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10 Defining Moments in Life (and the Importance of Each)

by Sean Ogle | Last Updated: January 15, 2020

As I sit here on a ferry from Koh Phi Phi, Thailand to Railay Beach (one of my favorite places on Earth), I can’t help but reflect upon what’s led me here – to the Andaman Sea in the middle of a Wednesday.

The same Wednesday that used to be spent in an office, dreaming of the day where I could go off gallivanting around the world for an indefinite period of time.

I play up my lifestyle and my ability to do this quite a bit.

Not because I’m trying to brag, but because this is my life.  This is my reality. When I started the site, I was very honest about my cluelessness about life and where I was going.

Working on this post at my hotel in Railay Beach, Thailand

Working at the Bhu Nga Thani on Railay Beach, Thailand

I continue that same honesty and openness now as well.

So for those of you who have called me out for bragging or don’t believe everything I write here, very politely: go somewhere else if you don’t like what I have to say.

Now that I’ve got that out of the way, I’ve come to realize there are ten very important life-altering moments that I’ve experienced in the last few years which have made my dream into a reality. Ten very specific moments, which I remember vividly that have helped shape who I am.

As you go on your own path, you undoubtedly will have similar defining moments.  In fact, I’m sure already have, sometimes it just takes a while to realize how important these moments are.

So here are the moments that have changed my life more than any other over the last ten years, along with some thoughts on why they are relevant to you and your goals.

Defining Moment Examples

Before I jump into my defining moments, I think it’s important to look at what a defining moment is and what different kinds of them are out there.

The dictionary definition of a defining moment is an event that influences or changes all subsequent related occurrences.

To put it more simply a defining moment is a fork in the road. It’s one of those times where depending on the moment, and how you react to it your life could go one direction or another.

Here are some common defining moment examples:

The list goes on, but these are some of the most common examples you’d expect.

Now, with those in mind, I want to share with you 10 of my most important “defining moments” in life.

These are the things that have put me on the path that I’m on, and frankly it was some of these decisions that have shaped not only my life, but Location Rebel and this business as well.

My Ten Defining Moments in Life

#1: Backpacked through Europe – Without the Backpack

This was my first global adventure.  This was a two-month backpacking trip that was not only cut down to 3 weeks due to employment reasons, but it also had to be experienced with next to nothing.

The fine folks over at Air Canada had lost my bag when I arrived in Rome.  It subsequently returned to my home in the U.S. two days before I did.

For as angry as I was about this, it had a very profound impact on who I am and how I travel.   This was the trip where I realized that I need very little to get by.  Along with that, I learned that all of these mishaps are all part of the adventure.  Whether you’re at home or traveling, shit happens.  When you can go with the flow, you’ll be far better off.

Think about this as you go on your entrepreneurial journey.   I promise you, things will go wrong.  There will be times that totally suck.  You will make it through, and chances are, you’ll have a hell of a story at the end of the day as well.  And if you know anything about me, you know that’s what I’m all about – having good stories.

#2: Began Location Rebel

Originally this point was “made my first dollar online” but I realized if it weren’t for starting this blog, I never would have made that money.

I began Location Rebel to hold myself accountable for doing the things I wanted to do in my life.  To be honest, I didn’t expect the site to live past the first month.

I’m awesome at starting things. You want to get a project off the ground? Get me involved.  I’m full of ideas and enthusiasm, and I always stay positive.  That said, when it comes to seeing long term projects through, I struggle a bit.

That’s why it’s so remarkable that we’re still going strong in 2018! This post was originally written in 2011…

To see that this is the 245th post on the site, I can’t help but think about the lessons this blog has taught me.  Not the least of which is persistence.  By staying persistent and continuing to blog, I’ve shown myself that I can indeed see things through to the end, and I’ve seen first hand just how valuable that persistence can be.

All of that said, it was that first $22 commission off an ebook called Source Control that I realized the potential of the internet.  To see that commission come in opened up a whole world of possibility that I knew nothing about – but I was damn sure going to learn about it.

Your takeaway? Persistence pays off.  If you’re working hard and aren’t seeing the benefits you want – keep working.  It’s all a matter of having the right combination of things come together.  For some people this happens right away, for others it takes longer, but in the end, it will work out.

#3: Quit My Job

I still remember this day like it was yesterday.  It was quite possibly the most terrifying yet exciting day of my life.  It was the first day in my life where I didn’t know what was going to happen next.

I went from being terrified of the uncertainty to embracing it, and eventually turning it into an asset.

I may be one of the few people who actually benefitted  from the tanking economy in 2009-2013.  Had we seem a bull run in 2008 and 2009, I’d be willing to bet that I’d be preparing to put my suit on here in a few hours.

Entrepreneurs see opportunity in a poor economies – many men and women have made their fortunes in such times.  I’ve made mine.  While it may not be a monetary fortune, it’s one much more important than that – I’ve built a fortune in time and opportunity.  I wish I could say that’s how I’d planned it from the beginning.

But rather I just look back and say, “wow that worked out better than I expected!”

Anything worth doing will terrify you.  There will be uncertainty.  However, taking the leap can (and probably will) be the best choice you’ve ever made – assuming it’s what you want.

#4: Ran a Marathon

It wasn’t until the last 200 meters of my marathon that I:

  1. Actually believed I would finish
  2. Realized what I profound impact it would have on me moving forward.

Running a marathon was without a doubt the hardest thing I’ve ever physically done.  I’m not a runner, and will never claim to be.  This was the one thing on my bucket list that I actually thought may never happen (ok, Virgin Galactic may be a bit of a long shot as well).

So when I entered Hayward Field for the last 200 meters of the Eugene Marathon I was overcome with emotion.  I wasn’t sure if I was fighting back tears or if it was the last 26 miles catching up with me, but I hit an emotional point I’d never experienced.  To know that I was seconds away from actually accomplishing something that I never thought possible, was so eye-opening.

Sean Ogle running the Eugene Marathon.

Strangely, this was one of the most emotional moments of my life.

All of a sudden, my reality shifted.  If I could do this, what else could I do? What couldn’t I do?

Maybe it’s a false sense of self-assuredness, but I really do believe I can do pretty much whatever I want.  I’ll do a better job of documenting this in my upcoming bucket list overhaul, but if it weren’t for the marathon I don’t think I’d have anywhere near the confidence I have now.

Confidence is everything.  If you’re confident in what you do, other people will gravitate towards you and share in your confidence – whatever it may be directed towards.

Go accomplish your impossible. Whatever it is, because afterwards, you’ll never look at life the same again.

#5: Released Location Rebel Academy

Location Rebel Academy is the culmination of the last eight years of my life.  It incorporates everything I’ve talked about in this post.  Overcoming fears, building a blog, starting a business, and living life on your own terms.

I was able to take all of the skills that I learned and subsequently applied to my life, and pass them on to others so they can make their own dreams happen.

The best part? In the last month that’s exactly what’s been happening.  Academy members are leaving their jobs, building businesses, finding clients, and most importantly, bonding as a community in a way that I’d only hoped could be possible

I knew it was a good program.  But it wasn’t until releasing it and seeing the success that everyone is having that I realized I was on to something.

Note: I originally wrote those words above when we had less than 50 members on the site. We now have over 2,500, and it holds true to this day more than ever.

This program has given me more confidence to continue putting out content and going farther down the rabbit hole and seeing what’s truly possible.

If you haven’t checked it out yet, I really hope you will.  Whether you join our community or just grab the free Arsenal ebook, I promise you will get value out of it.  I know I and many others have.

The five defining moments above I first wrote in 2011 when this was first published. They’re still major milestones in my life.

But since then there have been 5 more that have had equally as large of an impact as those.

#6: Got Engaged and Bought a House

I lump these two together, because they happened on the same day.

On April 4th, 2014 when I both bought my first house and got engaged, I was terrified of what that would mean for my brand and business. After all, I was the location rebel! The guy that travels and works from anywhere.

So to be settling down with both a house and a wife? I wasn’t sure how people would react…how would react.

What I realized though is that building a lifestyle business is not about being able to work from anywhere. Rather it’s about being able to do the things you want to do. For some that might be travel (I still travel 3-4 months out of the year), for others it may not look that different than their current life with a day job.

But the fact I was able to do these things and still grow this brand and business was huge.

#7: Got Married

It’s one thing to get engaged, it’s another to get married.

The extra level of commitment and support, is huge. The intertwining of finances, the discussions about kids and futures.

It’s no longer just you. 

And in my case having someone else to both share in the defining moments and the day to day moments as not only helped me to become more successful, but to be more fulfilled as well.

#8: Started The Eighty Club

At the beginning of 2017 I finally decided to try and monetize my golf site Breaking Eighty. I did this through creating a community called The Eighty Club, which I created for members of private golf clubs around the world.

Previously, while I’d had success here with Location Rebel Academy, and a bit of niche site success with HDR Software, I wasn’t entirely sure I’d be able to build another business in another industry.

Seeing how well this has grown (we’re up to about 200 members), and the people it has brought together has fundamentally altered much of how I travel and how I approach my businesses these days.

This post about building a membership site might be useful if you’ve ever thought about doing the same thing.

#9: Began My Golf and My Bar Quest

For most people, these might seem at best a little odd, and at worse downright shallow.

Let’s face it elite golf courses and expensive cocktails aren’t exactly making the world a better place.

However for me, these two things have taken me to places I’d never expect to go, introduced me to wonderful people, and helped me to add purpose and direction to my travels and websites.

As of this writing I’ve played 49/100 of the Top 100 Golf Courses in America, 45/100 Top 100 Golf Courses in the World, and after this upcoming trip to Singapore, I’ll have been to 48/100 Bars in the World.

More on that here.

Since adopting these I’ve changed how I travel, where I travel, who I travel with, and it’s made the journey that much more exciting and rewarding in the process.

#10: Shot the Desk

Of everything I’ve done at Location Rebel, the most interesting and the most defining may have been the video we shot called “The Desk”.

When we shot it, I had no idea how iconic it would become, or frankly, how much of our branding would be built around this concept.

The video proved to me that it’s worth it to do things a bit differently, and it also ended up being a once in a lifetime journey I got to take with my Dad and good friend, Jamie.

Build a Lifestyle Business Giving You Freedom You've Always Wanted

Our 6-part course gives you a strategy to start right now. Put control of your life back in your hands. Sign up below and let’s do this together.

By entering your email address you agree to receive emails from Location Rebel. We'll respect your privacy and you can unsubscribe at any time.

What is Your Most Defining Moment?

These are the moments that have shaped my life more than any others.  If it weren’t for these things I have no idea where I’d be.

So what are your life defining moments?  What’s led you to where you are? Or if you don’t feel that you’ve had a defining moment yet, what will it be? What do you need to do to make that happen?

Thank you for following along with me on my journey, as I continue to explore just how much is possible in life.

Want help building a lifestyle business that will help you do the exact same thing I’ve been able to do over the past 10+ years? I’d love to help you. Grab our free 6 day course and we’ll get started TODAY.

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
Build a Lifestyle Business Giving You Freedom You've Always Wanted

Our 6-part course gives you a strategy to start right now. Put control of your life back in your hands. Sign up below and let’s do this together.

By entering your email address you agree to receive emails from Location Rebel. We'll respect your privacy and you can unsubscribe at any time.