Sometimes ‘Living the Pursuit’ is an Uber Aggravation

Opportunity, Costs


Photo by JFXie

I was already exhausted when I pulled into the parking lot at the mall at 2:30 AM Saturday. With bleary eyes, I was searching for my last Uber passenger of the night. As usual, where he said he was and where he actually was were two different places, so I texted him. No response. I called him and – in a drunken voice – he told me that he was at Hooters not far away. Okay, no problem. When I arrived, he practically fell into my car with a bottle of beer and an unlit cigarette. I told him he had to leave both behind. He looked at me as though I was speaking a foreign language, but he managed to set the beer bottle on the ground and put the cigarette in his jacket pocket – all while cursing me with his bloodshot eyes. I asked where he needed to go. “Sun Prairie.” That’s a city, dude, not an address. I asked him again. Same answer. Listen man, I need an address. He pondered this difficult question for a while and eventually told me where he lived, so we set off. I sat through his offensive ramblings about women and heard all about how he sold some $90,000 piece of silver, and 15 long minutes later, we finally arrived at his house. But then he wouldn’t get out of the car. Thankfully – for his sake – he managed to sober up enough to get out of my car about three seconds before I was going to forcibly remove him, and we went on our separate ways.

My life as a late night Uber driver can be rough. Maybe not as rough as my passenger felt that next morning, but it takes its toll. Why am I subjecting myself to this punishment?

Sweet Home North Carolina

My family and I moved to Wisconsin 16 years ago and finally found our true “home.” There are certain things about Wisconsin that you just can’t beat. I even love the snow and cold in winter – until about mid-January. But our daughters are almost grown, and it’s time for a change. We’ve been “doing our thing” in Wisconsin for long enough. Like the Canadian geese we see flying overhead in late fall, it’s time to move south. Well, it’s not quite time. But it is time to start planning the migration.

We want to move to North Carolina. We have set our sights set on Oak Island – a small island just off the coast between Wilmington and Myrtle Beach. It is an absolutely gorgeous little island with tons of waterways and fantastic beaches. The fishing, kayaking, and scuba diving are all great, and the cost of living is reasonable. Sure, the occasional hurricane will send us running to the highlands, but we can deal with that in exchange for perpetual summer.

So now we have a goal: move to North Carolina. Simple, right? Just sell the house – and the snow blower – and drive south until the weather suits our clothes. Not exactly. I wish it was that simple, but the reality is that we’re a working middle-class family. Our goal of moving to North Carolina is nothing more than a dream if it lacks a plan to achieve it. But if we create a plan – and exercise personal initiative to execute our plan – then we have a goal. Which brings me to Uber.

I work as a software developer for a large corporation. It provides a good standard of living for my family, but – like many Americans – we have lived slightly above our means for many years. Nothing too drastic, but we do have some debt that needs to be paid off before we move. And – in addition to covering the costs of the move itself – we also need to save some money for a down payment on a new home. So I started driving for Uber to bring in a little extra money on the side.

Homeward Bound

On my drive home from Sun Prairie the other night – with windows open, 40 degree air blasting my face, and country music blaring just to stay awake – I took a peek at my phone to see how much money I had made during that shift. It was a bit better than average, a shade over $200. That’s not all that much money for working 10 hours, especially after you deduct the $20 I spent on gas, and the wear and tear on my car, but my family was that much closer to realizing our goal. In that moment, it dawned on me: I am living the pursuit – pursuing my happiness through hard work and sacrifice now so that later I can live the dream.

But let’s be honest. The pursuit sucks. It’s hard. You spend nearly all of your waking hours working, you miss out on family fun, and you get very little sleep. But it’s a gateway, a means to an end. “Living the pursuit” isn’t the goal. The goal is to live the dream. But you can’t do the latter without first doing the former. Each $3.20 minimum fare I collect from a college kid too lazy – or too stoned – to walk 1/4 mile home and each $20 fare I collect from a belligerent drunk from Hooters puts me that much closer to living my dream – and gets me that much closer to putting “the pursuit” behind me.

Home is Where The… What is?

In those rough moments as an Uber driver, it’s easy for me to question my choices. Is all this work really worth it? But then the dream floats through my mind and I remember that the pursuit is temporary. Then I smile just a bit and keeping Ubering on. Because while my heart might always be in Wisconsin, someday my ass will be on a beach in North Carolina!

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What “pursuit” are you living now in order to realize your dream later? How do you get through those roughest moments?

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Todd Osborne
Contributor at LTP
I am a 47 year old married father of 3 beautiful girls, and recently became grandfather to a sweet baby girl. I develop licensing software for Dell, Inc. and drive part time for Uber and Lyft. For fun I enjoy building and flying small planes and am President of the Middleton, WI chapter of the Experimental Aircraft Association. My wife and I are also the Young Eagles coordinators for the chapter and love to introduce children to the sport and aviation. We live in Cross Plains, Wisconsin and have plans to move in the next couple of years to Oak Island, North Carolina.