5 Inspiring Lifestyle Entrepreneurs to Follow

If you’re into lifestyle design and business, you must be following some lifestyle entrepreneurs for inspiration, learning from their mistakes, and reminding yourself it’s possible no matter how long it takes. If they can make it, so can you!

That lifestyle of freedom, travel, passive income and personal growth that you crave so much is available to you. And there are plenty of lifestyle designers who’ve shared the steps, mistakes, lessons and challenges on the way. Below, you’ll see 5 of my favorite ones.

Lifestyle Entrepreneurs to Follow

1. Sean Ogle of Location Rebel

Sean Ogle was an average person back in 2009 who admitted his life sucked. He knew university didn’t prepare him for real life and show him how to become successful, his job after that was a dreading experience with the long hours.

He wanted to live a completely different lifestyle so he did what he felt was right – quit his job, started his site Location Rebel to hold himself accountable, published his bucket list and started working on it, moved to Thailand and built a business.

In a few months he was making enough to have the lifestyle he had always dreamt about – to do whatever he wants, whenever he wants.

He’s lived on a tropical island, ran a marathon, climbed a mountain and much more.

Now his blog is all about helping others achieve the same. He shows people how to build a business they can run from anywhere and live their legend by doing whatever makes them happy.

Amazing, right?

And with today’s online opportunities, you can educate yourself to such an extent that you can be making a small income as a side project very soon.

There’s more to being a lifestyle entrepreneur.

You don’t really need to be that adventurous and have a bucket list like Sean, you can just live on the beach, feel good and work hard.

Digital nomadism goes together with living in a cheap country as a start – that’s why you won’t see someone who wants to become location independent move to Dubai. You’ll hear about places like Thailand, Bali, Vietnam, Philippines, etc. They are beautiful and exotic enough for you to completely change your way of thinking and approach to life and refind yourself.

2. Dan and Ian from TropicalMBA

Next on the list of lifestyle entrepreneurs to follow are Dan and Ian from TropicalMBA.

TropicalMBA is a super useful blog, podcast and community for those who are doing business at one of the places I mentioned above, or any other actually. It’s for creative individuals, entrepreneurs, hard working passionate lifestyle designers looking forward to form relationships with like-minded people.

The guys from TropicalMBA write and talk about the best places to live in, what to do there, how to handle your business, how to manage employees and work with virtual assistants, how to scale, come up with ideas and all you need to know about location independence.

But there’s one thing they think is a must – the desire to work more than the average person in order to achieve all that.

Many people have the misconception that the nomadic lifestyle means traveling all the time just sightseeing and communicating with the locals, or living near the ocean and actually sunbathing all the time.

That’s not true.

In fact, you always have the chance to do all that as you’re the one controlling your time. But it’s just that you choose to keep working on the stuff that got you there in the first place, simply because you’re a hustler and can’t just leave the business, even if it’s mostly passive income.

Here’s what Dan says about the actual amount of work such freedom requires:

“Many people I meet underestimate the incredible amount of effort required to get a business off the ground. If you aren’t clear on the effort required, me quoting you a figure would probably make you uncomfortable…

There are a million factors that stand between you and what you want. How much loot you have, where you were born, how good you are at Photoshop, how smart you are, what kind of family you grew up in.

The good news is that there is only one that you can do anything about:


Let people bicker about how much work is really required.

Let them gossip about how much work so and so *really* does versus what they say they do.

Let people sit around and run the odds. “If I do x work, what are my chances…” “Is it really possible to work 4 hours a week?” (BTW, of course it’s possible!)

Let them scoff. Let them “discuss.”

You’ll be busy.

If you aren’t where you want to be, for whatever reason, you are in the fantastic position of only having one question to answer.

How hard are you willing to work to get there?

3. Mish and Rob from Making It Anywhere

The 5 Types of Freedom a Business Can Give You

Mish and Rob are this sweet couple that left their jobs in London and have since then lived in 16 cities across 3 continents. On their blog Making It Anywhere they talk about every aspect of the location independent lifestyle and running a business from anywhere in the world making more money than in an ordinary job.

They do brand consultancy, copywriting, launched a property management company and publish books.

Personally, I’ve learnt a lot from them.

Here’s what they say about all the people out there who are concerned that you should be able to code or create softwares and apps in order to live anywhere in the world and make a lot of money:

“A few years ago you might have needed to be a programmer or designer to have this sort of lifestyle, but not anymore.

Not only does technology now make almost anything possible, but people are increasingly comfortable buying services from those they’ve never met. If an accountant is the best at what she does, who cares if she’s in Iowa, Ipswich or India?

We know people living this lifestyle who are recruitment consultants, psychiatrists, finance brokers, language teachers and startup CEOs… and yes, OK, we know a fair few programmers too.”

4. Clayton from Spartan Traveler

Clayton of Spartan Traveler has been traveling full-time since 2011 and for him that’s a dream he made a reality, which consists of first defining all the elements that create a satisfying life and then combining them into a system that works. 

He’s not focused on money or property, and doesn’t think success is connected to them either. He then became a lifestyle entrepreneur and joined a community of others like him.

He discovered something interesting – it was all easier and cheaper than he expected. Living the dream actually costs much less money that our current lifestyle, in terms of time and expenses. 

That’s what his blog is all about – living life on your own terms, doing more with less and not taking things too seriously so that you can enjoy this life at the same time.

5. Chris Guillebeau

Chris Guillebeau has visited every country in the world over the past 10 years while writing books and blogging.

The essence of his philosophy is this:

You don’t have to live your life the way other people expect;

You can do good things for yourself and help other people at the same time;

If you don’t decide for yourself what you want to get out of life, someone else will end up deciding for you;

There is usually more than one way to accomplish something.

He’s a strategist, a believer and one of the successful lifestyle entrepreneurs. On the blog he writes about personal development, entrepreneurship, doing unconventional work, and traveling.

There are many, many stories about such people you can find out on the Web.

Many include struggles, but I haven’t really found one who didn’t eventually succeed in becoming free from mediocrity and actually leaving home and traveling to whatever point in the world he feels like visiting.

But in most cases, it takes years. There won’t really be anyone in your surroundings to support you as they just don’t have the same goal and may even consider you crazy for wanting to escape such a comfortable life.

But if you develop a powerful mindset with a definite desire and a vision of you doing what you love while on the beach in Bali, for example, you’ll make it.

So I hope you enjoyed this list of lifestyle entrepreneurs worth following. Any other recommendations?