Odd Jobs

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Published on: July 18, 2011

Welcome to Odd Jobs. Every week, I’ll do something new to try to pay the bills or make ends meet, then blog about it. If I give plasma to earn a few bucks, you’ll read about it here. If I become an insane couponer to save money, you’ll read about it here. And even when I fail miserably, like if I bet $200 on the Cubs to win the World Series, you’ll read about it here.


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Week 52: Why You Should Never Drive a Beat Up 2002 Mazda (Or Try to Date People)

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Published on: May 14, 2014

Have you ever seen a taxi driver and thought, “That’s the life for me?” Sure you have. Who wouldn’t want to let total strangers into their car in the dead of night? Or deal with wasted people vomiting all over their carpets? Or spend hours a day stuck in traffic? Now you’re probably saying to yourself, “That all sounds great, Jonathan. But isn’t there some way I can have all the fun of being a cabby, without having to make as much money?”

Yes, hypothetical person that I made up for the sake of that sentence. Yes there is.

In the last couple years, three major apps have emerged offering to connect people with cars to people who need rides. The drivers takes the passengers wherever they’re going for a fee that gets split between the app developers and the driver. Now I’m sure you have some questions about this, so let’s stick with this already-introduced, mildly contrived narrative structure of questions asked by a fictional person followed by my answers…

Jonathan, isn’t that dangerous? Letting a total stranger into your car?

Of course not. Every rider is given a star rating based on how good a passenger they are. If someone is a serial killer, there’s a good chance they’ll only have one or two stars.[1]

I don’t understand. Doesn’t the average cab in Boston pay the government hundreds of thousands of dollars for the right to charge people for rides? How can these guys enter the marketplace for free?

Yes, the average cab does get charged a fortune, because the government will take as much money as possible from private entities every chance they get, but—

Actually, is there a way you can answer my question without forcing your political belief structure on me?

Sorry. Basically, if the passenger pays a “suggested donation” instead of a “fare,” their ride isn’t covered by the same laws as taxi rides.

Fascinating. Okay, so do you spend the rest of this blog post detailing your adventures giving rides to whackjobs and drunks?

Well, no. All three apps rejected me. But I was thinking that since I applied for the jobs, I could still write about the experience.

What experience? Getting rejected? Dude, if we wanted to hear about your experience getting rejected we’d just ask about your recent dating life. Ay-oh!

Come on. It’s only been one week since I texted that girl. She still might respond. Look, can we just stay on topic?

Which topic, the one where you didn’t get a job but still feel you can justify writing about it on a website that is supposedly about the jobs you work?

Yeah, I mean, the website is about the things I try to do to save or earn money, even if they fail. I’ve written posts before about jobs I didn’t get.

I know, I wasn’t crazy about those either. Like that one where you answered a bunch of questions on an application about pants. How was that a column?

Okay, you know what? Q&A over. Here’s what happened when I applied for a job turning my car into a not-quite-cab.


By all outward appearances, Sidecar is desperate for drivers. Every few days, I see a new job listing detailing how you can make $18/hour driving for them. But my application has been pending for weeks now. Here they are, begging for attention, and I can’t even get a response from them.

I thought we weren’t talking about your dating life.

I said Q&A over!


Of the three companies, Uber is the fancy one. Its website is black-and-white shots of hot people with fancy wardrobes slipping out of cars, presumably on their way to runway shoots in Paris. This is a problem since I have a hard time picturing a company like that hiring me to pick people up in my banged-up 2002 Mazda, with two years worth of junk clogging the back seats. Even their step-down option, called UberX, was too uber for me. When I applied, they didn’t take anyone with a car made before 2006.

I was ready to move on, but, for some reason, Uber started hounding me. They sent me a text a few days later telling me I had been scheduled for my onboarding Thursday at 6pm, followed by an eager “See you then!” I texted back that I had been told my car was too old and that I wasn’t free Thursday anyway. They didn’t respond.

Uber kept sending messages, first about the upcoming session, then about how they were sorry I couldn’t make it but there was another session later that week. I think, going forward, this will be my new approach to dating. If a girl says no when I ask her out, I’ll just send her a text that says, “Our date has been scheduled for Thursday at 8. See you then!” And if she no-shows I’ll just send another text saying, “I’m sorry you missed our first date, but don’t worry, another one has been scheduled for Friday.”

Might as well try something different.

Shut up!

I started to wonder if I had misunderstood my rejection. I called Uber and explained that I had been told my car was too old, yet I keep getting messages about an upcoming hiring session. The man on the other end of the phone checked my application and promptly told me that indeed my car was too old and I was unfit to work for them. Somehow, they had gotten me to ask, rejected me, then gotten me to ask again, just so they could reject me again. If you’ve ever dated in the 21st century, then you are properly prepared for what it’s like applying to Uber.


Lyft is like the teacher with a ponytail who turns his chair around and says, “Let’s rap” when he talks to his students. As if spelling lift with a ‘y’ wasn’t enough, their drivers are required to wear giant pink mustaches on their cars and to give new passengers fist bumps. Meanwhile, their promo video plays like a new-agey, we-are-the-world yoga session:

I felt like I needed a bottle of coconut water after I finished watching this. An attitude of zen and self-righteousness permeates the film, as though the drivers view their work as altruism. Like the guy who says, “Using my car for good, it’s made me a better person.” Using it for good? You’re not giving homeless people free rides to shelters, you’re getting paid to drive drunks home from Rhianna concerts at 2:00AM.

But I decided to drop my criticisms when Lyft became the first company to pass me through the application phase and onto the test drive. I was told that on Saturday morning, I would get a request for a ride from my “Lyft Mentor.” I would drive to him, pick him up and give him a ride as though he were a typical Lyft customer, while he would decide if I was qualified to wear the pink mustache.

Suddenly, I had a shot at this gig. Saturday morning, when I got the request, I raced to my car, turned the ignition, and… nothing. The car wouldn’t start. It didn’t even make that asthmatic I’m-trying sound. It just sat there.

All ready to go on a Saturday, and then nothing ended up happening? Sounds familiar…

I’m just ignoring you now.

I called my mentor and explained the situation, fearful this would lead to automatic rejection. But he told me it was okay, that he would drive to me.

“So, the fact that my car won’t start isn’t an obstacle to getting hired?” I asked.

“Nah,” he said. Lyft was clearly a top-notch organization.

He arrived and started filling out forms about my car, putting in the proper lies to make it seem like I had given him the test drive. We chatted about the job, the money, the hours, the convenience. He explained how you only drove when you wanted, as long as you wanted. It all sounded great. Lyft could really be a good fit. Currently, I work several jobs I love but that have unpredictable daytime hours and a lot of nighttime hours. Some weeks I’m super busy, other weeks I’m not, and most weeks I’m not left with a lot of free nights for hanging out with friends or dating.

Yeah, that’s your problem, not enough free nights.

Still ignoring. If I had this, I could work a bit more during the slow weeks and cut back on the number of night shifts. In my head, I was already a fist-bumping, mustachioed driver.

Of course, it didn’t work out that way. A few days later, I was rejected. I was so shocked that I called a representative from Lyft to figure out what happened.

“I just don’t understand,” I told him. “I thought I had the job.”

“Well, your mentor said you were a great driver,” I listened to the clear lies the mentor had listed to get around the fact that my car wouldn’t start. I wonder if he got paid for each test ride he took. “But he also said there were stains on the carpet, a dent in the back of the car and another on the hood, as well as worn out tires.” Yeah, but I mean other than that, it’s a nice car right?

“I guess I’m just confused because he acted like I was such a great fit.”

“Well, you may be. But we admittedly have very high aesthetic standards for the quality of cars that represent us.” High aesthetic standards?! Your company instructs its drivers to put giant mustaches on the grills of their cars!

“I guess that makes sense,” I said, defeated.

“Look, if you get a new car, let us know, we’d love to…” but I wasn’t listening anymore. I hung up the phone, another “no” added to the pile. In person, it had seemed like everything was going great, but I guess he was just waiting until he got home to reject me.

Sounds a lot like…

Don’t even.


Odd Job: Applying for jobs with various ride-sharing companies

Earnings: None

  1. [1] I am constantly amazed that a) this star system, despite being incredibly flawed, is every company’s answer to the question, “Is this safe?” and even more amazed that b) it actually works. That most people, if given the choice between losing their child and seeing their rating drop on a major website, would probably choose to let their rating drop, but not before at least asking, “Wait, which child?”

In some but not all articles, names or identifying characteristics or individual lines of dialogue have been changed to protect identities or because remembering exactly how things happened is hard. But in every case, an effort was made to maintain the integrity of these events that did indeed actually happen.

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Week 51: Why You Should Never Ignore Family Tradition

Categories: Living On The Cheap
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Published on: May 9, 2014

Growing up, my sister was the queen of sleeping in. Bears used to visit our house for tips on hibernating. And if you were the poor soul tasked with waking her up, you were embarking on a life-threatening mission only Navy SEALs could understand. But there was one thing that could get her out of bed before noon: Garage sales. When the weather was nice, she and my mom would wake up early every Saturday,[1] pile into the car, and cruise through the suburbs, looking for the best sales.


  1. [1] And by that I mean “teenage early,” so like 9:00.

Week 50: Why You Should Never Discount The Aphrodisiac That Is One Direction

Categories: Making Money
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Published on: February 28, 2014

Let me tell you about Denise.

You got your girlfriend flowers for Valentine’s Day? Ha.

You got your boyfriend tickets to a basketball game? Psh.[1]

Denise hired someone to come to her boyfriend’s place at 8:00 AM and serenade him with a rendition of “Kiss You” by the band One Direction.

Now let me tell you about me.

You think it’s bad when you sing? Ha.

You think your high notes crack and your low notes grumble like Jabba the Hutt? Psh.

I am the guy at karaoke who clears the floor. The guy who gets to the mic in front of a room full of people– people who had been dancing and singing along to the act that preceded me– and sings with a voice that sends them flocking to the restrooms, that reminds them to return that text from their friend, that encourages them to just sit silently and wait for the horror to be over.

This is the story about the day Denise hired me to sing to her boyfriend on Valentine’s Day.



  1. [1] Or you got flowers for your boyfriend and sports tickets for your girlfriend. I’m open to non-hetero-normative views of relationships! Don’t hate me internet!

Week 49: Why You Should Never Work Too Hard When You’re Eleven

Categories: Making Money
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Published on: February 21, 2014

Odd Job: Shoveling Snow

Pay: $44

For most kids, snow days were about sledding and hot cocoa. For me, they were about money. Starting at age eleven, every time it snowed, I would go door-to-door offering my shoveling services, and frequently clearing $150 for five or so hours of hard work.[1]

This year, when it snowed, I stayed in bed and watched a few episodes of House of Cards.[2] It is a sad moment when you realize your work ethic peaked at age eleven.

  1. [1] Or as $150 is known to an eleven year old: infinite money. I mean, that was enough for 300 plays on the X-Men arcade at the local bowling alley. There’s a line people like to use that money can’t buy happiness. If you’ve ever been eleven, you know that this line is total bullshit.
  2. [2] Or as it’s known to anyone who watches House of Cards: Planning to watch one episode, then suddenly discovering that you’re halfway through the season and your entire day has vanished.

Week 48: Why You Should Never Skimp On Dentists

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Published on: December 18, 2013

Denny The Dentist’s office was about what you’d expect from a company with such a classy name. Their door was adorned by a cartoon tooth triumphantly holding a toothbrush and giving a sparkling white smile. It was the kind of picture that was cute and charming until you started thinking about the idea of a tooth with teeth. The poster in the window advertised X-rays, cleaning and a checkup all for the low low price of $57, because apparently they didn’t think anyone would find it disconcerting to get oral care from a dentist who advertises specials like a mattress store run by Crazy Larry.


Week 47: Why You Should Never Believe Conjoined Twins

Categories: Making Money
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Published on: November 22, 2013

My friend and I stand in the middle of a convention center, the two of us squeezed into one jumbo-sized T-shirt, playing the role of conjoined twins for the amusement of the passersby.

At this point I don’t even find these gigs strange. They are just normal. This is my Friday.


Week 46: Why You Should Never Settle For Their First Offer

Categories: Living On The Cheap
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Published on: November 15, 2013

How often do we really haggle with someone? Maybe when we buy a car. Or a house. Maybe once every couple years. We’re always told not to settle for the first offer, but man do we do a lot of settling. But this week I decided to start asking. Asking if I could have things for less. Here’s what happened.


Week 45: Why You Should Never Make Balloon Animals Professionally

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Published on: September 20, 2013

The real victims of the time I learned how to make balloon animals were my roommates. Our apartment overflowed with deformed flowers and guitars that looked like strap-on dildos.[1] The constant nails-on-chalkboard sound of balloons rubbing against each other was only interrupted by the gunshot sound of balloons bursting. The place stank of rubber. But perhaps most annoying was my newfound habit of giving away my practice creations as gifts. Not just to my roommates, but to everyone I could find.

  1. [1] No, Seriously. Click here.

Week 44: Why You Should Never Reveal Your Shortcomings in a Craigslist Job Posting

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Published on: August 2, 2013

Perhaps the best job listing I ever saw was from a man who needed help scheduling a time for a doctor’s appointment. It read, “Please take a doctor’s appointment for us. Take 2-3 times from the doctor and check with me to see what works best. Once confirmed with me, confirm with the doctor and let us know.”

Now let’s break this down. This man needs to schedule a doctor’s appointment. For the average person, this is not an insurmountable task. He calls the doctor’s office with calendar open, figures out a time that works, then goes on with his day, almost as though this was really easy task and took almost no time. Not this guy. First, this guy wanted to filter through e-mails from a bunch of people interested in working for him and find the right candidate. Then he wanted said candidate to call the office for him, find multiple times that could conceivably work, then call him back, check in on those times with him, then call the doctor’s office back, hope those times were still available, book one, then call him back and tell him that his time was successfully booked. Presumably, sometime around 11:00 that night, he would finally have himself a doctor’s appointment without all that hassle of talking to the receptionist.

Week 43: Why You Should Never Be Famous

Categories: Making Money
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Published on: July 19, 2013

You may not believe this, but I’m not famous. I know what you’re thinking: A 27-year-old who spends a rather inordinate amount of his time in pajamas, cranking out blog entries that are primarily read by his friends and family, how is this guy not famous? I know. It’s crazy.


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