How to Actually Cross Things Off Your Bucket List in 2017

By Sean Ogle •  Updated: 10/25/16 •  12 min read

As I type these words I’m currently sitting on a Singapore Air Suites Class flight that retails for $10,455.

Yes, you read that price right.

Hold on one second, let me take a photo:

Singapore Airlines Suites Class

Not a bad office for the day.

Any moment now, my appetizer course is due to arrive which is made up of lobster, caviar, and is served with a side of Vodka.

When asked if I wanted Krug or Dom Perignon after boarding, I did what any sensible person would do: I asked for a glass of each. Then I washed it down with a glass of Blue Label.

Krug and Dom Perignon onboard Singapore Suites Class

At first I preferred the Krug, but as the flight went on found myself switching to the Dom.

And I still have 15 hours of fly time left.

Over the last 7 years the number of bucket list experiences I’ve ticked off has increasingly gone up.

Before this flight I had a personalized tour of the island of Islay in Scotland where I was treated to some of the most rare whiskey on Earth.

A private tasting at the Ardbeg Distillery on Islay.

A private tasting at the Ardbeg Distillery on Islay.

I played some of the most exclusive golf clubs in the world, and also played the most famous of them all, The Old Course at St. Andrews.

Swilcan Bridge at The Old Course.

Finally playing the most famous golf course in the world: The Old Course at St. Andrews

And now here I am on the most indulgent and lavish flight I could ever have imagined.

But why brag about this?

To make a point.

I’m no different than anyone else, but there’s one thing I’ve done repeatedly that has led to such amazing experiences, and that’s what we’re going to talk about in today’s post.

In this post you’re going to learn my biggest secret for actually accomplishing things on your bucket list in 2017, and other tips for showing you how to do more cool stuff in life.

How to Actually Cross Items Off Your Bucket List in 2017

About two months ago I realized I’d have to book a flight from Bangkok to Portland after traveling for a month on a round-the-world trip.

Naturally I started looking at my airline miles to see what the options were, and decided I wanted to try and do something, well, memorable.

A Suites Class flight on Singapore Air is one of the most sought after tickets in the world, and despite the astronomically high retail price ($10,455 to be exact), the experience can be downright affordable with the help of airline miles.

So I began telling people I wanted to take a Suites Class flight.

I talked all about the wonders of travel hacking, and how cool it would be to have your own little compartment with doors you could close.

I talked about it more than I probably should have, but by doing so it allowed me to do one very important thing: actually book the ticket.

And that’s the secret.

The more I talk about and joke about the big things I want to do, the more they actually come true.

Getting Custom Wedding Suits Made in Vietnam

For two years my wife Tate and I joked about what a cool story it would be if we flew to Saigon to get custom suits made for my groomsmen for our wedding.

18 months later I’m flying from Orlando to Hong Kong to meet her on a work trip before proceeding to Vietnam for a week.

Final price? Less than $100 a suit.

Getting custom suits made in Ho Chi Minh City, Vietnam

Getting fitted for my wedding suit in Vietnam

Playing the World’s Best Golf Courses

A couple years ago, I started telling people I wanted to play the top 100 golf courses in the world, and at the time I’d played exactly…zero.

But I talked about it a lot. One trip led to another trip, followed by invitations from people all over the world that wanted to help me on my journey.

I’m now a third of the way to my goal.

The 8th hole at Merion Golf Club

Giving a tour of where you shouldn’t be at Merion Golf Club: the #11 course in the world.

This hasn’t just been a recent thing either.

Quitting My Job and Moving to Thailand

Back in 2009 I started a website where I basically told everyone for months that I wanted to leave my job and travel – even though I had no earthly idea how I’d work up the balls to do it.

8 months later I was on a flight bound for Bangkok.

Just got back and look at the archives from May-September of 2009. I was clueless, but I kept saying I wanted to make a change. Then I finally did.

For more on this, read Chapter 3 in The Art of Non-Conformity. And here are a few more bucket list books that can help get you started.

Ryan Martin and Sean Ogle swimming in Thailand

My friend Ryan and I in Krabi, Thailand about a week after I arrived in Thailand.

Smoking Cigars in Cuba

Back while I was in my day job I made a bucket list goal of wanting to go to Cuba before the embargo was lifted and smoke a cigar.

This one I truly thought would never happen.

After planning a trip to Mexico three years later, I told a couple of the guys I was going with I thought it’d be cool to go to Cuba. A day later Clay was looking up flights and insisting we make it happen.

Then it did.

Derek and I with our buddy Clay at Hotel Ambos Mundos in Havana, Cuba.

Derek and I with our buddy Clay at Hotel Ambos Mundos in Havana, Cuba.

Why This Bucket List Strategy Works

Ok, that was a nice trip down memory lane for me, but why exactly does this work?

In each case, I firmly believe the reason that things actually came together was just because I talked (a lot) about doing them.

I’ve found that the more I talk about something, even if it begins as a joke, like our suits in Vietnam idea, the more it slowly gets engrained in your head that it could be real.

It’s kind of like in Napoleon Hill’s “Think and Grow Rich,” where he tells you to say words of affirmation in the mirror everyday like “I will be wealthy” , without being quite as deliberate, and well, weird about it.

I think my dad thought I was crazy when I first mentioned the Suites class ticket, and he rolled his eyes a bit like it would never happen.

I just called him from The Private Room in SIN while drinking a Blanc Des Millienaires 1995, to let him know I was about to board.

The brain is a powerful thing, and the more you talk about something, the more it will subconsciously look for opportunities to help you make your outlandish ideas a reality.

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Other Tips for Crossing Off Bucket List Items

While I firmly believe the absolute best way to continually have once in a lifetime experiences in your life is to tell people about your plans, no matter how crazy they may seem, there’s a number of other things I’ve done that have helped make so many of these crazy stories a reality.

Let’s look at a few of them.

1) Create Your Bucket List. Duh.

Here’s the thing, if you don’t have ideas of what you want to do in life, you’re probably not going to do much.

Or you may have a passing idea, but if you don’t document what that is, there’s a good chance you’ll put it off and forget all about it.

The very first step I took towards having this lifestyle was to create my own bucket list.

I wrote down all of the stuff I wanted to do in life (which is a constantly evolving list), and then I made it public to hold myself accountable.

Here are some additional strategies for creating a bucket list that you’ll actually accomplish:

2) Look for Hacks and Remember Experiences Don’t Have to Be Expensive

Often the most outlandish (and expensive) ideas can actually be accomplished for less money than you might think.

Take this flight for instance, here’s exactly how I was able to book a Singapore Suites Class flight.

  1. Sign up for Chase Sapphire Reserve to get 100k point bonus
  2. Spend $5,000 in the first 3 months. (If this seems difficult, it’s actually much easier than you might think with a few strategies) Note: I actually used Amex Platinum points for this particular redemption, but the Sapphire gives you more flexible points and a more widely available bonus
  3. Signup for a Singapore Air Krisflyer Account
  4. Transfer the Miles to your account.
  5. Select the redemption you would like to make, and waitlist yourself if necessary. I had to add my itinerary to the waitlist, and 2 days later I was told It was confirmed.

If people want more details on exactly how to do this, I can write another post about it. Let me know in the comments.

But there are all kinds of hacks you can do depending on what your goals are.

For instance, starting Breaking Eighty my golf brand has:

My top 100 quest would be much more difficult (and expensive) without it.

Sidenote: I’ve never had such attentive and friendly service in my life. The flight attendant just insisted she take my photo in just about every imaginable spot on the plane. You could tell, she’s done this before.

Working on a laptop in Singapore Air Suites Class

Writing this post at 37,000 feet.

3) Start a Lifestyle Business

Do you think if I were still working 50 hour weeks in finance I’d have the freedom and the flexibility to have all of these experiences?

Maybe, but it’d be much more difficult.

If it weren’t for building my business and this website, I’d most likely only have been able to do a small fraction of the things I’ve done in the last 7 years.

It’s opened doors in a similar way to Breaking Eighty, just take this trip to Jordan as an example.

But, by allowing myself the ability to work anytime and from anywhere, I’m able to leverage opportunities on a more regular basis.

If you’ve never considered starting a lifestyle business, or just haven’t been entirely sure how to go about it, then I highly recommend you check out “The Complete Beginner’s Guide to Starting a Lifestyle Business.”

4) Change your Mindset

Next to simply saying you’re going to do something, this might be the most important of all.

I’ve always been a glass half full person.

If there’s a problem, even if I don’t fix it myself, I do my best to not blame other people for the issue.

If something is really wrong, it’s my job alone to take responsibility for it, and get it fixed.

Often you see other people take more of a victim mindset where it’s always someone else’s fault, and rather than taking responsibility they place blame.

By shifting your mindset to one of embracing challenge and uncertainty, you’ll cultivate a habit of taking more action and getting more done.

And if you really want to start having more once in a lifetime experiences, that is exactly what you’ll have to do.

I’d recommend checking out Mindset: The New Psychology of Success.

5) Set Goals and a Timeline

This is something that so often gets overlooked. When I first created my bucket list, I had a goal of crossing off on average of one thing a month. I have similar goal, of at least 12 golf courses a year.

Think about a timeline that is reasonable, yet is also uncomfortable enough to get you to take action.

Bucket List: Accomplished

I recognize that this lifestyle I have is a privilege. It’s something I’ve worked hard to achieve, but it’s also something than can disappear in the blink of an eye, so I do my best not to take it for granted.

But it’s also not as unattainable as people so often think. Just ask the hundreds of people inside Location Rebel Academy who have made it happen.

Sure I had the gene pool on my side when I was born as a white American male into a middle class family.

But it’s not like I grew up with tons of money, connections or skills.

I’ve cultivated every aspect of my life and business, and I’ve seen just how much change is possible in even 12 months time.

So now I want to ask you a question.

What’s the one big thing you’ve been wanting to do? What do you constantly think about, but never talk about?

Well, let’s start having the conversation. Today, right now, choose one big outlandish thing that you’ve always wanted to do, and start thinking about how you’re going to do it.

Let me know what that is in the comments.

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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