Stride Stories: Switching gears with Uber

Stride: Matt, you’ve been a social worker for 19 years but you’re looking to make a change. Can you tell us more?

Matt: It started about a year ago. I was getting pretty frustrated in my current job and needed a change. I started writing down goals, and out of nowhere I wrote down this sentence: my current job will be my last as a social worker. I had a feeling whatever happened next was going to be a big change.

Stride: Many people view social work as an admirable job, what prompted you to want to make a move?

Matt: I work at a hospital so there’s a lot of variety – one day I may be working to get medications for an uninsured patient and that same afternoon I’ll have to explain to a patient who can’t speak English that we have to discharge him, which is frustrating. I love the work and helping people, but many days I’m just there to pick up the pieces… and I get yelled at for situations that are out of my control [laughs]. When I first started the 24-year-old, bright-eyed, idealistic guy was okay with that. I’m still idealistic, but now the 43-year-old knows he cannot do this everyday until he’s 65.

Stride: How did you start working towards that big change?

Matt: At first I didn’t [laughs]. Going against my proclamation, I started looking around for other jobs in the field of social work. This was back in June of 2014, and Uber had just come to Pittsburgh. Many Pittsburgh’ers were very skeptical of Uber at first, and I was one of them. I didn’t even understand what Uber was, but every potential job posting for social work that I came across featured a banner for Uber saying: “Uber, Drive for Uber!” At first I was like No, no, that’s not what I’m looking for! But I kept coming across signs saying things like – “Uber is a great side job - see if you like it.” They also put a suggested dollar amount you could make in a weekend… which really appealed to me, so finally I just clicked to see what Uber was all about [laughs]!

Stride: How did you ultimately decide that driving Uber full-time would work for you?

Matt: I took a week off of work to test what it would be like to be a full-time Uber partner. I had goals – monetary figures – that I set for myself to hit everyday. At the end of the week, I hit all my goals. I was really enthused, but the last big, daunting hurdle to make it work was – what am I going to do about health insurance? My social work is in a hospital, so I see people in uninsured situations, and I knew I couldn’t let that happen to me.

About that time, I got an email from Uber about Stride as an option for finding health insurance. I was under the impression that I’d have to pay COBRA’s $500/per month, which wouldn’t allow me to quit my job. But I looked online at Stride, and through the recommendation process, it appeared I could get coverage for $178/month! I was so excited about this, but I had to hear it from an actual representative. So I called the Stride number in California and talked to the wonderful Astrid. When she gave me the same $178/month quote, that was it!

I remember that I was looking at the tree in my backyard, and I knew my life had changed forever… I knew I could leave my job at the hospital and make driving work for me!

Stride: That’s awesome, what’s your favorite part about driving with Uber?

Matt: It’s the positive energy. I’m meeting more people who are doing the things they love. One person I drove to the airport told me they had decided to teach whitewater rafting in Santiago, Chile. Another girl and her boyfriend were about to cross the country backpacking. With Uber, I hear fewer people say, “I’m going to work a 9-5 job that I hate because I need health insurance and job security.” With Uber, it’s the “go for it” and inspirational-type stuff and I knew I had to follow these people’s example. Now I have a story like theirs and it’s great.

Stride: As an Uber partner are there any differences to being your own boss?

Matt: I think the one thing that I’ve gotten so used to is getting my taxes withheld then getting my refund check, so filing taxes this year will be a different experience for me. Although, as an Uber partner I now keep all the money I earn, instead of it being withheld and that does feel fairer.

Stride: Are you doing anything new to manage your finances now that you’re doing your own thing?

Matt: In taking a leap off the ledge, I made sure to have some cushion – I have a significant amount saved. Also, I paid off all my recurring bills – like car insurance – through the end of the year. This is Pittsburgh, PA and there will be nasty winter days where I won’t want to drive. I almost see myself as a fisherman – every day is different – there will be big harvests days and days where I only drive a little bit. On the big harvest days, like New Years and St Patties day, I’ll put away money which will be a nice bump compared to my regular days driving. When the ocean is full of fish, you gotta catch ‘em!

Stride: Any funny stories?

Matt: I often get up really early in the morning to drive. I have young ladies and men get into my car wearing yesterday’s clothes, and there’s no questions asked, I just take them home [laughs]. In 2015 “the walk of shame” has sure changed [laughs].

Stride: What’s been your most interesting ride?

Matt: One time I got a call from a mother, asking that I pick up her daughter from a doctors appointment. She said, “My 18-year-old daughter is at a doctor’s appointment but her phone died and I’m worried about her! Can you please find her and bring her home!” All she knew was the building where her daughter’s appointment was. I started there and did the detective work. I walked into the building and took the elevator up to the doctor’s waiting area. She wasn’t there but when I came down to the lobby, I saw this young girl eating a burrito bowl. “Are you Dyar?” I asked, and she said, “Yes, why!?!” “I’m Matt from Uber and your mother sent me here to drive you home.” Here was Dyar, nonchalantly eating her lunch, not remotely aware her mom was worried. The mom was a 10/10 on the emergency scale, and Dyar was a 2/10 – she was thinking I’ll go get some Chipotle after my appointment. So, I got to meet this wonderful girl and reassure her mother at the same time. That was 9 months ago, and it’s still the best trip I’ve had.

Stride: For people who might be stuck or thinking about life changes, do you have any helpful thoughts?

Matt: Don’t keep doing the same thing in the same way. Try to regroup, assess and think differently… there are answers out there. If you look for them, you’ll find them. I’m taking a leap into the great unknown, and while it can be scary it’s very exciting and rewarding too.

Stride: How’s your boss going to react to your resignation?

Matt: She’s going to be floored [laughs]! I don’t mean to brag, but people are going to be AMAZED that I’m leaving. People have this false assumption that I’m always going to be there, but eh-eh, Matt has other plans [laughs]!