Finding Happiness through Failure: How I Created Independence & Flourished in a Digital World

What did you want to be when you grew up? 

Inside all of us is a calling and a gift. But many of us never realize our passionate purpose or find true meaning in our lives. Why is that? 

When I was ten years old, becoming a doctor seemed like a great idea. 

After all, my next-door neighbour was a doctor, and he had a fancy house and a car. Very appealing to my ten-year-old self. Unfortunately, I would later discover that I hated the sight of blood. So I crossed that career pathway firmly off my list. 

But it was a conversation with my teacher in Grade 5 that I remember was a quiet hint and a promise that didn’t reveal itself until almost four decades later. 

She said, “Jeff, you’re a good writer. I love your stories, and you should write more.” 

To a ten-year-old, who had only discovered writing and reading a few years before, I didn’t know what to do with that statement. Would my stories allow me to one day buy a fancy house and car like the doctor next door could? As a child, I was too unaware to ask. 

So I continued with my schooling, remembering her words but failing to put them into action…

Chasing money

I navigated school rather directionlessly and graduated with exactly zero clues as to what I wanted to do with my life.  

So I decided to enroll in an accounting degree. It seemed as good an idea as any. Plus, I thought accountants made a lot of money, so that was my primary motivation for starting. But I soon discovered that I quietly despised accounting. I also wasn’t very good at it. Bugger.

Many of us spend our whole lives in careers we don’t enjoy. But I wasn’t going to be one of those people. So I decided to quit partway through my course and try something else. 

The teaching pivot

I then pivoted to teaching. Why? Well…because I came from a conservative religious upbringing that only had a small buffet of career options. I could really only pick from teaching, nursing and becoming an accountant because those careers allowed me to work within the religious ecosystem (more on this later). 

So I armed myself with a high school teaching diploma, and at the ripe old age of twenty-one I proceeded to instruct teenagers with my vast life experience and expertise (joke). Within mere days I discovered that teaching wasn’t fun, didn’t make me happy and was actually torture. Oh dear. 

But because I had invested four years of education and was under pressure from my conservative parents, the decision to leave was slow and drawn out. Giving up can feel a lot like failure.

I was worried what my parents would think about me ditching my second vocation, and looking back, I should have cut the cord sooner. 

If you’ve drifted into a life path that is more about security and what friends, family, and society think, you’re certainly not alone. 

I stepped right into that thinking, expectation and template. Our young self often enters a career more about comfort, security, and what others want for us. 

I also had the added pressure of organized religion. 

I felt pressure to fit into the expected role model of a conservative. I grew up with a closed and imposed flavor of Christianity, meaning that the career options were more typical than most. 

Another part of the reason I ended up teaching was that the church had a system of schools. Meaning I could work in the fortress of a closed ecosystem that kept us safe from the temptations of the outside world.    

After years of career agony, I took the brave step of making a decision for myself. The world felt too small and the opportunities too limited. I wanted to live a bigger life, and the mental and emotional pain of playing the game finally became too much. 

So I left. 

My parents weren’t happy about my decision and didn’t understand what I was doing. Neither did I. But I knew that if I didn’t make a change, life would be miserable for a very long time.   

You may also have an itch that needs to be scratched, a beckoning that you have ignored, a desire to create a life that you have dreamed about but never dared to act upon. 

What if I could show you how to bring that unexpressed part of yourself out into the light without any risk? Would you be interested?

Before we go into that, I had to learn a few more painful lessons to learn.   

What to do next?

As the career teacher at school, I was responsible for organizing work experience for the students. Work experience is where kids test out a potential career path for two weeks. So I decided to apply the ‘work experience’ model to my career search. During the summer holidays, I tested three types of industry careers. And for the first time, I listened to my heart rather than my parents.

This decision was the first step towards personal freedom and independence. It was freedom with a small ‘f’.   

“I did not intend to get rich. I just wanted to get independent”  – Charlie Munger (Vice Chairman, Berkshire Hathaway)

What I discovered next was the importance of low-risk career testing. The small voice inside me saying “yes” was heard and acted upon. So I tested out careers in the computer tech, life insurance and real estate industries. 

Here’s the thing about choosing a career, often you don’t know whether you’ll enjoy a job until you try it out. Exploring different career options through ‘work experience’ is a great, low-risk way to test out a career before going all in.  

Never one to waste a good crisis

So I chose a new career in sales in the computer industry. At the time, the personal computer sector was exploding. Apple and IBM were at war. And I discovered that the spoils of that battle were high commissions and adventure for some of the foot soldiers. My salary went from paltry to powder kegging. I basked in that industry and its downstream effects for a decade or so. 

But a few short years later, everything changed. 

I had an existential crisis sparked by the crumbling of my first marriage and a financial meltdown. It forced me to start again. I wasn’t going to waste a good crisis.

So, while trying to survive, I read and reflected on what to do next. A new business idea emerged, inspired by a few influences that intersected:

  • I read a book titled “The 4-Hour Work Week” by Tim Ferriss. This book opened my eyes to the fast emerging opportunities to create a digital business. 
  • During this time (2008), I also signed up for social media, including Facebook and Twitter. I noticed how obsessed people were and how much it occupied their time. I sensed an emerging trend that I thought would be powerful and change the world. These platforms were no fad. 
  • I also devoured a book called “The New Rules of Marketing and PR” By David Meerman Scott. He opened my eyes to the potency of publishing online content to attract an audience and potential customers. Today we call it content marketing.
  • The final piece of the puzzle that pushed me over the edge from inaction to action was an article by HubSpot. It said, “If you have an inkling of what sort of business you want to begin, start a blog.” Ok then!  

So in March 2009, I launched my blog, and I started writing. While sharing one post at a time, I remembered what my Grade 5 teacher had noticed as an innate ability. I had ignored it for 40+ years, and now I was finally putting my skills into practice.

I had discovered why I was on this planet. The writing was imperfect, and I was learning as I went. But I was consistently creating. 

The blog didn’t feel like work. It felt more like a mission that I had been called to. It was the intersection of my experience, innate ability and my passion. 

For four years, I set the alarm for 4.30 am and created, wrote, published and shared my (initially) amateur insights about the burgeoning revolution of social media. 

Was I making money from it right away? No. But my passion fuelled my desire to keep turning up to the page and hitting publish every day. 

The business model revealed itself two years later. 

A very short email from ‘Jonny’ popped into my inbox one morning. It said, ‘Love your writing and insights on social media. Would you be interested in running a workshop in New Zealand? We will pay you for it.’ 

He had my attention, and I suddenly stumbled into my first monetization opportunity. On checking Jonny’s “bona fides” (I googled him), I was surprised to discover that he was one of New Zealand’s wealthiest men. So my first ever paid speaking gig was held at Jonny’s golf estate, touted as having the world’s most scenic par 3. Not bad! 

From there, the opportunities continued to grow, the traffic to my blog had reached 5 million visitors a year, I had gained over 560,000 Twitter followers and I was invited and paid to speak all around the world. All that from my little side hustle.    

What is a side hustle, and why might you want to start one?

We may think the term “side hustle” is new and belongs to the digital age, but in fact, the first use of the term was in 1950 (according to Merriam Webster’s research). 

Its standard definition is: Work performed for income supplementary to one’s primary job.

But as work has evolved, technology has taken us globally. The nature of business has changed, and the meaning of side hustle has become a bit more muddled, mystified and glorified. 

It’s moved from the simple meaning of ‘An activity to make some extra money‘ to something bigger and more exciting.

Side hustles are born from the following motivations, desires and pain points:

  1. I’m successful but unhappy, and I want more from life. The small, gnawing voice that wakes you up in the predawn darkness. 
  2. I want an extra job to pay the bills and get ahead financially. You want more money. 
  3. I want an outlet to indulge my creative and curious spirit. I hope to be able to make money from my artistry one day. You could be a musician, photographer, blogger or creator. 
  4. I want a bridge from my dull day job to a career that provides the freedom to live where I want and work autonomously. You want Independence.
  5. I want to build and scale a startup that changes the world. You have the Big Dream. 

My side hustle was born from the third motivation, but we are all different and have different hopes and dreams. So your reason for starting a side hustle is yours to own. 

How did I find success?

So a few years into my side hustle passion project, I was being invited and paid to speak all around the world. How did this happen? All this traffic and attention?

There are a few factors here that contributed to my success.

I was operating from my strengths. This included an ability to communicate with words, both written and spoken. I was also able to sense and notice trends. 

So I was “Futuristic” minded and curious about what was around the corner and over the horizon. I was “Strategic” and big picture oriented (detail annoys me). I was also a “Maximizer” (this leads me to keep changing lanes to get ahead of the traffic). I am also an “Activator” that wants to go from an idea to action.   

My undiscovered strengths were revealed, and I was starting to receive some validation from other people. My side hustle had become my main hustle. I had independence and freedom. 

I had decided to choose happiness. I was doing something that I was curious about. I was creating, and my creations were getting a positive response. 

From that experience, I have created a framework to help you start your own side hustle, and we’ll get into that in a moment. 

Why you should create from your strengths

A few years after I launched the blog, I came across a book titled Strengths Finder. It was a revelation. The results it returned listed what I had felt, sensed and discovered through much trial and error throughout my career. 

My side hustle ticked almost every strength in my tool kit. On top of that, the new world of social media had affirmed that I was on track. 

Before you start any side hustle, I highly recommend you answer the 170+ questionnaire and find out what makes you tick and what your strengths are. Operating from strength is empowering, invigorating and revealing. I got it the wrong way around. 

I stumbled into my strengths after over 50 years of not knowing what they were. Until then, I had been operating and surviving because of what others wanted and not what I was actually good at.   

Here’s what the founder and father of Positive Psychology Martin Seligman says about the importance of your strengths in his book titled Authentic Happiness.

We all want a good life and Aristotle posed this two thousand five hundred years ago: “What is the good life?” …..I ask this great question anew, then provide a fresh and scientifically grounded answer. My answer is tied up in the identification and the use of your signature strengths.” – From the book “Authentic Happiness: Using the New Positive Psychology to Realize Your Potential for Lasting Fulfillment.

Introducing The Freedom Code

My side hustle journey has taught me many lessons that I have distilled into a philosophy and framework called “The Freedom Code”. 

My vision is to provide the inspiration, foundations, resources and community to discover and support your passion and claim your independence. It has five pillars. But before we unveil that, what is freedom?

What is freedom?

Freedom is a word tossed around a lot, and its meaning is distorted and fragmented.

Here are a few phrases and interpretations of Freedom with a capital F.

  • Freedom from tyranny
  • Freedom from autocrats and dictators. Humanity still has some more work to do on this. 
  • Freedom from being a slave and servant to the lord of the manor (or corporation). 

For the most part, the majority of the world has moved on from those places. Nowadays, Freedom might look like this: 

  • Freedom to be independent of a boss
  • Freedom to do what you love.
  • Freedom to pursue whatever brings you sustainable joy and gratification
  • Freedom to choose how you spend your day
  • Freedom to work from anywhere you want

Freedom to tell the boss, “I’m leaving the corporate treadmill and hamster wheel behind”. 

Freedom is the prize we are working for,” Seneca wrote, “not being a slave to anything—not to compulsion, not to chance events.” Then he said, “show me a man who isn’t a slave.” 

To money. To work. To fear. To whatever everyone else is doing. To alcohol, to cigarettes, soda, material possessions, bad habits, followers on social media, anchors on cable news. Indeed, we have many masters”.

My wish for you is the freedom to be fully human. To be free from the tyranny of the rat race of the industrial and corporate overlords. To create the life that you’ve imagined and dreamed about.  

In essence, I want you to be free to be you. True to you. Independent but connected. To realize your potential and purpose. 

Why should you care?

Many of us have successful jobs and careers. We have bills to pay and a family to look after. But starting a side hustle is a low-risk way to do what you love without giving up your day job. 

That’s what the “Freedom code” is about. Providing a pathway and framework to help you transition and start doing what you love with minimal risk. 

So what are the five pillars at the heart of the “Freedom Code” framework?  

Pillar 1: Discover 

Your biggest goal in life is to discover why you are here, act on that mission, and then the magic happens.” 

Discovering your life purpose and why you are on this planet means uncovering your gift. And they can be plural rather than singular.  

As Steven Spielberg reflected, “Dreams come from behind you… It is just a whisper and never shouts“. 

This means you will need to learn, observe, quietly reflect, and listen to the whisper. There is no template or exact formula for this, but some life habits and tactics will help you in this discovery phase. 

I would gently encourage you to start your Freedom Code journey. It may be a creation, a business or a side hustle built upon the intersection of your passion, innate gifts, and experience.

The Discover Pillar Principles

The Discover pillar is vital. It’s about finding out why you are here on this planet. If you find the key to unlock that door, life will be play and not work.

The core principles of the “Discover” Pillar include the following:

  1. Innate ability – What did nature give you – Your strengths. You may need to experientially explore more to unearth these or use some tools and science to mine the deep veins of your genius.
  2. Experience – What are the skills you’ve developed during your life journey? Can you apply them to this journey? 
  3. Passion – What do you love doing? This will sustain you during the marathon.  
  4. Attitudes – Your attitude will carry you from the initial idea and dream to the fulfillment of the goal. Positive instead of negative. Growth instead of scarcity. 
  5. Test and experiment – You don’t know what you like until you go into the world and see if it resonates with your soul and intuition. That dream job could be a nightmare career.
  6. Silence/Stop – Hear the whisper as it doesn’t shout. Distraction, busyness and noise will drown the whisper.
  7. Inspiration – You will need to find inspiration, and that will be from books, videos, podcasts and conversations with a tribe of like-minded colleagues. 
  8. Who is your tribe? – This is hard to know until you join in conversations and discussions. Join some clubs, online forums and groups. When you find your people, you will know and say, “I’m home. I belong. This is my tribe.”

Pillar 2: Create 

Art is anything that means creating and sharing your gift with the world”  – Steven Pressfield.

We are innately creative as humans, but somehow our creativity is lost as we get older. We are told to stop playing as children and reminded to get “serious” and be responsible. Go to school, get a job and look after your family.

So as adults, when we hear the word “create”, we usually think of artists. But we forget that the art and science of creating are not limited to the usual definition and accepted version of creatives!

Entrepreneurs (and side hustlers) are often left out of that conversation. We think more about painters, artists, writers and conventional art.

The reality is that the entrepreneur, the startup dreamer and the “side hustler” are all artists and creators. You are also a creator. You can take an idea and turn that into a business. 

Artists and entrepreneurs take an inside imagined idea and make it a reality. “The magic happens when the ephemeral imagination becomes a manifested visible creation.”

They know that dreaming, ideas and imagination can take form. As humans, we are all dreamers and creators. But some of us act, and others dither. The reality? If it isn’t visible, then it doesn’t exist.

Who are the creators? 

The reality is that we all are.

  • Architects are creators. They imagine a building. 
  • Builders are creators. They take a design from paper to production.
  • Scientists are creators. They see a world and the universe and then pose questions and possible answers to life’s big mysteries. This has led to the creation of devices and tools of magic and even Quantum Mechanics. 
  • Entrepreneurs are creators. They see a problem and create a solution that turns into a real service or product that can be seen and felt.  
  • Photographers are creators. They take us on a journey and allow us to see the world’s beauty. 

Once you’ve settled on the topic area you want to pursue, it’s time to do the work and create. Imagination is an inside job, and creativity is the external manifestation of your ideas. Creativity is about making the invisible visible. 

This pillar is all about the product, service or even art you will create. This pillar will require you to choose how you will create and the time and resources needed. This is where you go from ideas to action.

There is magic in motion. Don’t overcomplicate this step. Just start.

The “Create” Pillar Principles

Creating is where you move from imagination to action. Putting pen to paper or paint to canvas.

  1. Dream – imagination. This is where it all starts. But don’t stop here.
  2. Act – from imagination to creation. 
  3. Routine – Daily Habits that support creating. In his book, “Deep Work”, Cal Newport mentions the importance of setting aside dedicated time to do the work. That habit and routine changed my life. 
  4. Creative Space – Your creative nook for creation could be a dedicated desk or a dedicated coffee shop (that’s how J.K. Rowling wrote Harry Potter). You just need to find a space that works for you.
  5. Simplicity – Keep your creation simple and test different MVCs (Minimal Viable Creations) 

Pillar 3: Share

“The meaning of life is to find your gift; the purpose of life is to give it away.” Pablo Picasso

Creating a product is one thing, but to see if people care about it, you must persistently place your product or art in front of the world. That is the only way to find out if it solves a problem, is an object of beauty that is desired and wanted… or if it needs more work. 

Don’t wait for it to be perfect. Instead, create either a “Minimal Viable Product” (MVP) or “Minimal Lovable Product” (MLP) and see if people want it or share it. Releasing it into the wild is the only way to test your idea and see if it works. 

There are many ways to do that; social media, email, search engines (SEO), influencers and many more. You may also need to get into the trenches and set up a table at a local market or knock on doors.

When you share your creation with the world, it will change you, and you will change the world. It will also validate your idea and give you the feedback you need to evolve and grow.

“Share” Pillar Principles

There is only one way to find if your creation resonates and touches hearts and minds. So what are some of the benefits and principles you need to be aware of when sharing?

  1. Affirmation – Positive feedback that sustains and motivates you both face to face (Eg: conferences) and virtual (Eg: social media)
  2. Learn – from the tribe of followers’ feedback and sharing
  3. Digital platforms are the new village town square 
  4. Contribution – Share your time (help people who can’t help themselves) as well as your creation 

And if you like, you can stop right here!

Many people I have spoken to have raised this point: “But I don’t want to start a side hustle or start a business”. And that’s fine! 

The first three pillars of The Freedom Code, “Discover, Create and Share”, could be where you want to start and stop. 

You may not be motivated by money at all. Just discovering your innate abilities, creating art and sharing it with the world will be enough. Sharing your creations will be enough to provide a fulfilling and happy life. 

But if you want to make money from your side hustle, keep reading… 

Pillar 4: Monetize

“I did not intend to get rich. I just wanted to get independent”  – Charlie Munger (Vice Chairman, Berkshire Hathaway)

If you want to turn your side hustle into your main hustle and fire your boss, you may want to find out if the world will pay you for your creation. Being a starving artist is not a place of freedom but desperation. And I don’t know about you, but that is not a happy place.

Sustaining the sharing of your gift and amplifying your mission means you will need to get paid. In several words, that means “Sales”, “Revenue”, or, to be blunt, the bottom line is “Profit”. 

There are many different business models in a modern digital economy. It’s never been easier to sell your gift to the world. The internet and social media have provided us with low-cost and free tools, distribution networks and marketing platforms that we didn’t have before. 

The “Monetize” Pillar Principles

So how do you create something that the world will pay you for?

  1. Test different business models. What you think will create revenue may not work. Keep trying!  
  2. Embrace the new business models in our digital world. Ecommerce, FBA, Online coaching, Subscription-based models, Freelancing or even becoming an Instagram Influencer!     
  3. Start Simple – MVP (Minimal Viable Product) and MLP (Minimal Lovable Product)

Pillar 5: Amplify

“To make a bigger difference in the world, amplifying and growing your creation comes down to sales. And sales is where the magic happens.”  

If you want to put a dent in the universe, you’ll want to amplify your gift after figuring out the best way to monetize it. Ways to amplify include; Facebook advertising, Google advertising, Instagram advertising, and paid influencer marketing. 

Inside this tent, you will also need to ensure that you have the systems and processes to handle the scaling and amplifying of your art and creation sales. Processes and systems will keep you free from burnout and stress. 

The “Amplify” Pillar Principles

To make the most significant change and contribution to the world, you need to amplify your gift.

  1. Global is the new local – In the past, you could only reach a small world. Now you can show your work anywhere with paid online advertising. 
  2. Democratized Advertising – Paid digital media that you can access and control. 
  3. Process and Systems – Fall in love with the process of creating if you want to scale and amplify.

Wrapping it up

I designed The Freedom Code to help you find your purpose, meaning and mission in life no matter who you are, where you are, or how old you are. Inside all of us is our calling and gift. It may be dormant, or it is a whisper drowned out in the noise of life. Many of us don’t or never realize that passionate purpose or meaning. 

You may also have an itch that needs to be scratched or a beckoning that you have ignored. You desire to create a life you have dreamed about but never dared to act on. Yet. 

You may also be trapped in a career that you quietly hate and doesn’t fulfill you. You may feel like you are on a treadmill that you can’t escape.  

You may be successful but unhappy. But you don’t have to stay that way. 

I am creating a community designed to inspire you. To push you to act on the innate creator that lies dormant inside of you. 

I want to help you to launch and grow your side hustle.    

Side Hustle Strategies is an evolution of that I have always dreamed about. It is devoted to helping you grow personally and professionally (if you choose). Side Hustle Strategies exists to help you flourish.

Since I launched, it has been read by over 40 million people. That website and blog was originally a passion project that started as a side hustle. As I grew my blog, I discovered the financial freedom it gave me and how I designed and lived my life. 

After experiencing that freedom, I wanted to help others get control of their life. That is where the inspiration started for creating

So what will you get when you join Side Hustle Strategies?

For a low monthly fee, you will receive:

  • Ideas and inspiration to help you discover your mission and gift in life. 
  • A community that will help to act rather than procrastinate. To move forward rather than be stuck and paralyzed in doubt and fear.
  • The latest online startup business strategies to generate new revenue streams.
  • A weekly newsletter dedicated to specific topics to accelerate your personal knowledge and business growth.
  • Membership to a community of like-minded people wanting to start and grow a side hustle in our private Facebook group.
  • Proprietary research and the results for trends, business ideas and marketing generated from multiple testing, not available anywhere else on the internet.
  • Support and the opportunity to have your questions answered by experienced entrepreneurs who have forged the same path.
  • Access to our library of newsletter back issues and other resources to continue your education.
  • Bonus content is consistently added, such as expert advice and tools, so you are always up to date with the new technology and trends as they happen.
  • And so much more.

Register/Join Side Hustle Strategies today

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