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

By Sean Ogle •  Updated: 04/11/14 •  8 min read

I’m not even entirely sure where to start with this post, so I’m just going to start.

The last month has been, how shall we say? A whirlwind.

How you might ask?

Well, let’s just throw it all out there:

I feel like I became a grown up all in a span of about 3 hours.

So, let’s back up for a sec and I’ll recap everything as best I can.

The Engagement

This is far and away the most important thing that has happened. After over 5 years together, Tate and I are finally going to get married.

When we first started dating I wore a suit and tie to work everyday, and had a very traditional life.

She’s had to deal with me starting a business, leaving a job, moving to Thailand, moving back from Thailand, starting more businesses, and continuing to travel the world.

Talk about patience.

Throughout it all she has been my biggest supporter, and has had more patience than anyone I’ve ever met as I’ve figured out how to make this lifestyle work not only for me as an individual, but for us as a relationship.

We won’t officially tie the knot for another year and a half or so, but I can’t wait to start the next chapter of my life with her – none of this would have been possible without her support, so I’m excited to finally take this next step!

So how did I do it?

Well, I did it about 10 seconds after we walked into the second most important part of this story:

The House

For those of you paying attention you may remember my new years goals post at the beginning of the year.  One of the things I really wanted to accomplish was to buy a house.

I can hear what many of you are saying: “What?! You’re supposed to be the Location Rebel!”

Bottom line, the only aspect of my life the house changes is the level of space and comfort when I’m at home.

I currently travel about 4 months out of the year, and the rest of the time I’m in Portland. So that will all remain the same, I’ll just have a dedicated office, space for friends and guests, and a great view of the city as well 🙂

Tate and I have lived in 485 square feet for years, and when you work from home, this gets unbelievably small.

So for all of those reasons I’m pretty stoked.

Also, I think we made a great investment. It’s very much a “cheapest house in the best neighborhood” kind of situation, and I’m still within walking distance to downtown Portland which is a pretty big deal for me.

Pioneer Nation

In the midst of all of this, myself a few others put on the inaugural Pioneer Nation event.

Essentially it was a business conference for independent entrepreneurs.  Think a smaller World Domination Summit, with more of a business focus.

Overall everything went off without a hitch, and our attendees seemed to have a great time.  The jury is still out on what the next iteration of it is going to look like – but for now, I couldn’t be happier with the end result or more proud of our team that put it together.

Chris also did a fantastic recap of the event here.

Sean Tyler Caelan

Enter China

Finally, the day before Pioneer Nation started my friends Nick Ramil, Tim Nybo and I released the beta edition of Enter China.

This is my first new product in nearly two years, and I think it’s positioned extremely well to serve a small but growing niche of people that are looking to China to do business.

The community is already thriving, and Nick is throwing our first EC meet up in a couple weeks in Guangzhou for members that are coming out for the Canton Fair.

And for those of you who missed it, here’s a quick video of my experience at the Canton Fair in 2012:

That Part About the Kick in the Ass

This past month marks the most expensive month of my life.

Between buying the house and all that entails, paying my 2013 taxes, SEP contribution, and Quarterly payments for next year – I’ve had to write 6 figures worth of checks this month.

Ho. Ly. Crap.

That is terrifying to me. But to be honest, I think it’s the best thing I could have possibly done for my business.

When the Uncomfortable Gets Comfortable

I’m going on 5 years of entrepreneurship. Next month will be my five year anniversary of starting this blog (WHAT?!?!).

For the vast majority of those five years, I went through a bunch of uncomfortable phases.

First I worked up the guts to leave my job.

Then I moved to a foreign country.

Then I had to figure out how to support myself back in the United States.

I stress about money – a lot.

And during these periods of change, I was always just uncomfortable enough to keep pushing forward – striving to get to that point where I don’t have to stress out about money.

Then something really weird happened.

I got to that point.

In the last few months I reached a point where I had enough money in my bank account that I didn’t stress about how I was going to make my next dollar.

I could do what I wanted and buy what I wanted without those doubts hanging over me.

And you know what?

I didn’t know what to do with myself.

Your Success is the Only Reason for My Success

The drive I’d had for years to build and grow had waned a bit and I found myself feeling oddly comfortable in a life I’d built on the premise of discomfort.

It feels awesome to know that this great life I’ve built for myself was only because I was able to develop products and systems that helped other people build great lives of their own.

We have over 600 members in Location Rebel now, and a big percentage of them are living their own versions of the dream.

Just look at this picture that Tristan sent me.

Tristan Ao Nang

Or this one from Lise in New Zealand:

Lise Carter View

The list goes on. I’ve only been successful because they’ve been successful.

But as comfort set in, I was becoming less useful to everyone else. Sure I got to play more golf and spend more time with friends, but I wasn’t actively doing as much of the things that brought my success in the first place: helping others achieve their lifestyles.

Keep Your Back Against the Wall

It’s so odd to me that it took the things that most people consider very safe, traditional, and comfortable to knock me back into a place of discomfort and focus on the business.

It took zapping my bank account to near zero to get to the point where I remember, “Oh wait, there’s a reason I’m in this position, and it sure as hell isn’t because I slacked off and lived like a 28 year old retiree.”

I’ve found that for myself and so many other entrepreneurs the best work is only done when your back is up against the wall.

When things have to work, because you have to be able to keep the lights on next month.

When you’re at the point where failure isn’t an option.

When there are forces greater than yourself relying on you to be successful.

Those are the times the greatest work is created.

Now much of my cash is gone and I have a mortgage to pay. That scares the hell out of me.

But the minute I saw all that money leave my account, it was like a light went off.

The motivation I’d been searching for for months was finally back – and with vigor.

I’ve felt renewed and excited to refocus the business that has helped so many people these past few years.

Mentally, it feels as though back is up against the wall again.

Even though on the surface, by traditional standards, my life might be getting more comfortable and settled down – the exact opposite is happening.

I’m returning to the fight and excited to take what I know and apply it to as many lives as possible.

Life is a rollercoaster and as I mentioned in my 2014 goals post, this is will be a huge year for me, and one that represents the biggest series of changes I’ve had in 4 years.

Once again I can feel the creep of the fear of uncertainty. But now that I know this is an asset and not a liability.

For the next couple of weeks I’ll be moving into the new place and trying to get refocused on the blog and business – there’s been a lot of guest posts lately!

In May I’ll hit the road again for a couple short trips, and then I’ll be doing a longer trip in June to the east coast to continue knocking off more of my Top 100 Golf Courses.

Have you gone through any major life changes recently? How did you handle it?

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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34 comments on "A House, an Engagement, and a Huge Kick in the Ass"

  1. Matt Riley says:

    Congrats on the new house, the engagement, and everything else. These big decisions will just take you to another level and make you more successful in your future endeavors. OK enough with the well wishes I have to get back to work I have clients waiting for shit! Congrats again!

    1. Sean says:

      Thanks Matt…now get back to work!! 🙂

    2. Zorika says:

      Congratulations on your Engagement……..the house and to your success in all things 🙂

  2. Tristan says:

    Congratulations Sean . Fantastic changes are a’comin’ and I’m sure 2014 will be a great year for L180. What a start it’s off to already! Very happy for you guys and great to hear the business spark that’s been lit too 😉

    Good luck with the move!


  3. So many awesome updates, Sean! Congrats on the engagement and the house. Glad you didn’t have a heart attack from all this happening in one day 😉

  4. Liz says:

    I for one cannot wait to see all the next projects coming down the road, and to have a beer on the deck 🙂

    Congrats Sean and Tate!

  5. Yeah!! Great to read this ass-kicking and engagement recap.

    Indeed, it’s been a crazy ride for you. I’ll be looking forward to seeing what the next five years brings for both you and Tate.

  6. Sean – A HUGE CONGRATS on getting engaged…. that’s awesome!

    In addition, congrats as well on the new pad too. I certainly don’t see a problem with having a sweet place to call home while still being a location rebel. What a great concept as well with Enter China! No question it’ll be another successful endeavor for you.

    They say that you can get everything in life you want if you will just help enough other people get what they want. I can’t think of a more perfect example than of you and what you’ve created with Location 180. Awesome! Congrats man….. Cheers!

  7. Lorna says:

    Wow, congrats all around! You’ve been busy! I know what you mean about the juice drying up once all of your ducks are in a row… I thought retirement was going to be never ending bliss. Turns out I missed the engagement and challenge of stretching myself and the interactions with others. And while I wouldn’t want to return to an outside job, I’m thoroughly enjoying learning how to create a viable enterprise from home. Much more success to you!

  8. Cat says:

    Wow! That’s a whole lot of awesomeness to put all in one post. Congratulations! I heard a phrase recently on a Lewis Howes podcast about being a “life baller” – I think you qualify for that title as well. 🙂

  9. Kristof says:

    Congrats Sean, great post!

  10. Sheralyn says:

    Huge congrats on your engagement and the house! So excited for you! 🙂

  11. Dan says:

    Huge congrats Sean !!!!

  12. Dakota Gale says:

    Well played Sean! A big congrats to you and Tate. Fun knowing I was involved in one of three.

    As for being rooted with a house, no need to fret. Location independence is a choice, and if you can swing a mortgage and travel whenever you want, that’s some mighty fine cake you’re eating. I suspect there is a product line in there somewhere that could really help people.

    Here’s to location independence AND a place to call home! May the next five years be even more adventure-filled and exciting. I suspect they will be.

  13. Gunnar says:

    Congrats Sean! Line ’em up, and knock ’em down!

  14. Sergio Sala says:

    I’ve been following your journey since like 1 or 2 years, and it’s pretty cool to see how you are changing and adapting on your life’s road.

    Congratulations on everything! Having a house does not mean that you are sedentary.. It has benefits, too! Will you try couch surfing on it? I can be the first, ’cause I need for WDS haha.

    For me, I’m in process of being nomad the whole time, but I still need to create income out of my blog and design stuff – it takes time, because in the spanish world it’s so different.. Constance will pay off, I know.

    Anyway, enjoy your new adventures!

  15. Chas says:

    Congrats to you and Tate. I truly wish you much happiness and joy. Continue living your dreams. “An unfulfilled vocation drains the color from a man’s entire existence.” ~Honoré de Balzac, Scènes de la vie Parisienne

  16. YES!

    Although Liz spilled the beans to me on our call the other day, I’m happy to see you putting the big news out to the world, Sean.

    Just wanted to send you a shout out from South America, and thanks for the stories about your best work being created when it HAS TO WORK, when your back is against the wall. That’s been my experience as well –

    Having a life of comfort and every system running smoothly on autopilot sounds great on paper, but the real thrill of living this lifestyle is learning what we are capable of when we cross the great divide into the ocean of uncertainty, again and again – Nothing makes me feel more creative, driven and alive than those times.

    Looking forward to seeing ya in Portland in July, bro!


    I know for a fact that

  17. Alex says:

    Well done Sean! Great to hear your found some new motivation. Can’t wait to see what’s next.


  18. Super congratulations on all the exciting stuff happening for you! I think it’s awesome to be able to travel alot of the time AND have a house!! Happy moving! x

  19. Ana says:

    A hearty congrats, Sean, on the engagement AND the house! Having a firm home base is going to be one of my own themes in my biz, as I certainly have found out what it feels like not to have that when it’s needed. You have a home now … and you also have location independence. Awesome!

  20. Carl Bolland says:

    Wow Sean! Congratulations!

    I’ve been reading your blog for quite some time and must admit, you’re one of the better writers and motivators for Personal Development and Entrepreneurial material – You always get me hungry for making my own success!

    I’ve tried my own website and similarly to your story (mentioned in your first post), I’ve failed many times but learned something new from each of them. You actually played a pivotal role in my new website, as you inspired me to use my own name to externalize accountability and motivate me because who the heck wants such a personal URL becoming a link hub? – Not me!

    Congratulations on your engagement and house purchase! Honestly it’s really awesome to see you go from working on someone else’s pipe dream (9-5 job) to living your own!

    I’m looking forward to your new challenges and material as you enter this new stage of your life!

    I hope to be as successful as you one day!

    Carl Bolland

  21. Janine says:

    Congrats on everything! And I’m happy to read the back against the wall thing is not just something I am dealing with 😉

  22. Scott Asai says:

    Sean, congrats on getting engaged and buying a house! Thanks also for sharing what you’ve accomplished as it’s inspiring for fellow entrepreneurs to stop talking about it and start doing it!

  23. Congrats Sean Ogle! Those are some incredible milestones.

    And to answer your question: Yes, ever since I joined Location Rebel!

    In the past 5 months I’ve been able to:
    -Connect with some encouraging individuals from your community
    -Take a 12 week leap of absence from my well paying corporate job
    -Take care of my little sister suffering from a medical condition – spend more time at home to take help her and start my business
    -QUIT my corporate job!
    -Start a new product/business but FAILED
    -Started another more realistic online marketing consulting business… and so far it’s working out!
    -Now taking care of my little brother
    -Oh, and not to mention regular location independent trips the Rocky Mountains (my get-a-way work time from Denver)

    I can’t put into the words the “up against the wall” feeling I have every single morning over the past few months. Sometimes I just don’t want to get up and ask myself, “What the hell am I doing?”

    I get up anyways and remember my vision of having a successful business that legitimately helps other businesses. I write it down on paper: what I want and how much income I expect to make. I also wrote down motivating questions and read this every time I wake up.

    I’ve wanted this more than anything my whole life, and for once I can see my dreams unveil itself one day at a time.

    So here’s to “burning the ships” to the point of no return and creating something out of nothing when you most need it!

  24. Christina Marcus says:

    Hey Sean, I love how your journey keeps evolving. I agree that being location independent, traveling the world, and having a beautiful home is the best of both worlds. I am looking forward to reading more posts about the engagement and about managing a mortgage with a location independent lifestyle.

  25. kristopher ryan watson says:

    wow Sean, i couldn’t believe my eyes when i read about acquiring the house AND got engaged ! that is an amazing step forward, so congrats !

    But, i hope that doesn’t mean you’ve planned on settling down any time soon; i enjoy your travel posts and look forward to the wisdom you share from those journeys.

    again, congrats. you’re an incredible inspiration to guys like me.
    wishing you all the best in the future !

    Kris W.

    1. Sean says:


      Thanks man! And absolutely not 🙂

      Still planning to travel just as much as before, now I just have a bit more space and a better working environment for when I’m not on the road.

  26. Jason says:

    Sean, HUGE congrats to you on the engagement and everything else! Looking forward to following along while you’re ‘up against the wall’. Kudos for taking the plunge on the house and your life love all at once, awesome stuff! Keep up the great work, we love what you do man.

  27. Joel says:

    Awesome news Sean, congratulations on the house and engagement! I totally agree that the back against the wall scenario is the best motivator for an entrepreneur. I’m looking forward to seeing the results of your renewed vigour!

  28. ryan says:

    super inspiring, well done champion, as great as the last 5 years have been, here’s to making the next even sicker!!! Thanx 4 all the power info!

  29. dave says:

    Sean – congrats on the engagement. That’s super exciting. It’s so important to have someone there to support you year after year while you do your thing.

  30. nayar says:

    congrats on the engagement sean, great to hear your fired up again hopefully well see more stuff from you. i have been through most oft the major events life throw at us like getting married, buying a house, and having a child. and i don’t think that effects the location independent lifestyle at all as it just comes down to the fact that how uncomfortable are you willing to get. sure travelling with a child or a mortgage looming on your head is un-confortable but then thats what location independents thrive on right? i used to work day in day out trying to make something and thought maybe overtime etc will impress the boss to finally kick start my progression but i eventually realised that its not going to happen once i was on maternity leave i finally realised when i was free to do whatever i wanted whenever i wanted that thats the life i want! to be able to spend time with my kid as well as work from home on my own terms. i am hoping to get involved with location rebel but i have recently started my blog so i can get some writing practice behind me before i fully embark as a location rebel. many thanks for all your inspiration and help. i think i had better be adding the following to my bucket list ‘buy sean ogle a coffee, during a trip to the states’ haha regards

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