said to myself, “If I need to hire somebody to help, I’ve failed.” I’m not the world’s best manager, and I didn’t want to be responsible for anyone else’s success. While I’ve hired freelance experts in web design, graphic design, copy editing, PR, and legal work, I do everything I can myself, including marketing myself and billing.
6. Provide personal attention to each client and leave each client happy. This goes hand-in-hand with my other principles. If you get high compensation, don’t work long hours, and do work for which you are qualified, you can make sure every client gets what they need.

If my objective were to build and eventually sell off my business, this would be the wrong strategy. But that was not my goal. My goal was to make a good living doing what I loved and not be constantly bathed in stress. I did not maximize my revenues. I maximized my happiness.

The details of my business have changed, the principles have not. They worked when I launched WOBS in 2015, and they are still working for me now.

This was my journey.

2015-2016: Launching WOBS

I hit the ground running. Within two months of launching WOBS I was doing corporate positioning work and editing a research report for a local tech company.

WOBS made only $24,000 from consulting in 2015, and $69,000 in 2016. That would have been tough to live on. But as I described yesterday, I had a year’s severance from Forrester and a six-figure book advance to support me as well. Wise investing had insured my house was paid off and my college funds fully ready for my two children. Financially, I was fine.

In the first two years I was still trying to find my sweet spot for consulting offerings. I made significant amounts from corporate positioning work and writing value propositions, but I found the corporate back-and-forth associated with that work frustrating.

I did several corporate Writing Without Bullshit workshops and gave four paid speeches. I also started working on idea development and book proposals with several nonfiction authors who’d been referred by friends.

My editor at Harper Business suggested at one point that I could make a good living ghostwriting. I told her I’d never write a whole book for someone else. Dan Gerstein, the CEO of Gotham Ghostwriters, heard I’d left Forrester and called me out of the blue. I told Dan I wasn’t a ghostwriter, but I did do editing, idea development, and book proposal work with authors. I started to do book proposal work for Gotham clients.

2017-2019: Attaining focus

Starting in 2017, I knew revenue from my freelance business needed to fully support my family. And I also knew that freelance work succeeds when you focus on a few repeatable offerings. That kind of focus allows you to become efficient at delivering value. It also makes it possible to market yourself effectively and benefit from referrals. So, I asked myself, who was I and what did I do well enough to make a living?

More than half of my income in 2017 came from writing workshops, editing, and book proposals. So I resolved to focus in those areas.

I also paid attention to where my business was coming from. Half of my freelance income was generated through word of mouth, and the lion’s share of the rest was from my blog and from LinkedIn. I resolved to focus my energies on those platforms, where my daily posts would function as content marketing.

But something else started to happen that year. Two corporate executives I knew — one of whom was an old friend — had planned to become coauthors, and I was coaching them. Then they realized they were too busy to actually write the book they had in mind. So we changed our arrangement. Although I had been resistant to ghostwriting, these were authors I felt well connected to, and I was sure I could write the book they had in their minds.

I was deep into that ghostwriting project in 2018 when an incredible opportunity presented itself. Gotham needed an author who could ghostwrite a book on artificial intelligence for the CEO of a company pivoting to AI. (Unlike now, in 2018, a pivot to AI was unusual.) This project would allow me to learn more about AI and to gain experience as a ghostwriter for a CEO. Not only that, it would pay extremely well. So I took the work.

As a result, half of income came from ghostwriting in 2018. I continued to do book and article editing and corporate workshops. Ghostwriting two books at once along with all that other work was a challenge, and violated my first principle: I was swamped with work.

I learned two big things that year. First: I really enjoyed ghostwriting and would definitely do it again; it was fascinating and challenging work that was well-suited to my skills and paid well. And second, never again would I agree to ghostwrite two books at once.

By 2019, four years into my freelance journey, I had finally figured out what my business was about. It was mostly about helping authors with idea development, coaching, proposals, editing, and ghostwriting. There were still a few corporate writing workshops here and there, but it seemed clear I would be phasing those out.

2020-2022: COVID changes my plans

In early 2020, I did a writing workshop for Netflix at their headquarters in Silicon Valley. It was the last in-person workshop I’d ever do — COVID changed all that.

But COVID also changed corporations’ willingness to engage in remote training. After all of Netflix’s offices shut down in spring of 2020, the guy who’d hired me to do the in-person workshop referred me to their Asia-Pacific partner group, where the management was interested in investing in a workforce that was a little demoralized after being stuck in their home offices. I did a series of writing workshops for their Asian and Australian staff across seven different countries. More requests poured in from other teams at Netflix who’d heard about my workshops, as well as from people at other companies who’d spoken to Netflix folks. One-fourth of my income in 2020 came from writing workshops, and all of them except that first Netflix session were virtual.

Here was an ideal offering for me. I could charge the full amount, the same as I did for an in-person workshop, without having to leave my desk. I could conduct the exercises using video and chat, which was highly effective. And while I customized the workshops and exercises to each client, 90% of the content was repeatable.

The remainder of my work came from authors. I conceived the idea of writing a book for nonfiction authors and started to create it, in partnerships with Naren Aryal at Amplify Publishing.

I was on a roll, and had found a combination of offerings that fit well in a world shut down by COVID. The demand for workshops continued through 2022. I also heard from Rohit Bhargava, the CEO of Ideapress Publishing, who got me started on another ghostwriting project for one of his author teams.

2023-2025: WOBS serves authors, with a sideline of survey analysis

I published Build a Better Business Book in 2023. That was my way of telling the world that I serve business authors. The book continues to generate interest, leads, and credibility. In my most recent ghostwriting project, the client said they selected me in part because I wrote the book on the topic.

About half of my revenue from 2023 until now has been from ghostwriting. I ghostwrote the book for Rohit’s authors and another for a Gotham Ghostwriters client. I’m currently ramping up a ghostwriting project for 2025.

Each of these ghostwriting projects takes around a year and generates on the order of $100,000 for me. As you might imagine, at that level of commitment, I’m very selective about the projects I take. I’ve been fortunate: all five of my book ghostwriting projects have been fascinating, fulfilling, and lucrative with great client relationships. It’s a lot less work to market yourself when half your income in a given year comes from one large project.

I continue to do editing and other work serving authors to generate the rest of my revenue. As I predicted in 2019, the workshops are no longer popular. I was just wrong about the timing.

I also ramped up a new business in 2024: surveys. Working with Gotham Ghostwriters, Amplify, and others, I helped design a survey of business authors and wrote a report about it (you can download it at AuthorROI.com). This project tapped into my statistical and report writing skills. I’m scoping two other writing-related survey projects right now.

How to stay agile — and sane — in an ever-changing freelance business

Thinking back to my mindset in 2015, it would have been impossible to predict the twists and turns of a decade of freelancing. Year by year, I ended up specializing in editing, book ideas, ghostwriting, workshops, and surveys. But there is a simple strategy behind all of what I did:

• Don’t forget your fundamental principles. The principles at the top of this post still drive my business.
• Identify repeatable and referable work that I can refine, market, and deliver profitably.
• Choose clients carefully to maximize the chances of working with people I like on projects I like.
• Try new things that connect to the things I already do — similar clients, similar topics, or similar work — and see if they look like promising potential offerings for the future.
• Expand my content knowledge, because learning is fun, but also, because it broadens my appeal for more exciting projects.
• Learn what doesn’t work and don’t do it again.
• Be constantly alert about trends in business and publishing that will affect my clients.
• Do everything possible to leave every client happy.

Will WOBS last another ten years? By then I’d be 76 years old. But if it stays this interesting — and if my brain and body hold out — there may be no better way to productively spend the time I have remaining.