Original Orient Adventures

A Real-Life Look at Hustle, Gig Work, and Providing for Family

At 32 years old, I was working full-time — 80+ hours every two weeks — and pulling in around $55,000 a year before taxes. Not a fortune, but we made it work. My wife was the real breadwinner for our household, and she also handled most of the fun stuff for the family — vacations, birthday parties, weekend outings. I was more of the “boring dad,” keeping things steady.

But then life shifted. My wife was forced to change jobs, and her income was going to be cut. Suddenly, the pressure was on me to carry more of the financial load. I liked my main job — I work as a Sales Loan Associate, writing collateral loans, selling items, and handling cash. (If you haven’t guessed, I work in a pawn shop — one of the oldest professions around.) It’s a job that keeps me on my toes and lets me interact with all types of people and situations.

But as much as I liked my day job, it wasn’t going to be enough on its own. I’d tried working multiple jobs in the past, and I’d also dipped my toe into the world of gig work — apps like DoorDash, Uber Eats, and others that send you a 1099 instead of a W-2. These jobs are technically self-employed work, which means you have to do your own taxes and set money aside before it even hits your bank account.

I’d driven for DoorDash before, but honestly, I wasn’t a fan. The constant fast food runs and drive-thru waits didn’t appeal to me. But now, with my wife placed on medical leave and our household suddenly a one-income family, I was motivated to try again — and this time, I was determined to find something that fit.

I came across a few new delivery apps I hadn’t used before:

Amazon Flex Roadie (which I believe is now a FedEx subsidiary)

The first time I opened Roadie, it was a Friday afternoon around 4 PM. There were two deliveries available — one paying about $11.30, another around $23. Not bad for quick runs at the end of the day.

But of course, there were requirements. You need a valid driver’s license, a reliable vehicle, and the ability to lift and transport packages. I had all that. But when I checked the Roadie app again over the weekend, there were no deliveries. That’s when I realized Roadie probably follows a more traditional schedule — no weekend runs, likely because it’s connected to FedEx.

I decided to give it a real shot — check it multiple times a week, get familiar with the app, and see if it could actually help bring in some money. The app was simple to use and walked you through each step, from pickup to delivery. Payment is supposed to land weekly, just like DoorDash.

At that point, I hadn’t tried too many other gig platforms, but I was motivated. I wanted to see if I could grind away at the bills, save some money, and maybe even build some connections in the process. Gigs aren’t just side hustles — they can be opportunities to learn and grow. That was my hope, anyway.

But that’s just the beginning of the story.

Coming next: Part 2 — The Reality of Gig Work

Why things didn’t go exactly as planned — and what I learned from it.