Stride Stories: Full-time Uber for the family

Stride: Jay, tell us a bit about yourself.

Jay: I’m 34-years-old and originally from Hawaii; I’m now living in the San Francisco Bay Area. I held a job as a marketing manager for six years, but got tired of working for other people, so I decided to become a full-time Uber driver. I needed my work to be something more flexible, so I could spend more time with my family and work whenever I wanted to.

Stride: That sounds like a great move. How did you make that transition to self-employment?

Jay: I got burnt out working in the corporate world – waking up to hundreds of emails and the pressure of work. The company I was working for was so demanding. I knew I needed something more flexible. I tried out Uber for three months before going full time. I found that the income from Uber was the same (or more) than I was making at my full-time job, so after three months I decided to take the leap.

Stride: Interesting. Some drivers report that it’s becoming harder to make good income in the rideshare market. Do you have any secrets you can share?

Jay: I try to drive during peak hours to optimize when I can make the most money. My schedule fluctuates from week-to-week depending on when there are peak hours for Uber. [Author’s note: Uber raises the pay rate for drivers when the riding demand is high, i.e. peak hours]

Stride: What does the schedule of a full-time Uber daddy-driver generally look like? How have you optimized your driving time?

Jay: I generally work 7am-9am then take an 8-hour break and go from 5pm to 8pm. Uber is great at giving us a general idea when the demand is high. Uber also gives us a snapshot of our prior week's earnings, and shows when we can drive to make even more money, which really helps optimize your schedule to make the most money. Some days, depending on surge pricing or how I feel, I may drive extra hours. Most times I do – extra income always helps, especially if you have a wedding to plan for [laughs].

Stride: How has your quality of life changed driving full-time for Uber?

Jay: I’m able to spend more time with my daughter, who is almost 7-years-old. Now, I can go to her PTA meetings, take her on field trips, pick her up and drop her off from school… simple stuff, like being a real dad. I don’t have to worry about talking to my boss or asking for time off. In itself, that was a big decision-maker for me taking the leap.

Stride: Has your relationship with your daughter changed?

Jay: It’s night and day! She’s more excited to see me when I pick her up from school, and she wants to do a lot more with me. When she has events at school, she’s always looking for me because she knows I’m going to be there, rather than thinking Daddy won’t be here because he has to work.

I’m teaching her how to play tennis and basketball. I also take her to soccer practice and swim practice. Right now, we are working on a science fair project that’s due next month.

Stride: That’s so inspiring to hear. A good lesson for the rest of us taking our work too seriously. What did you struggle with when you transitioned from the corporate world to the driving life?

Jay: For me, it was the discipline to create my own schedule. In the corporate world, you have to be in by 8 am. It took me awhile to create the schedule I wanted (and needed) to optimize my driving time and make the most money.

Stride: Do you think you will always be self employed?

JayYes, I am psychologically unemployable at this moment. Now, the idea of working for someone makes me cringe. My lifestyle is phenomenal and I don’t see myself going back to to the corporate world ever.

Stride: Do you have any plans to do work other than drive for Uber?

Jay: I’m in the process of working on my passion project with my fiancé. We want to create a travel blog and website based on positive content, love, and relationships. We are coming up with the idea right now and laying the foundation. We love traveling so much, we want to find a way to travel and stay financially grounded.

Stride: What inspired your passion project?

Jay: My fiancé took me to the Philippines in 2014. I had never been there, and it was Paradise with a capital “P” [laughs]. During that vacation, we decided to get married in the Philippines in January 2017. Then we don’t want to stay in one place… we want to share our story and help as many people as we can. My fiance is a hygienist so she wants to travel the world promoting dental hygiene.

Stride: That’s such an inspiring plan, but we’re curious: how do you travel the world with a young daughter? Most people view that as a time to plant roots.

Jay: I'd like to take her with us wherever we go, but unfortunately we can't during school. I had my daughter in a previous relationship, and we split custody, so she mostly stays with her mother. My daughter is 7 and at the point in her life where she's really making sense of things around her. I'd love for her to come along with my fiancé and I once we start our passion project, but we know she won't be able to all the time. My fiancé and I plan to have 3 kids of our own, and we are definitely bringing them along with us. We both believe that being well-traveled, no matter the age, is crucial. Exposing our kids to the world first-hand will be great for them.

Stride: We totally agree! Now, switching gears: if you could fix one thing with the current medical system, what would it be?

Jay: Wow, one thing?! I’d like to a see more transparency in the fees charged for visits. As a regular person, there’s a lot of medical jargon that I don’t understand. I recently went in for some tests and got this huge bill – I still have no idea why it was so expensive. That’s my biggest fear in going to the doctor for a regular visit or test. We should all get a bill that explains clearly why things cost as much as they do.

Stride: What is your biggest health concern for America?

Jay: From personal experience, I’d love to see cancer get obliterated. I lost my father to cancer, so I’m hoping a research center or university comes up with a cure. It’s such a tragic disease… eradicating it would do wonders for us.