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65 Lessons From 14 Years In Online Business and Professional Blogging

I’ve been running an online business for 14 years now.

I started back in 1998 when I created my tech site, PCMech.com. I wasn’t full-time right away. In fact, I did other things at the same time and my online business was a “side business” for a few years. I graduated college in 2001 and pursued this “side business” full-time. Even while I built it up, I did some web development work for clients, too. It was probably around 2003 or so before I was actually making enough from my website to live from it.

In internet years, I’m an old man, I guess. I accept that. Its funny, even when I go to conferences and hang out with many of my peers in this business, I’m reminded that I’m one of the older people in the room. And I’m only 34. :)

In doing this for so long, I’ve learned a lot of things.

Here’s a list of 65 lessons I’ve learned during the last 14 years, in no particular order.


  1. Keep things simple. When you feel things getting complicated, stop and look for what you’re doing wrong.
  2. It is as important to work ON your business as it is to work IN it.
  3. Never, EVER fail to launch a site without building your email list. If you’re not building your email list, you are completely wasting your time and you’ve already failed whether you know it or not.
  4. Don’t worry about perfection. Make it good enough.
  5. Most of the time, your best work is done when you throw out all the details, give yourself a tight deadline, and just get a minimum viable product online.
  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.
  8. It is your blog and your list. Don’t worry about pissing people off. If they don’t want to hear from you, let them unsubscribe.
  9. It is more important to connect with the RIGHT people in your audience, than to worry about raw numbers.
  10. Who gives a shit how many comments you get? Comments don’t get you paid.
  11. Don’t go into debt to fund your business.
  12. Creation of valuable offers is how a business makes money. Ad income is just filler income.
  13. Be a real person. Don’t ever say “we” when it is just “I”. People see right through that.
  14. Building your social media follower lists is practically useless when compared to your email list. Focus on your email list.
  15. Start or join a mastermind group. It is invaluable.
  16. Get out from behind your computer and connect with people IN PERSON.
  17. Never spend too much time trying to save a few bucks. Your time is your most valuable asset.
  18. Technology changes. Platforms change. People don’t. Focus on the people and the rest of it is just a means to an end.
  19. Outsource before hiring employees.
  20. Change your work environment every so often. Coffee shops are nice.
  21. Don’t skimp on your computer and work equipment. If you plan to make your living with it, the least you can do is not cheap yourself out.
  22. Don’t be afraid to show your personality. People like it. It makes you REAL.
  23. Don’t play follow the leader in your marketing. What makes them the leader anyway?
  24. Those who make a point to flaunt their success are often not very successful in reality. The joy comes from the game of creating that success, not the end result of it.
  25. Don’t waste time comparing yourself to others. Instead, compare to who you know you can be. Compare to yesterday’s self.
  26. Don’t buy an internet marketing product because of hope. Buy because you know immediately what you’re going to apply it to.
  27. Passive income online is a pipe dream. There is nothing passive about it.
  28. Don’t feel obligated to keep up with the latest news and trends. Most of it is stuff you don’t need to know.
  29. Never compromise with your own reality. Never let others talk you into being “reasonable” or “realistic” about your goals.
  30. Don’t ever make promises in your marketing that you can’t deliver on.
  31. Your biggest periods of growth usually come when you’re most uncomfortable. Learn to accept that.
  32. Never be scared to fire a customer or client. Sometimes, the customer is not right.
  33. Don’t compete on price. Instead, keep your prices within reason and figure out how to compete on service.
  34. Don’t let your business consume you. The business is supposed to support you, not the other way around.
  35. If an email list you’re on never does anything except try to sell you, then unsubscribe.
  36. The first step to making money online is to stop searching the Internet for how to make money online.
  37. Take care of your health. Your business doesn’t mean jack shit if your body is messed up.
  38. Don’t put all your eggs in one basket. Have multiple streams of income.
  39. Always try to build a continuity income stream into your business.
  40. Take control of your time. Don’t let others control it for you.
  41. Never hire an outsourced worker without documented processes for them to follow.
  42. Marketing isn’t bad. It is the lifeblood of your business. Fail to market, you die. Those who think that all efforts to sell something are slimy… will remain poor.
  43. Manage by the numbers.
  44. Constant preparation for launch is just a search for excuses not to launch. Knock it off and deliver. The only way to catch a fish is to have your hook in the water.
  45. When you find that something you did was successful, then do more of that. Constantly be on the lookout for things you do which are not leading to results and stop doing them.
  46. Don’t create big products just for the sake of it being big. Focus on what is needed to deliver a result. The customer wants a result, not a big box of crap which will overwhelm them.
  47. Don’t throw everything and the kitchen sink into a product offering. It is too hard to market.
  48. Whenever possible, never create a custom solution that only you know how it works. Build your business out of systems. With software, use solutions from other companies so THEY maintain it. With internal procedures, make sure you make every job you do doable by somebody besides you. Otherwise, you’re a slave to your business for life.
  49. Don’t keep information in your head. You won’t remember it.
  50. Focus on how to make more money before you focus on how to cut your expenses. Income and expansion should be the focus, not only shortages. Focusing on shortages breeds more shortages.
  51. Learn how to say “no” and not feel bad about it.
  52. Set money aside for taxes. It sucks when you forgot to plan for it.
  53. Keep your tasks clear and concise and know exactly what you’re shooting for. Otherwise, you’ll spin your wheels and nothing will get done.
  54. It is better to do less and excel at it, then to do more and be only mediocre.
  55. Get plenty of sleep. Burning the midnight oil quickly leads to burnout, and your work suffers.
  56. Work in batches, and combine like tasks together. For example, write all your blog posts for the week in one sitting. Get it done so you can focus on other things for the remainder of your week.
  57. Blogging every day is, often, a waste of your time.
  58. The less time you spend on social media, the richer you’ll likely be.
  59. Keep your workspace clean. Cluttery offices make cluttery minds.
  60. Online business isn’t much different than regular business.
  61. A product means nothing if it isn’t delivered.
  62. Don’t fail to bring a product to market because you’re worried about people stealing it and redistributing it without paying. Employ reasonable safeguards then move on. Focus on your real customers, not on those unfortunate few who have already failed because they try to steal.
  63. Working smart is more important than working hard.
  64. Some people are meant to be employees and not entrepreneurs. And there’s nothing wrong with that.
  65. The only way to truly survive is through constant improvement. The moment you become comfortable with the current situation is the day you start withering away.

And, lastly, a bonus for life and business…

Be willing and able to accept responsibility. The moment you look to others to provide for you, or blame others for things which aren’t going right for yourself, you have failed. Taking responsibility doesn’t mean taking “blame”. Responsibility isn’t the same as blame. Responsibility is the willingness to CAUSE something. And if you’re not willing to cause things, pack up, go home and get out of the way.


I hope you found some value in this. It took me some time to put together. :)

If you did, I’d appreciate it if you share it or quote me out on social media. Thanks in advance!

Download These Lessons In PDF

A loyal reader of this site (Shlomo Skinner) voluntarily took the time to re-compile this list into common themes. I have made a few minor edits and am making that PDF available. If you want to take them with you in PDF, go for it! :)

65 Lessons From 14 Years In Online Business – 6 Page PDF


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