After climbing the corporate ladder for two decades, Johnny realized the ladder had been leaning against the wrong building. He was making great money, but he got a bad case of the Sunday Scaries (that dreaded Sunday night feeling knowing you have to go into work the next morning.)

He decided he needed passive income. After months of research, he invested $250,000 in a low-risk franchise system that promised he wouldn’t have to lift a finger. The investment made total sense. A safe bet.

When the business opened, he quickly started losing $10,000 per month and had to help operate a business that promised to be passive. It was a disaster. After losing more than $500,000 he shut the business down and decided he was just going to be content in his job. But the “empty feeling” kept nagging at him.

As his oldest son was preparing for college, he realized he had never shared his childhood passion of drawing with him. He decided to pick up the sketch pad and do one drawing a day with his son as a fun hobby. It had been years since he consistently drew and he remembered the feeling of losing track of time when he created something.

For years, he had a goal of sharing his art more frequently on social media but never made the time for it. Now that it brought him closer to his son, he committed to sketch and share his art every day on social media no matter how embarrassed he was with the drawing. He knew he wasn’t going to make any money with his creations, but at least he was having fun again.

Then one day he posted a buffalo drawing on a wooden canvas on Instagram and it went viral. A follower sent him a direct message asking if he took requests for custom artwork. He was hesitant to deal with the pressure of paid work so he told his follower a number that he knew they would turn down. “Sorry, it’s a $1K minimum.” The follower responded instantly, “What’s your Venmo?” 

When Johnny tried to solve his lack of fulfillment with spreadsheets and reason, he failed and felt miserable. When he trusted his heart, he found the Creator within that had been there waiting all along.

Johnny loved drawing as a kid and always wanted to do something with art as an adult, but it never felt practical. After his franchise business failed, he made a simple decision that changed everything. He committed to sketching every single day and sharing his work on a new Instagram account.

At first it started slow. Hearts from his mom and sister (the outcome that makes most of us tremble.)

His turning point was when he drew a buffalo on a wooden canvas and it went viral.

With a blossoming following and increasing commission requests, Johnny soon found himself navigating the unfamiliar terrain of art as a business.

For Johnny, the art venture was more than just a financial goal. It was a journey of self-discovery and fulfillment, offering a chance to leave a legacy beyond his corporate achievements. This pursuit was about finding meaning and identity outside the confines of a traditional career.

If you’re reading this you’re probably like us: decently happy with a job, but craving more. Maybe you aren’t really sure what “more” looks like. Sure, you want more money and freedom just like the next guy, but the path is unclear from where you are to where you’d like to be. 

It seems like all of the entrepreneurs and creators online know exactly what they want, who they are, and what energizes them. And here you are, wondering:

We wish there was a single, clear, golden path that leads directly to your shiny golden opportunity. You know, the perfect way to build something that feels like our own where the risk is low and the returns guaranteed. 

But that’s not real life. 

Figuring out what you should create is a single player game, but that doesn’t mean you have to do it alone.

For far too long, those stuck on the Default Path have had two options: Start a side hustle doing low leverage boring tasks like delivering Door Dash OR try to raise a bunch of money and roll the dice in entrepreneurship. Both are horrible options for people with careers and decent work experience that just want more without having to risk everything that they’ve worked so hard for. They aren’t desperate for cash, they are unfulfilled and know that there’s another life inside of them that is meant for more. 

Although every side bet is unique, we’ve found there are some common threads among those that find success.

These steps aren’t unique to selling art online.  They are principles that apply to any Side Bet. By following these principles you can navigate the journey from rediscovering a passion to building a successful and fulfilling Side Bet, just as Johnny did with his art.

Johnny’s story is a beacon for those who have felt the call and are ready to leave the Default Path and find their own path. His experience emphasizes the importance of starting small, focusing on consistent input rather than immediate output, and understanding market demand. 

Looking ahead, Johnny envisions scaling his art business, and exploring avenues like prints and collaborations so he can turn his Side Bet into his full-time thing.

Until next time,
Raleigh “Enter the Cave” Williams