84 Lessons From 20 Years As An Online Entrepreneur (Updated)

Over 20 years of running different businesses online, experiencing highs and lows, as well as dealing with all the struggles that come with it… I’ve taken a lot a lessons myself. I thought I would compile some of the biggies into one blog post.

Here are 84 lessons I have come to affirm over 20 years of online business, broken down into short, pithy takeaways…

  1. Keep things simple. When you feel things getting complicated, stop and look for what you’re doing wrong.  Power is found in simplicity. Complexity is a sign of failure.
  2. It is as important to work ON your business as it is to work IN it. Never get so entrenched in being the worker in your business that you forget to be the CEO.
  3. Never, EVER fail to launch a site without building your email list. Your email list is your source of leverage and momentum for a new site. Failing to build it means you will likely never get off the ground.
  4. Don’t worry about perfection. Make it good enough. Perfection is often undefined. We don’t even know what it looks like and likely wouldn’t notice it if it were. In reality, absolutes are unattainable. So, get it to “good enough” state then move onto your next project.
  5. When you want to accomplish more, give yourself less time to do it. I’m at my most productive when I’m about to go on vacation. I get a TON done beforehand because I KNOW I have a deadline. Tasks will expand to the time allotted. It is called Parkinson’s Law.
  6. This is a people business. They’re not pixels on an analytics graph. They’re people. Treat them as such.
  7. Never waste your time trying to make everybody happy. Some people are so busy making themselves unhappy that it is a waste of your time to try to fight them on it. There are some people who will complain no matter what. So, listen to them, evaluate, then decide if real action is warranted. If it is an outlier, forget about it.
  8. It is your blog and your list. You own it. You’re the one who does all the work. You pay the hosting bills. Keep that in mind if you have that stray person who complains you are charging too much or don’t do enough for them for free.
  9. It is more important to connect with the RIGHT people in your audience, than to worry about raw numbers. Raw traffic figures, comment counts, or even list size are not nearly as important as how many of the RIGHT people you have. Engaged subscribers are more important than raw subscribers. Number of customers is more important than raw traffic.
  10. The only proof of a product idea that matters is sales. It doesn’t matter what anybody tells you or how interested they seem… if they aren’t asking you to take their money, take it with a grain of salt.
  11. Never assume you know what your audience wants. Ask them. One of the most common mistakes I see is people who build a product because they think people need it. It is arrogant… and stands a good chance of falling flat.
  12. Who gives a shit how many comments you get? Comments don’t get you paid. Spending time worrying about how many comments your post gets shows you have the wrong priority. In fact, you might even be better just turning comments off altogether.
  13. Don’t go into debt to fund your online business. It is completely unnecessary and just adds stress. Don’t buy things for your online business with credit. This is the internet… you can literally make up an offer and make sales out of thin air. So, do it.
  14. Creation of valuable offers is how a business makes money. Ad income is just filler income. Affiliate income is a profit maximizer. It isn’t really a real business until you’ve got your own products/services on offer that you sell directly.
  15. Be a real person. Don’t ever say “we” when it is just “I”. People see right through that.
  16. Email list > Social Media List. Building your social media follower lists is practically useless when compared to your email list. Focus on your email list. If a social media “guru” tells you email marketing is dead, laugh at them then walk away.
  17. A blog is not a business. Blogs are a great marketing platform. But, they’re not a business. And they never have been.
  18. Start or join a mastermind group. It is difficult and limiting to try to build and grow your business as an “only one”, trying to be a hero. This would tends to operate best at a minimum of two. As a solo entrepreneur, it is important to have a peer group to discuss things with. Or hire a mentor to provide a second set of eyes.
  19. Being understood is more important than sounding smart. Communication is only effective if it is clear and understood by the people on the other end. Using big words to try to impress just makes you stupid.
  20. Balance out “real life” and virtual work. You can only be at your computer for so long before your world closes in and your productivity drops. It is important to balance that mental work out with activity in the real, physical world.

Want to check out the remaining 64 lessons that I’ve learned?

Check it out:

84 Lessons From 20 Years As An Online Entrepreneur (Updated)