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65 Lessons From 14 Years In Online Business and Professional Blogging

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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


There’s still a few more days to get in on the Demolishing Your Blogging Technical Confusions workshop series before the price hits its cap. Sign up today, save some money, and let me help you learn to be self-sufficient when it comes to the technical side of your blog. 


  1. Larissa says:

    It is Awesome!!!!!!!!

  2. lorrainegrula says:

    I guess 14 internet years is equal to 84 dog years.  You are an old coot!   🙂  I’m 54 so that makes me ancient.  This was an excellent post David.  No doubt you could take that post, expand on it and turn it into a one hour video.  There is so much wisdom in this list.  Thanks, as always.  I’ve been doing this for 6 years now and even with all the ups and downs, it has been rewarding and fun.  Compared to so many others who give internet marketing advice, you are a breath of fresh air.  You are practical and honest, not  just spewing swipe copy crap and giving false promises.   

    1. David Risley says:

      Thanks, Lorraine. And, yeah, some repurposing ideas for this list have already gone through my head. 🙂

  3. Tasi says:

    That’s awesome, Dave

  4. Will Atkinson says:


  5. Will Atkinson says:

    Excellent, excellent, excellent! Everyone in Internet marketing should read this post, regardless of skill or experience. Good job, David.

    1. David Risley says:

      Thanks, Will. 🙂 And by all means, spread the word. I like traffic as much as the next guy. 😉

  6. Matt says:

    Great post!  I’m relatively new to the blogging world and this post will most likely save me weeks of running in circles.  Blogging is pretty much a hobby for me now because I love doing it but haven’t really tried to make any income from it, yet:) Thanks for your insights!

    1. David Risley says:

      No problem. Just remember, doing it as a hobby and as a business aren’t necessarily the same. Doesn’t mean you can’t enjoy it like a hobby, but it does mean that the considerations are different.

  7. Are Morch says:

    Hi David.

    Now I think my mind is younger then what my birth certificate tells me.. lol

    It was a valuable list here of great lessons learned. And the cool thing about it that some of these lessons you passed on to us that drops in here either on your blog, or that taken part in some of your training. 

    One of the most important lessons I learned is that this journey is not about taking perfect action steps or have detailed map that guide you to your destination. 

    It is actually ok to take imperfect action steps, and yes sometimes it also totally ok to take a scary detour without really knowing where you are going. Sometimes even the best have hickups and they just move on. 

    One of the things I found incredible value was to get a mentor or accountability partner (not sure if this goes along with your MasterMind group). Here I learned that I was a perfectionist!!(?? never knew). So I can now conquer to your point to settle with ‘Good Enough’. Is it scary to do things I never done before? You bet it is.. but I have more fun then I ever had. So as I started out with my mind is now younger then my birth certificate. My good friend John Haydon told me that a child smile in average 400 times per day. So I everyday now I deliver some childish service 😉


    Are Morch
    Hotel Blogger

    1. David Risley says:

      Well said, Are. And I love that… childish service. 🙂

  8. Tatum says:

    Great info. Thanks!

  9. Nice list Dave. 
    – I need to remember #26 & #36
    – I’d love to be able to do more of #56 but it takes me too long to write sometimes to make that an option.
    – #59 Cluttered Desk = Cluttered Mind…What does an empty desk = ? 😉

    I’ve learned that I still have a lot to learn.

    – Chris

    1. David Risley says:

      Empty desk is usually a good thing, not to worry. 🙂

    2. PJ Brunet says:

      I agree with David, but there are exceptions and extremes.  Some intelligent people are capable of processing tons of information.  And there are some disciplines where you’re not working with cute apps all day.   Random example, if you write historical non-fiction, you might be working in an old library with old photos and books piled around you.  Just look at the cockpit of the space shuttle, it looks like clutter to the outside world but it makes sense to the astronaut.  Maybe the other extreme is a sensory deprivation chamber, j/k.

  10. Bernd says:

    Awful list, David. Excellent!
    Love 31: “Your biggest periods of growth usually come when you’re most uncomfortable. Learn to accept that.”
    It is so true!

    1. David Risley says:

      Awful? 😉 j/k, I know what you meant. Thanks, Bernd. 🙂

  11. Mk Akan says:

    thanks for this…very many golden nuggets here…my issue is with creating big perfect products…thanks 

    1. David Risley says:

      Just realize it isn’t necessary.

  12. Thank you for valuable lesson, thanks Dave. Good work!

  13. Peponne says:

    David, I’m truly impressed by your professionality, your down-to-hearth-no-nonsense attitude, and above all, your stupendous generosity. I expect to be doing business with you real soon. Best regards!

    1. David Risley says:

      Thanks so much, and looking forward to it. 🙂

  14. Kat Lessin says:

    Thanks David.  Today was the perfect day for this post.  So what I needed to hear.  Well thought out and very valuable insights especially from your experience being an “older person in the room” or in this space. 🙂

  15. This! #55: Get plenty of sleep – Working all night is a sure way for the following day to be almost entirely useless. Beyond that, it’s unhealthy. I choose sleep over work as much as possible because I perform better the next day, and I get more done in less time. #31 is always true, without fault. I wish there was an easier way, but great periods of growth seem to happen only when I’m uncomfortable.

  16. Cody Wheeler says:

    Lot’s of productivity tips in here. I dig it. Question for you Dave – What would your Top 3 of these be that are actionable today? I see keep things simple in there, but then I see 65 tips that sort of overwhelm me to read and 95% of which I’m not going to remember. Maybe it’s hard to narrow it down that much. What are the heavy hitters here dude?

    1. David Risley says:

      I’ll let you figure that out for yourself. 

  17. Daniel says:

    Why do you say being 34, you are considered the “old” crowd?  Aren’t most bloggers varying in ages anyways?  I read other bloggers and they all vary in ages, from early 20’s to 30’s.. and through 50’s +

    1. David Risley says:

      You’re right in the general area of blogging. I was referring mainly to the people in the same niche as myself, in other words the whole “blog about blogging” thing. Most of the people I know in this market – and people you may know, too – are older than I. Plus, there’s the experience factor since I’ve been doing this longer than most.

  18. Debbie says:

    Great article. Been indep contrctor about 20 yrs and now deciding to get website, blog, etc. Just have question about number 3 ….I want to come across like I have small business and am writing content as “we” instead of “I” so people do NOT think it is just some rinky-dinky co. However, sounds like I am way off. Right?

    1. David Risley says:

      I don’t know your business, but in general, there’s nothing wrong with embracing the fact you’re a one-person show. These days, people like doing business with real people and not feel like they’re just a number in a big factory.

  19. Danny says:

    Summary: be irreverent, make it rain.

  20. Mike says:


    It’s crazy to think that 34 is old in this business. I’m right behind you at 32.

    I liked # 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.”

    Everyone always talks about how important starting a list is. Why? Because it is!

    1. David Risley says:

      Yep. People don’t do it because they don’t want to pay the $19 for Aweber or something, but its such lame thinking if they’re at all serious about building a business.

  21. ES says:

    The point, ‘first step to start making money online is to stop searching for it online’, is an exemplary statement. It does require a few years to understand it though 🙂

    1. David Risley says:

      Yeah, I could elaborate on it. But, its also simple. Making money comes with delivery of an outcome to a market who needs it. When people search for “how to make money”, they’re starting with the end result. Nobody starts a business with the thought, “I’ll do whatever makes me money.”. People in the real world understand about delivering value to a customer. “Make money online” searches will just lead people astray.

  22. I could not agree more with the bonus Dave.  As an Officer in the Army for 8 years, I had many superiors.  The only ones I truly respected were those willing to accept responsibility.  I try and lead my life/business by that mantra.  It’s easy to blame others.  

  23. Thanks for the motivation! I just finished setting up the email list for my blog. Now I need to work on marketing.

  24. Your shared a huge and comprehensive list of tips. To get great results for business your tips are very important and workable, i will try to get benefits from your experience.

  25. MikeHaydon says:

    Is the choice of 65 because you’re so old in internet years that you’re ready to retire? Just kidding. Great list and something that bears further study. Thanks.

    1. David Risley says:

      Haha… didn’t even think about that. 🙂

  26. Ela Zyrek says:

    This was huge, David. I really like this article!

  27. Ela Zyrek says:

    This was huge, David. I really liked this article! Thank you@elazyrek:twitter

  28. As a side note, I wanted to share this on my Facebook page through my smart phone, but there was only a ‘like’ box. So I couldn’t share it..

    1. David Risley says:

      Not sure. If you paste the URL in there, it should work.

      1. Hi David..I have a new smart phone, and am not sure about the pasting bit. All I wanted was to quickly share it on my page (which would get a few extra readers ;).

        Tweeted it though..

  29. Thank you David for telling it like it is. I know I only discovered you a few weeks ago but you restored my faith in business that operate online. Yes – business is business – regardless of where it occurs – the same rules need to apply. 

    Taking your awesome advice (and mine) – I’ll be logging off for over 3 weeks to nurture my ideas and churn them out as realities vs. half hearted, exhausted brain farts … 
    To creativity and telling it like it is! 

    1. David Risley says:

      Thanks, Ameena. And good discussion on Facebook the other day. 🙂

  30. Swamykant says:

    That’s Awesome list, David

  31. Hello David,

    Too many similar thoughts 🙂

    I’ve started list building after reading one of your posts (about 3 months back!). And I’m not at all worrying about the comment count (before I used to worry about them, this pissed off me).

    But I’ve one question about the 9th point. How to find the ‘right’ audience for my blog? 

    Any help?


  32. Another great post David. #49 is one people need to remember 😉 

    My brain is a mass of wrinkly grey awesomeness, but it has so many great ideas locked away in it that I just can not recall. You need a great system that allows you to store and categorize your ideas in a way that will enables you to recall them and actually ACT on them.If you rely totally on your brains ability to recall those ideas, you will flush many great ideas away.

    1. David Risley says:

      Yep. I use Evernote for that. Its awesome.

      Hope you’re doing well, my friend. Lunch again anytime. 🙂

      1. Yes sir. We should hit up lunch after you get this great training hammered out

  33. Thanks for this awesome list David! I think I have to write down some of it in my notes as a reminder.
    One thing I need to put as my laptop wall paper is “The less time you spend on social media, the richer you’ll likely be.” hehehehe…
    Closing down my FB now 🙂


    1. David Risley says:

      Trust me, it is something I struggle with myself. 🙂 Many of these lessons were learned the hard way by me. 🙂

  34. Murray Lunn says:

    Number 28, all the way.

    “Don’t feel obligated to keep up with the latest news and trends. Most of it is stuff you don’t need to know.”

    I can’t even begin to tell you how quickly you can be swept up into this “need” for keeping up-to-date with every tid-bit of information. Doing so not only burns you out but has you chasing these goals that don’t truly matter. Yes, it’s important to understand trends but if they get in the way of business than they’re just a distraction. Keep your head down, work on what matters, get shit done. Plain and simple.

  35. Glynne says:

    Great advice David.  What I want to know is how can you build a list if you have nothing to sell?  We (yes it is ‘we’) have a humanitarian website raising awareness and funds for global charities.  Not certain how to encourage people to sign up to our list?  Any suggestions?

    1. David Risley says:

      You don’t need anything to sell to build a list. It is all about capturing the emails of people with similar interests. You could build a simple update list for global happenings to bring charitable events to people’s attention, for instance.

  36. Kathleendeane says:

    Those were amazing insights! All of them I believe are spot on! Thank you for compiling them for others benefit

  37. Evette says:

    Thank you David for putting this list together and sharing it, great info.

    Thank you!!

  38. robinhallett says:

    Wow, thanks for this, David. I can tell you worked hard 🙂 I learned more than a few dozen of these the hard way myself! I really appreciated your suggestions of what other pitfalls I might avoid (digital baby here). All the best to you, David!

  39. Manuel says:

    David, I found your blog by chance and I must admit that you have really done it. I read this post in its entirety and I agree with 99% of your statements. Thanks for sharing your knowledge.

  40. leckyt says:

    Wow! Awesome list!

    Now, on to the other great resources; so much to learn…

    If the rest of the free stuff is as good as this, I can’t wait to sign up for the paid stuff, too!

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