The Lifestyle Expansion Dilemma (And Why it Matters to You)

By Sean Ogle •  Updated: 06/30/14 •  9 min read

Starting a lifestyle business and earning income on your own is easy.

Seriously, it’s not complicated. It’s work, but it’s not difficult work.

One of the biggest shocks to me since beginning to see some a modicum of success, has been the difficulties that come after you have some income flowing in.

I tell people early on, don’t even think about what you want to do.

If you really want a lifestyle like this, screw your passion. I don’t care about that. I don’t care about taking all of your interests and merging it into one perfect, everything is unicorns and rainbows type of business (at first).

I only care about one thing when your getting going: generating income.

Once you can generate a little bit of income, you start to generate confidence.

Income and confidence are all you need to be successful with a lifestyle business.

This article isn’t about that though. (Check this out, if that’s what you’re looking for).

No, this article is for those of you who already have a business going. Whether you’re making $1k a month or $100k a month, I’m willing to bet that you have a similar dilemma to one that I face on a regular basis.

What’s that?

I call it the Lifestyle Expansion Dilemma.

Early on, at all costs I tell people to focus on the basics. You don’t need 10 different websites each with their own separate blog and You Tube channel. You just need to follow the simple steps to bring in income and build confidence.

But what happens once you have income and confidence?

All of a sudden you have something else as well: options.

The lifestyle expansion dilemma is what happens when you’ve built your foundation. You know you can bring in money, and perhaps you’re preparing to leave your job.  You may not want to do freelance writing forever, so you start to think about all of the different options open to you.

This is the dilemma, and it has a direct impact on what path your life takes. Mark Manson had a great post awhile back about the dark side of the digital nomad. In it he said:

“Economists say there is no such thing as a free lunch. I say there’s no such thing as a free life. Some of us just learn to choose better shackles than others.”

It’s just as easy to become trapped in your new life, if you aren’t careful. So making choices early on that truly reflect your core goals in life and business is really important.

The Four Ideals of the LED

So once you have those fundamentals (income and confidence) how do you make sure you stay on the right track?

I believe there are four key ideals that go into building a lifestyle business – and balancing each is one of the most difficult aspects of lifestyle entrepreneurship.

These four things are:

Let’s take a look at each of these and consider how they fit into this dilemma.


Obviously we need a certain amount of money to survive. But in a world where everyone thinks bigger is better, there’s a constant pressure to grow and make more.

So as you’re considering what direction to take your business, or what new venture to begin work on, money is a key factor. Are you going for the $30 million exit? Or are you cool making just enough to support yourself?

Be honest with yourself about how much money you really need/want. Is it your primary motivator for building a business?


If you decide to really go big and swing for the fences as it relates to money, then you take away some of the benefits of lifestyle.

For instance if I want to take my business from where it is now and scale it up to be a multi-million dollar business, inevitably I’m going to lose some of the lifestyle benefits.

What are these? Examples would be:

There are always exceptions to the rule, but generally as revenue goes up, flexibility and freedom of lifestyle goes down. Click to Tweet


Early on, the only thing most new lifestyle entrepreneurs care about is supporting themselves. But once they can do that, many people find that business is more fun if you have a team and aren’t working alone on an island (I say that both literally and figuratively).

So do you sacrifice some of the lifestyle and monetary potential to start working with a team of people that share the same goals? This in and of itself has it’s own rewards and can make business and life much more enjoyable.

Instead of working with others full time, do you split the difference via joint venture or one off projects?

Deciding how to incorporate others into your business life, is something that will become more and more important as you get out of the beginning stages of business.


What’s your end goal with everything you do? How are you changing lives? Do you even care about changing lives, or are you just in it for the lifestyle and the money?

For instance, I spend hundreds of hours each year working on the World Domination Summit for little money, because I believe in the people I work with and the impact that it has.  However, if I take on too many of these projects, I jeopardize my fundamental lifestyle and money goals, because I stretch myself too thin.

Why Is This Important?

Inside Location Rebel, we’re frequently having members get to the point where they’re starting to think about lifestyle expansion.

They’re bringing in a few thousand dollars a month, perhaps have left their day job, and now they’re saying “what now?” – which can be a very overwhelming question.

What I’ve found is that more often than not, they haven’t started to think through what they really want over the long term.

It’s easy to get to what you thought you wanted. Make some cash, be able to travel the world indefinitely. But what happens when you’re done traveling full time and you want to do something else? You need to have a plan, or at least some solid ideas of what you’d like your life to look like.

Being honest with yourself about your goals for money, lifestyle, people, and impact makes it much easier to decide which projects to get involved with.

For instance if all you care about is the money and the lifestyle (solopreneur, internet marketing), then you’ll most likely take a very different path than someone who chooses money and people (traditional startup, conferences etc).

An Exercise for Clarity

Because this can be overwhelming and there are so many intangibles, taking the time to do a little exercise can help make your decision process a little bit easier.

1) Order Your Lifestyle Expansion Ideals

First you need to know what drives you, and what is most important to you in your lifestyle business. So take a little bit of time and place the following in order of most important to least important: money, lifestyle, people, impact.

Be honest with yourself. If it really is all about the money, as opposed to impact, acknowledge this.

If you want to take this a step farther write  500-1000 words on each of those 4 topics, and your views about them.  This will allow you to think through each of them a little bit more and have a better understanding of why one is more important than another.

2) List Out Potential Avenues of Business Ideas

By now you’ve probably been building the fundamentals of your lifestyle business for 6-12 months. During that time you’ve probably had dozens if not hundreds of ideas for new ventures, or various opportunities that have come up. (If not, you’ve got other issues, and should read this.)

Write down as many of those as you can.

If you’re past the idea phase and are trying to decide between a couple different avenues, then just focus on those.

3) Rank Each Idea based on Core 4 Ideals

Now take your ideas, and being as objective as possible, rate how each of the 4 ideals  of lifestyle expansion apply to each.

To clarify, here is what mine looks like:

My Personal Ideals:

  1. Lifestyle
  2. Impact
  3. Money
  4. People

These line up perfectly with Location 180 and Location Rebel – which is why even years later, I’m still so excited about these aspects of my business.

It doesn’t line up quite as well with things like Pioneer Nation or WDS, because while they are huge for impact, in person conferences are much more difficult for my primary ideal of lifestyle.

Moving Forward

The biggest reason for writing about this today is to let you know that a lifestyle business is just that, it’s all about the lifestyle you want to live. If you’d rather work with cool people, make a huge impact, and only make $40k a year – that’s awesome!

If you want to build a million dollar business, that allows you to do all of the cool stuff you want to do in life – great!

You just have to understand which ideals are most important to you, and know why they’re important, so you can make the right decisions for your life.

Some opportunities will potentially to allow you to have all four of these, but you need to make sure that most of your efforts are playing towards the things that play to your unique goals.

So with that said, what ideals are most important to you and why? Let us know in the comments!

Image Credit: Businessman in Hat from Big Stock

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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19 comments on "The Lifestyle Expansion Dilemma (And Why it Matters to You)"

  1. Josh Denning says:

    Hi Sean,

    This is an awesome post and something that I am thinking deep and hard about now. As I have just exited the big business thing to build the lifestyle business thing as you know.

    I am now however finding myself drawn to building the big business thing as weird as this sounds (on the side) at the same time. Like having a little digital agency going on the side of the lifestyle business (how weird and backwards does that sound) but I mean it..

    What I found being in the big business thing was that once you get to a certain point. The big business actually becomes easier to put people and systems in place to free yourself up, sometimes even more than a lifestyle business allows, however that takes at least a good 3 years of hard work at least. Could be 5 years, could be more, but then depending on skills, luck, business selection and work ethic could be less.

    Once that team is in place though the choice is really yours. If you build that team right, you will suddenly find that you can go away for 10 weeks and come back to a business producing more revenue, that is bigger, stronger and better than it was when you left.

    Now, that! for many entrepreneurs is a strange feeling as they realise they’ve worked themselves out of a job!

    I just thought I would add that for all lifestyler’s out there because if you really think about it for a true freedom seeker, sometimes the 3 to 5 years of hard work and sacrifice is the only true way to absolute location independence and financial freedom.

    Food for thought! Best, Josh

    1. Sean says:


      This is exactly why I wrote this post 🙂

      For many people, what they really want isn’t necessarily what got them out of their typical 9 to 5 job in the first place. For many people, a small lifestyle business (and/or travel) is just a way for them to open up new doors – such as going the bigger business route you mention here.

      Really appreciate the thoughts.

  2. Bram says:

    Hi Sean,

    I can’t remember how I discovered Location 180 about a year ago, but your reading-list and blogposts literally changed my life.

    Today, I’m working as a freelancer here in Brussels, Belgium. The first days and months after making the decision to go all-in were like crossing a desert without knowing when and where you’d find water. Blogs like yours killed the loneliness and doubts when needed most.

    Lately, I’m looking at the horizon for a lifestyle expansion. Great post.

    Thanks so much.

    1. Sean says:

      Thanks Bram, so cool to hear about the transition you’ve made! Keep us posted on your expansion and where you take things from here.

  3. Hi Sean,

    You touched a few important points here. I remember a comic strip from Freelance Freedom I saw a long time ago in Freelance Switch. A graphic designer founded his own creative agency because he was tired of working for someone else.

    Ironically, his own employee was talking with someone on the phone about how much he hated the place.

    The thing is sometimes we pursue an idea but later we find out we’ve changed and what one day made us happy is no longer there.

    Right now I’m building my way out of my day job. So my primary goal is to make money. Eventually, money will be less important and my business will be about freedom and building products that matter.

    Great post!

  4. Hi Sean, I found this post great at it explains in a few words what I’m looking for. I discovered your blog about a year and a half, I read it frequently and I’m still on the process of changing my life, but you’ve just made see a clearer path towards what I’m looking for.
    Thanks Sean.

  5. Scott Asai says:

    Love this post! My order is:

    1. Lifestyle
    2. People
    3. Impact
    4. Money

    Since I’m a coach, I’m making my shift to programs because I like planning events and programs are like coaching as a product. I’m excited about the potential results!

  6. Ana says:

    I am not at the point yet where I must make those kinds of decisions. My priority is making money asap. But I know there will come a time, within the year, I’m thinking, when I will need to make my own list. Thanks, Sean, for reminding all of us where we’re going!

    1. Ana says:

      Hey Sean and others,

      Had to amend my previous response to your excellent post as my day job, a contract position, came to an end last week. Sometimes … you’re forced by circumstance to jump in when you were previously doing too much wading. Here’s my list:


      Money is by necessity on top, but that won’t always be the case. Lifestyle will hopefully get moved down, too. I’ve realized as I’ve gotten older how much people really do matter, more than I ever did before. Impact is a very close second to that. Hope that didn’t confuse you all.

      Where things are on the list don’t matter; making the list does.


  7. Awesome article Sean. One thing that I will like to add is that the same way that we work hard on our businesses, we need to work hard on deepening our relationships. I found that some digital nomad had issues in this area because they take relationships for granted (I am referring more specifically Marks article – The Dark Side of the DN).

  8. Ron says:

    Great post. I’m like Ana but just thinking about these issues will help motivate and keep me on track. Thanks!

  9. Great post Sean, definitely got me thinking. When it comes to making money, I’m definitely cool with making enough just to support myself and give me the ability to do my thing from anywhere. For me, impact and making a positive difference means everything to me, similar to why you invest so much time and effort in WDS for such little financial payback. My order then is:
    Thanks for the insight and thought provoking post, cheers!

  10. This post totally resonates with me as it matches with my push for uncovering your Ultimate Whys. Goals aren’t enough you need to dig for your whys. We need to build businesses that serve our lifestyle choices, not spend our lives serving our businesses. Great post!

  11. Ana says:

    Lisa-Marie, you hit it on the head so accurately it’s a virtual bullseye in every way. All my life I’ve asked why we don’t live within a system that services our needs, instead of one in which we serve the needs of the system. In business that’s true as well. Yes, we need to work; I’ve never been afraid of work, not even hard work where needed. My business will serve my lifestyle choices. What I’ll do is work in it as much as I need to for that purpose.

    When I listed money on top of my list, I did so only for the beginning, when it becomes self-supporting in a stable manner. That must be necessity come first, especially if there’s no day job to fall back on. But with success that will change. 🙂

  12. Such a timely post, Sean! After leaving WDS, I was overcome with a bit of an identity crisis — but not in a bad way. I just got the feeling that I want, and need, to do more. Just not sure what that looks like yet. Thanks for the advice!

  13. Romi says:

    Great post! I enjoyed reading it and it made me think about what my list would look like.
    Thank you for raising awareness and providing new insights.

  14. nico says:

    Hey Sean!
    I heard you are in Bali right now. How’s the quality of the internet connection? Everyone online its saying that it sucks and its really making me change my plans of living in Bali.
    Thanks man!

  15. It all comes down to opportunity cost. Would I rather do this than that, as you stated it.

    I think my ideals are being financially independent enough that I could take off a year and not have to work at all yet still be able to support myself well. I want to get to a place where I can branch out and try my other passions. I want to be able to travel and meet new people and enjoy life. I don’t want to have to answer to a boss.

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