This transcript was generated from the episode audio and may contain minor errors.
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This is a good story today, a contribution, a listener contribution from a friend of mine, in fact, and we're gonna call it We Accept Your Proposal to Resign, which is a true story, of course. It's part of our Failure Friday segment, where we hear about something that does not go well, at least at first, and in this case, it ends up being a life-changing, transformative experience for this guy. It ends up being an amazing thing for this guy. His name is Sean Ogle. But in the beginning, it was a little bit scary.
So I don't wanna give away too much of the story just 'cause he tells it really well. But basically, he is a college graduate, he's young, he goes to his boss with a creative proposal to work remotely. He thinks, "Oh, this is a great idea. "They're gonna love it." But the boss sees it quite differently. So without further ado, let's hear the story.
His name is Sean Ogle from Portland, Oregon. No stranger to side hustle school listeners or to anybody who's read my books familiar with my work. As I say, a long time friend. I'll have a couple words of wrap up at the end. But first, Sean.
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Hi there, my name is Sean Ogle. I'm the founder of Location Rebel, where I teach people how to build small businesses that you can run from anywhere in the world and spend more time doing the stuff you love. Unfortunately, to become the founder of that site, I first had to fail in spectacular fashion, and that's what my story is about today. So I started with a finance job straight out of school in July of '07. You may remember July of '07, peak of the market, by February of '09, complete financial meltdown.
Everything was a crisis. My bosses were unhappy, our clients were unhappy. I was unhappy. Everybody was losing money. And I ended up saving up all my vacation time for the year and begged my boss for months to let me go to Rio for the carnival celebration with my friend.
So me and my friend, Brian, we went down there. We went hang gliding over Rio. We danced in the carnival parade. We went to a Guazu Falls, one of the seven natural wonders of the world. We had the absolute time of our lives.
And the day I got back, my boss told me I was getting a 20% pay cut. He said, "Sean, it was either we take 20% pay cuts across the board or someone gets fired." And that would have been you. So, you know, the next few months go on, I'm struggling. Everybody's unhappy. My boss comes up to me one day and says, "Sean, if you can think of any creative ways to save the company money, I'd love to hear about them." So being the ingenious millennial I thought I was, I got creative and I put together a remote work proposal.
See, my buddy Ryan had quit his job three weeks after that trip and moved to Hawaii where he was living the life. And so I went to my boss and said, "I will take a 50% pay cut for three months if you let me work remotely from Hawaii. I'm gonna open us up to a new client base. You won't have a lot of expenses of me being in the office, parking, things like that. And it's gonna make our company more secure because we're gonna have to figure out how to make a remote work situation possible, which is gonna allow you guys to travel more in the process." So we went back and forth.
I truly thought this was gonna work. We had multiple meetings over the course of a couple months. And finally, one day he calls me into his office and he's like, "Sean, we've decided not to accept your proposal, but we will accept this as your resignation." And we went back and forth. I had an opportunity to save my job, but it ended up leaving with me having to exit the premises within 10 minutes and it was not a happy situation. And so I learned a variety of things that day, but a couple of the most important ones are that most people are happy with the status quo and they're gonna judge you for wanting to do something different.
My boss, he had had the same lifestyle for 30 years. And the fact I wanted to come in and change it up and do something a little bit different was frustrating. In that, I also learned you have to take responsibility for your own happiness. If it wasn't for that happening and if it wasn't for the financial crisis, I would probably still be in my financial job today, absolutely miserable. But what I ended up doing was after I left my job and I went home and cried because I was so terrified of what was gonna happen, I ended up selling my car and moving to Thailand for the better part of a year where I worked remotely and I built my business.
And it was the very best thing that could have happened to me. I also learned that the worst case scenario almost never happens. I was thinking about all these things if I moved to Thailand that could go wrong, but the reality is what's the worst case scenario? I lose all my money and I have to go back and get a day job. That wasn't so bad.
And there was a high likelihood of it happening, but usually the worst case scenario doesn't come to pass. So in that failure, that remote work agreement that I thought was going to work so well is my first kind of thinking outside the box, potentially entrepreneurial type venture, it failed in spectacular fashion, but it taught me I have to rely on myself. I have to be willing to trust in the things that I think are going to work and I have to put myself out there and put a lot of effort forth for the things that I wanna build if I wanna see success. So thank you for listening. Hope you enjoyed it and yeah, we'll see you later.
[Music]
Never confuse a single defeat with a final defeat. That's the theme of failure Friday here on Side Hustle School. But I also like what Sean said, your worst fear is probably not gonna happen. So very well told. Thank you so much again, Sean.
Listeners, check out Sean's golf project. These days he is a pretty much full-time YouTube golf influencer, Breaking80.com or Breaking80 on YouTube. I believe Sean Ogle elsewhere. Listeners, if you have a question and update about your hustle, sidehustleschool.com much more is on the way always seven days a week and you can access all 3,400 episodes of the podcast. I think several of them now at this point feature Sean.
All those are freely available at the website, sidehustleschool.com or just continue to listen for the new episodes. Thanks so much, my friends. My name is Chris Guillebeau. This is Side Hustle School. [Music]
