Eight years ago I was a horribly depressed, broke, fired security guard.

Today I am an island hopping pro blogger who’s been featured on sites like Virgin, Forbes, Entrepreneur and Fox News.

How did I make this Kafka-esque transition?

By breaking rules.

My Story

After receiving my security guard pink slip I drifted around for a few months. I lived off of government assistance, receiving unemployment insurance. I did appreciate the checks but felt humiliated and dehumanized to rely on the government to make ends meet.

I became terribly depressed during this time. I even contemplated suicide. I felt like a complete and utter loser; no money, no job, barely any possessions.

Here I was in my early 30’s with no money, no career, just drifting through life on the sea of circumstance.

The Turning Point

One day I got so freaking fed up with accepting whatever life threw at me I decided to take charge.

At that moment I had to break all the rules I’d been taught by society.

I wanted to live my dreams by building a thriving online business so I could circle the globe.

I decided:

  • Not to get a job
  • Not to devote my existence to paying bills
  • Not to buy a home
  • Not to start a family

Making these tough decisions turned me into even more of an outsider. It’s one thing to feel like a loser but quite another to have nothing to show for your rebel streak as was the case during those lean days.

I sucked it up, dealt with the painful barbs tossed my way and decided to build a blogging business from the ground up. I had zero entrepreneurial bones in my body. I didn’t even know what a blog was at the time.

I did know enough to plunk down a few hundred bucks I didn’t have to buy something called a domain and hosting. Which felt terrible because I was breaking even more rules in the process, taking a big risk that I’d probably regret in the near future.


Slowly but surely I built my blog into something that turned a profit.

Sure I struggled mightily during my first few years. This happens to rule breakers as you find clarity in your life and business. But I began to see something manifest in my life that absolutely floored me: all massively successful folks are rule breakers. I was following these world-changers.

Richard Branson. Bill Gates. Tony Robbins. The late, great Steve Jobs. All these disruptors who changed civilization did things that screamed “a full 180” from what society did.

You won’t win in life by following rules society sets for you because the general public largely does things from a place of fear.

You will never win if you act predominantly from fear. You will never live your dreams if confined by lack and limitation.

I had to work long, hard, exhausting hours despite seeing no immediate financial returns.

I fell deeply into debt, went bankrupt and lived off of 25 cent snacks from the discount rack of the local convenience store for weeks.

My life became a sustained nightmare as I struggled, strained and strived to survive.

But I won.

I became a world-traveling, Amazon best-selling, island-hopping professional blogger who inspires aspiring digital nomads to travel the world while building profitable blogs.

Almost every single breakthrough I experienced was based on me doing something society said I should not do.

“Get a job to pay the bills.”

“Find employment just to get good health benefits.”

“Build up your savings before becoming a full-time blogger.”

I followed none of these alleged talismans of wisdom.

Yet here I am.

I broke the rules.

I defied convention.

I won.

Tips for Breaking the Rules and Winning

  • Follow your passion life-wise or business-wise
  • Don’t be too practical (practical thinking is usually confining not freeing)
  • Pick one or two mentors in your niche to follow
  • Sprint outside of your comfort zone by diving into your fears on a daily basis
  • Surround yourself with fellow rule breakers
  • Start your day with meditation or prayer
  • Get comfortable with hearing your inner critic tell you what you CANNOT do then….do it
  • Devote your life to freeing yourself and to those whose lives you touch
  • Learn your craft inside-out
  • Do more things from a place of love and fun and less from a place of fear

Your Turn

Are you struggling right now because you are following rules society set for you?

Or are you winning by being a rule-breaker?

Ryan Biddulph is a blogger, author and world traveler who’s been featured on Richard Branson’s Virgin Blog, Forbes, Fox News, Entrepreneur, John Chow Dot Com and Neil Patel Dot Com. He has written and self-published 126 bite-sized eBooks on Amazon. Ryan can help you retire to a life of island hopping through smart blogging at Blogging From Paradise.



Image courtesy of Felix_Broennimann.