The Mental Evolution of a Cubicle Dweller

By Sean Ogle •  Updated: 12/21/09 •  8 min read

This post was originally published in December of 2009. It’s been updated to fix grammar and links.

For the past few weeks I have been reading Chris Guillebeau‘s annual review posts, and it has inspired me to do a bit of a personal review myself.

While I haven’t written a book, inspired thousands of people (scratch that, 10 years after originally writing this, this is the one thing I HAVE done), or almost been kicked out of Saudi Arabia, I have been thinking a lot lately about how much has changed in 2009 and reflecting upon where I was a year ago.

If you have been reading Location 180 for awhile, you have a general sense of what I have been through, but you probably don’t realize just how far I have come to get to the point where I am today.

If you had asked me a year ago, what I would be doing in December of 2009, I surely would have told you that I would be doing pretty much the same thing I was doing in 2008.  I’d still be working 40-50 hours a week at my job, living a comfortable life, and plotting some way to use the 10 whole days of vacation I’d have in 2010 to make it some place exotic.

There was a sense of obligation in my job, that I never thought I’d be able to shake.

The mindset of “you gave me work, so I should be eternally grateful” is something that I felt would lead me to a 30 year career at the same company.  It honestly wasn’t until after I lost my job a few months ago that I was able to get rid of that feeling, and honestly the guilt that’s still inside of me tells that, even now, the feeling isn’t entirely gone.

So back to last year, one of my best friends had already been talking for months about the world trip he was going to take in January of 2010.

I had dreams of joining him, and he made some pretty good arguments for why I should (scuba diving in Utila, World Cup in South Africa, Hiking the Inca Trail, you know, typical every day stuff), but the sense of obligation to my job was so strong that I hardly considered it at that point.

Then came Brazil.

Getting ready for the parade. Sorry buddy, I had to put this in here!

Getting ready for the Carnival Parade in Rio. Sorry buddy, I had to put this in here!

We’d been planning it for nearly 10 months.  I cashed in ALL of my vacation days for the year, and in February we hopped on a flight to experience Carnival in Rio de Janeiro first hand.  To say we weren’t disappointed would be an understatement.

However, more importantly than that, it was what triggered one of the rare “aha” moments you experience in life.  You know the ones where you realize that you do have options, and aren’t entrenched in whatever life you currently have.

I have extremely vivid memories of two moments in particular.

One was a Wednesday morning about 11 am walking down Copacabana beach and I just looked to Ryan and said “we should be able to do this everyday.” I want the freedom to work, when I want to, not when it is most convenient for someone else.

The second moment was near the end of our trip, and we were taking a jet boat down the Parana River after being doused by Iguazu Falls.  As we cruised the 7 miles down to our take out point, I couldn’t fathom having to go back to work a mere three days later.  It just didn’t seem right.  I think that was the moment where I realized a change needed to be made.  I had no idea how I was going to  go about it, but I knew something would need to happen.

I went back to work, longing for days when getting out for an hour to go exercise wasn’t the best part of my day.  I mean seriously, when you are counting down the hours until you can leave to go lift weights or run? Something isn’t right.  I don’t even enjoy working out that much!

Anyways, the next big shift came in April.  Ryan, on a whim, decided to move to Hawaii.

Do you know what it’s like to talk to someone 3 times a week, who’s working as a cabana boy, and routinely getting free “excursions” from his concierge roommate.  We are talking zip line rides, atv trips, diving outings, and even sunset helicopter rides, ALL FOR FREE!

If that isn’t enough to make you jealous I don’t know what is (see photo above for my version of payback).  Yet, as much as I wanted to go join him, I still wouldn’t consider the idea of leaving my job that I was so grateful for.

At this point, I’d been toying with the idea of starting a blog to help me gain some clarity about my life and goals.  Chris Guillebeau had just moved to Portland, and I was shocked when he agreed to meet me for coffee.  I honestly credit a lot of this blog’s success to him.  He provided me with resources for starting the blog, as well as gave some personal insight into some of the things that worked for him (reading other blogs, and taking action being among the most useful things I got out of that first meeting).

Chris Guillebeau Portland Meet Up in August (Click for Photo Credit)

Chris Guillebeau Portland Meet Up in August (Click for Photo Credit)

As I progressed through the months, and wrote post after post, I started to experience a slow evolution.  I had been in touch with so many people who were living remarkable lives that I was starting to believe maybe, quite possibly, I could actually be one of those people as well.

In September, I stumbled upon a blog post about how to propose a remote work agreement.  This is a concept that I never thought would work for my position at my job, but after thinking about it more and more, I realized that with some creative thinking, it could totally be done.

Submitting that proposal was the first real step I made towards a new lifestyle…even if it was a failure.

My failure however, was in actually believing that 1) It would work and 2) If it didn’t work, there wouldn’t be consequences.

By the time a month had passed and there was no response, I really felt like it was because they were figuring out all the details for how to make it happen.  In my mind, aside from not being able to answer the phone on a regular basis, I didn’t see a downside.

They’d save thousands of dollars annually, and I would still be able to provide nearly all of the value that I was giving while in the office.  It seemed like a no brainer to me.  But I guess I come from a new way of thinking.

In the end, they obviously didn’t accept the proposal, but it was the best thing that could have happened.  Sure, I experienced a few terrifying weeks with no income, or idea of what the future would bring, but then everything came full circle.

Like I mentioned, I started the blog with no real of idea where it would take me.

Well, my blog is taking me to Thailand.

Seriously, you want motivation for starting a blog, there you go.  In 6 months, I’ve gone from frightened conformist, to trailblazing adventure seeker (ok that might be exaggerating a little bit, but it isn’t totally far off).  The same amount of time has featured a number of slow but deliberate steps towards rewiring my brain, and adopting a new way of thinking.  Each step bringing me closer to my ideal lifestyle.

I have no idea if my next adventure ends with me having found that lifestyle that I am searching for, but I do know that I am closer than I have ever been.

Spoiler Alert: As I re-read this post that I wrote over 10 years ago, I can definitively say that this story has a happy ending. I did find the lifestyle I was searching for. And this post does a pretty good job of breaking down the journey.

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

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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23 comments on "The Mental Evolution of a Cubicle Dweller"

  1. Mary says:

    Wow, that is a lot of great stuff happening in a year! Your blog has really helped you grow and change your life, hasn’t it? That’s great Sean. Just think of all the wonderful things to come in 2010!

  2. Rob Blasko says:

    Sean: It sounds like 2009 was an awakening year for you. I had a couple of my own “aha” moments this year: herding sheep (or attempting) on a farm in Australia was but one of them more memorable. I’m hoping 2010 offers me the opportunity to act on those “aha’s.” Cheers to your search, and thanks for sharing your journey!

  3. Casey says:

    Congrats on the move! SE Asia is unbelievable. Enjoy the time out there. Everyday is an adventure to say the least.

  4. Carmen says:

    Wow! What a year! Congratulations on taking so many leaps not only mentally but personally and professionally. It seems like you are positioning yourself for even greater personal growth in 2010. Happy new year!

  5. I agree with Rob Blasko: 2009, a year of a-ha moments. Apparently, this is true for a lot of people, and it will be thrilling to see where 2010 takes us. Although I only found your blog recently, it certainly will be interesting to accompany your blogging ventures in Thailand!

  6. Nate says:

    This post is exactly what I needed to read today. Very inspirational. I’m really excited for you man. I want to get to the point where I can do whatever the hell I want everyday so badly that it keeps me up at night. Which is good so I can work on my projects that will get me to where I need to be financially before anything can happen. Anyway, really good post it was a pleasure to read.

  7. Kyle says:

    I’m aboard the same boat you were this time last year. Hoping my 2010 Carnival experience spawns the same afterthoughts. Thanks for the peace of mind, brother!

  8. Earl says:

    The idea is to make 2010 even more life-changing than 2009! Stay positive and there is no reason why you won’t be able to go walking down the beach (or anything else you wish) every single day.

  9. You, Sean Ogle, are my Chris Guillebeau. If that makes any sense. Former cubicle dweller? Check. Feeling guilty for not feeling grateful? Check. Trying to speed up evolution by blogging? Check. Keep it up, your experiences inspire all of us cubicle alumni.

  10. NomadicNeil says:

    Sean, you are a great example of someone changing the way they think about things and the effect that has on their life.

  11. Ryan says:

    Well I would have to say, NOT COOL for not even running this post by me before publishing it. Payback is gonna be hell in 3 days when im back in PDX! But seriously, congrats man. U’ve definitely earned everything u have going ur way. See ya soon 🙂

  12. Till says:

    Hey Sean!

    Here’s one more guy inspired by your honesty. You demonstrate that sharing your dreams, successes and let’s say bumps on the way to freedom is not harmful but the opposite: it inspires others and yourself!

    I’ve had the opportunity in 2008/09 to backpack my way through Chile in 10 weeks from the Atacama desert to wild Patagonia. Now the plan is to return there in 2010, become fluent in Spanish, explore South America, play beach volleyball in the warm evenings and build my freedom business. I’ll drop you a note when my blog is up 🙂

    Cheers & thank you!

  13. Alan says:

    Loved your “aha” moment in Brazil! Very nice reflection, Sean.

  14. Josh Sager says:

    Great post, Sean. Your move to Thailand has been one of many impetuses that has lead me to make 2010 the year I start working for myself, do a lot more traveling, and generally start dominating the world! Happy Holidays and keep going!

  15. Angela says:

    I can completely related to a seemingly gradual change in thinking that all of a sudden sneaks up on you in it’s full magnitude… It is amazing how fast it can happen too. I’m excited to see how your 2010 develops!

  16. That was fun and inspiring to read. I am so happy you were able to find the life you truly want. To many people don’t realize it until it’s too late. It has been fun getting to know you the last 6 months or so and seeing your growth as a blogger and individual. Can’t wait to read more in 2010.

    David Damron

  17. Nate says:

    Thanks for sharing your transformation, I appreciate it. I’m somewhere in the middle right now, going through a ‘transition’ period. I’m extremely excited to see what the next year brings for myself and for you!


    1. Sean says:

      Thanks everyone for such positive comments. I really do feel as though 2010 is going to bring some exciting things, not just for myself, but for all of you as well. I look at your blogs, and comments, and many of you are doing things just as exciting as what I am going through, and it is awesome to be able to share the journey together!

      @Till I would love to hear more about your adventures, so definitely drop me a line when the new blog is up!

      @Ami I think that may be one of the best comments/compliments I have ever received. To think that I have inspired any one, even a little bit, makes this whole project worth it. I really like what you have done with your site, and I am looking forward to seeing more from you in the new year!

      @Kyle You won’t be disappointed. I promise!! Go to Buzios and Iguazu if you have time/money!

      @Colin Glad to see you have found the blog! A beer would be awesome, I am always interested in talking with people about their different approaches to travel, and to do it with a family, certainly makes for a unique story! Keep me posted on your locale!

  18. Congrats, Sean.

    You have come a long way, baby! as the old cigarette commercial used to say.

    I have followed you and your blog from almost the start and seen you progress and have doubts and second thoughts along the way, but you hung in there and now you’re going to Thailand.

    I’ll be calling upon you for an interview for an upcoming project of mine, I hope you’re availale.


  19. Karen says:

    Congratulations on making so many changes in your life.

    It sounds as you are on the right path now, and are prepared for any road bumps along the way.

    I hope the move to Thailand is all you hope for (and more).

  20. Wonderful to see another cubicle flee-er! Good luck in Thailand!

  21. Cathy says:

    Found your blog from a chrisguillebeau tweet…

    Another cubicle alumni enjoying your post! Rock on.

  22. Hansen says:

    Great post! I am in a very similar situation right now and I already have the plans to move. Now to get a blog going.

    Hope to see you around the world somewhere.


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