What’s the luckiest thing that’s happened in your career?

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On more than a few occasions I’ve been asked what it’s like working remote. The inevitable followup is wow, you’re lucky. You can call it luck, but I just finished talking to 50 companies, put together proposals for all of them, and 49 said no to remote.

Lucky indeed!

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But to be sure, there have certainly been events that I look back on, that have had a seminal influence on my career. I thought of three. Here they are.

1. I got a newspaper route

Yes it’s true. Way back in the dawn of time, news was delivered on paper, and those would often be delivered to your doorstep, every morning. That and for only pennies.

At the time I think I was ten years old, and I was super excited because I wanted to be part of the world. And this was really the only job you could get at that age. It required a lot of organizing. You had a book with lists of all your customers, you had to keep track of who had paid, and so forth. Some wanted to pay monthly, while others insisted on weekly.

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I was lucky not only to get the paper route, but to have parents that encouraged me in this way, and could teach me how to be responsible and reliable. Yeah those were super important early lessons.

When I saw that I had a captive audience, it wasn’t long before I was selling incidental services. Do you need your driveway shoveled? I got it. How about mowing your lawn or raking those leaves? Or walking your dog? I spun this into a whole bunch of side businesses.

It was exciting because I was making my own money at such a young age, and felt the lure of self-determination. I loved that feeling.

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2. Linux happened

In the early 90’s Linux came on the scene. It might seem like a meaningless blip on the radar to you, but to me it was everything. At University I worked in the computer lab, where we were the operations staff. Those systems all ran Unix. So to go home and use a windows box, it was demoralizing.

Then out of nowhere this guy from Finland started building off of Tennenbaum’s book, Minix! I had worked on that at University, so I immediately saw the implications. I mean heck why can’t all that great software run on PCs, it’s just a matter of getting the drivers working. Big vendors didn’t want to do it, but millions of hackers around the world were happy to pickup the mantle.

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From there I build a tower, cobbled together hardware, memory, disk bus. Do you want to go IDE Or SCSI? Better choose a graphics card that is supported if you want to get X11 running on that. And of course an optical mouse so that it really feels like you’re sitting at a sun workstation!

“No one has as much luck around the greens as one who practices a lot.”  
–Chi Chi Rodriguez

To me that was pure magic. I mean from boot up to graphical interface, the entire stack was built by people just like me. And I could look at all of it. So cool! Even better that we were fighting the good fight against Bill Gates & the borg! 🙂

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3. Meeting the $65/hr consultant

This is a funny story too. One of the first jobs I had in NYC was not a consulting gig. It was a small design shop in the late nineties. Their biggest customer was Miramax Films. So they were doing really cutting edge stuff. And a lot of cool tech too. After their lead engineer quite, I became the defacto go-to person for all tech projects. I guess you could say I was CTO of a team of 5.

For one of our projects we needed help. The CEO had won business to do some Oracle development, which I didn’t have a lot of experience in. So he hired a consultant to help out. Very nice guy, a bit older than me. In fact I think he was about as old then as I am today.

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As he was a smoker, we stepped outside together at one point, and I chatted him up a bit. I was so eager to learn. I don’t recall if he shared his rate or I learned it some other way. But I was shocked and blown away. To me it seemed like an insane amount of money. I remember him saying something to me. “Don’t worry Sean, someday you’ll be consulting too, and making just as much.”

“No one is going to know or care about your failures, and neither should you. All you have to do is learn from them and those around you. [A]ll that matters in business is that you get it right once. Then everyone can tell you how lucky you are.” 
–Mark Cuban

Well I am a very competitive person. I also knew that I was smarter than this guy, but he had a bit more experience than me. So from there I started sniffing around. I talked to recruiters and anyone I knew. Within two weeks, I had gotten an offer for $80/hr. Shortly after that I gave my notice.

I have to thank that guy for challenging the way he did. And I’ve never looked back since!

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