What came first, the lifestyle or the career?

It’s an age-old question, and some people answer it by becoming a lifestyle entrepreneur.

It’s easy to get wrapped up in your career, and then, before you know it, your best years are behind you.

 Lifestyle entrepreneurs are a breed of businessmen and women who prefer to get paid in not just money, but in…

  • TIME
  • FUN

When you stack plenty of paper but are short on the other things that matter, is it really worth it?

Becoming a lifestyle entrepreneur isn’t for everyone, but I believe strongly that everyone should at least explore the idea.

Let’s take a closer look at what it takes to become a lifestyle entrepreneur and whether or not it’s for you.

Note: This in-depth guide how to become a lifestyle entrepreneur is several thousand words long, so you can check the table of contents below to jump to the section you’d like to dive in to more. 

What Is A Lifestyle Entrepreneur?

A lifestyle entrepreneur is someone who creates a business to improve their overall quality of life.

Believe it or not, you can create an incredible lifestyle and make seven or even eight-figures a year.

Richard Branson could even be considered a lifestyle entrepreneur, and he obviously does exceptionally well for himself.

A lifestyle entrepreneur focuses both on meaningful rewards and financial gains.

Your lifestyle business can involve something that you’re passionate about, but it doesn’t have to. As long as your work revolves around your lifestyle and not the other way around, you’re a lifestyle entrepreneur.

Most people prioritize profits over passion and security over lifestyle design, and honestly I can’t blame ‘em.

Life is first and foremost a game of survival, and it’s usually safest to hold a traditional job.

The lifestyle entrepreneur, though, puts fun and happiness in the “survival category” along with money and security.

After all, each breath could be your last, so you might as well get paid in awesome experiences as well as money.

My Lifestyle Entrepreneur Definition

For me, a lifestyle entrepreneur starts with the question “What type of life do I want?” before they ask “What kind of job do I want?”

Both are important questions, but I think happiness should be your #1 priority.

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Am I glutton for fun? Well…yes, but that’s not the main reason that I put happiness first.

When I’m happy, I’m more energized and more productive.

I problem solve more creatively and ask smarter questions.

If your business doesn’t align with the life you want to live, you’re selling yourself short.

When I stepped away from becoming a lawyer to build my personal brand, I was putting lifestyle first and taking plenty of risks along the way.

I knew that if I failed in the pursuit of my ideal lifestyle, I could at least live with that.

What I couldn’t live with was never trying.

With that said, the path of the lifestyle entrepreneur isn’t for everyone.

Here are a few tips to help you decide if becoming a lifestyle entrepreneur might be right for you: 

Signs You’re A Lifestyle Entrepreneur

When it comes down to it, becoming a lifestyle entrepreneur, or any type of entrepreneur for that matter, isn’t everyone’s cup of tea.

You might be a good candidate for lifestyle entrepreneurship if…

1. You always know a more efficient way to do things. 

A lot of lifestyle entrepreneurs are proudly unemployable, which translates to, “I can’t stand  being part of an ineffective system!”

Most workplaces are overrun with inefficiency.

When you’re forced to work in an inefficient environment, it’s near impossible to live up to your full potential.

When you break off on your own to build a lifestyle business, you get to optimize the hell out of your work and your life.

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“Work smarter, not harder,” is the quintessential motto of the lifestyle entrepreneur.

2. You’re a strong advocate for automating and outsourcing tasks. 

In the digital age, outsourcing and automating go hand-in-hand with working smarter, not harder.

Everyone has their strengths, so if you don’t have all the pieces to the puzzle on your own, that’s okay — there’s somebody out there who can do it better for a fraction of the price.

The end result of being a lifestyle entrepreneur?

More time to do the things you love.

3.  You can’t stand low-vibrational energy in the office. 

What’s the culture at your current job?

Do you leave feeling invigorated or drained by the people you work with?

Too many offices are wrought with negativity and complaining, neither of which increases productivity. A negative workplace won’t make you happier, and it’s definitely not going to help you accomplish more.

As a lifestyle entrepreneur, you’ll get to handpick who joins your team.

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Here are a few of my rules:

Rule #1: Positivity takes priority.

Rule #2: Laughter is mandatory.

Rule #3: Treat challenges as opportunities to impress yourself.

When you lay the groundwork for an enjoyable work environment, productivity happens naturally.

There’s no place for low-vibrational energy in your lifestyle business.

4. You’re drawn to the idea of passive income.

Trading your time for money is the old way of building the best life.

It’s labor-intensive, slow, and eats away at your freedom.

When you take your business online, there’s a million ways to front-load your work and create multiple streams of passive income.

You can make money while you sleep, while you vacation, and while you have dinner with your family.

I made roughly $30k-50k/month on my Virtual Summit Mastery course alone before I sold this part of my business to Jan Koch.

I initially put in a lot of work to create the course, but now the sales flow freely — mostly from organic search traffic and direct referrals.  

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I make money while I’m on the beach and while I’m 10,000ft in the air on my way to the next digital nomad destination. It’s a lifestyle that I try to introduce to as many people as I can.

5. Commuting sucks your soul.

I’d be shocked if even a few hundred people in the world actually enjoyed their commute to work, yet almost everyone has one.

Sure, you can listen to podcasts, but no matter what you do commuting will still suck.

Lifestyle entrepreneurship means that you can ditch the commute if that’s what you want, and if that isn’t priceless, I don’t what is.

6. You don’t like having a limited earning potential. 

Let’s face it, most traditional jobs have predictable limits to the amount of money you can earn in a year.

Where’s the fun in that?

Wouldn’t you rather work on something that gives you the opportunity to transform your income and your lifestyle?

7. You value freedom above all else. 

One of the lessons I’ve learned on my entrepreneurial journey is that I can never predict the future.

Priorities change and new opportunities present themselves.

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When I started law school, I thought that becoming an attorney was what I wanted to do.

I was wrong.

As a lifestyle entrepreneur, I get to pivot when the time is right and don’t have to deal with a ton of negative repercussions.

I value that freedom.

8.  You thrive in stimulating, constantly evolving environments.

If you go nuts in a stagnant, predictable routine and are motivated by the thrill of a challenge, then lifestyle entrepreneurship may be for you.

Lifestyle entrepreneurs have to stay on their toes. Curveballs are common.

You’re going to have unexpected obstacles, believe me, but that’s half the fun. 

Benefits Of Lifestyle Entrepreneurship

Think you’re ready to strike out on your own as a lifestyle entrepreneur?

These days, anyone has the ability to spend more time with their family, eliminate awful commutes, and gain financial freedom.

Here are some of the top benefits of becoming a lifestyle entrepreneur:

1. More Time with Family and Friends

It’s a grim thought exercise, but when you’re withering away on your deathbed, do you think you’re going to regret not spending enough time in the office?

My point exactly!

Something that you might regret, though, is not spending more time with your friends and family.

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Like everyone else, I have a list of things that scare the BLEEP out of me, but nothing is more terrifying than a life of missed opportunities and regrets.

When my younger brother unexpectedly died from an accident in 2013, it snapped me out of the traditional path and made me more willing to take risks that could enhance my life.

I committed to spending everyday working towards a more ideal life.

That same year, I started navidm.com and embarked on my entrepreneurial journey.

2. Discover Your Optimal Work Hours

Tim Ferriss, the author of The 4-Hour Work Week, is a one of the world’s most well-known lifestyle entrepreneurs.

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He’s a unique guy to say the least, and it didn’t take him long to discover that his most productive working hours didn’t fall between 9am and 5pm.

When it comes to writing, Tim catches his biggest waves of creativity in the late, late evening — sometimes well past midnight.

It would be pretty hard to make progress on his books if he held a regular job, but Tim doesn’t do regular jobs.

He sets his own hours, works when he’s most productive, and plays when it’s most enjoyable.

Timing is everything when is comes to crafting the ultimate lifestyle.

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3. Focus On Your Strengths

Anytime you have to learn a new skill, there’s a period of lost productivity.

You lose even more time as you improve that skill, and by the time you really know what you’re doing, you could’ve hired someone else to do it four times over.

Becoming a lifestyle entrepreneur allows you to focus on your strengths and outsource the rest.

If you don’t have a background in something or simply don’t like doing it, there are plenty of people who’ll be willing to do it for you.

4. Infinite Personal Growth Potential

It’s impossible for me to know where my motivations or interests will lie five or ten years from now.

Let’s pretend for a second that I never left law school and right now I was trapped behind a desk.

In this situation, it would feel hard to break free.

As a lifestyle entrepreneur, you get to switch up what you’re currently doing in the relative blink of an eye.

This fluidity is a priceless asset to personal growth.  

5. More Freedom and Flexibility 

Sometimes things come up.

When you have a regular job, you don’t necessarily get to go with the flow and take advantage of life-changing opportunities when the arise. 

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How many transformative experiences does the average person miss out on over the course of their career due to schedule conflicts alone?

10? 20? 50?

When you run a lifestyle business, you get to rewrite the script so that you don’t miss out on incredible experiences.

6. Build an All-Star Team

Most people find themselves surrounded by whatever random people get hired by same corporation, and the majority of employers all face the same dilemma — they’re limited to applicants who live within driving distance of the office.

What are the chances that these people are the top-performers who are going to bring out the best in you?

Next to none!

When you run your own lifestyle business, you get to build your team from the best candidates that the world has to offer.

  • You pick the team.
  • You have the entire world’s population to choose from.

I like those odds better than playing the workplace version of Russian roulette.

7. Potentially Unlimited Income

Income is the single most influential part of living the best life possible.

It can open doors you never thought possible.

When income is both passive and scalable, you have a recipe for almost unlimited income.

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The only limits are your imagination and your ability to solve important problems for your audience.

That’s an empowering reality — one that will get you out of bed early and make you hungry to seize the day. 

10 Steps To Becoming A Lifestyle Entrepreneur In 2022

Exactly how do you become a lifestyle entrepreneur and design the perfect online business around your desired lifestyle?

  1. First, you have to know yourself incredibly well.
  2. Second, you need to decide what you’re good at so that you can use it to provide value to others.
  3. Finally, you have to connect with the right audience, earn their trust, and improve their lives while enhancing your own.

Here are the steps you’ll take along the way:

Step 1: Design the perfect day and reverse engineer your ideal life.

If your life was on an endless loop that replayed infinite times, how would you live each day?

Before you can start brainstorming ideas for your online freedom business, you have to define what your perfect day looks like.

Once you do this, you’ll have a crystal clear image of how you want your life to be.

  • What time do you wake up?
  • Where do you wake up? a.k.a. Where do you live?
  • Do you meditate, workout, or go straight to work?
  • How much personal time do you have each day?
  • How much family time?
  • How do you finish your day?

Start from the second you wake up and lay out every detail of your perfect day..

Each time I do this exercise, I see myself waking up in different locations, so I know that travel is part of my ideal lifestyle. It’s one of the many insights that I get out of this exercise.

By the time you finish, you’ll have an outline of your perfect day, and it’ll act as a filter for eliminating business ideas that don’t sync with your ideal lifestyle.

Step 2: Make a list of lifestyle goals that are deal breakers.

This step should be part of everyone’s process for living a happy life, but most people slack on it or ignore it entirely.

Without defined boundaries, your work can easily take over your life.

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You need to draw a line in the sand when it comes to lifestyle design and refuse to cross it, no matter what.

For me, this was saying “NO” to working behind a desk for a law firm.

Sure, I would’ve had a secure income and fewer uncertainties, but it wasn’t going to make me the happiest version of myself.

I decided that this was a deal breaker, so in 2013, I got serious about designing an exit plan.  

Step 3: Make a list of your areas of expertise.

You’ll have the best chance of success if you focus on your strengths because they’ll give you a competitive advantage.

Coming from law school, my professional skills were pretty diverse.

I started my personal brand website with no real direction — the only goal being to share my entrepreneurial journey, make connections, and see where it took me.

Although this strategy ended up working out well for me, I recommend you take a more systematic approach.

Decide what you’re most knowledgeable about and start your brainstorming there.

Or you can always consider hosting a virtual summit in your niche where you bring on other experts in your field (that way you don’t even have to be the go-to expert from the beginning… you’ll quickly build your brand and business by association). 

Step 4: Make a list of your passions and interests.

As a lifestyle entrepreneur, you’re going to put a lot of blood, sweat, and tears into you work, so you might as well be passionate about what you’re doing.

There are going to be plenty of bumps along the way, maybe even some hair pulling and feet stomping. Your genuine interest in the work you do will be what pushes you through these rough patches.

Whatever you do, don’t settle on a business idea just because it’s in a promising market.

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That would defeat the whole purpose of becoming a lifestyle entrepreneur in the first place!

Find the happy medium where your expertise overlaps with your passions and interests.

That’s the sweet spot where you can create the ideal life. 

Step 5: Find your ideal customers.

It isn’t enough to have a great idea for a product or service if you don’t have a clear picture of who your customers are.

This is why starting with your strengths, passions, and interests can be so helpful, because it makes it easier to pick a profitable target audience.

Use your insider insights to make a detailed audience persona:

  • Where do they live?
  • Are they married or single?
  • Do they have kids?
  • What do they do for work?
  • How much do they earn?
  • What are their biggest problems?

This last question is the most critical because you’ll need to provide value by addressing their pain points.

Even more importantly, you’ll need to be confident that your audience can afford your services.

Instead of isolating a specific income group, I packaged my Virtual Summit Mastery course at different price points:

  • Virtual Summit Mastery allows lifestyle entrepreneurs of all levels to unlock the power of virtual events.
  • The VSM Coaching Accelerator program includes maximum support from myself and my team so that you have the best possible chance of crushing it with your first summit.

Mitch Asser was a personal trainer with zero experience online when he launched his first virtual summit.

He generated six-figures in revenue and grew his email list from zero to over 35K subscribers over the course of multiple virtual summits.

Selling all-access passes to his online events continues to be his primary business model. That’s one of the coolest things about hosting virtual conferences — they can be an entire business model on their own.

Step 6: Establish an online presence.

You’ll need to create a home base online where people can come and check out your services.

Here are some of the successes and struggles of my first 6-7 months online:

  • I did my first online interview with the notorious Pat Flynn from Smart Passive income.
  • Wrote over 40,000 words in one month alone.
  • Did quite a bit of blogging.
  • Started a podcast called The Lifestyle Architect.
  • Generated a mere $400 in revenue (significantly less than my expenses)
  • Gained only a few hundred email subscribers.

I had built a solid online foundation, and even went the extra mile with starting my own podcast, but it didn’t get me the results I was hoping for.

Then I started hosting virtual summits, and it put my lifestyle business on steroids.

Step 7: Connect with your audience and offer value.

Once you have your target audience, you’ll need to connect with them and offer significant value.

To do this, you’ll have to…

  • Connect on a personal level
  • Leverage your unique image and personal brand
  • Stand out from the crowd

This can be a slow and arduous process when you’re learning how to start a blog, podcasting, and guest posting to make industry connections and gain exposure.

By the end of May 2014, after almost a year of grinding the old school way, I came across virtual summits.

It seemed like hosting a summit could be a viable way to rapidly grow my email list, generate revenue, and build authority while growing my brand.

I decided to transition from just blogging and podcasting to hosting my first virtual summit.

My very first online event, The Branding Summit, transformed my entire life and business for the better.

The Branding Summit generated over $20K in profit and 3,000 new email subscribers.

I quit my part-time job at a bank in Sweden and moved abroad with my girlfriend to Cabo San Lucas, Mexico.

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The month after my summit, I generated $40K in revenue, mostly from affiliate sales of Ramit Sethi’s online course.  

It was a jolting moment in my life that helped me realize the incredible power of becoming a lifestyle entrepreneur.  

Step 8: Grow your audience.

Hosting my first virtual summit exploded my growth, but I realized that they could do a lot more than just jumpstart by business.

As of today, I’ve hosted and participated in dozens of of virtual summits.

One of my more recent summits, List Building School, generated over 26K new email subscribers and multiple six-figures in revenue.

It’s fair to say that the more summits you host, the more you’ll grow your audience, and virtual summits can work at any stage of your online lifestyle business. 

Caitlyn Pyle ran an online membership site where she taught people the ins-and-outs of making money from home.

Business was going well, but she felt that she was missing out on a lot of earning potential.

With her first summit, Caitlyn grew her email list by 60K subscribers and generated $500k in revenue in just two weeks. 

Virtual summits do more than just boost growth and generate revenue…

  • They give you immediate authority by associating your brand with the experts you interview.
  • They build meaningful relationships with industry leaders.
  • They deliver actionable advice to your audience and help you grow an army of loyal fans.

People were so interested about my success with virtual summits that it motivated me to create Virtual Summit Mastery 1.0 in 2015.

Step 9: Focus on what feels right and charge what your worth.

When you offer undeniable value to your target audience, you get to charge what your worth and focus on what feels right.

By the time 2016 hit, I was ready to launch Virtual Summit Mastery 2.0 and acquired tons of new case studies from successful students.

My knowledge of virtual summits became a highly marketable asset to dozens of lifestyle entrepreneurs.

You can accomplish the same thing in any niche.

Brian Appleton used virtual summits to generate $225K in revenue within the first year of his online business as lifestyle entrepreneur in the insurance industry.

Just as it happened for Brian, your income can scale along with the value you provide, and your lifestyle will improve along with it.

In 2016, I traveled throughout the USA to New York City, San Diego, and Austin.

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I lived in Barcelona and Cancun, where I moved into a dream penthouse right on the beach.

My first real affiliate launch for Virtual Summit Mastery brought in $200K in revenue that same year.

I was able to expand my team and further boost my growth.

It was an incredible year where I made over $600K in revenue (with very high profits), and I was crafting a life that would’ve never been possible if I had played it safe and stayed on the lawyer path.

Step 10: Study, Optimize, and Scale

Just because what you’re doing now is getting results, doesn’t mean that you’re getting the best results possible.

You should always be learning, optimizing, and trying your hardest to scale what’s already working.


Because it’s always easier to optimize what you’re doing now rather than starting from scratch.

During 2017 and 2018 I attended many masterminds and events around the world (I even spoke at a few as well)… I made some great relationships, and relationships are a resource that fuels growth even more than revenue.

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But don’t just optimize what’s working for your business, study what’s working for your happiness.

After all, the ultimate goal of becoming a lifestyle entrepreneur is to improve both your quality of life and you income.

The two should improve at the same rate.

Real-World Examples Of Lifestyle Entrepreneurs Who’s Living The Dream

Don’t think that you have what it takes to become a lifestyle entrepreneur?

Think again…

People from all backgrounds have gone on to crush it with their lifestyle business.

There’s no reason to think that you can’t do the same.

Here are some examples of lifestyle entrepreneurs who forged their own path and came out victorious:

1. Natalie Sisson

Natalie Sisson is a New Zealand entrepreneur and the best-selling author of The Suitcase Entrepreneur, where she teaches readers how to use their skills so that they can live life on their own terms.

Lifestyle Entrepreneur Natalie Sisson home page