The Business School of Hard Knocks

Over the last twenty years, I chased money everywhere. I obsessed over it and grew my career beyond what I thought possible for a guy with a minimal college education. I began my career as a cable guy and recently ended it as a Director of an IT department for a national healthcare company. I was making close to $200k per year. Then my PTSD skyrocketed and COVID restrictions started.

Then I decided to become an entrepreneur. Actually, I’m an introvert solopreneur, to be specific. I’ve learned a few great lessons along the way. Some of which I believe will ultimately help me reach my goals and perhaps they’ll help you reach yours.

Let me list the biggest lessons I’ve learned.

Push through the ‘Valley of Disappointment’

I’ve started many blogs, podcasts, YouTube channels, Fiverr gigs, 3 LLCs, a Udemy course, Facebook ads (which I got banned for life from), online surveys, and social media accounts specifically to make money as an entrepreneur. All of them failed because I did not persist long enough through what author James Clear refers to as the ‘Valley of Disappointment’ to blast past the ‘Plateau of Latent Potential’ in his life-changing book Atomic Habits.

Graphical representation of James Clear's Plateau of Latent Potential
Trudge through the plateau to experience success

Honestly, I haven’t mastered that yet. I’ve spent thousands of dollars on solo business ventures only to make a couple of hundred dollars in return (cumulatively). During that time I’ve swung into and out of deep depressions. Thank goodness for my wife and family because those days were dark. I would never wish those experiences on anyone.

However, I’m still working to improve and try to zero in my focus on what matters. I will eventually succeed. Plus I’ve learned a few things from my failures. Albeit, I didn’t learn them until much later than I should have…

Don’t go into business for the sole purpose of making money

Literally, every venture I pursued was solely focused on generating revenue and that was all. This is the most recent lesson I’ve learned and am grateful for it. The only way that makes sense to start and grow a successful business is to actually provide value to clients. That’s it. If you don’t start focusing on that from the start, you’ll never motivate anyone to give you their money. In the Army, I learned the NCO Creed and one of the lines went something like, “competence is my watchword.” In the case of entrepreneurship, value is your watchword.

The only thing I find believable about actually making money via an online/solo business is by networking – growing an actual group of people that you get to know and they get to know you by providing them more value than they ever expected.

In 2008, Wired editor Kevin Kelly wrote an essay called “1000 True Fans” that’s included in Tim Ferris’s book Tools of Titans.

To be a successful creator, you don’t need millions. You don’t need millions of dollors or millions of customers, clients, or fans. To make a living as a craftsperson, photographer, musician, designer, author, animator, app maker, entrepreneur, or inventor you only need 1,000 true fans.

Kevin Kelly, 1,000 True Fans essay from 2008

Kevin defines a ‘true fan’ as “a fan who will buy anything you produce.” My mom is a true fan of mine. Rather than growing a large number of impersonal followers that usually don’t actually care much about you or your product/service, focus on getting to know a small group of fans and give them exactly what they want. You know what they want because you developed a relationship with them. You simply cannot do that with tens of thousands (or more) followers.

Put first things first by prioritizing the tasks that actually create value

Dr. Stephen Covey, the late brilliant author and teacher of The 7 Habits of Highly Effective People taught me a very important lesson in Habit 3: Put first things first.

Watch this video to feel the same ‘ah-ha’ moment I did when I initially watched it.

There are so many things that I wasted time, effort, and money on:

  • Amassing social media followers
  • Changing WordPress website themes and appearance
  • Buying and trying shiny new apps
  • Taking online courses for a wide variety of purposes
  • Obsessing over Google Analytics
  • Obsessing over YouTube views and subscribers.

When I started off, those are the things that excited me the most. Now, however, I realize those were the easy things to focus on and they provide nearly zero value to actually creating and growing a profitable business.

You can’t create a successful business, no matter how small, without a team

No business, including those that we introvert solopreneurs love (blogging, YouTube-ing, podcasting, etc.) will become successful without help from other people. ‘Solopreneur’ should be a banned word, yet I cannot force myself to ask for help. Yet.

I swear I used to call myself a proud solopreneur. Now I’m embarrassed by that idea. My biggest problem is being an introvert. I don’t like working or talking with other people. Of course, once I do start chatting and working with others, I almost always love it. That’s how my career was so successful. I wish I made that association much sooner.

If you’re reading this, I hope you’re nodding your head ‘yes’ because we are peas in a pod. Perhaps we can help each other?

There’s a big difference between liking something and liking the idea of something

This is a huge life lesson for me. For example, I now realize I like the idea of living in a cabin in the middle of the woods. I would never actually do it, though. Sometimes you have to go through this lesson and learn things the ‘hard way’ but avoid wasting too much time and money in the process.

I thought I’d love being a freelancer on Fiverr and eventually work my way up to Upwork and then consulting. Nope. I hated the experience of working with clients that had different expectations of what they wanted and how much they wanted to spend on it. I also hated Fiverr’s rules for moving up the seller tiers. Ironically, that was also the most profitable venture I pursued. Still, it wasn’t for me. I only like the idea of being a freelancer.

Another example of something I thought I’d love but actually don’t: I hate writing. I struggle with writing blog posts yet I currently have 4 blogs. I even tried writing a few books. That was frustrating.

I should caveat that with this: I love writing these posts that I’m writing now. I know they’re super helpful to anyone who is just starting off where I was a few years ago. The satisfaction I receive by passing on this knowledge feels awesome.

PS: I love making videos. Why the hell didn’t I focus on that from the beginning?

Don’t trust everyone claiming to teach you the magic formula to success

Every successful business owner/blogger/etc. is willing to teach you ways to become successful but literally, none of them tell you every step they went through. 99.999% of the time the advice/lessons won’t work. Think of it like a carrot and a stick. If they give you the carrot straight away, they only get your money once. That’s why they keep that carrot dangling in front of you – ie, only giving you tiny spoonfuls of what actually works and charging more for ‘add-ons’ and ‘mastermind groups’.

In Closing

Today I found a popular Twitter account from a guy named Naval. Here’s one of his tweets that inspired me to write this post:

For some reason, Naval‘s posts struck a chord with me, the same way Eckhart Tolle‘s talk on living in the present did. It’s taking me a long time to understand and espouse their ideas (mental models), but I’m working on it.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Scroll to Top