How to Achieve Long Term Success as a Lifestyle Entrepreneur

By Sean Ogle •  Updated: 02/14/17 •  11 min read

I’m coming up on my EIGHT year anniversary of starting this blog.

Do you know how old that makes me feel?

Facebook memories of my time living in Thailand have been popping up on my newsfeed saying, “this was seven years ago”.

Mind blown.

It truly does not feel like that long ago.

Ryan Martin and Sean Ogle swimming in Thailand

SEVEN years ago?!

Yet, I think back to all of the wonderful stories and memories I’ve created since then, and the amazing success stories that have come out of Location Rebel Academy, and well, I guess yeah it’s been a long time.

I woke up this morning in a state of reflection, and more than anything one of gratitude (I promise, that’s about as woo woo, as I’ll get).

But I wasn’t just grateful of the life I have, but everything (and everyone) that has helped me get here as well.

Because let’s face it, while the steps to build a legitimate lifestyle business aren’t overly difficult, putting them all together, sticking with it through the down periods, and having faith in yourself can be a really difficult thing.

So after eight years, how do still have the freedom to live this lifestyle, where so many others haven’t had as much success or have moved on to other interests?

I hope to answer that with this post.

There are a few counterintuitive things I’ve learned that I think will be beneficial to those both starting out, as well as those who have had some success who simply need a reminder for how to keep this lifestyle going.

So let’s jump into it, here are the 10, ahem, 11, things I think everyone should do in order to sustain longevity as a lifestyle entrepreneur.

1) Take your ego out of it

Recently I was invited to attend a really special conference. It’s for a very limited number of people, and the people I knew who went last year are some of my most successful friends, and they all raved about it.

So when I got the invite, and was referred by another successful friend, I felt like I had no choice but to go.

It cost $5,000.

I’m not the best in investing in myself and spending big sums on coaching, conferences etc.

And while I certainly have the money, and I do believe I would have gotten value out of it, I came to the realization that my primary reason for wanting to go was to satisfy my ego.

I wanted to be included in that group of successful people so much that I was willing to pay just to make myself feel good (ok, not just for that reason, but it was a driving factor).

By realizing this, I was able to take a step back, and invest that money in something that I think will be more directly beneficial to what need.

Part of the secret of longevity is “you do you.” Don’t focus on other people and what they’re doing. Focus on what will grow your business, what makes you happy, and don’t let your ego run the show.

2) Write daily

This might be the most important piece of advice on this list.

Just about everything I do in my business is some form of content creation. The more I write, the more content gets put out, the greater the chance to reach someone and have an impact on their life.

The vast majority of all we do online is written, so sharpening that skill, and also simply using it as an outlet for your thoughts is incredibly valuable.

Lately, I’ve gotten out of this habit – and I’ve felt it. Not necessarily monetarily, but I haven’t felt as clear on my direction or focus. Writing helps me get there.

This post will help you cultivate a daily writing habit.

3) Double down on what’s working

These next three all go hand in hand, and contradict each other a bit, but keep reading..

In 2012 I made the decision to stop focusing on additional products, and just focus on the one thing that was working best, Location Rebel Academy.

It was the best decision I’ve ever made in my business.

It allowed me to stay focused on the thing I knew I could teach best, give attention to the one thing that had the most income potential, and it freed up headspace to be able to make time for more of the things I enjoy doing in life (like travel).

When I did this I immediately grew our membership with in LRA and our success stories saw a boost as well.

So rather than trying to monetize in 10 different ways, focus on the one that is working best.

4) Remember, what got you here, won’t get you there.

I know that’s a book title (one I haven’t actually read yet), but it’s an important message.

I doubled down in 2012, and it was the best decision I could have made.

In 2016, I knew in order to continue to grow the site, I had to remember what got me here, won’t get me there.

Specifically the Location 180 and brand, had become confusing for people with the strength that Location Rebel had gained.

So we merged them into one.

On top of that, our audience had grown to the point where I couldn’t ignore the fact that we had quite a few people who Location Rebel Academy, wasn’t a perfect fit for – so we rolled out a handful of other products to help serve them better.

We’re still focused primarily on the Academy, but for others that need help with writing emails, overcoming fear, or just want the basics of this whole lifestyle – we now have stuff for them.

It was a tough decision to implement those changes, but 6 months later, it’s already clear it was the right choice.

5) Start new things. Slowly.

Ok, so double down on what works, when it makes sense.

Then remember, that once you do that, things will still need to evolve.

One last bit of advice in that vein is to start new things slowly.

Once you have one business or brand chugging along, you might be compelled to start something else.

That’s great – but do so slowly.

I started Breaking Eighty in early 2013. I wrote once or twice a month and took a couple golf trips a year to take photos and generate content for the site.

I didn’t worry about monetizing it at all for the first year or two.

I built the brand slowly.

That allowed me to not lose focus on Location Rebel, which is most important, but it also allowed me to build my reputation and build trust with that audience.

You don’t necessarily need to wait as long as I did to try to monetize (years), but remember, for most people niche sites, brands, audiences, whatever you want to call them, are not built over night. So don’t try and build it over night.

6) Get a #2 as soon as possible

I often tell people there is nothing solo about being a solopreneur.

You need a community of people you can lean on for help and who can support you during both the highs and the lows.

That’s what Location Rebel Academy provides.

But the same is true for people once they have a successful business.

LR member Mike, Liz, myself, and my adorable wife Tate.

LR member Mike, Liz, myself, and my adorable wife Tate.

I’ve been working with Liz Froment since 2012. She is my right hand girl, knows the community even better than I do, and is what allows me to stay sane and continue doing this.

When you’re working on your own, frankly, it can get lonely. Yes, the freedom is great, but often my days are spent in sweats moving my laptop from one room in the house to another.

Liz helps me vent, helps work on aspects of the business I don’t have the time for, and has become a great friend.

Here’s more about her.

7) Be as accessible as possible

Part of what sets what I do apart from others is that I spend half my working time answering emails from people in our community.

I do my very best to be as accessible as humanly posssible. Not only does that allow me to build more real relationships with people in our community, but it also builds trust, and inevitably the business grows because of it.

These days since so many are coming in, I’m not able to respond to some emails as quickly as I would like – but I still do my best to respond to every single one.

I think the best thing you can do to grow your business from 0 to $100k a year, is encourage interaction every single step of the way. Ask your readers to respond with answers to questions, give them thoughtful feedback, hop on Skype if asked etc.

It takes time, and you can’t be quite that open with your time forever, but for businesses doing under $250k a year, I think it’s one of the most overlooked ways to grow.

8) Play deliberately

I truly believe this is one of the biggest secrets to my success.

It can be so easy to sit down and spend 10 hours at a computer, while essentially just pretending to work.

Maybe you get 3-4 hours of real work done in that time.

But then for those extra six you leave feeling exhausted and don’t have anything to show for it.

Rather than wasting those times in front of my computer, I try and recognize when I’m no longer being productive, and I go deliberately do something fun.

Usually it’s golf:

Other times it might just be going for a walk, or even playing a video game.

But as long as whatever fun activity I’m doing is deliberate it makes going back to work that much easier later on.

Whenever possible I still try and wake up at 6am, and stop working at noon.

9) Not everything has to be passive

I get it, passive income is the holy grail – and once you get a little bit of it, it can be easy to become complacent.

Your niche sites are bringing in a few grand a month, you’re traveling the world and loving your life.

But I still remember being in the middle of nowhere in Yangshuo, China when I got an email on my dial up connection from a business partner telling us all of the traffic for our HDR photography site had disappeared.

Overnight $3k/month in passive income went down to $300.

You never know when that might happen.

By diversifying your passive income with freelance jobs or more active income, you’re able to protect yourself in the event something bad happens.

It may not be as sexy as being fully passive, but when things go sideways? You’ll be glad you’ve got a client or two to fall back on.

10) Niche down. Then niche down even more.

The internet is a big place. There are literally tens of thousands of people trying to do exactly what you’re trying to do – no matter what it is.

So the more you niche down, the more successful you’re going to be. Even if you feel like you’re alienating a lot of people, what you’re really doing is making it even more of a no brainer for your target market to get on board.

With my new golf project, I started something called The Eighty Club.

It’s a golf society for members of private clubs across the United States.

Take my entire audience at Breaking Eighty.

Probably 15% of them are members of private clubs.

Then only a portion of those people are interested in potentially hosting strangers on their course.

Fewer still travel on a regular basis.

And then even fewer of them like to communicate in online forums.

So in the end, I’ve created a community that is probably only a good fit for 1-2% of my audience.

But for that 1-2%? It’s a perfect fit, and one that doesn’t take much in the way of selling.

How can you take a market and niche down, and then niche down again, to make it a total no brainer for that target market?

11) BONUS: Never take what you have for granted

I’ll be the first person to admit it, this lifestyle is a privilege – not a right. Not many people have the ability to do whatever they want, whenever they want.

And as soon as you start to take that for granted, it can all start to slip away.

Take a few minutes every day to be grateful for what you have – that goes for all things in life and regardless of what phase your business is in.

Sure I might “play” more than the average person, but I don’t do that to the detriment of the work that got me here in the first place.

Check out this infographic of all the tips in one easy to digest form from Julie at Nest Egg Chick:

Location-Rebel-Long-Term-Success (1)

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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9 comments on "How to Achieve Long Term Success as a Lifestyle Entrepreneur"

  1. I like your article Sean Thanks!

  2. Michael L. Preiss says:

    Excellent article, Sean! Thanks so much for sharing it.

  3. Luke Thomson says:

    Really inspirational article Sean, it’s really good to keep motivation high!!

  4. linda says:

    Good article Sean, I felt the one of writing daily is the back bone.Thank you

  5. Great Article Sean!
    Helps us stay motivated on this difficult journey! There are many ups and downs, and I believe having some off time is totally crucial for success (and sanity :P)
    Hugs from Greece

  6. Dakota says:

    Congrats on eight years! That is no small accomplishment. I’ll second a few of those – doubling down on what’s working, hiring as SOON as you can, and deliberate play.

    Here’s to eight more years of designing an awesome life. Speaking of that, let’s ski Bachelor before this amazing winter is over!

  7. Alpa Pandya says:

    Happy belated blog anniversary! 🙂

    I agree that a lavish lifestyle is a privilege.
    But then… life is about choices. It’s about how we want to spend our days. So by deciding what we want to be, to do and to have we can make steps toward our ideal lifestyle.

  8. Phil says:

    First article I read and I gotta say I agree with everything you said! Keep it up, I will be joining your ranks soon enough!

  9. Sean, your 10 (or 11) tips on how to be a lifestyle entrepreneur were really good. When I first started reading it I wasn’t so sure, but after just one or two I was really impressed. I ran a small (83 person) hands-on software development company for almost 30 years, and after selling it I’m now a freelance consultant to small start-up business owners. I’m learning how to be a lifestyle entrepreneur at the same time I’m advising them on how to successfully do a start-up. Thanks for your tips.

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