What I’ve Learned from a Decade of Spending 10s of $1,000s on Online Courses and Self-Education

What I Learned Taking Online Courses

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Entrepreneurship requires extreme self-education. 

We don't have the luxury of a training department that has a structured itinerary for us to master or bosses who are personally invested in us mastering the skills needed to succeed. 

Rather, we depend on books, podcasts, YouTube, masterminds, seminars, courses, and of course trial and error. 

We need to be self-motivated to learn the skills that make us successful.

In this post, I want to discuss my experience with e-learning and the 8 things I've learned about online courses after spending tens of thousands of bucks on them over the past decade. 

Let's get into it.

#1 You Won’t Complete Most Courses You Buy, BUT That's Alright

I get it. Buying an expensive course that ends up collecting dust makes you feel a little stupid. 

But do you know what’s way worse than that? Being too afraid to pull the trigger on courses that you will take and can change your life.

I’ve spent a fortune on self education, but what I learned makes it seem inconsequential.

Check out all these Udemy courses, for instance, that I bought but never finished.

Not completing online courses

You may forget to take a course (or 12) and you might buy some bad ones, but at scale, the winners pay off and make up for the duds. 

I count those as a self education tax. I keep moving and buy the courses I feel have potential to help me grow. 

It’s quite liberating. 

#2 "Yes, Most Things Are Available for Free Online BUT That Doesn't Mean Paid Courses Aren't Worth It"

This is the favored talking point of most anti-gurus. You will typically find statements like this in the comments of ads for anything educational. 

This logic is not wrong, but it’s incomplete and misguided.

Yes, you very likely CAN collect all of the same information online for free through YouTube, podcasts and videos instead of buying a course. However, there is a reason why courses have value.

Paid vs- Free Courses

Here’s what you get from a course that you typically won’t find for free online.

Note: I say “typically” as there are exceptions to each of these points. 

(1) A-Z training. A topic like Google Ads requires much more than a 30-minute YouTube video. Likewise, no one can pack all the information into one blog post.

(2) Order. Videos, podcasts and blogs are amazing but they typically cover one narrow topic at a time. This means getting a holistic view of a concept or topic would require you to piece together content from all over the place.

(3) More incentivized creators. Course creators want you to succeed, even if it’s just for the sake of their own wallets. If you don’t like the program, you will refund it and/or spread bad word of mouth for them.

(4) More up to date. If you sell a course online and it becomes popular, you will want to keep it up to date. Things change and information should be regularly updated. Videos about Google AdWords from 10 years ago are not helpful anymore. YouTube is a major thumbs down in the arena of keeping content up to date. They don’t allow creators to change anything except their thumbnails!

Old YouTube Videos with Views

No offense to Neil Patel (he's one of my all time favorites) but this is an example of dated content ranking highly on YouTube.

So, if someone makes “the ultimate google ads training,” in 2010 and it gets millions of views, should we be surprised that they don’t delete it and create a new video that starts from scratch in terms of views (which drive clicks thanks to adding credibility)? 

(5) Skin in the game. There's a saying in my industry, "People who pay pay attention." My experience has always been that I'm more likely to complete a paid program over a free one. Yes, this is almost entirely psychological, but it's a thing!

#3 Software Products USUALLY Have Amazing Free Training

The best thing a SAAS company can do to reduce churn on their products is to educate their users quickly, completely and efficiently

The best companies know this so they invest big money into creating training videos, hosting webinars and more to ensure their users master their software.

SAAS Free Training

Tools like Surfer SEO bend over backwards to train their users. 

Heck, the training above is actually free for everyone, not just users.

#4 Doing Is Mandatory to Retain 

Toxic self education is a real thing. It feels productive, and it is, but there is a point of diminishing returns.


Full disclosure, this pyramid is hotly debated and contested among academics. Use it as a rule of thumb vs. a law.

If we consume and don’t act on what we’ve learned, we forget most of it. 

When self education takes priority over action, there is an issue.

Disclaimer, the learning pyramid isn't accepted by everyone, but as a rule of thumb, I think it's safe to start with.

#5 General Self Help Becomes Redundant Quickly 

I love a good self help book as much as the next bro-entrepreneur, but let’s face it: there is little new information after you’ve read the heavy hitters like "How to Win Friends and Influence People" and "Atomic Habits".

I suggest focusing on specific skills once you've dialed in your mindset. 

#6 Accountability Is a Cheat Code 

I’ve “gone halvsies” on a couple of high ticket programs with my friend and business partner Christopher multiple times.

I’ve completed every course we’ve purchased together.

Oh, and we don’t even talk about it. I just feel an extra sense of urgency because we bought it together and I’m not alone on it.

Take courses with another person or group of people and you will likely find yourself completing them more often.  This has been proven time and time again in studies. 

Increased chance of meeting goal with a partner!

The American Society of Training and Development found that people are 65 percent likely to meet a goal if they committed to completing it to another person.

Increased chance of meeting goal with a partner you check in with

Furthermore, their chances of success increase to 95 percent when they build in ongoing meetings with their partners to check in on their progress. [Source]

#7 Price Rarely Matches Quality

It’s sad to see people sell their knowledge short while others with less value to offer dramatically over value and over price their own programs.

But, it’s as common as the sunrise.

I’ve bought some amazing high ticket programs but I’ve had equally amazing programs that cost $14 on Udemy.

#8 Live Events often Have the Most Value Per Minute Than Courses

If you can attend an event and can engage fully and pay attention to all the speakers, that’s about as good as it gets.

There are a few reasons for this.

Reason #1: Good event coordinators know you probably won’t come back next year if you don’t learn things 

Reason #2: Speakers go hard on making their talks stand out. It’s their chance to bring you in as a customer or follower so they really lay it on thick with actionable advise. Also, they want to be invited back to the next event so they need to impress. 

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