The Hardest Decision I’ve Had to Make All Year

By Sean Ogle •  Updated: 10/11/12 •  5 min read

I’m going to get some crap for this one, I’m sure.

However, I’m going to write about it anyway – because as you continue building your lifestyle business, traveling, and doing more cool stuff – you’ll face similar issues.

I always said I’d be honest on that site, so here’s honesty at it’s best.

The Decision

So, for the last month I’ve been wrestling with the hardest decision I’ve had to make all year. What is it?  Well, luckily it wasn’t anything serious.  It wasn’t life or death, there wasn’t large sums of money on the table, and really in the end, it didn’t matter which way I went with it.

The decision was whether or not I should go to Thailand this month.

Go ahead, I can hear the collective “are you kidding me?!? THAT was the hardest decision you had to make this year?”

It’s ok, I’d expect nothing less from you.  I’ll admit that I must have made some pretty good life decisions if that qualifies as the most difficult decision I’ve had to make.

But hear me out, once you get past your thoughts of “screw you, Sean” – you’ll see what I mean…I think.

One Crazy Year

2012 has been more intense than I ever could have expected.  I’ve done more traveling than anticipated, met dozens of new friends, and I’ve been working a lot throughout it all.

My initial plan was to head out to Thailand for three weeks in October to see a bunch of old friends (most notably the team over at the Tropical MBA), go to a little conference, and meet a bunch of others that I’d never had the chance to meet in person.

I was going to spend a week in Chiang Mai after the event in Bangkok, and see an area of the country I hadn’t yet experienced.

So what was the problem?

It can be summed up in one word: momentum.

The Importance of Forward Momentum

After getting back from Fashion Week in NYC with my friend James, I was ready to build some momentum.  I’d been eating like crap, not working out, and it was time to put some serious focus into the next phase of my business.

The day after I got back I went and got a gym membership.  I actually went to the grocery store and picked up some healthy food. I began mapping out the plan for Location Rebel that I’ve been dragging my feet on since January!

In the last few weeks since then, I’ve gained a lot of forward momentum.  I’ve brought someone on board to help me out with the transformation of the program (more on that later), I’ve been featured in a number of big publications, and I can feel myself getting closer to the goals I’ve set for myself.

Now, I know if I went to Thailand right now I’d have an incredible time. I’d make incredible memories, with great stories.  I’d meet a ton of people who I know would have a positive impact on my business going forward.

But I’d kill the momentum.

These three weeks would be more about the adventure than it would be about specifically building off my forward momentum on the business.

I’ve always said that I’ll choose work over play whenever possible.  I have a fairly loose “yes” policy with most of what I do – but while normally Thailand would be slam dunk, this one was more difficult.

It wasn’t even about the money. In fact, its probably cheaper for me to spend 3 weeks in Asia than to stay in Portland.

It was the cost of killing the momentum that kept sticking in my head.

I’m Not A Travel Blogger (Usually)

I’m a blogger who happens to write about travel on a fairly frequent basis.

While many people look at travel bloggers and think they have the best job in the world (and I’ll admit, it seems pretty great) the amount of time and energy they put into what they do is staggering.  I don’t think I’d be able to sustain a travel schedule that rivals the likes of Gary Arndt, Nomadic Matt, or Mike Richard.

While I can do it for periods of time, and hope to do more of it next year, you can’t deny that working from the road (not just abroad), will wear on you with time.

I knew if I went, I’d kill the momentum.

There Will Always Be Opportunity

From the very day I quit my job, I’ve never had any shortage of opportunities.

When people know you’re open, and looking for opportunity, they will find you.

Is going to Thailand to hang out with some of my favorite people, and meet even more an amazing opportunity? Of course it is.

Maybe I’m getting wiser in my old age, but there are times where you have to decide what’s in the best interest of the business and put it first.  After all when you have a lifestyle business, life and business go hand in hand.  What’s best for the business is usually what’s best for your life.

I know there will be other opportunities. Lots of them.

By not going I’m also able to save the miles and perhaps go some place new in the new year with full confidence in my business due to the changes coming in the next few months.

Perhaps this post is my way of rationalizing a missed opportunity, but I guess the moral of the story is as this:

Most of the time you should say yes. Except when you shouldn’t – and you’ll know when that is.

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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36 comments on "The Hardest Decision I’ve Had to Make All Year"

  1. Janet says:

    saw your tweet about this and sort of assumed you decided to go. but momentum is better, too. i was trying to decide on whether i should go to the same gathering in Thailand.. but I’ve decided to focus my energies on WDS this year and see if I can get round 2 tickets.

    1. Sean says:

      Nice! Would be great to finally see you in person somewhere!

      Where are you at these days?

      1. Let’s meet there next year instead Sean. I’d love to meet Dan Andrews and hang with you again, plus I have a big ass travel plan coming together.

        Btw congrats to saying no, we need to do more of it to the right things

        1. Sean says:

          Looking forward to hearing about the travel plans 🙂 And for those of you who don’t know Natalie, check out her 100 Change camapaign

  2. Lindy says:

    Hey Sean, I can imagine the temptation of going away on an adventure/holiday, kicking back with ice-cold beers on a white sandy beach and chilling out with old friends. It’s what I would do, if I had the funds anyway! Good on you for deciding on the alternative. You’re absolutely spot on! When you’ve got the momentum going, you should absolutely run with it.

    PS Hope you don’t mind me pointing out something. You’ve got a little spelling error in your post :p It should be ‘The decision was whether (not weather) or not I should go to Thailand this month.” Just thought I should point that out 🙂

    1. Sean says:

      haha you weren’t the first person to point that out 🙂

      Just got it fixed!

  3. Nate says:


  4. I think you made a wise choice. Thailand will always be there, at least in the foreseeable future.
    If you have the impetus on a project you need to do it. It’s pretty easy to push a car that’s already rolling, “how can one guy push a 4000 lbs vehicle? It’s so easy!” But if that car is stopped and you have to get it going again…
    I can’t count high enough to recollect the number of projects I’ve started and not finished simply because they dragged a little at some point, or something shiny came along and distracted me.

  5. Andrew says:

    The decision was whether or not I should go to Thailand this month.

    Go ahead, I can hear the collective “are you kidding me?!? THAT was the hardest decision you had to make this year?”

    LOL, that’s what we call a “champagne problem” Sean 😉

    On a serious note though, kudos to you for having the discipline to continue with the forward momentum.

  6. Bob Buskirk says:

    Sean, I’ve had the same thing happen to me. You are building a business or waiting for a new site to launch and you have all of this excitement surrounding it. If you decide to leave it sort of ruins some of that. Good post!

  7. Cherie says:

    I totally get the decision, and we make similar ones often ourselves. One of the great things about creating a lifestyle like ours is that we have real choice in being where we want we be. And with choice, comes great responsibility.

  8. Nathan says:

    This is a pretty timely post for my wife and I as well. We live in Thailand (with our online businesses), and we’ve been travelling so much this year that we have also lost our momentum. My wife has to go speak in Malaysia in a few days, and she doesn’t want to leave, even though that used to be her dream!

  9. Bob Buskirk says:

    I know this feeling, when you are working really hard on a business or website and you are excited about it and have all of this motivation towards it. Going away, while would be amazing you would sort of lose that excitement towards your business.

    Great post

  10. Sean, you will be missed.

  11. Hey Sean,

    I’m a little confused. Maybe it’s just me. I thought the whole idea of your lifestyle business was having the ability to work from anywhere? I guess you’re saying that going to Thailand would be more play than work. Is it possible to dedicate enough time in Thailand to get your work done, i.e., have your cake and eat it too?

    Or are you saying that you need to stay put, find some solitude, and get your nose to the grindstone in Portland?

    Whatever you do, I know you’ll do it well. Blessings to you, friend!

    1. Sean says:

      No matter what I can always work from the road – however depending on the type of trip, I may have more or less time to devote to real creative work. It can be easy to maintain on the road, but when I’m working on high level marketing that is going to make a dramatic difference in my business, doing it on the go is more difficult.

      With this trip, there will be a lot of socializing, late nights, and moving around. None of which are conducive to the kind of work I feel I need to get done right now.

      If I were just going back to Bali for 2 months, then no problem. I’d be able to get into a routine and get a lot done – however in this case, the trip just didn’t lend itself well to the type of work I want to get done this month.

      1. Got it. I guess I was thinking this trip could be more “Bali-ish” where you could get away and get some work done too.

  12. I think it’s a sage decision. I wish I could go to the BKK meetup but it didn’t work with my 2012 goals…

    Am I right to think your decision wasn’t really about Thailand but more about the BKK meetup there?

    1. Sean says:

      Well depends on what you mean by that. The whole reason for going was the meetup yes, but that was the aspect that made it difficult to say no. I’ve spent a lot of time in Thailand, so I’m getting to the point where I’m excited to try out some new places.

  13. Awesome your life is so great Sean!

    How are you doing financially?


    1. Sean says:

      Doing just fine 🙂

  14. Ah man, bummed you won’t be here, I was getting all excited too thinking you were gonna say you were coming out for DC>BKK. We’ll miss you here buddy. Chiang Mai lives up to the hype, it’s one helluva place to live man, and Thailand misses you… but hope we run into you somewhere in the world soon. 😉

    1. Sean says:

      Yeah bummed as well. There are a LOT of people out there this week (yourself included) that I wanted to meet or re-catch up with. That being said, there will definitely be other trips!

  15. Joy says:

    Well. Truth is that as I read this article Mumford and Sons “I Will Wait” came on, synchronicity (as in Thailand will be there for you?).

    When you create from this momentum, an abundance of opportunities will come your way, including time in Thailand that you can enjoy with full presence, perhaps celebrating and creating a new wave of momentum 🙂

  16. Brent says:

    Yep, I know how you feel. Keeping up with the momentum is hard. When the gray rainy cold hits Portland like it did this week, it’s even harder. But you are right, the only one who knows what’s best for Sean is Sean. Always moving your dream forward is the master plan, always. Sometimes you can create momentum, but other times it’s a wave that hits you and you need to ride that sucker for as long as you can.

    If you wanna get lunch or a coffee and stay motivated, ping me.

    1. Sean says:

      I know exactly what you mean. And I actually didn’t mine the rain this weekend. It’s the next 30 weekends that have be worried haha. That’s why I usually take off somewhere around January. Right when it gets unbearable 🙂

  17. When people know you’re open, and looking for opportunity, they will find you.



    1. Sean says:

      Life has proven this to be true time and time again!

  18. Gary McElroy says:

    Hi Sean,

    Got to hear about you from Natalie, as I am doing the $100 change campaign. Which by the way is fantastic and really keeps me focused. I firmly believe that life is about decisions, good and bad, looks like you made a good one here plus you seem to have a great bunch of friends to support you. Nice to meet you virtually, Sean.

  19. David says:

    That’s true, maybe you’ll kill your momentum, but you’ll get new inspiration, new ideas, meet new people and learn about new opportunities. When I went first time to Thailand couple of years ago, I learnt what word freelancer means. After my last big travel to India I quit my job 🙂
    Still respect for choosing momentum. Cheers!

  20. Sam says:

    Hi Sean, just came across your blog for the first time. Thailand would be a hard one to pass up, I’ve been once and look forward to heading back there some time, but there are always trade offs unfortunately.

  21. Just to add a little gas to the fire.
    Your decision was smart. No doubt about it.
    What is happening now in Bangkok is off the hook. The amount of smarts, cool people, ideas and awesomeness per square foot is overwhelming. You pretty much missed the beginning of the revolution #dcbkk

    1. Sean says:

      Thanks for rubbing it in 🙂

      1. That’s what friends are for 😀

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