Harrison Alley


I’ve pursued lifestyle entrepreneurship ever since I learned about it in 2013.

I don’t have lifestyle entrepreneurship all figured out.

But I’m happy to share what I’ve learned about this type of entrepreneurship over the past several years.

So what is lifestyle entrepreneurship?

Lifestyle entrepreneurship involves building a business to prioritize your ideal lifestyle first, profits second.

Plenty of people pursue “lifestyle entrepreneurship” without knowing about this term or caring that it has a label.

These entrepreneurs often do what they love and can’t believe they get paid to do it.

However, if you’re searching online for lifestyle entrepreneurship, I’m guessing you’re probably one of the 85% of people worldwide who isn’t engaged at work.

Perhaps you’re looking for a way out and investigating lifestyle entrepreneurship as an alternative.

Let’s dive into what makes lifestyle entrepreneurship different from conventional entrepreneurship and career paths.

Lifestyle Entrepreneurship and Lifestyle Design

Like lifestyle entrepreneurship, lifestyle design is another 21st-century buzz-word.

And the concept has actually been around for a long time.

But Tim Ferriss pushed the idea of lifestyle design into the mainstream in his book, The Four Hour Workweek.

In short:

Lifestyle design is just what it sounds like: deliberately designing your ideal lifestyle.

Part of lifestyle design involves mapping out what you want your life to look like.

It also involves estimating how much money it will take to get there.

Many people assume their ideal lifestyle requires so much money that they couldn’t possibly achieve it.

In fact, some people would rather never try lifestyle design for fear of realizing their dreams are out of reach.

However, many lifestyle designers will tell you that the life of your dreams doesn’t always cost as much as you think.

Regardless, lifestyle design is a critical first step in lifestyle entrepreneurship.

Because before you build a business to facilitate your ideal lifestyle, you need to know what your ideal lifestyle is and how much it costs.

Lifestyle Entrepreneurs, Products, and Services

Lifestyle entrepreneurs are all about building a specific lifestyle.

Usually, this lifestyle involves the freedom to work when, where, how, and on what they want.

For this reason:

Many lifestyle entrepreneurs sell products instead of services.

For instance, lifestyle entrepreneurs typically don’t pursue the path of web designers, doctors, and lawyers (who sell their services).

Instead, their businesses more closely align in offerings with e-commerce website owners, information product sellers, and bloggers.

Sometimes figuring out whether an entrepreneur sells a product or a service is tricky.

But usually, it’s straightforward.

And if you’re an employee, you are almost certainly a service provider.

Why Lifestyle Entrepreneurs Don’t Usually Provide Services

Service providers typically have more constraints on their time than those who sell products.

Anyone who has worked a regular 8 to 5 knows these time constraints well.

As an employee, you provide services for your company.

You sell your time to your company and your company pays you a wage in exchange.

While all employees may be service providers, not all entrepreneurs necessarily sell products.

There are plenty of service-providing entrepreneurs like freelancers and agency owners to name a couple.

And although their businesses may allow for freedom than an employee’s lifestyle, they typically aren’t the businesses lifestyle entrepreneurs pursue.

How Selling Products Fits Nicely with Lifestyle Entrepreneurship

One of the primary reasons lifestyle entrepreneurs prioritize selling products is because of how they scale.

The way businesses scale is easiest to think about with an example.

Imagine an entrepreneur who sells a product like an e-book on his website.

He puts the same amount of effort into the creation of the e-book whether he sells five or 500,000. 

Also, more sales also don’t necessarily require hiring more people or fundamentally changing his business operations, unlike service providers.

In other words, he could potentially sell 500,000+ copies without hiring employees.

Plus if his content is timeless, that e-book can continue earning him money for the rest of his life.

This likely sounds too good to be true.

But I’m actually describing a situation like Mike Geary’s.

Mike created the information product, The Truth About Abs.

He makes $5 – $10 million per year selling about 500,000 copies of his e-book annually.

Mike could be the poster boy for lifestyle entrepreneurship.

He realized he wanted to be a lifestyle entrepreneur after looking for a way out of his corporate job.

Mike also had a passion for health and fitness.

The desire to break free of his corporate day job motivated him to publish his health and fitness information product.

Even after publishing the e-book, it took years for Mike to leave his day job and work on Six Pack Shortcuts full-time.

But with this product, he built the lifestyle of his dreams.

Hardly any lifestyle entrepreneurs experience the financial level of success that Mike has.

But plenty of lifestyle entrepreneurs have been able to quit their day jobs and lead similarly independent lifestyles.

Lifestyle Entrepreneurship and Independence

You will often hear the term “indie” (short for independent) or “indie hacker” in the same breath as lifestyle entrepreneurship.

In fact, if lifestyle entrepreneurs had an official website (besides this one), Indie Hackers would be a strong candidate.

Why does independence go hand-in-hand with lifestyle entrepreneurship?

Like I mentioned:

Lifestyle entrepreneurs usually want the freedom to work when, where, how, and on what they want.

This typically means independence from a typical job, working in a large team, and particularly, independence from outside investors.

Funding your startup in a low-cost, no-outside-capital way is very popular with lifestyle entrepreneurs.

It even has it’s own buzzy term in the startup culture, I’ll discuss in the next section.

Bootstrapping and Lifestyle Entrepreneurship

If you look up the definition of bootstrap, you’ll probably find something like:

get (oneself or something) into or out of a situation using existing resources.

The definition of bootstrapped according to the Oxford dictionary

In entrepreneurship, bootstrapping means that you use your existing resources of time and money to start a company.

So instead of getting a bank loan going to investors for money, a bootstrapper will use his own time and money to get his business started.

Books like Eric Ries’ The Lean Startup and inexpensive technology have helped popularize the concept of bootstrapping in business.

Some businesses need outside capital and a large team to get off the ground.

These sorts of businesses like space exploration companies, green energy, and others aren’t good candidates for bootstrapping.

But for the lifestyle entrepreneur, bootstrapping his business is usually an excellent idea.

Perhaps the most important reason for the lifestyle entrepreneur to bootstrap instead of raise funds is that outside investors would make him a service provider.

He would be providing the service of turning his investors’ money into more money.  

And as I’ve mentioned, lifestyle entrepreneurs prefer selling products over providing services.

But bootstrapping as a philosophy is also about freedom.

And the fewer investors, employees, and people you have to deal with in business, the more freedom you have.

Lifestyle Entrepreneur or Lifestyle Solopreneur?

There isn’t exactly a hard and fast definition of a solopreneur.

But it essentially refers to a business owner who runs his business largely by himself.

I think anyone without any full-time employees counts as a solopreneur.

There are plenty of solopreneurs who aren’t necessarily lifestyle entrepreneurs like freelancers and indepedent consultants.

But lifestyle entrepreneurs seem particularly attracted to solopreneurship.

And it makes sense.

Solopreneurs, especially those who sell products instead of services, often experience many of the freedoms that lifestyle entrepreneurs are after.

Check out this post for my list of favorite solopreneur business ideas!

Lifestyle Entrepreneurship and Technology

As you’ve probably gathered, most lifestyle entrepreneurs rely heavily on technology.


The web has made online sales possible anytime, anywhere, to a global audience.

Or as entrepreneur and investor, Tyler Tringas puts it, certain types of online businesses are:

location-independent, high margin, [and] low-risk with predictable recurring revenue. 

Tyler Tringas blog

These sorts of online businesses perfectly facilitate the lifestyle many lifestyle entrepreneurs want.

Also, most lifestyle entrepreneurs have a technology-first mentality when brainstorming business solutions.

For instance, a lifestyle entrepreneur typically considers outsourcing businesses processes in this order with:

  1. code or other technological automation,
  2. a freelancing company,
  3. a freelancer,
  4. (and ideally never) a full-time employee.

Lifestyle entrepreneurs have a technology-first outsource mentality because people management often limits the sort of freedom they are after.


I hope this gives you a better idea of what lifestyle entrepreneurship is.

And I hope you realize that building a lifestyle business isn’t easy.

But with consistent, high-quality work, you can stack the odds of success in your favor!

What other lifestyle entrepreneurship qualities should I discuss in this post?

Let me know in the comments!

Leave a Reply

Your email address will not be published. Required fields are marked *