3 Massive Mistakes Digital Entrepreneurs Make That Keep Them Out of 6-Figure+ Territory


There’s 3 massive failures almost every digital entrepreneur makes, 3 deficiencies that never fail to cut them short of the 6 figure mark.

I make $100-$150 per hour, BUT — and believe me, this is a big butI do not make 6 figures per year.

Weird right?

I mean, just do the math:

$100 times 40 hours per week is $4,000.

Multiply that by 4 and you get $16,000 a month.

Multiply that by 12 and you get $192,000 a year.

But I don’t make that much.

This letter to you is about my failures, and perhaps the biggest failure I’m STILL trying to correct – the reason I make $100 to $300 per article, but fall miserably short of 6 figures.

Pain is a harsh but effective teacher, and while I’ve gone through some very real pain learning these 3 things, my goal is keep you from burning through time, energy and crushed hopes by telling you what these mistakes are and how to avoid them.

Let’s back up a bit, way back actually, to my first failure as an entrepreneur.

Failure #1: Nightcrawlers

I had my first business failure was when I was 6, maybe 7.

We lived in a gray, crumbling old duplex on a busy road — the roof leaked and the heater barely squeaked out enough heat keep us from freezing in the winter.

But that decrepit little cottage had one huge redeeming factor — it was just a short walk from my favorite fishing hole.

If there was any one label I would’ve willingly put on myself, it was that of a fisherman.

At night, the biggest worms ( we called them nightcrawlers) would come out of the ground, and if you were fast enough, you could pounce and snatch them from their holes before they zipped back into the bowels of the earth.

After weeks of practice, for hours each night, I got good enough to fill a bucket with worms in a single night.

As much as I fished, there was no way I could use even a fraction my supply, so I got the brilliant idea that I’d sell the surplus on the side of the road. Like a lemonade-stand….

…but with worms.

Car after car rumbled by without a second glance.

By the third day of standing for hours with my sign, I was miserable. My legs were tired, nose was burnt, and worst of all, I felt like a failure. Unnoticed, unwanted, inadequate.

But then something amazing happened. A friend of the family stopped by to buy some worms.

I was thrilled.

I gave him the bucket of worms I’d hunted all night for, and pocketed my profit, grinning from ear to ear.

As he drove away, I uncrumpled my first glorious payload.

It was a dollar. One. Measly. Dollar.

I didn’t know what bartering was at the time, let alone have the stones to play hard ball with a grownup, but I knew enough to feel ripped off. And with that, my bait shop dream disintegrated into cold reality.

Failure #2: Primal Trade and Barter

I had a few other escapades bartering baseball cards and marbles with the kids in my neighborhood, again getting ripped off by the older kids who knew what the cards were actually worth.

I always left feeling shamed and confused, wondering if I’d done the right thing.

By the time I started junior high, I thought I had learned a thing or two, and decided to give entrepreneur-ism another try.

Failure #3: Submarine Savant

This time, I sold sub sandwiches, and while I barely turned a profit, it felt good. I was no longer that doe-eyed, naive little kid. I was a shark tank entrepreneur; a sales savant, a savvy merchant.

But this time, it wasn’t my poor bartering that killed my dream. I got lazy. It wasn’t fun and I got bored of it, and after a month or two, I stopped altogether..

That turned out to be my trademark for years to come. I’d get a brilliant idea — one of those ideas that would clearly make me millions — then, after a few months of passion-fueled work, my motivation would dry up, leaving me questioning myself, wondering why I hadn’t made my millions yet, or even thousands or hundreds…

Failure #4, 5, 6, and 7

Later, I started an army surplus sort of e-store. It failed. I tried selling airsoft products. That lasted a few weeks. My hookah e-store actually got a few solid sales, but not enough to keep my interest. It also failed miserably. I tried dropshipping, affiliate marketing, Amazon stores, Ebay — you name it.

I wrote on a blog for about 6 months without seeing a drop of profit, but then it hit me.

I knew I wasn’t dumb, and I wasn’t lazy. I woke up at 4 every morning and put in more effort than anyone I knew. I wasn’t unlucky or some kind of bad karma magnet.

Whenever I failed, I made excuses to avoid the pain of being a failure.

The timing wasn’t right, the market was saturated, I didn’t have money to throw at my marketing like everybody else had.

Maybe there was a grain of truth there, but I was missing the greatest insights that would utterly change my life.

I don’t know when it happened, but something clicked. LOUD.

I realized that I hadn’t found my passion, and even more important, I had failed to be consistent.

Most people give up right when they’re on the verge of success, and I was one of those people.

I didn’t know how close I’d been to the tipping point, but I figured I’d better push hard and non-stop next time. Go big or go die — there could be no in between.

So I did some soul-searching (whatever that means), and landed on a career I knew I could pursue forever, just for the sheer love of it, even if I failed at it for the rest of my life.

Failure #8: My Pride and Joy

That craft was writing.

I didn’t know why or how people would pay for my writing even if it was good, but I set out with a new vision — to write professionally or die trying.

I was a starving artist and proud of it. Rice, beans and ramen noodles were my only friends, and I gypsy’d my way through the countries with the lowest cost of living, places where I could survive off of my sad content mill wages.

My fledgling scribbles met cutting criticism, clients who refused to pay, and more than a few sneering rejections.

But for all the pain and legitimate hurt I felt from those rejections (I know it’s lame, but hey, truth is truth), something inside me changed.

I was creating a career I loved and was proud of; I was finally being true to myself and that made me feel alive.

For the first time in my life I didn’t care about getting stinking filthy rich and impressing my family and friends with my prestigious success.

I simply knew what I was meant to do; what was written in the genetical story of my DNA.

And that’s when I started making money — GOOD money.

I’m not telling you this to show you how I went from rags to riches, as much as I love those stories.

I’m telling you this story to highlight the 3 major mistakes I made that initially kept me broke and literally a starving artist, and 1 monumental mistake that kept me from breaking the 6 figure mark.

Mistake #1: Lack of Passion… and Stuff…

Lack of passion, motivation, belief, momentum. I know those are 4 different things, but there’s so much overlap. Self-belief is your primary fuel that fuels passion, motivation and momentum, which are forms of fuel that drive your actions.

Mistake #2: Craftsmanship

Lack of pitbull tenacity in honing your craft.

My craft is writing.

I’ve spent years with a hyper-focus on writing a lot and writing well; constantly improving my craft. I want every article, blog post, sales letter or whatever it is that I’m writing to be a masterpiece.

And people are willing to pay good money for masterpieces.

My motto used to be “money follows quality,” and while I still say that and believe it, that’s only part of the truth.

THIS is the final piece to the puzzle — the mistake I’ve made for about 7 years — and the reason I don’t make 6 figures a year despite making $100 to $150 per hour.

Mistake #3: Self Promotion

Lack of self promotion. Call it sales, personal branding, marketing whatever you call it, this single mistake has vicious consequences.

You’ve probably heard how Van Gogh only sold a single painting in his lifetime, for 400 francs, the modern equivalent of $1,800 .

One of his paintings (Sunflowers if I remember right) sold for $39.9 million, but he died in poverty, a no-name, despite his masterful skill and dedication to his craft.

If you can’t get your work and ability in front of people, it doesn’t matter how much self-belief you have, or how much passion and time you put into your craft. Without marketing or sales, you won’t make a dime.

And THAT my friends, is my greatest failure to date — one I’m glad I caught onto early in my life, so I can correct it, and one I hope you’ll correct too, now that you know it.

Once I figure it out completely, I’ll let you know and show you exactly how I overcame that single most toxic mistake any digital entrepreneur can make.

Hopefully sooner than later (:

My final message for you is this unbridled truth:

The path to success is rife with failure and pain, and those are two of your greatest teachers.

If you let them be.

Recently I heard someone say that “failure is not an option,” that you don’t have to fail if you just do things right to begin with.

That’s a lie.

No one in history has EVER done that, not even the most brilliant minds the world as seen.

So I want to leave you with 2 quick mini-stories on that note.

Some Motivating Success Stories You Might Want to Digest

I’m sure you’ve heard these stories, but they’re worth repeating.

Let’s start on the writing side of things, since it’s arguably the best career a digital nomad can pursue (I know, I’m biased.)

JK Rowling was a single mother on welfare who wrote in cafes to stay warm and write as her baby slept.

She pushed through the pain of severe poverty and 12 publisher rejections until she hit her tipping point, and went on to make millions off of her passion.

Oprah Winfrey, love her or hate her, is another shining example of pushing through failure.

She was abandoned by her parents to live with her grandmother, who was so poor she had to dress the child in potato sacks. Needless to say, going to bed hungry was just a part of her life at the time.

On top of that, she was molested by two family members when she was only 13. She ran away in hopes of a better life.

Her newborn baby died when she was 14.

Despite one of history’s roughest starts, she kept beating her head into her metaphorical brick wall until it shattered.

Forbes now estimates her worth at roughly $2.7 billion.

Alright, I know I said I’s give you 2 success stories, but let’s count this one as a bonus.

Have you heard the story about the trader who started with a match and traded his way up to a palace?

Well that pretty much happened in real life.

Ingvar Kamprad was born in a small village in Sweden called Pjätteryd.

He was a humble door to door salesman, selling — you guessed it — matches, riding from house to house on his bicycle.

After some success, he started buying them in bulk to get the bulk-rate discount, and his profits grew.

It wasn’t long before he’d saved enough to buy and sell fish. Then Christmas decoration, and then seeds, and then low-cost, high-return ballpoint pens and pencils.

Finally, he pooled all of his resources and began selling furniture.

The furniture and home decor powerhouse IKEA was founded by Ingvar in 1943 at his uncle Ernst’s kitchen table. IKEA is made up of the initials of his name (Ingvar Kamprad) plus those of Elmtaryd, the family farm where he was born, and the nearby village Agunnaryd. His IKEA chain is now worth well over $6 billion.

All from a box of matches.

Remember, the journey to 6-figure success as a digital entrepreneur is only possible by maintaining your motivation, passion, and self-belief, and channeling that drive into mastering your craft, and promoting your craft.

Find your passion and never stop improving and promoting yourself.