• Chris OBrien

Starting that Long Overdue Business: Chapter 1

Updated: May 12, 2019



What's the difference between a dream and a delusion?


For instance, let's say tomorrow Elon Musk announced his dream of having 100% self-driving cars by 2022. We'd think, "Alright, that's bold, but if it's Elon saying it, it's probably going to happen." We might even buy Tesla stock in anticipation of all their future success.


But if a random homeless guy said the same exact thing, we'd shrug it off as crazy talk. There's nothing to support their claim. Especially if the homeless guy said he would be the one building the car.


One of the hardest parts about starting a business for the first time is believing that it can actually work. There's nothing to support the belief. No proof. No customers. On a scale of Elon Musk to Homeless Guy, I definitely felt more like the ladder.


Especially once you start putting skin in the game. It's a nice little daydream during a 9 to 5, or the times when I would think, "You know, I could do this once I retire in 20-30 years."


But once you pay a few hundred bucks to get setup on Legalzoom, or start buying ads on Facebook, or even when you put it as a title on LinkedIn, now it's getting real and that realness feels pretty uncomfortable.


Props to all of the founders who are able to dive in head first. My approach was more "dipping my toes in." As much as I believed in the idea and the dream of Long Overdue, I looked at it rationally and said, "If I don't have a day job in the beginning, my wife and I will run out of money in a matter of months." Or we would at least need to sell our house. I literally would become the homeless guy!


The problem with the dip your toes in approach is all about time. Your windows to work on the business are before work, after work, and the weekends. But before work is the only time I can work on my own writing. After work I'm a slug. I just want to lay on the couch and watch TV. And then weekends, that's supposed to be the break. That's when I want to spend my time with Ashley having fun in Chicago.


I was, and still am, left trying to balance all of these areas at once:

  • Religion

  • Time with Ashley

  • Time with family

  • Friendships

  • Day job - The thing that actually pays the bills

  • The Dream Business

  • Playing with the dog / going on walks

  • Writing - Or any other hobby

  • Reading

  • Watching the Kansas Jayhawks

  • Watching NBA

  • Watching Netflix

  • Going to see movies

  • Going to see shows at the iO and Second City

  • Taking a class at Second City

  • Oh yeah, sleep

  • Whoops, probably need to get to the gym too

And this is the easy part! God-willing, if we start a family in the next year or two, that new baby is going to be like Thanos snapping his fingers, immediately wiping out half of the list.


At first, I had this belief that I could do everything successfully all at once. Found out real quickly that doesn't work out. That's a recipe for complete burnout. So, in the last six months, I have a sliding scale that changes around. I missed a few Jayhawks games this year, something that pretty much never happened before. I don't watch nearly as much NBA. Haven't been to the movie theater in at least a year.


One of the hardest parts, for me, was accepting that I could only be "okay to good" at my day job. I show up at 9 a.m. because I'm writing til 8 in the morning. I don't work on anything after work. Nothing on the weekends. I'm truly a 40 hour a week guy and there's a certain ceiling you hit with that schedule. I'm like late-career Tim Duncan playing with a minutes restriction.


There have been plenty of times when the sliding scale impacted the most important parts of my life. When the sliding scale leaned more business and writing and, as a result, I was a mediocre husband, mediocre son, mediocre friend. It's in those moments when you think, "It's not worth it." So you adjust the scales again, take more time away from the sleep bucket or the writing bucket.


But that's when you know you're serious about the idea; when you go through all of that and the business/dream category never hits 0 on the sliding scale. Now it's time to find the right motivation.

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