Why You're Not Successfully Self Employed - 7 Reasons

Why You're Not Successfully Self Employed - 7 Reasons

I built a niche website about online teaching that made over $30,000 from Amazon Associates over the course of it's life before China banned online teaching (thanks China) and that topic all but died off.

I've also created multiple Skillshare and Udemy courses, this blog you're on now, paid courses that people find very helpful and I'm also a top rated Fiverr seller.

No one told me to do any of this

I just had to figure it out bit by bit from free resources, products I bought (courses and ebooks) and most importantly - trying and failing.

Spencer Hawes built software tools that he sold for over a million dollars, created an Amazon FBA business selling pillows (which he later sold) and now runs a massively popular blog.

Justin Welsh used Twitter (now X) and Linked in to grow a massive email list that helps him make a million dollars a year by selling helpful products to his audience and running sponsorships on his email list.

Matt Giovanisci of Swim University built a massively popular pool and hot tub brand that includes a blog, YouTube channel, email list, social media channels, white label physical products and digital guides.

They had to do what you and I have to do.

Figure it out through trial and error.

The value of online courses, ebooks, blog posts and YouTube videos is not that it's some magic bullet - it's that it will save you years of trial and error, but the fact remains, you still need to do the work.

Why do people fail at online business

So why do so many people fail at online business?

Here is what I have observed from my 10+ years of experience of working online:

  1. Not taking action - Professional planners.
  2. Lack of consistency.
  3. Being an echo (copycat syndrome).
  4. Keeping at a losing idea for too long.
  5. Not being resourceful and "figuring it out."
  6. Cheap, unwilling to spend money and always looking for shortcuts.
  7. Not getting out of your comfort zone.

Not taking action - Professional planners

The most common mistake I see from beginners is simply not taking action and actually trying. It's easy to plan and say you're going to do something because then you feel like you are making progress.

But you're not.

Instead, too many beginners become professional planners. Great at planning everything out in detail - spreadsheets, mind maps, drawings etc; but not very good at doing the thing they're planning.

They plan out the design of their website, the name of their podcast, heck, maybe they even do one or two podcasts but then never pay for podcast hosting to actually launch their idea (is their a free option bro?).

It's always some complicated plan of a website, product, YouTube channel idea, podcast, domain names and associated branding for each item.

But at some point you need to stop planning and actually launch.

I'm a highly rated Fiverr seller, I've worked with people who wanted to launch a gig on Fiverr and I've literally had people not even complete their profile on Fiverr because they did not have a camera to record an introduction video or they wanted me to hand hold them through the process of setting up a gig.

What serious people do by contrast is that they launch and go through the process of trying and failing like I did and like everyone else does and then asking me for pointers to help optimize their gig performance.

Lack of consistency

Consistency is the name of the game with online business. A great example of this is how Steve Scott built a million dollar Kindle ebook business.

Do you think he just woke up one day with 80+ Kindle ebooks to his name, a high traffic website and an email list?

No, it took a consistent amount of work over the course of a few years.

Yet too many beginners get excited about starting a blog or a YouTube channel, creating an online store or launching a service, but then give up too quick by not following through properly.

The internet is awash with WordPress blogs that have 10-20 blogs posts, who's owners liked the idea of making money from a blog but not the actual work of being a publisher.

If you can't be consistent for a period of time with one business model for at least 6 months, you're never going to have success long term.

Being an echo (copycat syndrome)

BoldandDetermined.com (now defunct) was one of the most copied blogs I have ever seen in my life.

It was a personal development website for young men on the topics of weight lifting, making money, dating and personal growth.

But in the comments you would see a plethora of copycat bloggers leaving comments, or as I like to call them, echo’s of a superior blogger.

For example:

There is nothing wrong with modeling after someone because, as the saying goes, “success leaves clues.”

But being an outright copycat of someone else is never going to work because you’re always going to be a second-rate version of something better.

Instead of choosing a niche where you can add value, beginners tend to launch ideas about topics they are currently interested in but cannot provide value on.

Like, guys who watch dating content on YouTube then want to launch their own YouTube channels about dating even though they have no useful insights.

With Bold and Determined, the founder Nick Kelly was an excellent writer, he is actually big and strong and lived the life he wrote about.

Copycats modeled after him (from his WordPress theme to ripping off his blog content) but lacked the authenticity to back up their content.

Instead, choose a topic where you can actually add value

Select a topic that you know and understand better than others, one where you can share helpful insights, tips, and advice so you solve problems and pain points for you audience.

Then, build a brand around that topic that has it’s own unique style to help set you apart from what currently exists.

Keeping at a loser idea for too long

The total opposite of having a lack of consistency is the beginner mistake of keeping at a loser idea for too long.

I’m all for giving yourself 6 months of consistent work, but after 6 months if you’re not seeing engagement with what you’re doing it may be time to stop and pivot.

Notice I said engagement and not simply growth.

Building an online business, blog, YouTube channel, ecommerce website or personal brand through free traffic is a grind and it does takes longer than 6 months to see real results (and you should be open to testing out running paid ads, at least $5 a day to an offer).

Engagement is the metric I would pay attention to more than anything else because that is what will tell you if you’re onto something.

Are you getting emails from companies wanting to sponsor or work with you?

Do you get comments and questions regularly?

Are things in general growing or are they stagnating?

I bring this up because it reminds me of a blogger I know from Rhode Island where for over 10 years he’s been running his personal development blog. Starting when he was 24 old to now being in his 30s.

His blog gets a handful of visitors a day, his Kindle books don’t sell and what he is doing online does not work and has never worked.

In part because his content does not resonate with any audience:

I help emergent though leaders, creatives and change makers refine and align their authentic personal stories through self knowledge techniques in a holistic open approach.


What does this even mean and who is this for?

He rewrites this convoluted mission statement on his “about me” section for his blog every few months.

Blogging away hoping that “this is the year” things turn the corner. It’s been over 10 years, it’s sad and it’s time for him to stop and apply his energy towards something else.

In short, try your very best but be open to your idea failing and you needing to pivot to something else. Don’t get too emotionally invested in a project that is failing.

Not being resourceful and “figuring it out.”

I’ve created well over 200 tutorial videos on YouTube, the most frustrating comments I get are from people asking questions I literally answered in the video.

People who fail at starting an online business be it a service, blog, ecommerce website etc, fail because they require too much hand holding. They can’t just try, fail, adapt and figure it out along the way.

They need everything to be perfect and spend way too much time learning and planning before they can even launch a minimally viable product.

Just figure it out

This goes beyond internet business and can apply to all aspects of life. As many who read my business blog know, I’m an expat and have been one for 10+ years.

When I went to live in Ho Chi Minh City Vietnam for the first time a few years ago, I did my basic research.

But at the end of the day, I bought a ticket, flew to Vietnam, stayed in a hotel, and looked for an apartment. I just figured it out, making many mistakes and wasting time and money along the way.

With the internet, there are countless blogs, videos, courses, and resources to help you do and understand pretty much anything.

If you lack the ability to figure things out on your own and be resourceful, you’re going to struggle to have success online.

Cheap, unwilling to spend money and always looking for shortcuts

I called out AI auto blogging platforms numerous times on both X and my main YouTube channel.

I was inspired to write this because I saw countless YouTubers hyping up these spam producing platforms as a way to create content quickly – making YouTube videos about how they created “100 blog posts in under an hour” about topics like fern trees, birds or any other random niche and then running ads on them as a way to monetize their websites.

Shortcuts never work!

Every year it’s the same old story, just with a new dumb shortcut that maybe works for a few months, but long term sabotages your ability to build a sustainable, long term income.

Please stop looking for shortcuts.

They never work for the long term, all those individuals talking about auto-blogging platforms have had their websites penalized for spam and their traffic nuked to oblivion.

One of my competitors to my blog about online teaching that leveraged AI content heavily. At one point they broke almost a million visitors a month, now under 10K visits a month.

The whole point of SEO is to optimize your content for to rank well and be useful to people. Not to create dumb websites on exotic birds, gardening tools, or outdoor yard games using AI.

They may have made a quick buck, but really all they did was waste time. Instead, do the work to build a brand, position yourself as a helpful guide or authority about a topic and solve problems for people.

That’s all you have to do. It’s not easy, but this consistent long term work is the barrier to entry and it’s what separates the winners from the losers.

Stop looking for free

Finally, another reason why beginners fail at online business is because they are just to cheap to invest in their idea.

Even when I create videos and blog content about using Google Sites (the best free website builder I’ve used), people still want to know if they can get a free domain name in some way and are upset that they have to spend $12 to buy a domain name.


Get your .com domain name today.

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There is nothing wrong with being cautious on how you spend money, but when you start refusing to spend the money required to launch your idea (web hosting, podcast hosting, buying a camera for YouTube, running ads for ecommerce) then you’re going to struggle to make progress.

This ties back into looking for shortcuts because instead of paying for web hosting and launching a blog on WordPress or paying for a website builder like Squarespace or using an alternative blogging platform like Ghost, you instead want to find the cheap and free way to do everything.

Not getting out of your comfort zone

Finally, the last reason people fail to be successfully self employed is because they don’t want to get out of their comfort zone.

For example, a lot bloggers just want to only blog, not deal with other people and then magically make a lot of money by ranking organically on Google.

Sorry, but it’s the internet and you need to network with other people. When you look at anyone with a big online presence they always serve one audience in multiple ways.

YouTube, blog, email list, paid ads, courses, offering a service, social media. As the saying goes, “what got you here, won’t get you there.”

Take for example YouTubers Kara and Nate (3 million+ subscribers).

They have a very popular YouTube channel that makes enough to support them full time.

But did they stop there?


They founded a service called Fare Drop, a newsletter called Daily Drop, a travel blog, and various social media profiles.

Let’s look at Mark Manson.

He has built a high-traffic personal development website over the course of a few years, written multiple books, and earned a full-time income from it all.

Did he just only blog?

At first yes, but he did not just stop at being yet another “blogger.” He now also runs an email newsletter, creates private members-only content, and runs a YouTube channel.

Continually develop your skill stack.

You need to learn how to hire people to complete tasks for you, understand email marketing, create products and sales funnels, diversify your traffic sources, and serve your audience in multiple ways.

I’ve noticed that people who fail are those who don’t get outside their comfort zone and continually develop their skill stack.

Like running a webinar for the first time, creating a bi-weekly coaching call offer, or running ads. Whatever it is, getting outside of your comfort zone is doing the thing you’re avoiding but know you should be doing.

Why people fail to become successfully self employed – conclusion

I think anyone of reasonable intelligence with a good work ethic can figure out a side income.

It is possible to turn your knowledge into income if you’re able to avoid some of the mistakes beginners make that I laid out here.

Just pick an audience, solve problems, be in a topic you understand better than others and be willing to give a solid effort for at least 6 months - then evaluate and make a decision to push forward or quit and do something else.

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