Are you sick and tired of your 9-to-5 life? Then lifestyle design might be for you. Here, you build a life around the things that excite you.
For example, if you love surfing, you might convert a van and drive to the best surf spots. You pay for your adventures while working from your laptop in the evenings.
This is just one of many exciting options there are. Learn about the different models, their advantages and drawbacks, and the best strategies to make it happen.
My Story
Almost all people who get into lifestyle design were originally living very conventional lives, trying to fulfill the expectations of others. I am no exception to this rule.
Up until my mid-twenties, I was well-headed for the white-picket-fence life. I was studying to go into academia and become a professor. I had been with the same person for almost eight years. I was thinking about buying property.
I wasn’t doing any of these things because they particularly excited me. I simply had no idea what else to do. And I was also afraid to disappoint those around me. Until it all fell apart.
In 2006, my relationship of eight years collapsed. It hit me hard. For a year afterward, I was essentially out of order. I ate, slept, cried, and thought about killing myself.
But it also made me reconsider my life choices up to this point. I began to question everything. At the same time, I completely stopped caring about the expectations of others. I was so down that all the pretenses fell away.
That failed relationship became the single most important turning point in my life. I started to look into alternative career paths. It was then that I first heard about the digital nomad lifestyle, which led to me starting an online business and traveling the world. I began to experiment with talking to strangers and alternative relationship models. I got heavily into minimalism, eventually getting rid of almost all my physical belongings.
Paradoxically, the most painful moment in my life was the key to happiness. It shocked me into seeing things more clearly and taking action. I was no longer to follow the readymade life path that society had in store for me. I was ready to let go of it all and design my own life. This article will help you to do the same.
The Origins of Lifestyle Design
The term lifestyle design was coined by Tim Ferriss in “The 4-Hour Workweek,” published in 2007 — or at least he was the one to popularize the term and turn it into a pop-culture phenomenon.
At its core, lifestyle design questions the work-retirement paradigm — the idea that you must supposedly work for 40 years first before you can finally do all the fun things that you would like to do, like traveling or indulging in your hobbies.
This logic is fundamentally flawed. At 65, doing all these fun things won’t be so much fun anymore. Your vitality will have taken a significant hit. You might even suffer from one or several severe health issues at this point. You should be doing fun things when you are still able to enjoy them, not when you are nearing the end.
To make matters worse, we also have an unhealthy obsession with material things and status symbols. We think we need to buy all kinds of crap to be seen as a success in life. This further chains us to our miserable 9-to-5 existences.
Ferriss summarizes our dilemma by citing the short story of the tourist and the fisherman. Here is the short version:
A tourist spots a shabby-looking fisherman taking a nap in his boat at the beach. He approaches him and tells him, “You know, if you went out to fish several times per day, you could soon buy a motor for your boat.
The fisherman replies, “Then what?”
The tourist goes on, “Then you would catch even more fish. Two years from now, you could buy a second boat.
The fisherman replies, “Then what?”
The tourist explains, “Eventually, you could have your own fleet of vessels, your own fish factory, and your chain of fish restaurants.”
The fisherman replies, “Then what?”
The tourist enthusiastically exclaims, “Then, without a care in the world, you could sit here in the harbor, and soak up the sun.”
To which the fisherman retorts, “But I’m already doing that.”
The nonchalant fisherman understands that there is little sense in putting life off until the last moment. He also understands that material things don’t matter. We might think we want riches, but in the end, all we value are the experiences we had. This is what decides if it was life well lived.
Ferriss concludes that you must break away from this faulty work-retirement logic. Instead of placing all your hopes on a far-off paradise (retirement), you must design a life around the activities that excite you. If you want to dance tango in Argentina, you should move to Argentina. If you love deep-sea fishing, you should go live by the sea and charter a boat. In this model, your life is a series of mini-retirements — exciting adventures that you have now, not later.
To put this into practice, Ferriss proposes to start an automated online business (what he calls a “Muse”), which can be maintained on just four hours per week. The goal is passive income. This will allow you to escape the rat and give you your time back. It will also allow you to live a location-independent lifestyle. It doesn’t matter if you are spending your time in New York, Prague, or Bangkok. As long as you have an internet connection, you can run your digital business from anywhere.
The Modern Version of Lifestyle Design
The original definition of lifestyle design was ironically somewhat narrow. You were supposed to start an online business and then go live life as a digital nomad. The end.
The modern version of lifestyle design is more inclusive. Essentially, anyone who consciously breaks away from the social script, aka how things “should” be done, is by definition a lifestyle designer.
This begs the question — what exactly is the social script? The term refers to a readymade life plan, pushed onto by others, like your parents, your teachers, and society as a whole. The six pillars of this script are:
- You go to college → formalized education
- You get a job → employment
- You get married → monogamy
- You buy a house → property
- You have kids → procreation
- You buy things and amass debt → consumerism
Anyone deviating from this script is a lifestyle designer. This includes the van life dweller, traversing the country in a stealth camper. It includes the couple practicing ethical non-monogamy, i.e., sleeping with other people outside the core relationship. It includes the extreme minimalist who sold their physical belongings and now lives in a virtually empty apartment.
All of these people are creating a life following their own values and ideas — not to please other people.
At the same time, it has become apparent that the passive income model proposed by Ferriss is a pipe dream. There are no automated cash cows that can be run on just four hours per week. This has given rise to a bunch of alternative solutions to the cash flow problem:
- The passion business model. Here, you turn your passion into your business. The reasoning — if you love your work, it will stop feeling like work.
- The FIRE model (= financial independence, retire early). Here, you aggressively save money (typically around 70% of your income) to retire when you are still young.
- The frugality model. If you spend virtually nothing, e.g., by sharing your living space and dumpster diving, you can quit your 9 to 5.
- The off-grid model. If you become self-sufficient by owning the land and growing your own food, you can leave the system behind altogether.
The other area that has been significantly improved since the early days is your living environment. There are now many more options than just renting an Airbnb in Chiang Mai. Some of these options include van life, the tiny house movement, stealth camping, off-grid living, and communal housing projects (communes, ashrams, etc.).
This is the spectrum of lifestyle design as of now. I am sure it will evolve even further, as the digital transformation picks up speed. Which brings me to my next point.
Lifestyle Design and the Digital Transformation
Lifestyle design is inherently linked to the digital transformation.
Don’t get me wrong — there have always been lifestyle designers. In every age and culture, there were people tired of playing by the rules. This goes back as far as Diogenes of Sinope, who famously lived in a barrel, making it his mission to question contemporary customs. He was a lifestyle designer if there ever was one.
However, lifestyle design as a “mass movement” is a recent phenomenon. Only with the advent of the digital age became it possible to run a business from anywhere in the world, make use of geo arbitrage, and automate crucial processes via software.
However, this is only half of the equation. While some people like Tim Ferriss were advocating for digital nomadism as early as 2007, it was still a looked-upon phenomenon — if people knew about it at all. I became a digital nomad in 2015 and I clearly remember the reactions. Most “proper” folks thought me not quite right in the head.
Then the pandemic happened and all the newspapers that previously had published ironic pieces about these digital nomad weirdos suddenly changed tone. It was emblematic of society as a whole. Suddenly, remote work was all the rage. People who previously would have never considered leaving the office suddenly went to work from Playa del Carmen. Lifestyle design had arrived in the mainstream.
The Future of Lifestyle Design
I predict that this is just the beginning. There are at least two more major revolutions on the horizon for lifestyle design.
Crypto
The first one is cryptocurrency. We are nearing a future where there will be a decentralized world currency. Of course, governments will do their damnedest to control this currency. But it is unlikely that they will succeed, at least not completely (just like governments struggle with controlling the internet). This means it will become possible to move your business and other assets around the world at a whim. A lot more people who are currently chained to a certain location for juridical and administrative reasons will be able to leave.
On a side note, I think that this future is still several years off. Cryptocurrency is still in its early stages. The recent bust of the crypto bubble has clearly shown that. It is very much comparable to the bust of the dot-com bubble which the internet went through before it emerged as a more mature technology.
Virtual Reality
The other upcoming revolution for lifestyle design is VR/AR. Some professions still require an expert to be physically in the room, e.g., a doctor during surgery or an engineer conducting a repair on an airplane.
These requirements will eventually vanish. It is hard to imagine now, but virtually any type of work could eventually be conducted remotely. Using VR headsets, VR gloves, and robotics, we will be able to cooperate on critical projects as if the other person were standing next to us — even though they are de facto thousands of miles away.
This will lead to utter freedom, at least in terms of mobility. The story will come full circle — we will return to our nomadic roots. Provided we have the funds, we will roam the world at will, just as we did pre-agricultural revolution.
The sidenote here is that VR will also eventually lead to the death of lifestyle design. If we can’t tell the difference between the virtual and the “real” reality anymore, what incentive is there to travel to Bali in person? You can also just go there from the comfort of your home.
Obviously, this level of immersion is even further off into the future than a crypto-based world currency. Most of us won’t live to see it. But it’s not hard to imagine how this will play out. Until then, though, we are still left with seeking our thrills in real life.
Let’s look at the mechanics of this now.
The Mechanics of Lifestyle Design
There are certain constants that every aspiring lifestyle designer will run into. If you know them, you will be better able to deal with them.
1. The “Aha” Moment
This is how it all starts. Every lifestyle designer at some point has had an “Aha” moment. It is when you decide you can’t go on lying to yourself about your life. You can’t keep pretending that everything is dandy when deep down, you are chronically depressed about your sad cookie-cutter existence.
For me, it was the breakup with my girlfriend. It woke me up, not just to the hypocrisy of the monogamous relationship paradigm, but to the hypocrisy of the “good life” in general.
I know of other people for whom it was getting laid off from a job that they had been giving their everything for years or decades. I know of a few people for whom it was hitting rock bottom in their struggle with substance abuse.
The worst kind of “Aha” moment is always when a loved one dies, especially if the circumstances are tragic.
This is what it comes down to — pain. Pain will get you moving. It cuts all the nonsense in your life instantly; you have no bandwidth for these delusions anymore. Pain is the great clarifier.
With that extreme level of clarity, you won’t care about what others think of you anymore. You will see through your self-lies. It feels like you have nothing to lose anymore, so you might as well just do what you really want to do.
I always half-jokingly tell aspiring lifestyle designers to wait for the next major life crisis to come around. But it’s true. If you use that pain wisely, it will propel you forward. It will create that “Aha” moment for you.
2. The 3 Stages
Lifestyle design typically plays out in three consecutive stages:
- “Freedom from”
- “Freedom to”
- “Freedom being”
1. “Freedom from”
In the beginning, it’s all about shaking off the yoke. What the yoke is depends on the person. Person A wants to be free from their tedious 9 to 5. Person B wants to be free from their boring, monogamous relationship. Person C wants to be free from consumerism, i.e., get rid of their physical belongings.
“Freedom from” is how everybody starts, and it is nothing to look down upon. It feels fantastic to get rid of your shackles; most people never do. You should enjoy the heck out of it.
However, after a while, you start asking yourself, “What now?” This is when you graduate to the next stage.
2. “Freedom to”
Where before you were just focused on removing constraints, now you start moving towards positive outcomes. You get to choose what you want to do with your life, and that choice is exciting.
For person A, that might mean starting that passion business that they always dreamed about. For person B, that might mean experimenting with different unconventional relationship models and finding what is right for them. For person C, it might mean traveling the world with just a backpack.
This is a fantastic place to be in, and this is where most true lifestyle designers are at home. But there is also a bit of a danger here — the danger of too much choice. Lifestyle designers are prone to hopping around. They try one fun activity after another, meet with countless people, and attend event after event. Life becomes this endless chase, where you let your FOMO get the best of you.
This is when it’s time to graduate to the third stage.
3. “Freedom being”
At some point, you must make a choice. You must lock something in. Otherwise, your freedom will turn against you.
You don’t need to have 10 businesses. You can have or two, and give them the attention they deserve.
You don’t need to have a new hobby every month. Pick one or two that excite you the most, then go full in.
You don’t need to go on 20 dates per month. Have your one or two main relationships and the occasional fling here and there.
Less is better. By slowing down and becoming aware of what you are doing, you multiply the pleasure you get from your chosen activity. You will regularly experience these flow states — periods when you are fully present and everything clicks. Like a virtuoso exploring the possibilities of their instrument, you will be exploring the endless possibilities of your chosen activity. By limiting yourself, you have actually a new dimension of freedom, one that you were previously barred from. It’s the most satisfying of them all.
3. Hedonism vs. Responsibility
Lifestyle design is often a euphemism for unchecked hedonism. It attracts a certain type of person. Their two main characteristics are:
- They don’t want to do anything that is not fun
- They constantly want to feel stimulated
Lifestyle design enables these tendencies. You get to quit your restrictive 9 to 5 and are now free to do whatever you want. You can live wherever, date around, try lots of different hobbies and activities, play around with drugs, explore your spirituality, etc.
In short, it tends to be a bit of an ego trip.
This is also why lifestyle design tends to be a solo sport; it is not very compatible with a family structure. Traveling the world with your backpack, staying at Airbnbs, and working from your laptop is pretty doable if you are by yourself. But try to do the same thing with children, and you will likely hit a wall. What about schooling? What about a stable social circle for your kids? It is not impossible, but it is a lot harder.
To be clear — I am not saying you should do the “right” thing, “grow up,” and “take on responsibility.” When you hear these phrases, you can be sure someone is trying to manipulate you, be it a parent or a partner. They want a certain model for you — the white-picket-fence life, i.e., the model they prefer — and they are trying to guilt trip you into it.
You should absolutely not listen to these people. If you want to be free like a bird, fly. What I am saying is that you have to be strategic about your freedom. Overindulging your hedonistic tendencies like so many lifestyle designers do is not going to make you happier. Quite the opposite. If you want to optimize for happiness, you need to look at the vast buffet of options and make a choice. And then you need to go deeper, not wider.
Regarding the family question, it depends on your gender. For most female lifestyle designers, there is really only one model — the sequential model. They go off and explore the world for a few years, but then settle in one place. It makes sense, as raising children on the road is a hassle. Some female lifestyle designers decide to skip children and keep traveling indefinitely, but those are few and far between.
With male lifestyle designers, the distribution tends to be more evenly. Many do the same thing, aka travel for a while, then settle down. But quite a few also can become perpetual travelers, foregoing the family experience.
It depends on who you are and what you value the most. You must listen to yourself here, not the societal narrative. If you want to be the eternal bachelor (or bachelorette), embrace it. But if you dream about children, don’t suppress that thought either.
How To Go About Lifestyle Design
Here is how to get the most out of lifestyle design.
1. Adopt the Right Mindset
To go through with lifestyle design, you need to have the right mindset.
The first thing — you need to get in the habit of questioning the status quo. Most of us make our decisions based on what everybody else is doing. But the herd is rarely right. In fact, you are usually better off doing the exact opposite of what everybody else is doing.
Everything popular is wrong.
Oscar Wilde
The second thing to realize is that you are in charge. Unlike what most people want you to believe, you are not just a cog in the wheel. You have choices. For every problem you face, there is a solution that only depends on you. You are not a victim.
The third thing is to consider your mortality. If you don’t do this now, eventually, it will be too late. You will have wasted your life away being a “good” boy or a “good” girl. You will come to bitterly regret your timidness.
2. Define Your Goals
The very core of lifestyle design is choosing your own goals, independent of what others think you should do with your life.
The point is not to be a contrarian. The point is to truly get to know yourself. What are my values? What excites me? What am I good at? Then build a life around these findings, not around some cookie-cutter social script.
Do this in writing. Be specific. “I want to build an e-commerce store selling my own spray-painted skateboards and make a living in 12 months from now,” is specific. “I want to make money online,” is not.
It can be helpful to imagine what you want your ideal day to look like. It is usually a lot easier to develop a vision for that. Once you have done so, you can then extrapolate that vision to your life as a whole.
Think about hobbies and fun activities. If you are an avid surfer, your lifestyle design should represent that fact. You should research countries, coastlines, and local surf scenes. Plan around what excites you.
It is important to learn to differentiate between the things you think you enjoy (because they sound cool on paper) and the things you actually enjoy. For example, you might think it cool to travel the world in a van. But when you actually do that, you don’t particularly enjoy it. On the other hand, you might really enjoy writing romance novels, but not go through with it because you think it’s beneath you.
Don’t make that mistake. Be true to what makes you feel great.
Think about what you want. But also think about what the market wants. The more you go in the direction of your passion, the harder it will be to make money, at least initially. The more you play to what the market wants, the easier it will be to make money. It’s not a black-or-white thing. There are all kinds of shades of gray in between. But it’s a decision you need to make.
Final tip. Think of your life as a story that you are one day going to tell to your grandchildren. Will your current goals make for a good story? If not, it’s time to be more daring.
3. Ensure Cash Flow
To escape your 9 to 5, you need to create cash flow. There are a couple of different ways of doing this.
You could start an online business. I always recommend going with offering a service like copywriting, graphic design, marketing services, or programming. These services are very sought after. Do a good job and you can replace your current income in 6 to 12 months, if not faster.
Alternatively, you could consider the FIRE model. Here you stay with your current job but save north of 70% of your income. Obviously, that requires you to live extremely frugally for a couple of years. The upside — you can retire at age 40 (or earlier).
Another option is what I call the Robert Wringham model (after the writer and comedian). Here, you also dramatically cut your costs, so that you can get buy only working odd jobs. This way, you get most of your time back.
If you are interested in the ins and outs of these models, check out my article on escaping the 9 to 5.
4. Think About Mobility
This is one of the core questions as a lifestyle designer — do I want to be able to travel at will or not?
If you do want to travel, you ideally want to start an online business. Yes, you can do odd jobs in the places you travel to, but it’s not a good solution. These jobs pay badly, you are competing with lots of underqualified locals, and you are likely to get exploited. Start an online business, and save yourself the hassle.
It’s important to consider what places you plan to visit. For example, if you run an online business that requires a lot of communication with customers, you might be limited to countries in a certain timezone. Personal preferences also play into it. For example, I love the beach but couldn’t care less for the mountains.
If you are a stationary lifestyle designer — and there are plenty of those too — you don’t need to do the online thing. What you probably will want to do is to turn that passion of yours into a local service business. So, if you are passionate about martial arts, start a martial arts gym. If you think paintball is the coolest thing ever, start a local paintball shop or run a training field.
For the stationary lifestyle designer, housing options are important to consider. Oftentimes, they are in love with a certain type of housing like tiny houses, communal living (eco/smart villages), or an off-grid lifestyle. This housing model will in turn influence all your other choices. For example, if have a hut in the wilderness and can live off the land, there is no need to think about online business models. But then your job becomes to learn how to hunt and forage.
5. Plan for Geo Arbitrage
If you are the traveling kind, you want to make use of geo arbitrage, especially during the early stages of your entrepreneurship journey. For example, you could do what tens of thousands of digital nomads have done before you and move to Chiang Mai and live on $800 a month, while working online and earning in dollars. That will give you a lot more runway when it comes to getting your business off the ground.
6. Think About Your Social Life
If you become a traveling digital nomad, there will be real consequences to your social life.
First, your existing group of friends will not be able to move with you. And while you can try to stay in touch, let me tell you from experience that it is tricky. Slowly, as the years go by, you will grow apart.
To counteract this, you want to build a group of friends with the same lifestyle. This way, you can meet up several times per year all over the world. It will significantly help with the social isolation that all digital nomads at some point experience.
A good way to do this is to join designated digital nomad communities online. Make sure there is a live component to these groups, e.g., a yearly conference where everybody goes. One starting point is the “Dynamite Circle” but there are many more of those groups.
Last but not least, think about your sexual and romantic relationships. Many people will be hesitant to date you if they know you will be gone in two months.
There are a few ways to deal with this. You can make your peace with having lots of short flings. You can try to date another traveler. This is not as easy as it sounds, though. There tend to be a lot more male than female digital nomads. So, if you are a guy, the competition will be rough. Finally, you can date people locally but agree to have an ENM relationship (ethical non-monogamy). This way, they are free to explore other options when you are not around. It can work out quite well if your communication skills are on point.
7. Work Hard
Most people get into lifestyle design because they want to indulge their hedonistic tendencies. This rarely works out, especially long-term. Eventually, their lifestyle businesses fall apart and they have to return to the corporate world.
Understand — if you want to build a business to finance your adventures (online or offline), you must work really hard for a couple of years. For a while, you will get the exact opposite of what you were hoping for. No hedonism. No parties, no social media, no dating around, no pointless socializing. Just hard work.
It’s the price of admission. Pay it now, and you will be better off later. You will have a passion business that you are proud of and which you enjoy (and that also pays you well). You will enjoy life while everybody else is miserable because of their 9 to 5s. But you can’t skip to that part. You must go through hell first.
8. Prepare for Pushback
If you deviate from the social script, there will be a price to pay. Your parents, your friends, and even your lovers will not be appreciative of your black sheep tendencies. They will try to guilt trip you into changing your mind first, and if that doesn’t work, they will punish you by withdrawing their affection.
Don’t get angry with them. Understand — you are a threat to their way of life. If you can do all these adventurous things, it begs the question why they couldn’t. Without intending it, you have rubbed their noses in their own fear and narrowmindedness. Of course, they don’t appreciate that.
At the same time, you don’t want them to let you deter you. That is why it’s so important to surround yourself with other free spirits like yourself; ideally people already further along the journey. They will act as living proof that it can be done (and should be done).It will help you with staying the course.
9. Iterate
It is unlikely that you get it right the first time. You might think you want to kite surf in Egypt but then discover you are really into South American plant medicine. Don’t sweat it. Just change course. I went through at least four of these iterations before I finally arrived at the thing that was “it.” None of these iterations were wasted. With every single one, I gathered more data points that allowed me to move closer to my ideal lifestyle. It will be the same for you too. You learn through experimentation, not by coming up with the perfect plan on the drawing board.