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

By Sean Ogle •  Updated: 01/03/21 •  16 min read


When I originally wrote this post in 2010,  I was sitting on a ferry from Koh Phi Phi, Thailand to Railay Beach. I was floating in 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.

Here at Location Rebel I play up my ability to do this quite a bit.

We shoot videos from all over the world, and post those fun laptop photos. Like this one from Cabo last month:

Laptop and ocean view

Getting some work done in my hotel room at Pueblo Bonito in Cabo San Lucas.

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.

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.

What is a Defining Moment?

A defining moment in your life is an occasion where your life’s path has undeniably changed.

It could be something that changes within yourself. Maybe you experience and injury or illness that changes your perspective in life.

It could be an external factor like a career or relationship change.

But a defining moment is one of those times that you know you’ll look back on and say “If it weren’t for that, things would be different.”

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

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 12 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.

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My Ten Defining Moments in Life

#1: Backpacked through Europe – Without the Backpack

This was my first global adventure.  It 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.

Related: How Backingpacking Through Europe (Without a Backpack) Changed My Life

#2: Began Location Rebel Blog

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…

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

Working at the Bhu Nga Thani on Railay Beach, Thailand less than 7 months after starting this blog.

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.

Related: The Very First Blog Post I Ever Published at Location Rebel

#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 seen 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 economy – 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.

This is all just as relevant these days we we enter into year 3 of the pandemic. It’s made things very difficult for a lot of people, but if you embrace the uncertainty we’re facing, it could turn into a wonderful chance to make a change.


#4: Moved to Thailand

This was the first time in my life where I first consciously thought about the idea of a “defining moment.”

In fact, I remember the exact date and time.

January 5th, 2010.

I was sitting at the Portland airport, about to board a flight to Thailand – where I’d live for the next 7 months.

Victory Monument in Bangkok, Thailand

Victory Monument, taken on my last day living in Thailand. This was about 5 minutes from my apartment.

I even wrote a post about it: “Embrace Life’s Defining Moments.”

Never in my life had I lived more than an hour from my family.

I’d never even been to Asia.

This was the biggest, scariest thing I’d ever done in my life up to that point. And honestly? It may still be the scariest thing I’ve ever done.

#5: 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.  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. Afterwards? You’ll never look at life the same again.

Related: How to Run a Marathon with (Almost) No Training

#6: Released Location Rebel Academy

Location Rebel Academy is the culmination of the last 11 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 along the way, and share them with others in hope you can do a similar thing in your own life.

Work from Home Jobs

This was the week I officially launched Location Rebel Academy. I spent 2 months living in Bali while I did it.

The best part? That’s exactly what happened. Thousands of members and success stories later, I truly feel like the Academy has made an impact.

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.

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.

Related: Location Rebel Academy

#7: 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.

Sean and Tate House 1

In front of our new house – 30 seconds before I proposed.

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.

Related: A House, an Engagement, and a Huge Kick in the Ass

#8: Got Married

Sean and Tate Wedding Day

My wife Tate and I on our wedding day.

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.

Related: Sudden Loss, New Beginnings, and Three Simple Words

#9: 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.

Slide11 Merion 1

Me at Merion Golf Club – one of the top 10 courses in 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 over 250 members), and the people it has brought together has fundamentally altered much of how I travel and how I approach my businesses these days.

Related: Rogue Financial Analyst Makes $34,000 a Year from Golf Business

#10: 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.

"Cashew Everything Around Me" - One of the top 50 bars in the world in Singapore.

“Cashew Everything Around Me” – 28 Hong Kong Street is one of the top 100 bars in the world.

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 52/100 of the Top 100 Golf Courses in America, 45/100 Top 100 Golf Courses in the World, and at it’s peak, I hit 59 of the top 100 bars in the world (based off the 2017 list).

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.

#11: 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”.

Work from anywhere, even in the middle of a desert

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.

#12: Had a Baby

I tried really hard to keep this list to 10, but honestly? I’ve had 12 major defining moments in life, and this most recent one?

It’s by far the biggest.

This is one of the ultimate defining moments: having a kid.

Our daughter was born on January 5th, 2021. I had no idea what I was in for, how much my life would change, or how much love I was capable of giving. It’s been one of the ultimate defining moments in my life.

More than anything else, Elliot has changed my routines, my habits, and my thoughts.

I can’t wait to see the woman she becomes, and I’m more thankful than ever for these previous 10 moments. Because it was this path that has allowed me to spend so much time with her during the first year of her life.

Related: Turning 36 and Some Advice for New Parents

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 11+ years? I’d love to help you. Grab our free 6 day course and we’ll get started TODAY.

Sean Ogle

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.
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17 comments on "12 Defining Moments in Life (and the Importance of Each)"

  1. Great moments, Sean. A few of mine:

    – The first day I picked up a basketball at my cousin’s house as a 13 year old. Little did I know that I would become obsessed with the sport, and that obsession would lead me to become a web designer (so I could create a website about my favorite team), and live in New Orleans for three years (home of my favorite team, and one legendary city).

    – Moving to the US on my own seven years ago. I knew nobody and I was extremely shy. My time there changed me immensely.

    – Quitting my day job last December. I don’t think I could ever go back to being an employee now.

    – Tomorrow, when I leave Ireland again and take my biggest leap yet. The plan is to circumnavigate the globe in three years, without flying. Should be one hell of an adventure 😉

    Here’s to many more life defining moments for you, me, and all the other location rebels out there!

  2. Angie Orth says:

    Great post. There’s nothing so validating as looking back on your decisions and realizing just how far you’ve come.

    Quitting my job & traveling around the world alone are on my list… now on to the business opportunities!

  3. Wow, this is an interesting thing to go back and think about (especially when you’re at the relatively-young age of 25). Here’s what I would say:

    1) Transferring out of business school after 1 semester – I was unhappy and a little scared to make a big change, but I knew I had to do it. This taught me that it’s okay to take a leap sometimes, and that things can turn out okay even when we don’t know where we’re headed.

    2) Discovering the world of internet business – I’m not how it even happened, but I stumbled across a blog about making money on the internet (in legit ways) about a year and a half ago. It’s changed my way of thinking and my life since.

    3) Taking a whole summer off after grad school – Summer 2010 was literally the first summer in 11 years that I wasn’t employed in some way. And I loved it! I really enjoyed making plans on a whim and traveling to wherever I wanted to enjoy the great weather. It’s really what’s motivated me to out of the working world and unchain myself from a desk. I hope to repeat this in 2012.

  4. Tristan says:

    Hey Sean,
    Great reflective post. Nice to see the progressive moments to living the lifestyle you always wanted.

    A few of mine:
    1) Backpacking through Europe, then become a tour guide in Munich for three months. This helped me come out of my shell (I never was into public speaking), made me realise the type of people I want to be around, and expanded my thinking.

    2) Exchange program in Japan which opened my eyes to a completely different culture and way of thinking, and solidified my passion for languages

    3) Travelling to Africa last year. I can’t quite describe how this changed me yet, but I think about it most days and feel so lucky to have had the chance to go there.

    Look forward to reading others’.

  5. Matt says:

    Nice! It’s been awesome to get to know you and be a part of your transition Sean.

    A few of my life altering moments:
    1) Meeting my wife online then 4 months later taking my first International trip to Indonesia to marry her. People thought I had gone off the deep end but we’ve been happily married 10 years now.
    2) The birth of my boys – definitely life changing!
    3) Reading Location 180 from the beginning and realizing there is so much more to life than what I’ve been experiencing.
    4) Deciding to make the big move with the family to Indonesia where my wife and I plan to start a bakery (among other things).

    I have to say I’m really interested to be following the global adventures of Niall.

    1. Sean says:

      haha well its nice to see #3 on that list – but I have a feeling all of those other ones were much more defining moments than reading my blog haha. It’s been awesome to see your progress as well, and looking forward to seeing many more adventures in the coming months!

    2. Loving your journey, too Matt! Some great moments you’ve had there. Here’s to many more 🙂

  6. Sounds like you’re having fun!

    My most defining moment was getting a position at one of the companies I most wanted to work at after 55 interviews. I knew if I just survived for 10 years, I would be set. Being able to do what you want to do and earn a living is priceless.

    1. Sean says:

      That’s awesome to hear – there’s few great accomplishments than being able to make a living doing what you love in life.

  7. Jill says:

    My decision to move from Michigan, where I’d lived my entire life, to Tahoe so I could ski more was definitely a defining moment. I’ll be giving this more thought; thank you for inspiring me to think about this.

    1. Sean says:

      Glad I could help Jill! Sounds like a move I’d love to make someday as well 🙂

  8. Without a doubt, my biggest moment was my double-lung transplant.

    But, more than that, what really focussed me on life was discovering that death held no fear. I feared – dreaded – the process of dying, the idea that were my transplant not to come I would have endured a slow, suffocating death in a hospital bed with the anguished faces of my family looking on. Death itself had no sway over me.

    Knowing that, and knowing now that this second chance is here to be grasped, helps motivate me to do even more with my life.

    I want to know that the person who died and let me live with the most selfless choice one can make is looking down on me with pride at all I’m trying to do, whether or not I succeed or fail.

  9. My defining moment was when I had the courage to say to my colleague (in our mutual startup) out loud that I wanted to live location independently – and he responded: “Sure!”

    That moment I knew I couldn’t turn back.

  10. Darlene says:

    My defining moments hmmm. . . I’ve perhaps had a few more than you younger counterparts as I’ve been around the marble a few more times, LOL. This is what comes to mind:

    #1 – at age 21 quitting my job working for another photographer (who shall remain nameless but suffice to say I learned how NOT to run a business from him). Going full-time at my own photography business (with my then boyfriend/husband) in the early 90’s during that recession. And we rocked it!

    #2 – getting a divorce from above husband/partner in 2001 and leaving behind the studio I spent 12 years building. Having no idea what I’d do for income, a contract job being a rep for an international photography album supplier fell in my lap. Spent 9 years with them, travelling the world for them but meeting some great people and having a great time. Was my first real international travel when they took me to NZ to the offices there.

    #3 – quitting the above job/contract (which paid a high 5 figures) in 2009 when I got remarried. Renting out our house for 6 months and travelled Canada/US in an RV.

    #4 – now! reinventing myself yet again as a photography teacher this time. Once again I sort of fell into doing workshops locally and it’s given me confidence that I can do this and a possible ebook is in the works as well.

  11. Lois says:

    awesome and though-provoking post. my defining moments so far

    -quitting my job to work and live in America
    -quitting that job to follow my heart all the way to Europe
    -quitting another job to go backpacking through Asia

    wow, so far what has defined me as a person has been quitting to travel. thanks for the realization!

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