Build awareness and adoption for your software startup with Circuit.

15 Lessons Learned in 15 Years of Online Business

Practical, honest insight and advice.

Group of three business people discussing documents while working at table in office, copy space I’ve spent the past 15 years running my online businesses (mostly content-based websites).

While I love the flexibility and freedom, I also appreciate the opportunity to learn and grow through my work. The work is always challenging and never dull.

Things have changed drastically over the past 15 years, and the lessons I’ve learned from one project have often proven incredibly valuable for future projects.

 Sometimes, the world of online business changes so fast that it’s easy to lose sight of all the transitions and everything that’s happened. When I crossed the 15th anniversary of leaving my full-time job, I decided to look back and reflect on the lessons I’ve learned and how they relate to anyone starting or growing a business today.

Here are 15 specific lessons that stand out.

1. It’s Better to Be a Specialist Than a Jack of All Trades, Master of None

Most people want to be well-rounded, but mastering a particular skill is the best way to drastically increase your income and earning potential. A world-class SEO can earn far more than someone who’s good but not great at SEO, social media, writing, content marketing, web design, etc. 

For example, Matthew Woodward charges $1,497 for a one-hour SEO consultation, while the average SEO specialist earns about $55,000 per year (equivalent to less than $30 per hour).

It doesn’t matter if the world-class SEO has skills in those other areas. Clients will pay a premium to work with a master. And if that SEO runs his/her own sites, outsourcing other aspects of the work aside from SEO will lead to the best efficiency.

I have experience with most aspects of running an online business, and for a long time, I didn’t really have a focus or specialization. Eventually, I started focusing on content creation, and the results have proven this to be a better approach.

2. Partnerships Create Incredible Value

Most of the websites I’ve worked on over the years have been individual projects. I’ve outsourced work to freelancers but never had a partner or co-founder for a project until recently.

In 2023, I partnered with a friend to work on a new site,, and it’s been an awesome experience getting the business ready to launch.

There are so many benefits to having a partner, including:

  • More and better ideas
  • Benefits from different areas of expertise
  • Ability to get things done faster
  • Expanded network
  • Motivation
  • Accountability
  • Fun

I wish I had worked on a project with a partner earlier, and I definitely plan to do it again in the future.

3. The Only Constant is Change

The world of online business changes and evolves rapidly. Blogging, SEO, social media, and e-commerce were completely different 15 years ago. When I started my first blog, I got thousands of social media visitors from Digg, Delicious, and StumbleUpon. None of those platforms exist today (Digg still exists, but it’s changed hands and is completely different).

Not only do things change constantly, but the pace of change seems to accelerate. Just look at how far AI has come over the past few years.

It’s easy to get upset when things change (like when a Google search algorithm update wipes out a huge chunk of your site’s traffic), but change is inevitable.

4. Adaptability Is Essential

Adaptability is essential to deal with and manage the constant changes. You can’t get complacent or stuck in your ways. When change is needed, you must be able to adapt.

This is especially true for SEO and social media, but it relates to all areas of online business. What works today may not work five years from now, or even one year from now.

5. Build to Sell

A decent percentage of the money I’ve made over the past 15 years has come from selling the websites and online businesses I’ve built. I’ve had 6 different six-figure exits for a total of more than $2 million. Of course, I’ve made money while I owned and operated those businesses, but a few of them generated more from the sale than they did the entire time I owned the business.

After selling my first website, I learned to build each website or business with an eventual sale in mind. This involves things like:

  • Creating a business that someone else can run (not dependent on me)
  • Focusing on monetization methods that most buyers prefer (ads, affiliate marketing, product sales)
  • Building brands that stand on their own rather than branding them around me personally
  • Diversifying revenue so it’s not dependent on one source

Selling a website or online business can result in a life-changing amount of money, so it’s worth keeping the end goal in mind.

6. Passive Income is Rarely Truly Passive

Everyone seems to be after passive income. Of course, it makes sense. Who wouldn’t want to make money without any work or effort?

Plenty of articles and videos cover passive income ideas, but very few of those ideas are truly passive. I hate to be the bearer of bad news, but blogging is not passive income. Yes, there’s a passive element to it (if you have a successful blog, you can take a month off and probably continue making about the same amount). It may produce passive income for a short time, but it will start declining and eventually end.

You can hire people to do the work for you, but the same can be said about any type of business.

Instead of passive income, I prefer to look for ways to leverage my time and get the most out of the hours I work.

7. Persistence Pays Off

When it comes to online business, most people give up very quickly. In my opinion, the biggest difference between the successful and the unsuccessful is that successful people don’t give up easily.

I’ve had some websites and businesses that grew quickly, but others took a while before they showed any signs of life. If I hadn’t been persistent and stuck with those projects, they would have never turned the corner.

8. Never Underestimate the Value of a Strong Network

Regardless of what type of business you run, building a network is essential. Having a strong network will help you in so many different ways, including:

  • Advice and feedback
  • Collaborations and partnership opportunities
  • Referrals
  • Link building
  • Help with promotions
  • And much more

Of course, it goes both ways. If you want to benefit from having a strong network, you need to help others as well.

One common mistake is trying to network and make connections only when you need something. Effective network involves making and strengthening connections that may or may not benefit you at some point in the future.

9. You Must Be Continually Learning

Because everything related to online business changes so quickly, there’s always something new. Even if you’re an expert in your field (see point #1), you must stay on top of the changes.

Going back to the example of an SEO expert, frequent Google algorithm updates, new search features, and other industry changes require continual learning. If you get complacent, you’ll be left behind.

10. You Must Stay Focused

If you run an online business, you’ll face constant distractions that can easily pull you in the wrong direction if you’re not focused. Shiny new objects, tactics, and approaches are tempting, but if you chase too many of them, you’ll never make progress.

I see articles and ads every day about people making loads of money with some new method or business model. And, of course, plenty of online courses make it seem like riches are just around the corner if you invest a few hours of your time. 

While some of these methods may be as great as they’re made out to be, you have to be able to focus if you want results. That means you can’t chase every new idea. Choose your approach and stick to it.

11. Communication Matters

Communication is an essential skill regardless of what type of business you run. You have to communicate effectively with prospects, clients/customers, partners, employees, freelancers/contractors, journalists and PR professionals, other people in your network, and more.

Of course, both written and verbal communication skills matter, and listening/understanding is equally important.

When I started working online, I overlooked the importance of communication skills because I felt like I worked independently. But I quickly realized just how important good communication skills are.

12. Mental and Emotional Health Should Be Prioritized

Most entrepreneurs work long hours. On top of the long hours, many, myself included, struggle to “turn off” and really get away from their work.

Unfortunately, it’s very common for the grind to take a toll on mental and emotional health in the form of stress, anxiety, fear, and burnout. After running my business for about ten years, I went through a difficult period of anxiety and burnout. Thankfully, I got through it with the help of some people close to me, but I learned through the experience that I must be more proactive to protect myself from the same challenges in the future.

Now, I’m careful to set aside more time for things away from work and allow myself to get refreshed and recharged when needed.

13. The Importance of Time Management

Time management is the biggest challenge I face in my work. There’s no one to tell me what I should be working on, so I have to be careful to manage my time effectively. There are endless things to do, but some are more important or urgent than others.

Learning how to manage time and maximize efficiency made a big difference for me, but staying sharp in those areas is a never-ending challenge.

14. There’s a Difference Between Being Busy and Working on the Right Things

Just because you’re busy and working long hours doesn’t mean you’re working on the things that will actually make a difference for your business. Putting in a lot of hours and working hard won’t lead to success if you’re focused on the wrong things.

I think many people who don’t have experience with their own business or self-employment tend to see being busy as a sign of success. People ask me all the time, “How is work? Are you busy?” Yes, I’m busy, but that doesn’t necessarily mean my business is doing well or that I’m making money.

Staying busy isn’t a challenge. But keeping busy with the right things can be.

15. You Don’t Need a Big Business and Employees to Be Successful

A few years ago, a friend who runs several brick-and-mortar businesses said something to me to the effect of, “A business isn’t really a business if there are no employees.” He wasn’t talking about my business, but his logic still applied to me. However, I don’t agree with him.

I’ve always felt that you don’t need a big payroll to have a successful business, and that’s more evident today than ever. Thousands of solopreneurs and independent creators are achieving incredible success without a more traditional business structure.

In fact, there are many advantages of running a lean operation. Building a large organization and team simply because you think it validates your business is a bad idea.

Final Thoughts

Running an online business requires constant learning, growth, and development. It’s a never-ending process. I’m sure plenty of other lessons could have easily made their way onto this list. Feel free to comment with the lessons you’ve learned. I’d love to hear your own stories.

Continue Learning