The Lifestyle Entrepreneur Blog

What’s stopping you achieving your goals?

Recently I watched a local family on the island Okinawa light one of those flying lanterns as the sun set. For a good 5 minutes they held on to the lantern as the flame warmed up the balloon that would eventually take it into the sky.

When the balloon finally reached the right temperature, they let go and, with cries of delight, the lantern soared into the night sky carrying with it their hopes and dreams far out into the East China Sea.

People often ask me “how do I do that?” when looking at my location independent lifestyle as a lifestyle entrepreneur.

Well, the first step is education. I recommend reading Tim Ferriss’ 4 Hour Workweek and Chris Guillebeau’s The $100 Startup as starters.

I wish they could have seen that lantern too. If they did they’d see that the lantern flies not by the power that carries it into space but by us letting go.

You made the commitment to go.

You designed a travel goal.

You decided the type of travel lifestyle you want.

In that sense, your lantern is ready to fly. You have all the power you need.

So what’s stopping you?

You’re holding on.

What comes next is a test of your ability to step outside your comfort zone.

Firing your boss, selling your car and traveling the world – that’s the easy part.

Taking the next step isn’t about finding out what to do – you have most of the skills and answers on board. What you need to do is to discover what’s stopping you.

Perhaps you are worried about what others will think.

Perhaps you are scared of leaving your comfort zone.

Perhaps your worries are financial.

Perhaps you are afraid you might fail.

And so on…

Here’s a few tips to help you avoid being consumed by the “what ifs” we often face in these situations:

You may be worried about what others think.

If the people around you aren’t fans of your plans, keep quiet about them. You can’t change your family or friends but you can forgive them. Don’t go round preaching and justifying your plans, nothing’s going to change except you’ll get frustrated. Save your energy for those who count, those who will re-energize you in the process.

You may be worried about things going wrong.

You could get sick, you could lose all your money, you could even lose your partner. Sure, all these things could happen. Think of all the things that went wrong in the last 12 months of your life: a hundred problems and a few crises thrown in for good measure. My point is that things go wrong whether you travel or stay at home. That’s the price of living.

Travel won’t relieve you of problems. You’ll have exactly the same amount of problems you did as when you started.

You may be worried about where to start.

There are a million things you can change and you can’t control about travel. Don’t focus on these things.

Instead, ask what can I do now?

You might not be able to find accommodation until you get there. But what can you do now?

You can save enough money to pay for 1 month’s rent. If you don’t have enough money, what can you do now? You can set up a regular payment of $50 a month from your bank account. If you can’t afford $50 a month, what can you do now? You can set up a second bank account for your travel fund so when you do have that $50, you are all ready to start saving. Don’t know how to set up a second bank account? Pick up the phone and speak to your bank right now. You might not have the money but you have the time to get started.

You’re worried about your daughter’s education in Hong Kong but you can’t inspect the schools while you’re living in the States. What can you do now?

You can get your daughter using the iTalki website and find a similar aged English-Chinese language partner for free. Your daughter is too busy studying for exams to learn Chinese, so what can you do now? You can get your daughter to sign up for the website so when she finishes her studies, she’s all ready to go. Even your daughter has 5 minutes to do that.

My point is, there is always something you can do right now to move forward in your travel plans.

There will never be a perfect time to start traveling. When we hold on to a perfect time or a perfect situation, our travel lantern never flies.

So, don’t wait for perfect because you’ll be waiting forever. Start moving now and fix things as you go on. Small things every day. And if you aren’t able to do what’s in front of you, break it down into something smaller. Keep breaking it down until it’s do-able right now.

It’s easier to steer a moving bicycle than a stationery one.

Write down on paper what your major barriers are.

For me, my major barriers were my son’s education and not being able to run the business while abroad. But thinking it through and doing my own research I realized these fears were unfounded. Travel was the best education I could give him. And with hindsight, we were right. Putting him into local schools in both Spain and Japan has instilled him with a boundary-less world-view that the 21st century will demand of the next generation of workers.

90% of the power of fear is that it goes unrecognized; fear operates at the level of the subconscious. Once you write it down and get it out into the open, however, it doesn’t look so scary after all. That’s the first step to addressing the things that hold you back.

The more I was able to define these fears the more I could deal with them until they didn’t stop me anymore. I found answers. I found resolutions.

The second part is breaking down your fears into actions you can start and finish today. Worried about money? Start calculating how much money you’ll need. Use my Guide to Location Independence for that. Not sure how you’ll make ends meet? Start a new income stream on the side. D

on’t know how to start a business?

Find someone who can and ask them for advice.

Don’t know someone?

Join a meetup or a forum. Join my Facebook Page to interact with likeminded entrepreneurs. There are always options.

Be the player, not the audience

In life be the traveler, not a tourist.

Be the player, not the audience.

Be in the game making it happen, not at the sidelines watching.

It’s so easy to sit on the sidelines and snipe at those who take a risk with their lives. These people want you to fail not because they dislike you but because it reconfirms their own convictions that doing nothing was the better option.

Tony Robbins started out running seminars. His first event was a complete failure. People said he should quit. Did he listen to the voice of the people on the sideline? Of course not.

I wonder what the people on the sidelines thought about Cassie De Pecol – the first woman to visit all countries in the world. I’m sure on the outside they were cheering her on but inside they were eating their hearts out.

Tourists come to see. They see everything but learn nothing. They come back with souvenirs not experiences. They eat what they eat back home and connect with nobody. Everything is planned, everything is scheduled.

The traveler, however, experiences, connects and makes mistakes. She faces the unknown and it’s in these gaps the magic of life happens.

Get off the fucking tour bus and get lost in the backstreets.

So what exactly do you do?

“What do you do?”

I face this question a lot as a lifestyle entrepreneur.

Networking events, friends, family. Then there’s immigration officials.

It would be easy to answer this question if I was a software engineer or a teacher.

Just fill “software engineer” in the box, stamp your visa card and walk on through.

That’s another story you tell yourself.

If you keep telling people you’re a software engineer, what happens when you lose your job? You lose your identity too. That’s like dying a social death. It’s so scary we do everything possible not to make it happen. So, we work crazy hours, suck up to boss people we hate and go with the flow, because… “I am a software engineer.”

Mine is a long story, but then that’s the price you pay when you choose to do different. You could live a much more interesting life but you have to face the furrowed brows when you answer the question, “what exactly do you do?” I have trouble explaining this to my dear mother some times.

Immigration officials often don’t like this approach. I tried it once at the Canadian border. The official looked at me like I was on drugs because he wanted a one word answer rather than a story.

“So, you travel a lot… visit companies… invest in these companies, eh? Like a manager? Look, it makes my and your life easier if I just write ‘manager’ in the box here.”

I nodded. Sometimes you have to know when to just smile and tell people what they want to hear.


But, I don’t report to anyone. I don’t manage anything or anybody. I outsource all my management to dedicated managers but nobody turns up at my desk every morning and asks “what would you like me to do today?”

In Robert Kiyosaki’s cashflow quadrant, I’m an investor / entrepreneur. I don’t trade my time for money anymore. But, that doesn’t make it easier for the average person who wants to put you in a box.

Honestly, what do I do?

Well, I travel, explore and write. I am an adventurer at heart. That is what I do. But, can you write “adventurer” on the immigration card? Sounds a bit cranky.

I make my money in real estate (thank you Rich Dad Poor Dad for getting me started on that journey and helping me become financially free by aged 40). So, I could also be a real estate investor. I invest in elsewhere too including precious metals and other businesses.

I write books. I also run a radio show. Two radio shows in fact. And, a venture business for mobile entrepreneurs.

I swim, bike and run a lot. I completed an Ironman once.

But I’m not a manager. That’s not my real story, easy as it is.

I don’t have a normal life, or a normal job with a normal title. I don’t commute to an office, take a salary or write email memos copied into 20 people.

Life is easier when you fit in a box, but easier is rarely better.

Next time someone asks, “what do you do?”, play with them a little.

Throw them a curve ball. Rather than nodding their heads, get them to say “seriously? ” Life’s absurd. It’s a game. Play it by your own rules.

Questions you should ask instead of “What do you do?”

Bianca Bass wrote an interesting article on Medium “23 questions to ask instead of ‘So…what do you do?’”

There’s a great question on that list, one to remember at the next meeting / party / networking event:

  1. What’s the best thing that happened to you this year?

You see, that’s so much more interesting than “So… what exactly does a digital marketing manager do?” Because the asker is obviously just being polite. Nobody is interested in this answer (not even Mom).