Diary of an Uber Driver: Why did I start driving for Uber?

Over the past 27 years, I have found myself in many truly bizarre situations. However, if you had sat me down when I finished high school and said, “Listen, in ten years time you will be broke, have grey hairs in your beard and will be driving for a new age taxi service called Uber,” I wouldn’t have believed you. In fact, I would have been rather offended. I was supposed to be retired by now and drinking Pina Coladas on a beach in the Bahamas, not ferrying around abusive drunkards on a Saturday night and sculling cans of energy drink to stay awake.

My 17-year-old self envisioned a tall, bronzed statue of a man with perfect white teeth and a full head of hair. I am still tall, but pale and far from statuesque. I am not overweight but have a midsection like a plastic bag full of warm custard. I’m by no means bald, but my hair is slowly running away from my translucent face. My teeth aren’t white, straight or close to perfect. They are more of a McDonald’s fries yellow, slightly chipped and in need of attention. Dentists are expensive and my bank account is as empty as a schooner glass on ANZAC day. By now I was supposed to be a man who could speak several languages. I am fluent in English and Australian slang.


I haven’t traveled, well not really. England for two months before flying home to a girl I thought I loved doesn’t count, so my friends like to remind me. And maybe that’s my problem. The reason why I haven’t made it to The Bahamas, fuck, I haven’t even made it to Fraser Island. I have never seen things through, never persisted with anything long enough to make them a success. I like to tell myself otherwise. I deliver rousing speeches inside my head lauding myself as a man of great ambition. A man who doesn’t settle for mediocre but strives to be different! To be better! Two failed businesses and a boneyard of jobs “I didn’t like” and the speeches dim to whispers. I spend half my time depressed, the other half dreaming of what could be.


I am starting to feel the pinch. A stopwatch floats above my head counting down the seconds to an acceptable reality. My inbox taunts me with unopened job alerts I signed up to as a fresh-faced University graduate; a constant reminder of the illegitimacy of my current path. Weekends once spent with friends in a blur of cheap beer, strobe lights and cigarette smoke now replaced by sit down meals in suit and tie with strangers who are just dying to know: “what are you doing with yourself these days?” “How is your career progressing?” I scan the crowd for a familiar face to drag to the corner of the party to talk about anything else. It feels like overnight my FaceBook feed changed from videos of fridge to fridges, beer bongs and festival shows to weddings in the Hunter and standing in front of SOLD signs. As I mindlessly trawl through friends and acquaintances LinkedIn profiles, I am starting to get that sinking feeling life has passed me by.

The second of those failed businesses hurt the most. I partnered with an old friend from school to build a business called Guerrilla Eats. Our website sold progressive dining experiences through Sydney’s culinary hotspots. “An entree’, main and dessert at three quality restaurants within walking distance of each other,” our website still reads. I quit my full time job and picked up some bar work so I could focus wholeheartedly on the business. I would work from 8am till 3pm signing up restaurants and bars to the site and then work from 4pm through till midnight pouring schooners at a sailing club. The business launched spectacularly with rave reviews in the Sunday Telegraph and a resounding thumbs up from the foodie blogosphere. The bookings came flooding in and for a brief moment, we had made it. I could sit here and tell you fifty reasons why we closed the business six months later. “We had an investor who strung us along” or “the restaurant’s tried to squeeze us too much on the margins”. Every single reason for failure I spewed out to anyone who would listen was total bullshit. I’m addicted to instant gratification. The business started to show signs it wouldn’t be a multi-million dollar success overnight so I gave up on it. I’m the type of guy who reads those articles, “12 things successful people do before breakfast,” for that dose of “yes I can”, before doing the opposite. Every other week I’m buying monthly planners from the corner store to give myself the illusion my life has some as-semblance of order. I buy expensive headphones and running shoes to validate the me of today to sit on the lounge tomorrow. I tell people the reason I’m broke is because I invested money into the business. “I took a risk!” I say defiantly, “but it didn’t pay off.” I’m broke because I buy $25 salami rolls from inner-city deli’s because I’m hungry now and I want to eat now. I don’t even have the discipline to wait thirty minutes till I get home to eat food from the fridge like a normal person.

So here I am; broke, with grey hairs in my beard and driving for a new age taxi service called Uber. Why Uber? Why didn’t I just open the Aladdin’s cave of job adverts glowing in my inbox? The thought of writing a cover letter, tailoring my CV to the advertised job and then turning up to the interview made me feel sad. I didn’t have the energy to lie anymore. I couldn’t sit across the desk from someone and feign enthusiasm for their company and their vision. They would buy my bullshit answers and cheesy smile and I’d be back at square one. I wouldn’t love the job and I wouldn’t be a millionaire tomorrow so why bother with the effort to start with?

I’m tired. Tired of emails and expectations, deadlines and disappointments. More than anything, I’m tired of not knowing what the hell I believe in. I lay awake at night willing myself to figure it all out. I wish I could say I’m driving for Uber to take some time out to think about what I’m going to do next. I’m driving for Uber because I don’t know what comes next. I haven’t given up on life I just know what I have been doing so far isn’t working.

For now…..I’m just going to drive.


  1. Hey Ben, you’d be surprised how many of us feel like this now or in the past. Anyway have you read Jack Canfield’s “The Success Principles, how to get from where you are to where you want to be”? If not I think it would help a lot. Also Brian Tracey’s book on goals is pretty great too. Good luck

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  2. Hey Ben.
    I think we may be living the same life…..

    I’m 30, drive full time for Uber in Sydney and my life is, as I put it, “like I’m sitting in a stalled car at a crossroad with no sign posts”.

    I do love the the job, to be honest it’s probably the only thing keeping me sane. As an extremely chatty person I find the conversations with riders almost like a drug. It’s moreish and it makes me forget about everything else other than the conversation at hand.

    I don’t know if you recieve my email address on here and I’m putting myself out on a limb here but if you do shoot me an email I’d be keen for a chat either through email, phone or over a beer if you’re interested. If you don’t have access to my email then respond on here and I can send it.
    It gets harder to meet new friends with similar interests/experiences as one gets older.
    Things were much easier bonding over a shared common interest with a transformer toy in preschool.

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    • Hey David, thanks for getting in touch. Happy to chat over emails mate:

      I can definitely relate to getting lost in conversations with passengers and forgetting your own troubles for a while.

      Safe driving, Ben.


  3. Relatable as a fellow Uber driver who is still majorly controlled by the instant gratification monkey, which lead me to this. But I do enjoy driving with Uber even though the experiences have started to blend into a single experience with a good side and a bad.

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