“Screw it, Why Not?” – The Next Big Adventure

By Sean Ogle •  Updated: 09/04/13 •  6 min read

“What would it look like if I moved to Thailand for 7 months?”

“I’ve always wanted to live on a tropical island, Bali looks great!

“7 countries in 4 weeks? Cool!”

Over the last few years I’ve had some freaking sweet adventures. It usually begins with a basic idea and then makes the following progression:

Every big idea or grand adventure you come up with is totally doable – the biggest problem is most people simply don’t do it.

How many things have you said you were going to do at some point? How many of those have you circled back around and actually done?


I have a lot of big ideas, but like most other people, there are times where I fall into the trap of thinking, oh that’s not possible, or that’s too much work.

I was thinking about this recently, and you know what happened?

I finally said: “screw it, why not?”

The Next Big Adventure

As many of you know, I started a golf website a few months back.  So far, it’s gone even better than I’d hoped.  The main goal of the site was threefold:

When I launched the site I had the original goal of playing the Top 100 Public Courses in the US.  However, for as much as I want to do that, I really want to play the Top 100 Courses.

Two separate lists, and the vast majority of the Top 100 are private – hence the separate lists.

So I said, screw it, cool, I’ll just do both.

I’ve made some progress. Since March I’ve played 5 of the Top 100 Public and 1 of the Top 100.

Not bad, but frankly anyone can do that. I’ve put together some great write-ups, taken some great photos, but there’s nothing that exciting.

If I’m serious about this goal, then I’ve got some serious work to do.

So this got me thinking. How can I cross off as many of these courses as possible in a short period of time? How can I do this in a way that’s interesting to my readers, and potentially benefits the courses I’ll be playing?

What about a golf road trip?

I started thinking about this. I know so many golfers who have said they want to do this – yet no one I could find has actually done it (or at least they haven’t documented it very well).

I mean how hard can it be, you hop in a car, and go play golf!

The more I thought about this, the more I liked the idea – but I still wasn’t sure where I’d go.

So I started looking at where the courses were.  I found this map from Golf.com.  I’m personally going off the Golf Digest lists, but this got me pretty close.  There were two areas that stood out: The Southeast and the Great Lakes Area.

I’d already been to the Southeast this year – and hey, I’ve never been to Wisconsin or Michigan…Hmmmm.

Between the two lists there are around 20 courses that would be on my potential path.

What if I went and played all of them over a 2(ish) week period? 16 days, 16+ rounds of golf, 1 trip.

That sounds exhausting. And awesome.

Screw it, why not?

I knew I wanted to do something in September/October.  The original plan was to use 65k Ultimate Rewards points to fly from the US to Germany, use my stopover and spend 10 days at Oktoberfest, then fly on via the same ticket to Bangkok to go to a conference and see some old friends.

For as exciting as this was, for some reason I kept coming back to the golf idea.

People would ask about my fall business/travel plans and I’d tell them: Well it’s looking like either Germany and Thailand or Wisconsin and Michigan.

You can imagine the weird looks I got when I told them which one I’d decided on…

But for me, if I’m looking back on this 20 years from now, the whole roadtrip thing just sounds awesome. Every golfer has thought about it at one point, so why not be the guy to do it.

How Can You Follow Along?

First if you want the full details of the trip including my schedule and full course list, you can see all of that here.

My goal is to make this just as interesting to follow along as it is to do it – even if you don’t like golf.

I’ll be shooting a daily video blog about my experience on the road, what’s like to play so much golf, and don’t worry, we’ll be mixing in some good lifestyle business videos in there as well.

If you just want a few of the business videos, then subscribe to the Location 180 You Tube Channel.

However if you want all the daily updates, all the stories, and all the fun, then check out our new Breaking Eighty You Tube Channel. I decided to create separate channels, because let’s face it, a lot of you could really care less about golf.  That said, the goal is to make both channels interesting to my readers, so I’d love it if you subscribed to both.

You can get photos from the trip on the Breaking Eighty Facebook page, and all of the in depth reviews will be posted on our site over the weeks during and after the trip.

What Does This Mean for You? 

If there’s one thing I hope you get out of this, it’s that you should stop putting off all the stuff you want to do.  Why not find a way to do it now? Get creative, start a business, make yourself uncomfortable, do whatever you have to do in order to start living your life on your terms.

Sure it may be odd for someone who writes about being a digital nomad and location independent entrepreneur to be so in to golf – but hey, that’s my thing! I built this business and blog to allow me to enjoy my life more and help others do the same, so if there’s anything I can do to help push you over the edge, don’t hesitate to reach out.

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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