This transcript was generated from the episode audio and may contain minor errors.
[Music]
What's up? Welcome to Side Hustle School. Hey there, my name's Chris Guillebeau. So glad you're out there. Now we're doing something new every Friday.
I believe we can learn as much from failure as we can from success, if not more in fact. And that's why we're running this new segment called Failure Friday. Conveniently it comes out every Friday. It is a collection of short stories, all about mistakes, missteps, disasters, and of course, failure. And just like our Throwback Thursday segment, you will hear directly from side hustlers who have struggled to get something off the ground or have otherwise had some major setback or detour.
And they'll tell you the story of what went wrong as well as what they learned from it. The stories will vary, but often they start with an idea, some kind of preconception of like, well, I've got this idea, here's what I think is going to happen. And then here of course is what really happened along with what they learned from it. So as we are just getting started with this series, I wanna say that I applaud their courage. Anybody who's willing to step forward and say like, yeah, this was a tough one, right?
So I'll try to share some of my failure stories along the way as well, but we really can learn from this process. So today's short story features Sean Ogle from Portland, Oregon. Now he is no stranger to side hustle school listeners as well as anybody who's been following my work for a long time. I first heard about Sean in The Art of Nonconformity, my first book. And I actually know some of this story that he's gonna tell pretty well, but I don't think I knew all the details, including how he was effectively walked out of his office the day he left his job forever.
So I'll let him tell that story, all the details as well as what happened next. All right, here's Sean. [Music]
Hi there, my name is Sean Ogle. I'm the founder of Location Revel 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 Rhyme, 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, 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 Rhyme 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 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 want to build if I want to see success. So thank you for listening. Hope you enjoyed it. And yeah, we'll see you later. Never confuse a single defeat with a final defeat.
That is the theme of this new series, Failure Friday. In fact, in some ways you could say that Sean's defeat being walked out of his office on 10 minutes notice, you could say it was actually a victory. It certainly turned into a victory, but even just the stance that he took in being willing to come up with this creative proposal, put it forward, as you heard from him, he thought it was going to work out. And it did work out, just not quite the way he expected. Now, I want to say that, of course, all of our listeners, not everybody here wants to quit their job.
So many of our listeners are happy in their jobs. They're just trying to find a way to make extra income or build a bridge to something in the future. So I totally acknowledge that. But I think the point is Sean wasn't happy in his job. So if you're not happy and you make a change, it's also true, like he said, that your worst fear is probably not going to happen.
Like if you do lose your job for whatever reason, or if you do decide to kind of walk out on what feels like a cliff, most likely the worst thing that will happen is you have to get another job. And in this case, Sean ended up creating his own job, which you can check out now at locationrebel.com or his golf project, breaking80.com. He's got lots of stuff going on. We will link it up in the notes. But again, his main site, locationrebel.com.
If you have a question, if you'd like to update us about your side hustle, if there's something else, you know, whatever it is, come to sidehustleschool.com/questions. Those notes today are at sidehustleschool.com/1518. Thank you, Sean. Thank you, listeners. I hope you subscribe wherever you get your podcasts and come back tomorrow.
My name is Chris Guillebeau. This is Side Hustle School. [Music]
From the Onward Project.
