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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