Reflection

Each new decade transforms me in ways I never imagined.

I began as a shy kid, content tinkering with code in quiet corners. Ten years later, I was the driven entrepreneur who measured worth by work. Another decade flipped me into a restless night owl, chasing laughter and living on impulse. Now, as a world traveler devoted to giving back, I see these shifts not as detours, but as steps toward understanding what matters most. Each stage carved out a new facet of who I am—proof that change can light the way forward.

Early Years

 

Friend Moves to the USA

The second best friend of my life, whom I had spent years with, moved away to the USA. I don't remember exactly how I reacted, but I ended up staying close to family and didn't branch out much for many years after.

 

Meeting Ross and Discovering Computers

I met Ross in grade four, a new kid in town. For the first time since kindergarten, I had a best friend. We hung out all the time and spent countless hours using Spiderman Cartoon Maker! Recognizing my passion for computers, my mom hired a local kid to give me lessons. He introduced me to HyperCard.

 

Creating My First Computer Game

I created my first black-and-white HyperCard computer game, a point-and-click adventure where players navigate a spaceport maze to launch a ship. This project ignited my passion for software development.

 

Uploading HyperCard Games

I uploaded some HyperCard games I had made. I hoped someone would send me $2 for registration but didn't think much of it. I’m pretty sure I put them on the InfoMac archives.

Business Begins

 

First Sale for a License

My first sale came when someone sent $2 cash via postal mail for a game license. I wanted to deposit it, but my mom encouraged me to frame it. She knew it would be special one day.

 

Family Changes and Growing Confidence

My mother left my father, and we moved in with my grandparents. I spent the summer playing on Hotline. Without my father’s oppressive attitude, my confidence began to grow.

 

Launching My Online Portal

I created an online portal for my apps. Using Kagi as a credit card processor (they didn’t know I was 16), I made my first $5 alarm clock app sale on May 27th. This started my software business.

 

First Overseas Trip to Hawaii

My mom took my brother and me to Hawaii. I spent most of the trip in internet cafes sending license codes and updating my apps. When not there, I relaxed on the beach with my Palm Pilot knock-off.

 

First Real Girlfriend and Academic Success

I met my first real girlfriend. Although my grades dipped slightly, I still managed to make the honor roll.

 

High School Graduation and Scholarship

I graduated high school and received a scholarship for having the highest GPA in my field of study.

 

Moving to Burnaby for Post-Secondary

My girlfriend and I moved to Burnaby for an intensive new media program. I breezed through it but felt it was overpriced and under-delivered.

 

Starting My First Internet Marketing Job

I was hired by a man subletting an office after I didn't get my first choice job. I even got two friends hired. The boss never came in, trusting us to work while we often goofed around.

 

Winning a Trip to New York

My girlfriend secretly entered me in a radio contest, and we won a trip to New York to meet Kylie Minogue. It was my first adult trip abroad without my parents.

Young Adult

 

Buying My First Condo

After a breakup, I decided to buy rather than rent. My mom co-signed, and I purchased my first piece of real estate.

 

Estrangement from My Father

My dad and I had our first real fight as adults. Our relationship ended that day and never recovered.

 

Focusing on My Software Business

I quit my internet marketing job to focus full-time on my software business. I sold my first condo for a profit and bought another near my mom.

 

First Solo Vacation to Hawaii

I returned to Hawaii solo for my 22nd birthday, escaping a night out of drinking by going on a true adventure. A mysterious stormy night encounter still haunts me today.

 

Getting My Driver's License and First Car

Living in a small town made procrastinating on driving impossible. At 22, I got my license and bought my first car, greatly expanding my freedom.

The New Me

 

Personal Transformation

After a breakup, I attended my first house party, tried alcohol, dyed my hair purple, embraced punk/grunge style, and shifted my music taste to Green Day and late 90s rock.

 

Creating a Board Game

A friend and I created a board game combining elements of Life, Monopoly, and The Sims. Players strive to win at life by earning points in various categories. It's now available online as a free print-at-home download.

 

Launching and Shutting Down an Internet Cafe

I opened my own internet cafe without proper feasibility studies. It lasted about three months before I closed it, realizing the industry was fading.

Okanagan Life

 

Beginning Real Estate Investment

I moved to the Okanagan and kept my old house as an investment property. Over the next 13 years, I bought, renovated, rented, and sold properties as an investor.

 

Starting Hiking & Social Clubs

I started a hiking club in the Okanagan, offering free weekly hikes and later expanding to other social events. It grew into the tens of thousands, earning media features. In parallel, I launched a general social club where I host cook offs, paint nights, board game events, road trips, and much more. Most of these events are either done at-cost or at a loss at my own expense for the sake of building community.

Travel Bug

 

Salkantay Trek to Machu Picchu

I joined a Groupon trek to Machu Picchu, embracing an Indiana Jones-style adventure. Traveling where English wasn't common no longer scared me. I launched AdventureJosh.com to blog future trips.

 

Life Abroad in New Zealand

A friend and I tried life in New Zealand, doing extreme sports I never imagined. After five months, we returned home low on funds but rich in unforgettable experiences.

 

Breaking Free and Expanding Travel

Feeling stagnated, I broke up with my girlfriend and traveled extensively (Jamaica, Puerto Rico, Cuba, Turks & Caicos, and the UK). I pursued my childhood dream of possibly living in Ireland.

 

International Adventures Become Routine

I traveled to Thailand, Singapore, Malaysia, Vietnam, Cambodia, China, Finland, Israel, Jordan, Egypt, India, and Nepal. While in SE Asia, I volunteered on an archaeological dig. Later that year, I filmed a travel video in India—a grueling journey that opened my eyes to global inequities.

 

Moving to the Island and Personal Challenges

I moved to Vancouver Island with hopes of new adventures, got a hair transplant, yet shortly returned to the Okanagan hoping to enact positive change. After a brief foray into politics, my best friend Ross died of an overdose. I took time away to grieve and reflect.

 

Moving to Ireland and Health Challenges

I moved to Belfast with a UK Ancestry Visa but left after three months due to unfriendly attitudes and harsh weather. Considering another UK city, I was hindered by gout, making it hard to host hikes.

 

Completing the Last of the 7 Wonders

I road-tripped through Italy, finishing the last of the 7 Wonders, and learned Final Cut Pro to release my second travel video. Italy became a favorite country. I followed this up by volunteering at an animal reserve in South Africa.

Lockdown & Introspection

 

Rooting Down in Alberta and COVID Impact

I settled in Alberta, started new clubs, and looked forward to hiking the Rockies. Then COVID-19 hit, ending any plans to use my UK Visa again.

 

Volunteering at the Local Zoo

I volunteered hundreds of hours at a local zoo but was horrified by the treatment of animals and staff. The experience left a bitter taste in my mouth.

Adulthood

 

Reflecting After My Father's Passing

My father passed away while I was in Greece. Although we were not close, it caused me to reflect deeply. I extended my Europe trip to two months and 11 countries, traveling solo on what I once thought would be a honeymoon itinerary.

 

Transitioning Focus and Ending Event Hosting

As I neared 40, I promised myself that if I remained single, I’d step back from hosting events and invest that energy into my career and personal life. I kept this promise. I chose to bring that chapter fully to a close in September 2024. Though it felt bittersweet, it also brought a sense of relief and renewal, paving the way for a future more aligned with who I’ve become.

 

Loss of My Best Friend Darryl

My best friend Darryl died in a car accident. Of my long-term childhood friends, only four remain, scattered worldwide. May they all outlive me.

 

A Close Call with "the One"

I believed I’d finally met the woman I’d marry, only to see my father’s familiar shadows in her. Recognizing the pattern, I chose self-respect over passion and excitement, broke free, and kept moving forward.

 

Discovering "How I Met Your Mother" and Embracing Nomadism

After binging How I Met Your Mother, I noticed uncanny parallels to my own life—even old rumors about me seemed lifted straight from the show’s scripts. The absurdity made me laugh, but it also nudged me toward a new chapter. I sold my last investment rental property, escaped winter for the Philippines, and embraced a nomadic, entrepreneurial existence. Now, I run my travel page like a business, value my health and work more deeply, and save the wild nights for moments that truly matter.

Check out my highlight reel on YouTube for travel inspiration!