The 7 Decisions: Become The Ultimate Lifestyle Entrepreneur

lifestyle entrepreneur

Conformity is the jailer of freedom and the enemy of growth.

~ John F. Kennedy

I remember well the first time I was asked:

What do you want to be when you grow up?


Where do you want to go to college?

I was a child the first time I was posed either of these questions, and I – of course – hadn’t a clue as to what I wanted, or how to respond.

Or, when I moved to New York City in 1994:

What will you do there to make money?

(Kinko’s was my first job in NYC, which I promptly quit after 3 days, once I witnessed a colleague loudly berated for mis-stapling a document)

Or, when I needed a place to live:

Do you want to buy or rent?

Followed by a long-winded commiseration over the impossibility of the former and the financial black hole of the latter.

I remember well the water cooler conversations at various day jobs I’ve held, during which I and others would longingly discuss our plans for the weekend and upcoming vacations:

Just two more weeks until my vacation
Thank God it’s Friday!
I live for the weekend

It never felt right to say these things. I would always feel a twinge somewhere in my gut as I spoke. Something inside of me knew that the thinking supporting these comments was off. Somehow, I knew there was another path, an alternative way of approaching life to one where my weeks needed to be endured to get to the weekend or to vacation, when I could really live.

Each of these questions is supported by a mainstream worldview or “paradigm” which is proliferated by the vague, largely unquestioned belief that “this is how we do things.”

That is, for many of us in the western and westernized world: we go to school until our early/mid-20s, settle down somewhere where we rent or buy a home, and get jobs that we hunker down in for years until we can “retire” when we’re older.

That’s the story that we’ve been told (and sold).

But, more and more, people are stepping back and questioning this picture. Is this model really a given? Does it have to be this way?

Is there another way that embraces more freedom, abundance, flexibility and… fun?

Seven broad questions – or decisions – seem to punctuate the mainstream path, and most of us will inevitably face them. Each of the typically binary options presented assumes a well-worn direction, which is what we refer to as the “mainstream” or traditional way of doing things.

None of these classic decisions or their limited answers are “wrong,” as long as they reflect a person’s true wants, values and excitement. But often, they do not. It is common for people to be unhappy with the choices they make within this framework, but see no other option or way out.

Yet, there are infinite options. Now, more than ever before, there are paths and models emerging that present real, viable alternatives to the mainstream choices presented.

More and more, people like you and me are boldly designing lives that consciously question the mainstream path. The common parlance for such individuals is “lifestyle entrepreneur,” meaning one who consciously designs his or her lifestyle. A newly styled creator, of sorts, who prioritizes his or her preferences over the well-worn way of doing things.

So, what are these seven decisions? They go something like this:

  1. Do I attend this or that school?
  2. Do I pursue this or that career path?
  3. Do I settle in this or that place?
  4. Do I buy or rent my home?
  5. Do we get a bigger house or a storage space for all our stuff?
  6. Do I go on this or that diet to “get healthy” and lose weight? (or, do I see this or that doctor to cure me if I’m not?)
  7. Do I subscribe to this or that religion?

The majority of us will face each of these decisions in some form or another in our lifetimes. The questions themselves seem to offer an either/or answer. You either become a doctor or a lawyer. You live in the city or the suburbs. You buy or rent that first home. You try Atkins or South Beach.

For more and more people each day, however, the assumptions behind these questions are flawed. Erroneous. Unnecessarily Limited. They are based on the broader mainstream paradigm that is becoming less and less obligatory.

Now, we can choose differently.

This article aims to present each of these false choices and the alternatives being explored today by trailblazers who are defining their (what we call) ownstream.

~ Do I attend this or that school?

Mainstream: Public or private grade school? College or university?
Ownstream: Home school/road school/world school, gap year, online specialty courses

Does the mainstream educational system actually work?
Do we learn enough in high school or college (about either ourselves or a particular trade) to start a career that will last a lifetime?
Is it ideal to saddle a 22-year-old college grad with a mountain of debt and a career path of which he or she has little understanding?

The college system in much of the western world is structured such that the majority of students have to select a major (which implicates one’s job opportunities post-graduation) at the age of 20 (or, at the outset of one’s junior year). Does anyone actually know what they want to do at that age?

And, is a singular career path even healthy or realistic today? Most of us change our career trajectory many times throughout our lives. Yet, the mainstream path pressures us to follow a very narrow line by hamstringing us with considerable debt, making getting a job priority #1 the day after graduation. And due to this debt, this job is likely to be necessary for many, many years.

When it comes to grade school, the singular, outlier alternative has always been home-schooling. But, technology has now opened up two new models that are very exciting: road-schooling and world-schooling.

They are nearly the same idea, with world-schooling being – as you might guess – international, and road-schooling happening domestically, often in RVs or other mobile living dwellings. Many parents support this lifestyle – which might seem incomprehensible to many who are rooted to the traditional educational system – through online businesses that enable location independence, some of which are grounded in their own story as road and world schoolers.

Is it more useful to learn about Renaissance painting from a worn out textbook or standing in front of the Adoration of the Magi? The act of travel and living in other cultures has constant, experiential learning at its core.

Should one desire more formal training, it is wholly possible to take topical courses online via a multitude of platforms, which can prepare you for a chosen career path., for example, employs industry experts to share their knowledge in various creative and business fields. CreativeLive offers courses in specific creative and artistic niches taught by working experts in these fields.

These courses can be had at great value, and train you on precisely the content you want to learn, rather than requiring you to commit to a 4-year curriculum, which in many cases includes courses outside your interests and is not relevant to or a guarantee of any career in the long term.

~ Do I pursue this or that career path?

Mainstream: Doctor or lawyer? Business path or creative path? For-profit or non-profit?
Ownstream: Muse business, online business, passion business, freelancer

Formal education and work choices have been inextricably linked in our mainstream culture. One goes to school to learn a trade, which one can then apply in the world, exchanging time for money.

With the recent rise of the internet entrepreneur, the notion of career has changed dramatically, however. In Tim Ferriss’ seminal book, The 4-Hour Workweek, he outlines an entirely new paradigm for work. Namely, that one can set up an online business – which essentially runs itself (save 4 hours per week, in his example) – and kicks off enough income to support one’s preferred lifestyle, rendering a standard job or career obsolete.

This “muse” business may or may not be a passion project (an e-commerce business selling t-shirts is one example from the book), but it allows for travel, pursuit of passion projects, and other experiences that can’t be had in the standard day job structure. Most importantly, it enables one to set up a lifestyle and then build a business to serve that lifestyle choice, as opposed to the other way around.

The internet has also enabled many individuals to create coaching businesses around their passions, and to recruit clients from around the world. In support of this path, a fleet of digital marketers has emerged to train these coaches on the art of connecting and selling to clients online.

These businesses don’t require a college education and they can be very lucrative. Entrepreneur, Eben Pagan has created multiple seven-figure online businesses all from his laptop computer and with a virtual team. (BTW – If you’d like to explore creating your own online business, I recommend learning from Eben himself)

Many are opting for a freelance path in which they contract their services to a number of clients, affording a measure of ownership over their time and work location.

Each scenario offers the flexibility to change direction if desired, and to have more control over your time, lifestyle, and location. It is simply no longer necessary to schlep off to an office for all the daylight hours, should you desire something different.

~ Do I settle in this or that place?

Mainstream: The city or suburbs? The beach or the mountains?
Ownstream: Location independence. Travel through Asia building my online business? Woof through South America, working as I go?

Look around you. Do you live near where you were raised? Did you leave your home only to return after, say, college or military service? Interestingly, 54% of Americans live in the same communities where they grew up (according to this report), with 46% moving elsewhere.

Have you ever thought of moving abroad? Many people fantasize about becoming an “expat,” yet only .001% of people do it (3,415 worldwide, in fact, in 2014). Most Americans, therefore, call home someplace rather close to where they were raised, and almost always within our borders. When we do move, it’s usually for career or work reasons – not often for reasons of lifestyle.

Our notion, therefore, of “where” is decidedly local. Most people never move from where they were raised, or they move somewhere else only to find themselves locked in, due to a nearby job.

Experiencing the world, travel and receiving the unique experience of other cultures, then is confined to perhaps our favorite word here in the US, certain to raise the corners of any full-time employee’s mouth:


Usually, one is allowed by their employer a certain number of days each year to take as vacation, after which they must swiftly return to the office. This time frame is usually barely enough to fully exit one’s work life and its stresses, and is often spent counteracting these effects in the form of much needed relaxation.

And due to the advent of the smartphone, many employees have their jobs in their pocket while on vacation – unable to fully unplug due to the ever-expanding role of work in our world. Money must be made.

The model then has people veering from one extreme to the other – severe stress to catatonic on a beach…

Does this sound right to you??

Combine that with the Standard American Diet (SAD), our 60+ hours per week work (and stress) load, and it’s no wonder that we’re a country passing out at the end of the day and dying from heart attacks.

But, the rise of mobile technology and the internet has also allowed for a new, more empowering phenomenon:

Location independence.

digital nomad
Checking email while having lunch in Goa, India.

Freelancers can now work from home or cafes, avoiding the often stressful (and distracting) corporate office environment. Entrepreneurs can build businesses in beautiful places (Thailand and Vietnam currently amongst the most popular).

The wise build businesses that they love, and would do anyway, that are “virtual.” These online businesses (covered above) can allow one to work from anywhere there is a good wifi connection.

And, most importantly, these businesses can be systemized. Software exists nowadays that allows your business to become a system that makes money for you – independent of your time.

Imagine that for a moment – creating a system that simply makes money for you, freeing you up to do what you want.

Most entrepreneurs that we know report that it takes a bit more than 4 hours/week to run their businesses, but many of these businesses begin from a true interest and – this is key – the income they generate is not tied to the number of hours spent working on them (i.e., exchanging time for money in the traditional day job structure).

Given that the ability to build actual wealth online is now a very real factor (which is typically far more motivating than working a job, hoping for a bonus, and…making someone else rich) AND that the work itself is something one is truly interested in, many desire to work as opposed to having to work. 

Huge difference.

This systemized structure allows for location independence, longer-term travel, deeper immersions into cultures and the ability to live and work (on your own time) from anywhere in the world.

On a recent trip to India, for example, I worked with clients via Skype, wrote blog posts, and recorded and uploaded multiple podcasts all from my laptop computer.

The internet has also given rise to other fascinating travel possibilities. Namely – woofing and couch-surfing. In the latter, people can crash with others for a night or two at far less than the cost of a typical hotel (or can housesit for free, as Ownstream podcast guest, Stacey Murphy explains here on Episode 2, time stamp – 50:30). With woofing, you work off your lodging by getting your hands dirty in an organic farm (something many people – including Theresa – WANT to do anyway).

Finally, many hackers have uncovered ways to rack up airline points to travel for free and for cheap, or to upgrade to higher classes of service. The Points Guy, Brian Kelly, has created an entire online business devoted to the subject of points and offers a bevy of creative ways to build these…and often very quickly.

In fact, in 2014, we traveled to – and through – Asia and back to the US completely for free using his tips.

The days of the travel agent are rapidly ending, and more and more people are finding ways to spend more time on the road, experiencing the world, tasting real adventure.

Popular blogger Seth Godin puts it best:

“Instead of wondering when your next vacation is, maybe you should set up a life you don’t need to escape from.”

~ Do I buy or rent my home?

Mainstream: Buy or rent? Fixed rate vs. adjustable mortgage?
Ownstream: Tiny house or RV? Refurbish a van, bus or RV for extended living/travel?

One of the few non-negotiables in any lifestyle paradigm is the need for shelter. But, is it mandatory that it be a dwelling situated in one location that one rents or incurs long-term debt to support in the form of a mortgage?

Enter the tiny house (or tiny house on wheels, aka THOW). Tiny houses are usually somewhere between 200-300 square feet, are often built by the residents, and typically rest upon a towable trailer, enabling movement and travel.

These homes are certainly cozy, but allow for tremendous customization and creativity. Because there is little space, every inch is maximized and utilized. Given the low cost of building and owning a tiny house, residents often have the freedom to design and furnish their tiny homes with top line appliances, furniture, and other items.

tiny house on wheels
This THOW was designed and built by, neighbors of ours here in Southern California.

The thinking behind a tiny house is to create a personalized home that is to scale with what we truly need to live and thrive. In our addicted society, it is very easy to default into the thinking that “more is better” and, in the realm of homes and living, “bigger is better.” As those who once lived unhappily in 2,000 sq. ft. homes and went tiny will tell you, neither is necessarily true.

Tiny houses bring families together, often creating stronger connections while – in many cases – eliminating the need for a mortgage or monthly rent payment. Many individuals are even now converting old school buses into moveable homes.

If building your own home is not appealing to you, check out one of the many prefab tiny home sites that have risen to meet this market, or the growing population of people moving into residential vehicles (RVs) and vans (yes, vans). One of the more amazing hashtags on Instagram is #vanlife. Our pal Tynan (Ownstream Podcast guest #3) lived in his RV for many years, which limited his accumulation of “stuff”, and forced him to focus on what was truly essential.

Most of the time, people making the shift from the mortgage/rent paradigm to one of these more nimble and mobile options are doing so by choice, not because they cannot “afford” the other. Many are waking up and realizing that their money and resources should go towards experiences – toward living – rather than towards accumulating things.

In Tynan’s case, for example, while living in an RV in San Francisco, he traveled half the year (or more), living and working from all corners of the globe, opting to cultivate his most precious resource for the experiences he truly desired in life. That non-renewable resource?


~ Do we get a bigger house or a storage space for all our stuff?

Mainstream: How many pairs of shoes/shirts/dresses can I fit in my closet?  Where can we store all the toys/gadgets/kitchen stuff we don’t use anymore?
Ownstream: Can I get one or two awesome pair of shoes that I love? Can I get one awesome jacket? Can I reduce my “stuff” down to what I actually need?

We live in the age of consumerism. From where we sit right now, working in a cafe in downtown Encinitas, CA, we can see outside the window a multitude of signs and businesses appealing to us to come in and spend money on things.

A few years ago, we chose to eliminate much of our clothing, books and other things simply because we didn’t need or want them. They were just “there” taking up space. Often these things had been impulse buys, or gifts we had received (and never truly wanted) that we guiltily held onto, when we could have given them to someone who actually wanted or needed them. The things that fill your closet or drawers not only take up physical space, but mental/emotional space and energy as well.

A pivotal moment for us was when we traveled through Asia for 3 months in 2014 with only 24 liter backpacks (the size of your average high school backpack):

digital nomad
Theresa in Koh Lanta, Thailand, with the two backpacks that contained everything we needed for 3 months of travel.

It was extremely freeing to know that we did not need more than a few shirts, pants, socks and a jacket for months of living, including a variety of outdoor activities, and climates ranging from the tropical beaches of Thailand to the cool mountains of Nepal.

Since the trip, I have successfully minimized my wardrobe to 5 pairs of pants, 5 dress shirts, 4 t-shirts, 2 blazers, one jacket vest, one light jacket and one rain jacket. I own 4 pairs of shoes, each for a very specific and unique purpose. I LOVE each of these items, feel great in them, and adore wearing them out into the world.

Minimalism is a growing trend, first popularized (at least to us) by Leo Babauta and his most excellent blog “Zen Habits”. Minimalism is a movement not away from things or “stuff,” but towards more freedom, choice and flexibility. It’s not about a poverty mindset, as many minimalists opt for buying very high quality items that they truly love.

For many, it starts by asking a few tough questions:

Does this “thing” add value to my life?
What do I truly need?
Do I really want this?

For many, the choice is to eschew material goods for the ability to be lighter and more flexible. To be able to travel with a backpack, rather than weighed down by multiple checked bags. To have open space at home rather than common clutter.

The market has responded. There are now a multitude of brands that have emerged that offer stylish clothing that doesn’t need constant washing or (even worse) dry cleaning. These clothes are easy to pack, can be worn in various conditions and… they look and feel AWESOME.

Here are just a few:

Mizzen & Main (men’s shirts)
Wool & Prince (men’s shirts)
Icebreaker (men’s/women’s activewear)

Minimalists realize that they can have everything they need and want without being overloaded to the point of excess and without sacrificing their values of freedom and flexibility.

There is considerable crossover here with the tiny house movement and its essential question: what do we really need? Think about your stuff and your home: how much time is spent working a job you don’t even like just to pay for these things? Does that seem right?

For many, the answer is no.

~ Do I go on this or that diet to “get healthy” and lose weight? (or, do I see this or that doctor to cure me if I’m not?)

Mainstream: Atkins or South Beach? Cardiologist A or B?
Ownstream: Embrace a lifestyle that is inclusive of healthy, whole foods, not a fad diet

The Standard American Diet (aka, SAD, which has spread throughout much of the modern world) is primarily made up of processed foods, animal products (meat and dairy), sugar, caffeine and very little actual food — and specifically, very few fruits and vegetables.

The usual pattern, unsurprisingly, is to gain weight, feel bad, then look to some trendy, fad, and often extreme and unsustainable diet to shed the pounds. This choice often has very little to do with optimal health and is more about satisfying vanity and appearance in the short term. Usually, these diets – and the much-desired results – don’t last.

So, we oscillate back and forth, eating the standard western diet, gaining weight, then adopting a drastically different fad diet to shed the excess pounds only to then return to the original diet that caused the weight gain in the first place.

Alongside this feeding frenzy is a corresponding increase in the experience of chronic disease and death directly tied to this diet. Cancer, heart disease and diabetes are the main culprits – all of which have dietary causes and solutions. Our medical system “treats” these diseases by addressing the symptoms (carving out tumors, removing arterial plaque, and adjusting insulin levels with medication), not by addressing the root cause (or therefore providing any long-term cure)…

Our diet.

Powerful, alternative lifestyle diets have emerged that not only allow for a fit physique and appearance but also promote long-term health. We refer to these as “lifestyle diets”, as they are meant to be lived for the long term rather than used periodically to lose weight. Two of the most popular are:

The Paleo Diet
The Whole-Foods, Plant-Based Diet (WFPB)

These diets differ along their respective views of animal products – namely, meat. We are whole-foods, plant-based ourselves and find the diet immensely helpful in feeling good, maintaining a powerful and consistent high level of energy, focus and more.

They are similar in that they promote the consumption of real, actual food and a massive reduction in sugar intake – a hugely unhealthy eating habit in our society.

The whole-foods, plant-based diet was made popular by the superb film, “Forks Over Knives” which features the pioneering work of Dr’s. T. Colin Campbell and Caldwell Esselstyn who, independent of each other, arrived at very similar solutions to our western health woes.

Whole-foods plant-based diet
We had the pleasure of meeting Dr. T. Colin Campbell at the NYC showing of “Plant Pure Nation”.

Namely, that the western diet, filled with meat, dairy and processed food is the primary driver of cancer (Campbell) and heart disease (Esselstyn) and that adopting a whole-foods, plant-based diet has the power to prevent, stop, and even reverse these fatal diseases. This film can be viewed streaming on Netflix anytime you like. There are plenty more of these films too…

Change in this area begins by taking a hard look at one’s eating habits and the world around us. Do we seem like a healthy, thriving population? To what can we attribute the rise of chronic disease (mainly in the west)? How are our dietary choices affecting our environment? And, perhaps the most important:

Do I feel good?

It’s easy to begin making changes in this area. And it always starts by eating more whole foods. From here, feeling good tends to create its own momentum leading to more healthy, conscious decision-making around what we choose to put into our bodies on a daily basis.

~ Do I subscribe to this or that religion?

Mainstream: Am I Christian, Muslim, Buddhist? Where should I attend church this Sunday?
Ownstream: Where can I learn meditation? What spiritual path speaks to me? How can I daily connect with God or a higher power? How do I follow my excitement today?

Which leaves us with spirituality and religion (perhaps the most important).

For many of us, spirituality is an essential aspect of who we are and how we live. It offers both community and a “code” for living that helps guide our decisions, actions and relationships.

In the west, God is largely experienced via the lens of church. Typically, we head off for an hour or so on a Sunday to learn about God and scripture, and for a dose of community. Sometimes, our practice and connection with something greater than ourselves is limited to that one hour a week.

Church sometimes comes fraught with limiting, punishing rules and lingo that is more about what we can’t do rather than what we can. Too often, these institutions preach a gospel of fear, which to many seems dated and irrelevant in these times.

Not all churches function this way. In fact, we know many people who go to a traditional church and are thriving, happy and living vibrant lives. So, it’s not about church as much as it is about the obedient “duty” to join and attend one without contemplating whether that particular path and faith is what one truly wants, believes in, and resonates with.

Fortunately, now – more than ever – there are a bounty of choices in terms of where and how we worship, connect and celebrate God, spirit, the universe.

Yoga studios offer a glimpse into the vast connection between spirit and the body. Meditation classes reveal our monkey mind – so dominant in western culture – and what lies behind and beyond it.

In the last 20 years or so, the law of attraction has emerged as an alternative way of viewing the universe, God and our position within this vast cosmology. Instead of eschewing desire, we now learn to embrace it. Rather than viewing the world as a place of limit and lack, we are shown abundance and empowerment. 

Each spiritual path comes with community, enabling us to connect with others who share a similar view and who can support our individual path.

Spirituality is no longer separate from our outer lives. More and more, people are waking up to the fact that we create our own realities and that our inner lives show up on the outside.


These seven focal life decisions now present a vast array of alternatives. And, by the time you are reading this, there are almost certainly more options to choose from. These new paths and paradigms are not being driven so much by a desire to exit the mainstream as they are an innate, intuitive wish for more empowerment, abundance and freedom in life.

Knowing about these options, many continue consciously to choose mainstream solutions – but willingly so, because something about those choices excites and fulfills them, not because it’s the only way to live.

Each of us as individuals is able now to create a life of more and more freedom and forge something truly our own. The cookie cutter mainstream is not the only design.

Most who question one area of the prescribed map, eventually question them all. The Ownstream Podcast is meant to be a place where these individuals are featured and elevated so that you can learn their creative solutions to the challenges that life presents.

It’s truly an exciting time to be alive. It has never been easier to live in a way that harmonizes with our desires and values. Doing so usually begins with a choice to do something differently. Perhaps differently than your parents did it, or than your friends and family are currently doing it, but a choice to approach life devoid of the notion that there’s one way to do this.

There are many ways and you get to choose.

Your move.

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