As an employee, your job dictates your life.
When you get up in the morning, what you must work on, which people you spend your day with — all of that is determined by your 9-to-5 prison.
Lifestyle entrepreneurs question that paradigm. They believe that your job should enhance your life, not worsen it.
Learn about the benefits of lifestyle entrepreneurship, what business options you have, and how you can make the transition.
Definition: What Is a Lifestyle Entrepreneur?
For most corporate drones, work comes first. Their personal life is an addendum.
For a lifestyle entrepreneur, it’s the other way around. They create a business to serve their personal lifestyle.
A typical example would be someone selling courses online.
Unlike a corporate drone, you don’t have to abide by office hours, do nonsense work, and put up with annoying colleagues.
Rather, you can set your own hours, work on projects that interest you, and choose your own team members.
Generally speaking, lifestyle entrepreneurs value experiences over profit. They would rather go surfing for two hours each day than bring home a big paycheck.
That doesn’t mean that profit is out of the question. I have met some highly affluent lifestyle entrepreneurs over the years. But for them, wealth was a byproduct, not the goal.
Lifestyle businesses usually take place online, as this allows for location independence. As long as you have an internet connection, you can work from wherever.
This criterion is not set in stone, though. For example, I have a friend who is running a local martial arts gym. The business completely supports his personal inclinations. In my book, he is still a lifestyle entrepreneur.
The 3 Types of Lifestyle Businesses
There are three competing models of lifestyle businesses:
- The Passive Income Model
- The Passion Hustle
- Hybrid Models
Let’s examine what each model has to offer.
1. The Passive Income Model
Tim Ferriss, in his 2007 book “The 4-Hour Workweek,” champions a passive income model, what he calls a “muse.”
A muse is an automated cash cow. You set it up once and then spend little time maintaining it (supposedly only four hours per week).
An example would be a dropshipping business. You could be selling iPhone cases via your website, and then let another company do the fulfillment for you.
With all that free time, you can then focus on the things that truly excite you, like competing in the world kickboxing championships in China or studying tango in Argentina.
So, the idea is to keep your moneymaking activities separate from your passions in life. Your business is just a means to an end.
2. The Passion Hustle
There is another camp of lifestyle entrepreneurs arguing that your business should be completely based upon your passion in life. Their most well-known spokesperson is Gary Vaynerchuk.
According to Vaynerchuk, the notion of passive income is a pipe dream (I agree with that assessment). If you want to make it as an entrepreneur, you must put in the hours.
Hence, it’s best to do something you are truly passionate about since you’ll have to do it nonstop anyway.
As a result, work stops being a chore. You start looking forward to it.
Let’s say you are passionate about shredding. So, you start a YouTube channel to teach aspiring guitar heroes. You then monetize through paid memberships.
With the passion hustle, your business is not a means to an end; the business is the thing.
3. Hybrid Models
Finally, there are hybrid models.
Here, someone starts a business based on their passion but also keeps the workload relatively light, like the Tim Ferriss model.
As a digital nomad, this is the model that I observe the most during my travels.
Living in a cheap country like Thailand, someone might work for 3–4 hours on their YouTube channel, then spend the rest of their day training Muay Thai or partying it up.
The upside is the fun factor.
The downside is that this model doesn’t provide much financial security. Most hybrid entrepreneurs make just enough to cover their expenses but have no reserves to fall back onto.
Lifestyle Entrepreneurs vs. Traditional Entrepreneurs
So far, we have only talked about how lifestyle entrepreneurship compares to a 9 to 5.
But how do lifestyle entrepreneurs differ from traditional entrepreneurs (founders, small business owners, etc.)?
Here is a quick overview.
| Traditional Entrepreneur | Lifestyle Entrepreneur |
| Is not passionate about what they offer | Is passionate about what they offer |
| Rents a brick and mortar business | Works remotely |
| Tends to be less technology-savvy | Tends to be more technology-savvy |
| Listens to the market | Listens to their ego |
| Is motivated by a strong work ethic | Is motivated by hedonistic impulses |
| Often depends on funding | Is usually bootstrapping |
| Hires full-time employees | Hires freelancers |
| Aims to make more than they spend | Aims to just cover their expenses |
As you can see, both models have their pros and cons. As a lifestyle entrepreneur myself, I think there is a lot to learn from traditional entrepreneurs, especially when it comes to work ethic and financial foresight.
Typical Jobs
Some typical professions for lifestyle entrepreneurs include:
- Copywriter
- Ghostwriter
- Blogger
- Self-published author
- Traditional author
- Graphic designer
- Website designer
- YouTuber/vlogger
- Podcaster
- Social media influencer
- E-commerce shop owner
- SEO specialist
- SEA expert
- Social media manager
- Marketing consultant
- Developer
- Life coach
- Affiliate marketer
- Stock market investor
- Real estate agent
- Athletic coach (fitness, yoga, martial arts, etc.)
- Fashion designer
Benefits
Here are some of the benefits that you will enjoy as a lifestyle entrepreneur.
More Time With Loved Ones
As a lifestyle entrepreneur, you are free to attend your child’s soccer game or take your mum out for lunch.
You can be there for your loved ones. This means fewer regrets down the road.
More Spontaneity
When your friend calls you and says, “Let’s get ice cream at the beach. I’ll pick you up in 10 minutes,” you’ll be able to go.
More Control
With a 9-to-5 job, you have little control over your work. Your hours, your colleagues, the projects you get — all of that is determined by “the man.”
Not so for the lifestyle entrepreneur. You make the rules.
Performance-Based Compensation
While Dave from accounting is playing fantasy football all day, you are putting your shoulder to the wheel; yet you both get paid the same.
Being your own boss remedies that. If you put in more effort, you will earn more. If you want to take it easy, you will earn less.
Whatever you choose, it’s fair.
Free Allocation of Time
With a lifestyle business, you can flexibly allocate time from one area of life to another.
Let’s say you always dreamed of getting your pilot’s license. So, for the next 6 months, you cut back on work to learn how to fly an airplane.
Vice versa, you might be set on taking your business to the next level. So, for the next year, you put in 60 hours per week.
It’s up to you where your time goes.
Better Experiences
Studying ikebana in Japan? Shark diving in the Red Sea? Training Muay Thai in Thailand?
You don’t have to keep putting off these experiences until it’s too late. You can have them now.
More Passion
When you turn your passion into your job, you stop dreading work. Rather, you start looking forward to it.
I remember my first passion business, teaching BJJ for a living. Rarely would I ever think, “Damn, it’s 6 pm again. I must go teach jiu-jitsu now.”
On the contrary, most days, I would be giddy with anticipation.
More Personal Growth
With a traditional 9-to-5 job, you usually get paid to do one thing and one thing only. Nobody cares much for you branching out.
However, as a lifestyle entrepreneur, you are free to explore new skills, like learning digital marketing or project management. You can make your work about your personal growth.
Location Independence
By starting an online business, you are no longer bound to a certain geographical location. It does not matter if you work from your home office in North Carolina or if you are sitting at a beach café in Vietnam.
You can experience everything the world has to offer.
Setting Your Own Hours
As a lifestyle entrepreneur, you are free to set your own hours. The only thing that matters is that the work gets done.
This allows you to work when you are most creative. For some people, that will be 7 o’clock in the morning, for other people, that will be 3 o’clock at night.
It also allows you to schedule around important events. If your daughter’s birthday falls on a Wednesday, you can still spend the day with her, and do your work before and after.
Efficiency Over Hours
Employment emphasizes time over efficiency.
For 40 hours each week, you must show your face at the office. But nobody cares much about what you get done during those hours.
With lifestyle entrepreneurship, it’s the other way around.
If you can create lots of high-quality output in 20 hours per week, that might very well suffice.
No Income Ceiling
With a 9 to 5, there is a limit to what you can earn. Even as a highly qualified specialist, you are unlikely to make more than $200,000.
Lifestyle entrepreneurs have no such income ceiling. If they choose a scalable business model and are willing to put the work in, the sky is the limit.
Choosing Your People
As an employee, you don’t get to choose your coworkers. You are stuck with whoever is already there. This often results in office drama.
With a lifestyle business, you can handpick the freelancers you want to work with; not just based on their qualifications, but also on their personalities.
No Commuting
Each day, the typical office drone spends about an hour in their car, getting upset at the traffic. That is a giant waste of time.
When you work for yourself and don’t need to commute, you can invest that hour more wisely, e.g., in working out or learning a new language.
How To Become a Lifestyle Entrepreneur
Do you dream of becoming a lifestyle entrepreneur? Here is how to make it happen.
1. Define the Parameters
The first step is to get clear about what type of life you want to live.
For example, do you want to travel the world? Do you want to do volunteer work? Party a lot? Seek enlightenment?
A helpful exercise can be to imagine your ideal day. Ask yourself what your perfect life would look like on an everyday basis.
Are you getting up early or late?
Are you in the city or the countryside?
Are you living a solitary life or do you have lots of friends around you?
Are you living a minimalist life, spending little? Or are you throwing your money around?
Once you have come up with your daily routine, you can then extrapolate your ideal lifestyle.
2. Identify Your Passion
I always recommend starting a passion hustle. Here, you base your business model on what you are excited about in life.
However, many people have a hard time figuring out what their passion is.
These four strategies will help.
First, imagine what you would do if there was no chance of failure. Would you tour the world playing music? Become a professional surfer? Write the next great American novel?
This thought experiment is fantastic for stretching your imagination beyond its current limits.
Second, understand that your passion has already manifested itself; you are just not aware of it.
Maybe you always enjoyed doodling as a child and then later did graphic design for the student newspaper. And even now, you always end up at a museum on the weekends. Guess what — your passion is related to visual art.
Unfortunately, it’s much easier to identify these patterns from the outside. The trick then becomes to interview people who know you. They will quickly see through you.
Third, understand that nobody gets it right the first time. You come up with a hypothesis about your passion in life, then try it, only to find it was a little bit off. So, you modify your hypothesis.
This is how you get there — by making mistakes and course correcting.
Fourth, have the courage to pursue your own dreams. If your parents always imagined you as a doctor, but you want to be an adult movie star, go ahead and start that OnlyFans channel. Happiness, to a large extent, is the ability to overcome social expectations.
3. Get a Reality Check
So far, we have only talked about what you desire. But you must also consider your limitations.
Here are six questions you should ask yourself.
a) “What value can I provide?”
For example, you might dream of becoming a social media influencer. But if you are fumbling for words as soon as a camera is pointed at you, that won’t happen any time soon.
Note: I am not saying you can’t get there. If you dedicate the next 5 to 10 years to perfecting your craft, you can become almost anything. But you need to have a realistic notion about where you are currently at.
b) “Is there a market for what I want to do?”
There is no point in starting a business if there is nobody willing to buy from you. Fortunately, with the advent of online businesses, this is a smaller problem than it used to be. Since your audience is now the world, at least some people are bound to like your stuff.
The question now is more about how big or how small that market is, and if you are comfortable with that size. Which brings me to my next point.
c) “How much money is in my chosen activity?”
The more obscure your market, the less money you’ll make.
That is not necessarily a bad thing. If you are okay with earning relatively little from something you are absolutely in love with, you are golden.
But if you are not, you might have to compromise on your passion a bit and go for a broader audience.
d) “What can I keep doing without growing tired of it?”
In order to succeed with anything, you need to have staying power.
This is especially true for passion-based businesses. Many more people dream of becoming musicians than of becoming accountants. Hence, the competition will be much more fierce in the music industry.
If you can’t see yourself investing most of your time into your passion, it is probably not your passion.
e) “Am I good with self-responsibility?”
Being an entrepreneur means taking radical responsibility for yourself.
You cannot rely on your colleagues or your boss anymore to clean up after you. You can also not rely on the system anymore, e.g., for health benefits or your 401(k).
Everything is up to you now. Whatever you want, you need to make it happen yourself. Whatever goes wrong is your fault.
Can you handle that?
f) “Am I okay with social isolation?”
Especially during the first few years of your journey as a lifestyle entrepreneur, you will have to put a lot of hours in.
That means you will have little time to spend with family and friends — even less time than you currently have with your 9-to-5 job. As they say, it will get worse before it gets better.
Can you deal with this kind of social isolation?
4. Do Your Market Research
You need to get a clear idea about who your customers are.
The first step is to create content around your passion. Once you have posted a certain number of articles or videos, people will start to get in touch with you.
When they do, always engage. Write back and forth with them. Better yet, hop on a video call with them.
The goal is to get an idea of who they are — their backgrounds, their values, their desires, their fears.
Based on these interactions, create customer personas. Be as specific as possible:
- Give each persona a name.
- Determine their age.
- Determine their gender.
- Determine their level of education.
- Determine their desires.
- Determine their pain points.
- Create a visual avatar for each persona, so you can actually look at them.
From now on, always take these personas into account, so your marketing efforts don’t fall flat.
5. Choose Your Business Model
There are three ways you can make money as a lifestyle entrepreneur:
- Selling a service
- Selling a physical product
- Selling information
Let’s say your passion business is about fitness.
You could work as a personal trainer (=service), you could sell fitness equipment online (=physical product), or you could create a video training course (=information).
I always advise people to get started with services, as it is the quickest way to create cash flow.
If you sell something like copywriting, graphic design, or programming, you can literally start earning today, even without prior experience. That’s how much of a demand there is for these services.
Also, the skills you learn from running a service business will nicely transfer to a product-based or an information-based business model. In this sense, a service business acts like a well-paid internship.
One caveat — when I am talking about selling services, I am not talking about coaching.
Even though coaching is technically a service, it doesn’t sell like one. In terms of marketing, it is closer to an information-based business. That means you need to build an audience first, which is much harder to do.
If you want to learn more about setting up a service business, I have a free in-depth guide.
6. Get Your Marketing in Order
When it comes to starting your own business, people talk a lot about how you need to have a business plan, secure funding, get the right software tools, find the best tax advisor, etc.
I say most of these things don’t matter initially. The only thing that truly matters, the thing that will make or break your business, is that you get your marketing in order. If you have no paying customers coming in, you have nothing. Hence, focus all your energies on that one area, then worry about the rest later.
That being said, marketing is complex and it is hard. If it wasn’t, everybody would be making bank.
So, there is no way to explain successful marketing in just a few short paragraphs, not least because it’s highly dependent on your target audience and your business model.
There are a few hard-learned lessons I can pass on to you, that will save you a lot of time:
Don’t have too many irons in the fire. That is by far the biggest mistake I see — people are trying to do everything at once. Instagram. TikTok. Facebook groups. Google ads. Blogging. Vlogging. SEO. This is a recipe for disaster. If you are trying to do everything at once, you will not reach critical mass anywhere. Pick one channel, the one that is most likely to resonate with the audience. Then give that channel your all, until you start seeing results. Only then do you add another channel.
Don’t be too vanilla. Trying to please everybody is never going to work out; you are always going to offend someone. Also, it makes you look fake and disingenuous. It is much better to show yourself as you are to your customers, even at the risk of potentially alienating a significant portion of your audience. But those few who stay will be loyal to you forever. Quality over quantity.
Choose organic over paid traffic. Most lifestyle entrepreneurs have limited funds to start with. Instead of wasting that money on paid traffic, start creating high-quality content regularly which will eventually result in organic traffic. Not only will you pay much less per lead, but your leads will also be of higher quality.
Play the long game. Despite what I just pointed out, most lifestyle entrepreneurs don’t produce content (or not nearly enough). For one, it is tiresome; but even more so, it requires patience. When you start blogging or vlogging today, you can’t expect to see real results before two or three years have passed. That is way too long for most people to wrap their heads around. But if you are one of the few people who can, you will eventually surpass most of your competition.
7. Be Realistic
There is a major hurdle that I have observed with most lifestyle entrepreneurs I have ever met (including myself). And that hurdle is entitlement issues. We think we don’t have to work hard, but should still be able to enjoy all kinds of luxuries and privileges.
That should really come as no surprise. Naturally, the benefits of a lifestyle business attract hedonists.
Here is a little anecdote to support this point. Whenever I travel to a new place, I join the local WhatsApp group for digital nomads. And it’s always the same panorama — 90 percent of all threads will be about the best places to brunch, the best places to rent a yacht from, the best local yoga studios, the best ice-bath meetups, the best clubs, etc.
It becomes obvious real fast that most of these people are not serious about work. They might pretend to be, but the reality of how they spend their time looks different. They are in full-on holiday mode.
I am not arguing for forgoing pleasure. I’m a lifestyle entrepreneur myself, after all. But you need to understand that in order to make real money, you need to hustle, especially during the early stages of your business. If you think that’s compatible with going surfing every day, hanging out at the beach bar at night, and hooking up twice a week, think again.
There is nothing wrong with these activities. If you feel they are worth it and you are okay with having little financial reserves, you are doing the right thing. But don’t become one of the many lifestyle entrepreneurs who think they can “hack” their way to wealth while not having to compromise on the fun. That is wishful thinking.
That being said, it is not a black-and-white thing. There are many shades of gray. As a lifestyle entrepreneur, you really can allocate time from one area of your life to another. One year, you might go all in on one work, and the next year, you might only do fun stuff. During other years, you might prefer some kind of mix.
All of these are legit choices. Just realize that you get out what you put in. And acknowledge that at least during the early years of your business, work will have to take precedence.
8. Find Support
I highly recommend that you find other people to connect with over lifestyle entrepreneurship.
That is for two reasons:
- Accountability
- Community
During the early stages of your journey, it will be hard to make yourself do all the hard work. Until now, as a corporate slave, you were just following orders. Also, there were other people around you doing the same thing, which helped with compliance. And as soon as the clock struck five, you could forget about it all and go home.
This fundamentally changes once you become a lifestyle entrepreneur.
Suddenly, you have to make all the hard decisions. If you are wrong, you don’t earn. Also, there is no group of colleagues you see every day to exert peer pressure. You must muster the discipline to put in the hours every day all by yourself.
On top of that, during the early years, you will sometimes have ungodly amounts of work to deal with. Think 12-hour days, working the weekends, and even the occasional all-nighter. And finally, you will always be tempted to just ignore it all and go hang out at the beach like all the other cool digital nomads.
That is a difficult situation to navigate all by yourself. Hence, why you should join an accountability group (or even consider hiring an accountability coach). By setting a certain quota for yourself, e.g., the minimum number of hours you have to work each day, and reporting back to your accountability buddy, you make sure things get done.
You might want to join a community of other lifestyle entrepreneurs, not just to hold you accountable, but also to deal with the loneliness that every entrepreneur experiences, especially the traveling kind.
Think about it — how many lifestyle entrepreneurs did you know before you started looking into this? Probably very few. Even with the rise of remote work, it is still a rare mode of living. This means there will be very few people currently in your life who know about your struggles firsthand.
As a traveling entrepreneur, this disconnect becomes even stronger. Now you are constantly in new places, always having to build your relationships anew. It can feel exciting, but also exhausting at times.
There are ways around this, though. Online communities of lifestyle entrepreneurs like the “Dynamite Circle” (terrible name) provide a certain consistency. On top of that, many of the members regularly arrange to meet in different cities all over the world, so that you end up seeing the same people in person as well. It is a surprisingly workable model.