The Joys of Being Your Own Boss
Why I Work for Myself in the Gig Economy
I began my rideshare journey in the spring of 2017, driving part-time on weekends and occasionally after work. At first, I never viewed rideshare as a sustainable full-time gig. But then, the post-pandemic spending boom and driver shortages created an opportunity I couldn’t ignore—enter the Golden Years of rideshare.
In late 2021, during the Great Resignation, I made a bold move: I quit my corporate job and dove into full-time rideshare driving. The main motivation? To become my own boss and choose my own hours.
The Freedom to Choose
With rideshare, I can sleep in or take a day off to spend with family without asking for permission. I’ve traded the corporate grind for a flexible schedule that fits my life, not the other way around. For the first time, I felt zero stress—no deadlines to meet, no bosses to impress, and no coworkers to navigate. Each morning, I worked on my terms, and that autonomy was incredibly satisfying.
While the gig economy comes with its own challenges—like being solely responsible for my success and managing my own finances—the benefits far outweigh the drawbacks. I’ve escaped the misery of micromanagement, rigid schedules, capped salaries, and the constant need to ask for time off.
Finding Balance and Growth
The flexibility of my rideshare schedule was crucial for my well-being. It allowed me to balance work and personal priorities, freeing me from the constraints of my two decades in corporate life. By paying off debt and keeping my expenses low, I achieved my goal of thriving as a full-time gig worker for over two and a half years.
During that time, I discovered new opportunities for growth—like listening to podcasts while delivering Amazon Flex packages and even starting my own YouTube channel. Eventually, I returned to the corporate world but now drive rideshare part-time as a weekend warrior. That two-and-a-half-year break was transformative and helped me grow as an individual.
Embrace Your Path
I’m not suggesting everyone should quit their job to drive rideshare. The gig economy is more competitive than ever. However, when people scoff at your choice to work for yourself, remember that you’re embracing a flexible lifestyle that many envy.
Responses like, “Get a real job,” or “You answer to the customer,” are common. But the truth is, as a gig worker, you owe nothing to anyone, and you don’t have to answer to anyone. You’re living life on your own terms—happily in the position of “Fuck You.”
Key Benefits of Independence
Freedom — You are in control of your work life. You decide when, where, and how much you want to work. This freedom fosters a sense of responsibility and fulfillment that’s hard to replicate in a traditional job.
Flexibility — Life can be unpredictable, and having a job that accommodates that unpredictability is a blessing. Whether it’s a family commitment or a spontaneous trip, your schedule can adapt without the hassle of requesting time off.
Opportunity — The gig industry is ripe with opportunities for growth. You can expand your services, explore new areas, and connect with diverse people, all while making money and providing for your family.
Key Considerations of Independence
Benefits — Independent contractors typically lack employer-provided benefits (health insurance, retirement plans, etc.). Without these safety nets, gig workers must take proactive steps to manage their health and financial security.
Balance — While the flexibility to choose your own hours is one of the most appealing aspects of rideshare driving, it can also result in the temptation to overwork. Many drivers find it challenging to establish boundaries, often pushing themselves to work longer hours in pursuit of higher earnings—leading to burn out.
Sustainability — Reflecting on the long-term viability of gig work as a career path is essential for those considering rideshare driving. While the immediate benefits of flexibility and autonomy are appealing, it’s important to evaluate potential career growth within the rideshare industry and beyond.
So, if you’re considering the gig economy, know that it’s not just about earning money; it’s about gaining freedom and embracing a life that aligns with your values. Cheers to living life your way!
