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
- Freedom
- Flexibility
- Autonomy
- 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.
Table of Contents
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.
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.
“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.
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.
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.
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.
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.
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.
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.
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.
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.
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?
- First, you have to know yourself incredibly well.
- Second, you need to decide what you’re good at so that you can use it to provide value to others.
- 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.
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.
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.
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:
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:
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 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…
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.
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…
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.
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.
Why?
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.
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.
Roughly eight years ago, Natalie left the high-paying corporate job that was sucking the life out of her.
After briefly working for a startup, Natalie decided to start her own lifestyle business.
In April of 2010 she went all-in to work full-time on her blog, The Suitcase Entrepreneur.
Natalie now lives on her dream property in New Zealand, travels the world, and is a sought-after speaker.
The best part is, she gets to prioritize her life according to what matters most:
Did I mention that Huffington Post named her one of the 50 Must-follow Women Entrepreneurs of 2017?
Most of these accomplishments wouldn’t have been possible if she’d stayed at that corporate job that was stifling her creativity and making her miserable.
2. Chandler Bolt
Chandler Bolt started his lifestyle entrepreneur journey the same year as I started mine.
In 2013, he was a 21-year-old sophomore at the College of Charleston.
Like most college students, he was staring down the barrel of several years of school, a lot of debt, and no promise of seeing any returns on his investment.
That same summer, Chandler and his business partner wrote their first self-published book called The Productive Person.
The first month after publishing the book in November 2013, it brought in $7k and continued to steadily earn $2k-$5k a month.
Chandler delayed dropping out of school until his junior year, and later went on to found The Self Publishing School.
Today, his business is arguably the world’s leader in online education for writing and self-publishing books, but this wasn’t always the case.
Prior to hosting virtual summits, The Self Publishing School was doing well, but Chandler knew it wasn’t living up to its full potential.
His first virtual summits did incredibly well.
Between two summits, Chandler brought in 60K new email subscribers and $700K in revenue.
The Self Publishing School went from a low six-figure business to a multi-million dollar business thanks to the exponential growth that came from his summits.
3. Ryan Lee
Ryan is an excellent case study of someone following their passion, knowing their audience, and building a loyal fanbase.
He’s the lifestyle entrepreneur, speaker, best-selling author, and personal trainer behind RyanLee.com.
Ryan had grown a solid client base as a personal trainer before taking his knowledge online with his first website back in 1999.
Eventually, he grew his site into a six-figure membership site, then a multi-million dollar publishing business.
In one of his most successful books, Passion to Profits, Ryan shares the insights he learned from his own entrepreneurial journey.
It just goes to show what can be accomplished by buckling down, working hard, and serving the right audience through the power of the internet.
Ryan is now focusing mostly on his new nutrition company called Rewind which is on track to become an 8-figure online business already.
4. Stu McLaren
Some people take the “lifestyle” side of lifestyle entrepreneurship to the next level.
Stu McLaren is one of them.
I’m doing my best to keep up with his wild adventures by skydiving and zip-lining, but he’s got quite the impressive list of fun accomplishments:
Is this guy even real?
Today, Stu is a coach and consultant for high-level experts who want to further grow their businesses while improving their quality of life.
He’s a master at helping people turn their knowledge into recurring revenue and scaling it into seven and eight-figure membership sites (he’s also the creator of the TRIBE course).
Back in 2008, Stu co-founded the world’s most popular membership site platform for WordPress (WishList Member). During that time, he learned how to consistently keep members coming back every month.
Stu’s a guru when it comes to profitable online businesses around your ideal lifestyle.
Take what Stu did for New York Times best-selling author Michael Hyatt:
The best part of of Stu’s success as a lifestyle entrepreneur?
He’s realized that the more money he makes, the more impact he can have on world.
Since 2009, Stu’s helped build schools across Kenya and housed thousands of kids.
Becoming a lifestyle entrepreneur gives you the killer combo of more money and more time, so you can accomplish your philanthropic goals.
5. Lewis Howes
Sometimes being in a tough spot is the best time to make a big change, and in 2008, Lewis Howes was in a tough spot.
His professional football career came to a screeching halt with a severe wrist injury.
With no back-up plan or savings, Lewis ended up sleeping on his sister’s couch for a year.
What Lewis did have, though, was a laptop and the internet.
Lewis networked like a maniac on LinkedIn until he found a job in the sports industry, but as he continued to network online, he realized that there was a lot more potential than just finding a job.
As he mastered online networking, he realized that he could teach people how to do the same.
Lewis learned how to make money online with podcasting, books, videos, online courses, virtual conferences, and public speaking.
Just three years after sleeping on his sister’s couch, he built a $2.5 million/year lifestyle business around helping other people become successful online.
Not only has Lewis been able to excel financially, but he’s also been able to return to high-level athletic competition as part of the USA Men’s National Handball Team.
6. Lost LeBlanc
Canadian travel-enthusiast Christian LeBlanc has made a living out of connecting with people through the stories he tells on social media.
He loves traveling, taking pictures, and traveling more than anything, so he took his passions and turned them into a profitable lifestyle business.
The idea of entering the corporate world after college made him cringe, so instead of hitting the job boards, he hit the road.
Just a couple of short years later, LeBlanc has a profitable online travel business.
He travels around the world documenting his journeys on Instagram (lostleblanc) and YouTube (Lost LeBlanc).
LeBlanc blew up on Instagram when he grew his account from 700 followers to 30K followers in just seven months.
Leblanc’s Insta-success came from:
Roughly 5-6 years after his initial success, Leblanc’s YouTube channel is fast-approaching 2 million subscribers.
In this video LeBlanc breaks down exactly how he makes money online with social media:
LeBlanc’s secret sauce to success?
He creates personal connections through his storytelling.
When people feel connected to your content, they follow it.
7. Steph Gaudreau
Steph was a school teacher for over a decade when she started her first blog to document and share her mountain biking adventures.
Every once-in-a-while, she’d post a recipe or two.
People loved her paleo recipes, and with the encouragement of a friend, Steph decided to create a blog about the paleo diet called Stupid Easy Paleo.
When Steph’s blog was a year old and still not making any money, she decided to go all in and quit her teaching job.
She struggled to get early traction with traditional digital marketing and SEO tactics, and during her research she came across virtual summits.
Steph new that hosting summits had a ton of potential, but interviewing a bunch of experts in a niche as competitive as health and nutrition seemed like a long shot.
With a little effort, I was able to convince her otherwise, and she enrolled in Virtual Summit Mastery.
In the end, she gained nearly 20K new email subscribers and sold over 600 all-access passes to her first summit.
Steph’s lifestyle entrepreneur journey has now migrated to her personal brand website StephGaudreau.com.
She enjoys an incredible work-life balance and still loves teaching others how to get healthier and live a more fulfilling life.
Your Next Steps: Get Started To Become A Lifestyle Entrepreneur Today
Are you ready to take the first steps towards becoming a lifestyle entrepreneur?!
Ultimately, your product or service has to help your audience solve their biggest problems.
If you scratch their back, they’ll scratch yours by supporting your business and transforming your life.
FAQ: Top lifestyle entrepreneur questions answered
What is a lifestyle entrepreneur?
A lifestyle entrepreneur is someone who prioritizes personal fulfillment and a desired lifestyle over traditional business goals.
They build a business that aligns with their passions, interests, and values, allowing them to have more freedom and flexibility in their life.
