What Would It Look Like If…

What would it look like if…

…I ran a marathon even though I’ve never done it before?

I moved to a tropical island for two months?

…I built a business that has the potential to help thousands of people?

…I golfed all of the top 100 courses in the country – in a year?

There’s one thing that sets successful lifestyle entrepreneurs apart between most other people:

Their ability to imagine something most people would say is impossible.

What Would It Look Like If…

This is quite possibly the biggest mental reframe I’ve ever made in my life.

Before I was running an online  business and traveling all the time, I used to spend a lot of time daydreaming.

I’d pretend that I was running down a beach as opposed to the bike path in Portland.

I’d imagine that I was playing a round of golf in Bali as opposed to the local muni course.

I’d imagine that I was working on a business that really inspired me, rather than just making someone else rich.

The problem with all of those things was that for a long time I never actually thought that my daydreams could be reality.

It wasn’t until I got a random email from Dan Andrews telling me to apply for the Tropical MBA that I realized maybe there was something to this after all.

I put myself in a good position to make things happen, but at the time, I didn’t have any clue what I was preparing myself for.  Even today, I’m not entirely sure what’s going to be next.

However in that first 6 months of living in Thailand I made a profound switch.  Instead of thinking “that’d be cool” I started saying “what would it look like if?”

Why This Is So Important

You may be thinking, “yeah, yeah, big deal.”

But it is a big deal.

If you don’t have the ability to imagine something incredible that doesn’t currently exist, or the ability to imagine a life that you’re not yet living, you’re never going to achieve those things that truly excite you.

Most people thought people like Steve Jobs and Bill Gates were crazy. How about Alexander Graham Bell? The Wright Brothers?

For most of the things that we use on a daily basis and take for granted, there was someone behind it who people deemed crazy.

In my case I’m not inventing something that’s going to change the face of humanity as we know it. However, I have created things that have made a huge difference in the lives of many people – not the least of which is my own.

Once you believe anything is possible, you begin looking for ways to achieve it.  Once you achieve a small goal it gets easier and easier to achieve a larger goal. Before you know it, you’re not only doing all the things you thought you had to wait until retirement for, but you’re getting paid to do it in the process.

What have you always wanted to do? What have you believed would be impossible and therefore haven’t even thought about pursuing?

Do me a favor. Today, ask yourself one question:

“What would it look like if?”

Go down the rabbit hole. See how far it takes you. You may be pretty happy where you end up.

Sarah Russell April 15, 2013 at 6:25 am

I love this – the idea of asking “what if” is so much more powerful than most people realize, because it totally changes your perspective. Instead of automatically assuming that something is impossible or out of reach, asking what it would look like forces you to seek out actual information (rather than assumptions).

So many seemingly-difficult things in life are much easier to do than most people realize, but they won’t ever make this leap if they aren’t first able to envision themselves in the scenarios they desire 🙂


Sean April 15, 2013 at 6:31 am

Couldn’t agree more. I’ve found just by asking, something most people never do, you’d be amazed at just how much is possible.


Scott Nelson April 18, 2013 at 7:23 am

I too have adopted this mindset. My current mantra is “wouldn’t it be cool if”. In my (current) experience, this comes with one caveat; like many goals and anything worth having, they usually involve sacrifice. Currently my two ‘wouldn’t it be cool ifs’ are; wouldn’t it be cool if I ran a marathon sub 4hrs and wouldn’t it be cool if I could make a living off my websites. Now yes, both of these would be cool(!), but the physical and mental sacrifice is exhausting. So I guess my main point is, choose your goals wisely!


Monique April 15, 2013 at 6:39 am

You’re amazing, and you inspire me MORE every single time you write a post. I’m going down that rabbit hole, and I’ll let you know what I find!


Katie Jane April 15, 2013 at 7:23 am

Yes to this. When you start asking “what if” it will literally change your life. There’s an entire conference – What If Conference – dedicated to this idea, which I attended earlier this year. It completely altered my worldview. It’s such a simple concept… “what if…” but it opens up an entire universe.


Siegfried April 15, 2013 at 8:03 am

Hi Sean!
Thanks for posts like this, they really help when I get tired of online struggle 😉
Best Regards!


Matthew Riley April 15, 2013 at 10:49 am

I too got by with daydreaming for a long time and removing myself from reality. You never think it is possible because you just make excuses. This year alone I have knocked tow things off my bucket list (traveled internationally, and drove across the country). Things I only daydreamed about before.

The sense of actual accomplishment is far better then the artificial enjoyment you get from daydreaming.

Yesterday went out and hit a bucket of balls at the driving range for the first time in years (going over again today) and this morning started my day off with fishing. That’s two personal enjoyments in two days, most people don’t get to do two things in a month for themselves. Great post! BTW hope you had a great time at the Masters.


Caelan Huntress April 16, 2013 at 9:16 am

This mindset is essential in the fight against stagnation and mediocrity.


Sarah Li Cain April 22, 2013 at 12:29 am

I love this post. I don’t think I would be where I am now if I didn’t ask those questions. I think that people are too scared to ask themselves “what if”, sometimes because they don’t believe in themselves enough, or sadly, some are scared of success.


Chas April 23, 2013 at 8:51 pm

Thank you for that. Feed your head.


FERNANDO June 15, 2013 at 12:54 pm

The start of this post gives the dreamer that it’s possible to achieve the lifestyle they dream. Great to hear about Bali, my best place I loved to the 30 days I spent. The Kuta beach and the 10 days there are some the most epic times of life.

Great to see your sharing your Asian exotic travels Sean. Loved your YouTube video where you show how to stay for free in a luxury Vila in Bali.

Just asked the question and myself and my girlfriend while she’s designing an eBook which I wrote for the FERNANOD BIZ readers.

Always great to have a good read Location 180 in the weekend.


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