My Five-Year Journey Creating, Launching, Failing & Succeeding With Online Courses

I created my first online course because I didn’t want to help any more people with resumes. I called this course “Crushing Your Resume.” Little did I know that this small act of creation might lead me down a path where I might not need a resume for the rest of my life.

A Bit About Me & A Warning About Online Courses

As you read this you may be a bit surprised at how obvious some of my failures or are why I seem to shy away from pushing things further or doubling down on trying to make more money.

Throughout this entire journey I was on a broader exploration of how one might design a life not centered around work. While I’ve seen clear opportunities to make more money at several points along the journey, I almost always optimized for a simpler life and more time to write and do the things that bring me alive.

The creation of courses and coaching were downstream of many years of intense coaching and consulting work as well as hundreds of conversations and thousands of hours of writing about these topics. For the most case, I created these courses after I had some validation that people were struggling with these things and that I had some sense that my way of thinking about these issues was helpful for people.

I see many people aiming at creating courses without first finding the things that they enjoy doing or directly helping people first. The following journey is a five year journey and knowing what I know now I’m a bit embarrassed by how poor some of my thinking and decisions were at the beginning of this journey.

I am sharing my journey below of creating digital content and several online courses and meeting mixed success along the way. I am not the most successful or the flashiest online course creator but I am in it for the long-term, really care about doing these things in a lasting way and want to see others find ways to create their own work.

I write this with the intention of saving you some time on your own journey.

Chapter 1: Idea For A Resume Course

It was 2015. I had decided to dabble in my first side gig as a career coach. Careers with Paul was born and I started writing and sharing what I knew publicly. 

When you decide to call yourself a “career coach” everyone wants help with their resumes. After helping 100 people I decided I couldn’t do 101.

Inspired by the Massive Online Open Course movement and learning about things like Udemy, I thought I might dabble with creating an online course. 

My background in consulting blessed me with the ability to create content quickly and to be able to have a good sense for how to sequence and structure that knowledge. Over the course of a few weeks I created a bunch of slide:

Lesson #1: Creating content with the intention of teaching others enables you to learn something in a much deeper way than simply “knowing” how to do something. I had helped many people with resumes but never approached it by thinking about how to clearly explain what I was doing and why. Creating the resume course forced me to sharpen my thinking, develop an easy to understand framework, and actually helped me get better at what I wanted to teach

I bought my first microphone, a Blue Snowball ICE and set out to record voiceovers with the slides. Given that I was still employed and working with my work computer, I didn’t do any video. For me, I just wanted to ship this thing and get it out there.

I had all sorts of roadblocks and issues with recording voiceovers as well as audio and video editing. When you are first starting never discount how much time you will spend tinkering and fixing really minor things.

Chapter 2: Getting Rich!

Just kidding. 

I posted the course on Udemy in May 2016 and I ended up making $30–$40 in that first year.

While I didn’t expect to make a lot of money, I was surprised at how little you could make on a platform like Udemy. Udemy controls a lot of the pricing and even if you priced something at $20, they might sell it at a discount of $0.99. Not really the kind of platform that’s going to support your life.

I did make my first paycheck from selling things online which was a huge confidence boost as I was thinking about potentially leaving my job.

Overall I was still pretty proud that I was able to create and launch something on my own after having my work tightly controlled by overzealous managers for the previous decade in my consulting jobs. 

I ended up using this as something I could send to anyone who asked for resume help too, which felt pretty good. 

At this point I was still thinking a lot about the depth of materials, the quality of video and audio and the “features” of a course. This led me to want to upgrade the content and make it a little more visually appealing and also to upgrade the audio voiceovers. I have a lot of fun messing with content so I thought this was a fun use of time. 

Lesson #2: It doesn’t matter how good your slides or course are if you are competing on a massive platform where there are 25 other resume courses who are priced at $0.99. Udemy was a great place for some early adopters but probably wasn’t a great place long term if I wanted to make money.

At this point I was still thinking of a course as something that could be consumed asynchronously and as a potential passive income product. I was aiming at helping someone make a change but had still not thought about a LIVE cohort-based course until I stumbled upon Seth Godin’s altMBA.

Chapter 3: “Digital Course Experience”

I’m not sure when I first heard about the altMBA but I remember thinking that this was definitely something that needed to exist. 

I was in my first year of self-employment and discovering that although I had worked in some of the best companies in the world, the skills I had developed were inadequate to creating my own work. I had always written or created things to please others and now I was figuring out how to channel my curiosity into something different.

I talked to alums like Cody Royle who credited the program with enabling him to write his own book. He found the support of others and the focus on creating your own work transformation and for only $2,000 at the time it felt like this might be more promising than the two years and $100,000 I spent on business school.

In 2018 I had started creating and was inspired by Godin’s general advice to focus on finding the people who want your help and to do it with generosity. I took this approach and announced to my newsletter that I was going to launch a “LIVE” course called “Solopreneur Shift” and let people sign up using a pay-what-feels right approach. This felt right in terms of balancing generosity and dealing the the terrifying fear of charging people money for the first time. Here is the announcement from my newsletter:

I paired this with a landing page which mapped out my vision of the course. 

To my surprise I ended up getting eight people to signup up at a mix of different price points. A few people paid the full tuition price (>$300!) which felt both amazing and terrifying. “These people really believe in me, wow!” and “Holy crap, can I do this?”

Here’s a secret you should know: I only built about 20% of the content before “launching”

I don’t recommend this for everyone. My superpowers are creating content and figuring out how to fit different ideas together. I knew that getting signups would be rocket fuel to motivate me to build the course, which turned out to be true.

Instead I focused on getting the sequence and structure of the course right and making sure it made sense to others:

Lesson #3: The biggest motivator for me is helping other people and getting people to pay me up front for a course was the biggest motivation in the world to not let them down. It was also terrifying and there’s probably not a good way to fast-track this step. It’s just something you’ll need to figure out how to power through.

A side note: Traditional vs. Online Courses

In this same summer At this time I was also a Teacher’s Assistant for a class at MIT for the MBA program, helping out a professor I knew. I found it striking to compare this kind of Professor-at-the-front type of “school” with my digital course which was interactive, collaborative, enthusiastic and part of an ongoing conversation on Slack. Many of the MIT students were interested in figuring out what they had to do to barely pass the class while the participants in my digital course were craving a transformation and really wanted to improve their live.

Chapter 4: Dreaming Bigger

Coming off this successful course experiment I was excited. I had made about $2,000 and was convinced that I was on to something. The online course felt alive whereas the class I was helping out with at MIT felt like it was from another era.

While I had given up on making money from my resume course, I made it free and kept it on Udemy and forgot about it. Out of the blue, I received the following graphic in an e-mail that made my brain explode. People from 94 countries had taken the course, what?!

This is when I started to realize that the opportunity of online education might be a lot bigger than simply training Americans in my backyard. 

Online courses shifted from something that I saw as a fun experiment to something that I wanted to place a bigger bet on for the future.

Chapter 5: “Strategy Toolkit”

My background before I quit my job was working in the strategy consulting industry for nine years from 2008 to 2017. One of the things I loved while working in the industry was taking extra time to participate in developing content and leading trainings for new hires and colleagues, teaching them the “consulting process.” 

In addition to this, I had started advising an undergraduate consulting group and over a few years had figured out how to backwards engineer a lot of the things I had learned and explain and train them in a way that was making a real different in their skills.

So when I went solo I thought that one thing I might do was to lead internal company trainings and I did exactly that as one of my gigs in the first year. I helped to design and lead a training for first year analysts at a software consulting firm. This was a month before I ran “Solopreneur Shift,” however, and I had never imagined that I might do this online. 

After Solopreneur Shift, I changed my mind about consulting trainings and quickly adapted some of the ideas for a virtual setting. I ended up moving to Taiwan in the fall of that year and when my consulting work evaporated and I was rested after an extended period of non-doing mode, I decided that I would embark on what I was then calling The Strategy Toolkit.

The first thing I did was to purchase a year subscription to Teachable (affiliate) which felt quite bold at the time for someone that had made less than $1,000 in three months. However, what it was was a bet on myself and a way of raising the stakes to guarantee that I would follow through.

I’m a bit embarrassed by the first iteration of the course but not about the Ninja.

I launched this after a steady month of creating and shipping and I got rich!

Just kidding, again.

I sold a few copies of the course to friends that believed in me and then considered it a failure. I stopped thinking about it for a bit and assumed that it might be time to move on from this dream of being involved in online courses. 

Chapter 6: Re-Branding As StrategyU + Think Like A Strategy Consultant

A month before I left my job a company flew me out to Los Angeles to have a conversation about leading an Academy that would help train consultants. I told them that I thought we should go virtual and call it “StrategyU.” They wanted me to merely be a salesperson for the course. They already had the materials and they thought people don’t want virtual trainings. I said no and left to self-employment a month later.

Fast forward 18 months later and I had created my own consulting course but I had launched it under “BoundlessU” which was the home of my main blog. As I mentioned, I had figured this might earn me some money here and there but that it was a lost cause. I was hoping merely to recover the $39 a month teachable fee. 

I moved to Bali after my failed launch and luckily I was joined by Jay a freelance digital marketer who quickly made me realize I was a marketing moron (he’s since moved on to launch a woodworking business in Colorado). He was really impressed with the course and believed in what I had. Simply seeing him excited about it was encouraging. It made me want to pick it up and give it another go. Together we brainstormed four things I would do immediately:

#1 Video: Shoot high quality videos introducing myself and giving more of a personal explanation why this course mattered to me and how the pieces fit together along the way

#2 New Brand and Course Name: Move the consulting articles I had written off my main blog and on quora to a separate site, which I planned to call StrategyU and change the course to “Think Like A Strategy Consultant” to more clearly communicate the shift I was selling. I had the advantage of already having SEO traffic of many of these already as well as many other “validated” posts I had written on Quora that received a lot of attention, including a post upvoted by Ramit Sethi which gave me another confidence boost.

#3 Give away high-quality content: Create a lot of valuable content for people to get an understanding of what kind of skills I was teaching in my course

#4 Free e-mail course: Create an e-mail signup and create a multi-day free e-mail course previewing content in the course.

Excited by this second chance, I started writing like a maniac and had rebuilt the course and site within a few weeks.

By the end of April 2019, I landed my first sale of the course from a stranger on the internet and the excitement of having something that might work motivated me to keep working to improve the course. 

In that first month I ended up selling 10 copies of the course (which I was still pricing at $99) and was kind of shocked that my strategy had worked. Throughout the rest of the year I had a steady stream of sales.

It’s hard to understate how shocking this was to me and how much it shifted my attention away from working as a freelancer and towards the creator economy. I was equally excited to see that less than half of the course sales were from the US and the rest spanned across 23 other countries:

Australia, Austria, Canada, China, Denmark, France, Germany, Hong Kong, India, Indonesia, Kenya, Malaysia, Netherlands, Norway, Peru, Saudi Arabia, Singapore, South Africa, Spain, Thailand, Turkey, UK, USA, Vietnam

Lesson #4: Digital products need some form of distribution. For me, SEO worked really well because this was an in-demand topic via google but other strategies like e-mail marketing, audience building on platforms like Twitter, and partnerships all seem to be viable strategies.

Chapter 7: My First Live Cohorts Of Think Like A Strategy Consultant

Although I was finding success with my course as an evergreen course, I wanted to run it as a cohort-based course to work directly with the students and use it as a way to keep improving and upgrading the course. 

In July 2019 I ran my first cohort to launch my first cohort and used this as an excuse to upgrade the course including adding challenging assignments and structuring it around a four-week cadence. This four-week schedule would pay bigger dividends down the road when I shifted it back to an evergreen course. 

I ran two cohorts and used a discord chat and also added a discourse forum. I enrolled about 10–15 people in each sessions and it went pretty well yet the entire time it felt like something was missing.

The biggest challenge about the cohorts was that almost everyone was a beginner in terms of the skills and they all wanted direct access to me and my feedback. It’s not easy for a novice to identify clear opportunities for improvement as easily as a novice might be able to point out opportunities in something like writing or speaking. 

After running two cohorts, I decided to shift the course back to an evergreen format with the new assignments and four-week structure. I created two clear options. One that was self-paced and another where they could work directly with me to get feedback.

  • $429 “Consultant” — Self paced and minor feedback
  • $699 “Partner” — Coaching Call + Feedback On Weekly Assignments

With this pricing and structure, I was in a great place when my target audience was forced to work remotely. This lead to a sustained spike in sales from April onward and for 2020, the course was able to fully support me and my wife’s life off, with more than $50,000 in revenue.

While I had made a decent amount of money in 2019 it was nothing like what happened in 2020 and for the first time I started to think that running online courses was something I could really lean into to support my life for the next several years.

Lesson #5: Just because “cohort-based courses” are all the buzz right now does not mean other models won’t work well for your course. I’ve been fascinated by the cohort-based course movement but I think there is room for a number of models to work with online courses.

Chapter 8: Re-launching “Solopreneur Shift” as “Reinvent”

While it was amazing to be gaining traction with my consulting course in 2019, I knew that the course I needed to put into the world was the updated version of solopreneur shift. Since I quit my job in 2017 I have been increasingly drawn to helping people navigate and make sense of this new world of work.

As someone that loves the act of creation, creating a course has the added benefit of forcing me to simplify, synthesize, and communicate my ideas for other people. While the course has only had minor success since I launched it, it has had an incredible downstream impact on my writing and the quality of my ideas, helping me reach many more people through my ideas in 2020.

I had learned my lesson of not validating my course before launching so this time I decided to build it in public, inspired by the approaches of people like Nat Eliason and Ryan Kulp who both took similar approaches with course.

For me this was a great strategy because it channeled my motivation for helping individuals as a push to “keep going.” By tweeting and sharing my progress, asking people for feedback and sharing my progress, I was able to passively sell 10–15 spots in the course before I had built most of the materials.

To raise the stakes for myself I also decided to invest in a $100 light and also signed up for Podia as a way to make another financial commitment. These small purchases seem to have the effect of committing me to following through and once I spend the money I am thinking about running the course as a micro-business where I need to earn back the initial investment. Your mileage may vary. .

The course was designed around a five-week structure and the biggest component was an “action challenge” that would require students to publishing something in week three. 

Several people launched things that they are still working on to this day which is pretty much all I could ask for.

(Side note: I have a much more detailed writeup of the process of creating this course on Podia’s site)

In October of 2019 I finished the course in time to spend a relaxing few days in Japan before I launched the cohort with 35 people from around the globe. I ran two different sessions for the different time zones, had a co-facilitator join me, more actively encouraged sharing in a Discord group and overall it is the best experience I’ve had running an online course. 

Creating and running this cohort of Reinvent was one of the most rewarding things I’ve ever done and although I haven’t run a proper cohort again (mostly due to health issues), I’m excited to potentially run it again in 2021 or 2022 or whenever I find someone that might be interested in re-launching it with me.

Lesson #6: Not every course has to be a monetary success. The biggest benefits for me in creating reinvent have been going much deeper in a number of topics I plan to keep writing about for many years in the future. In many ways creating this course helped me improve my thinking and writing and helped me build the courage to pursue writing a book in 2021.

Chapter 9: Gift Economy Approach

With all the material I’ve created I’ve always tried to integrate a gift economy approach. I’m not going to go in-depth here but my goal in creating is usually for my own selfish reasons of making sense of the world, joy of creation, and then if I’m lucky, helping others. I want as many people as possible to benefit regardless of how much money they have.

It’s taken a few iterations to get right but I have landed on an approach that seems to deter most people from taking advantage of the system and encourages people with less to apply.

Here is the current language I have on my site

This directs people to a small exercise where they can share their motivation and offer a “gift” that feels right. I nudge people to offer something because in previous iterations where I offered it for free no one finished the course!

Here is an example of some of the amazing applications I receive:

Nothing inspires me more than people with the motivation to learn from all parts of the world. I find over and over again that the people with the least are often the most hungry to learn and this makes me incredibly optimistic for the future.

Chapter 10: Ongoing Tweaks and Opportunities

The success of my consulting skills course has continued. At the end of 2020 I was offered a chance to take part in an accelerator program to re-launch the consulting course as a cohort-based course. While it was increasingly clear to me that I had a lot of upside potential, I decided against it and doubled down on making my course even stronger. I invested in experimenting with ads, learned how to upgrade my landing page (h/t to Julian’s guide here) and have continued to slowly upgrade videos and content based on student requests. 

At the beginning of 2020 I crossed $100k in total sales which would have been unbelievable two years earlier when I had all but given up on my course and also reached 300+ students in 36 countries

The money I’m making from this course is more than I need and for now I am spending time writing, learning Chinese, and writing a book. I might decide to take my courses to the next level at some point, but I’m not in a rush. 

That doesn’t mean I’ve ignored all opportunities. I recently kicked off the first cohort-version of my course with a small data consulting firm in the US and am hoping this turns into something I can run with more organizations in the years to come. My hunch is that running it within a single organization solves a lot of the challenges I had with running it with random people across the globe. Time will tell. 

With Reinvent, I’ve turned it into a self-paced course as well but there has not been much interest. I’ve more or less broken even on this experiment which I’m happy with because this is the material I enjoy the most. I’ve recently launched a high-end coaching version of the course which I’ve having a lot of fun doing with someone in Mexico right now.

I’ve had a ton of fun doing all of this and if I never made another dollar from online courses I would have zero regrets from any of this. I feel incredibly lucky that I’ve been able to to build a life and work doing things I enjoy doing and get paid for it. 

Lesson #7: While it can seem like there is a lot of pressure to capitalize on the zeitgeist immediately there is probably also a benefit in playing the long-game and building things in a way that are sustainable and in a way that integrate with how you want to live and work. It seems after five years of doing this that I’m down to keep exploring for another five and I’m excited to see where things go!

Hopefully this guide will help you do the same.

To Learn More & Some Links

If you’re interested in learning more about my courses you can check them out. I’m always open to hearing ideas, or suggestions and definitely open to hearing about ways we might be able to partner on something:

If you are interested in supporting my journey or launching your own course, you can check out my affiliate links for Podia, or Teachable. Here is more I’ve written on creating courses

Some must-read links:

About Paul Millerd

Paul is a writer, creator, and curious human that is passionate about how people can reimagine their relationship with work to do things that matter. He published The Pathless Path in 2022.