9 Mindset Differences Between Entrepreneurs and Lifestyle Entrepreneurs

Is This the Way of the 21st Century Entrepreneur?

It seems like everyone wants to be a lifestyle entrepreneur these days.

Lewis Howes first coined the term a few years ago and it has grown wildly in popularity.

Do you know exactly what it means though?

You probably know it has something to do with traveling the world and working for yourself.

Maybe you’ve read books like Tim Ferriss’s 4 Hour Workweek,  or Jesse’s Lifestyle Entrepreneur and you’ve been building your own location independent business for a while.

Or maybe you’re new to the whole concept, and you’re just realizing that it’s possible to travel the world, swim with stingrays and run a business entirely online.

Either way, it’s all good. You’re learning about the best possible way to live your life, and I respect and admire you for taking the time to consciously create a life you want to live.

But if you’re like me, you get a little bit confused or frustrated sometimes with all the information.

There are thousands of books and blogs out there about being an entrepreneur, but not all of them are tailored towards people who want to live the type of lifestyle you want to live.

For example, if you wanted to build a motorhome, and you could find were instructions on how to build a 2 story red brick house, you would get confused and frustrated.

There would be a couple similarities, but everything from the foundation, to the roof to the sewage system would be different.

One would have a foundation made out of concrete and brick, while the other would have wheels and a chassis.

It’s the same with building a business. A business that will work in one place will not always work if you want to have freedom. The instructions for building a traditional business do not always apply to building a lifestyle business.

So how can you tell what approaches will help, and which approaches don’t apply?

It’s quite simple.

You have to create your mindset to create the lifestyle you want to live.

Then you can choose what type of business, and life you want to create.

Do you want a motorhome, or a 2-story red brick house?

What Do You Want: Your Money or Your Life?

Here are the main differences between the mindset of an entrepreneur and a lifestyle entrepreneur:

  1. Entrepreneurs seek investors. Lifestyle entrepreneur’s don’t. – Investors care about one thing, that’s a return on their investment. They don’t care about you wanting to explore the countryside in Bali, they want your business to grow, so their investment will grow also. Lifestyle entrepreneurs don’t want to answer to investors about how the business is growing. This often means bootstrapping a business or starting a business that has almost no initial cost. Many entrepreneurial books and blogs are focused almost entirely around wooing potential investors, seed rounds and forming business plans. That’s cool stuff, but not useful if you just want a lifestyle business.
  2. Entrepreneurs have an exit strategy. Lifestyle entrepreneurs don’t WANT to exit their business. –  An exit strategy is a way to get out of your business, so you can work 100 hours a week, make a nice big valuable company, then sell it before you go completely insane. Lifestyle entrepreneur’s don’t care about an exit strategy because they are creating something simple that they are passionate about to support the life they want to live.
  3. Entrepreneur’s are limited by location, lifestyle entrepreneur’s value freedom and will make sure they can run their business from anywhere in the world. – If you started a bakery, and you took on the role of head baker, you would have to be present every day, making sure that bread gets baked properly. If you took on a bakery as a client for your marketing business, then automated what you could and let your virtual assistants take care of the rest, then you could travel absolutely anywhere and your profit would still come in.
  4. Entrepreneurs just want profit. Lifestyle entrepreneurs crave adventure – Entrepreneurs typically want to grow profits as fast as possible. Both for their business and their investors. That can mean sacrificing a large amount of time, and location freedom to chase financial freedom. Lifestyle entrepreneurs want to make enough money to travel the world, play in rock bands or just plain kick back on a beach.
  5. Entrepreneurs will give money to charity… when they’re rich. Lifestyle entrepreneurs can give of their time. – You’ve probably heard about CEOs and business owners making massive donations to charitable organizations. But most of the time when these businesses are in the initial growth stage, the entrepreneur just doesn’t pay him or her self enough to donate to charities. On the other side, lifestyle entrepreneurs create a flexible schedule where they can donate their time to organizations they care about.
  6. Entrepreneurs focus on business goals. Lifestyle entrepreneurs focus on life goals. – In the next five years, do you want your business to grow 200% and to receive $5 million in new funding from investors? Or, would you rather spend time with family, re-form your old rock band and travel the world talking to beautiful women? Jesse has a great post asking what you would do if you had one year left to live. It’ll help you realize what goals matter, and what goals are just distractions from what you truly care about.
  7. Entrepreneurs focus on managing organizational structures. Lifestyle entrepreneurs stay involved at the transactional level. – Once you get an employee or ten it starts to take up your time. You have to deal with managing the people, and oftentimes entrepreneurs forget why they started their business in the first place. On the other hand, you can choose to stay involved with your customers, connecting and getting to know them personally. This will probably mean your business wont grow as fast, but you will develop more relationships, and keep doing what you care about.
  8. Entrepreneurs form a huge corporation. Lifestyle entrepreneurs form a sole proprietorship, an S Corporation or an LLC. – The difference is that most of the profit for lifestyle entrepreneurs is generated as the owner’s income. Keeping costs low, and personal profit high will make for a very sustainable lifestyle without massive business profits. That means only hiring perhaps one virtual assistant, instead of building a huge team that requires a lot of management and organization.
  9. Entrepreneur’s are willing to work 80 hours a week to avoid working 40 hours a week. Lifestyle entrepreneurs want to work 4 hours a week. – Entrepreneurs are willing to sink all their time into their business, staying late, waking up early, doing all the tasks no-one else wants to do. Lifestyle entrepreneur’s aim to simplify and automate to have more freedom.

Which one are you?

So, now you know the main differences, you can probably relate to both mindsets a little bit.

Whatever you want, that’s totally cool. I don’t want to sound condescending, or judgmental of those who take the traditional entrepreneurial route. I have a tremendous amount of respect for anyone who creates something new and works hard at it.

Also, realize these are not strictly defined categories, with harsh dividing lines. Instead, it’s more of a spectrum with traditional entrepreneurs on one side, and lifestyle entrepreneurs somewhere between them and hippies.

If your business grows right now, if it gets larger and more profitable will that involve you working more or less?

In other words, is it a system that works for you, or is it a system you work for?

Are you sacrificing the best years of your life to chase a dream for your later years?

Perhaps you call yourself a lifestyle entrepreneur, but after analyzing it a little more it becomes clear that you’re building a business that doesn’t support your freedom.

To know if you are where you want to be, you have to know exactly where you are.

Who Do You Want to Be?

So which resonated more with you?

Do you want to push yourself to the limit for 5-10 years to get a huge paycheck and then cash out and live like a king in paradise?

Or would you rather focus on generating enough to have cool experiences without necessarily having millions in the bank?

This is where you gotta get serious with yourself.

Do you want to start the next Instagram and make billions?

Sure, who wouldn’t. But do you want to invest 10 years of your life working like a slave for a small chance at those billions?

The fact is that hard work has little to do with the success of billion dollar companies, yes it is necessary, no it is not a guarantee of success.

That’s mostly determined by random factors over which you have no control. (Read Nassim Taleb’s book Fooled By Randomness for a scientific explanation of the actual factors that influence the unprecedented success of a billion dollar businesses, hint, it has a lot more to do with timing and luck than hard work and brilliance)

Putting off living your dreams for years is foolish. Starting a business can be a form of escapism.

What if you get paralyzed and can never go skiing on the Alps like you want to?

What if your market changes, and your business suddenly fails, even though it was growing like crazy for a few years?

What if you end up working 80 hours a week for 10 years and never make millions?

If those things happened, and you put off doing what you really wanted to do, then you’ll never get another opportunity. 

This is it.

You get one life. You can live your dreams and travel the world.

So do you choose to get experiences, or chasing wealth?

How You Can Get a Lifestyle You Love Fast

Tim Ferriss came up with the term Dreamline.

This involves planning out how much you need realistically to do what you want. It’s probably a lot less than you think.

I just came back from Peru in December. Beautiful country. Highly recommend it.

I was telling my friend how cheap everything was there.

He said “Damn, if you just got a couple million dollars you could move there and live like a king.”

I replied to that, “Who needs a couple million? You could live like royalty on $10,000 a month.”

Thinking that you need a million dollars to live a sweet lifestyle is nothing but a pesky limiting belief that will hold you back from actually getting out there and doing sweet stuff.

You don’t need a million dollars, you don’t even need $10,000 a month. You can survive quite well in countries like Peru, Thailand or the Phillipines off of a just $2,000 a month.

Now, if you’ve never made money online before then even $2,000 a month can sound like a lot.

So start out by figuring out a way to make $50 online, then you can build up from there.

Then you’ll have time to build towards that $10,000 a month.

The biggest thing is to take action. Start doing something that will provide monthly cashflow without a huge investment.

A canoe has to be in motion before you can steer it.

Once you’ve started, you can adjust your course.

Just start.

Come hang out at the Adventupreneur blog if you want case studies, and strategies on how to build a business while traveling. I would love to help you get started.


  1. Those 9 points are EXACTLY what I’ve been looking for. They sum it up. Thank you. I AM A LIFESTYLE ENTREPRENEUR, now I get it.

    Thanks Jon

    • Hey Martos,

      Glad to help out! It really provides a lot of clarity when you know EXACTLY what you’re going for, and exactly what you want.

      Good luck on your journey and let me know how I can help!


  2. Jon,

    While I agree with what you wrote, I think there is a middle category or two though.

    For example, a person who is willing to work hard, but wants to do so while living a lifestyle most dream of “later in life” – if they “make it.”

    I know of several entrepreneurs who have built very profitable businesses, some with investors, but most without, but they all live in very nice locations, typically in the Caribbean, because they want to live there and have built a business model that allows them to do so. Is it unconventional – absolutely, but can it work – for the right type of person and company I believe so.

    When you look at the economic benefits of working from the US Virgin Islands or Puerto RIco for example, you can ultimately work hard, have an educated workforce (if needed), and live a great life that also includes travel to other destinations and the benefits of being in a US territory, and still living close to the CONUS.

    They simply choose to work from a non-traditional location. They still want an exit strategy, and may or may not want or need angel or VC funding. While lifestyle guys want to ride it out, these guys see the benefits of an exit, typically because they are running a larger revenue company and want to walk away from the liability and responsibility.

    I think its also important to note that MANY entrepreneurs do not seek nor get offered any outside funding – they grind and make it solely on their own, which was not one of your categories. These guys/girls are willing to pound on doors and get the sales they need to make payroll and cover their bills. Regardless of the location they work from, they work hard day in and day out to become successful.

    In this day and age of blogging and tech, I think it is easy to forget how many entrepreneurs are opening a plumbing company or inventing the next widget to make learning to play a guitar easier or a restaurant franchise. Many of these style entrepreneurs don’t seek angel or VC funds, and many don’t travel the world. They grind day in and day out to make their businesses successful.

    Just some thoughts.

    Great article.

    Greg Colton

    • Hey Greg,

      “While I agree with what you wrote, I think there is a middle category or two though.”

      You’re right man. There definitely are tons of people who are somewhere between traditional entrepreneurs (who I would say are the ones that go out and grind, knock on the doors, work 80 hour weeks and don’t travel) and the lifestyle entrepreneurs who are kickin’ it in Thailand watching the sales roll in online.

      ” it’s more of a spectrum with traditional entrepreneurs on one side, and lifestyle entrepreneurs somewhere between them and hippies.”

      – I think a lot of people missed this point in the article, and it really summarized how I feel. It’s more of a choice of what matters more, the success of your business, or integrating your business with all parts of your life.

      Thanks for the insightful comment!


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