Lifestyle Design 101: What is Lifestyle Design? (& 35+ Questions to Ask Yourself)

It’s been over a decade since Tim Ferriss helped popularize the concept of “lifestyle design” in his book The 4-Hour Workweek (Amazon).

After doing some recent research on the topic, I’m genuinely surprised how little quality information exists today. I assumed lifestyle design would have achieved some compounding momentum by now, but in many ways it seems to have fizzled out.

Perhaps that’s due to a narrow understanding of the concept. Lifestyle design doesn’t always mean working from your laptop on a beach, traveling full-time as a global nomad, or becoming a monk.

This post is intended to give you a more well-rounded view of the (literally) life-changing concept of lifestyle design—along with a bunch of questions to spark thinking about your own lifestyle.

The average lifespan is roughly 30,000 days. That’s a lot of repetition and experimentation to figure out your ideal way of life.

“If you are lucky enough to find a way of life you love, you have to find the courage to live it.” — John Irving

Post Contents: Click a link to jump to a section below

• Lifestyle Design Defined
• Lifestyle Design & Yourself
• Lifestyle Design & Your Day
• Lifestyle Design & Work / Leisure
• Lifestyle Design & Location
• Lifestyle Design & Home

Lifestyle Design 101: What is Lifestyle Design? (& 35+ Questions to Ask Yourself)

Lifestyle Design Defined

Lifestyle design is intentionally crafting a way of life (or style of living) that aligns with who you are.

Let’s start with the biggest popularizer of lifestyle design: Tim Ferriss. In this short video with Ryan Holiday, Ferriss shares his most recent definition of lifestyle design:

• “Lifestyle design would effectively be a contrasting, philosophical lens through which to look at career and personal development that is juxtaposed with ‘slave, save, retire’—I’m going to cash in my chips in 20-30-40 years that will then redeem this period of doing many things that I dislike doing.” — Tim Ferriss
• “Effective lifestyle design is effective testing and awareness.” — Tim Ferriss
• “Are you designing a life you actually like living in?” — Ryan Holiday

Work is obviously a huge part of life. Let’s quickly cover the “slave, save, retire” approach that Ferriss mentions. Here’s how a traditional career breaks down:

• If you work 40-hour workweeks for 40 years: Work is 34% of all your waking hours for 40 years (yes, this even factors in weekends and two weeks of vacation each year).
• If you work 50-hour workweeks for 40 years: Work is 43% of all your waking hours for 40 years.
• If you work 60-hour workweeks for 40 years: Work is 51% of all your waking hours for 40 years. This is the equivalent of a career and a half.

None of these numbers even include commute, time getting ready for work, time thinking about work, or many other areas of the phenomenon of “total work.” No matter the scenario, this is an incredible amount of time and energy.

Can you really blame people for wanting a third (or more) of all their time awake and the bulk of their energy to be more purposeful, meaningful, and fulfilling?

Instead of doing things you dislike for decades and deferring living to the future, lifestyle design is figuring out the life you want and living it in the present. It’s highlighted perfectly in the short story of the tourist and the fisherman.

But, lifestyle design is more than work—it’s all-encompassing. Here’s a thought from Mihaly Csikszentmihalyi that was shared in Greg McKeown’s book Essentialism:

• “Most creative individuals find out early what their best rhythms are for sleeping, eating, and working, and abide by them even when it is tempting to do otherwise. They wear clothes that are comfortable, they interact only with people they find congenial, they do only things they think are important. Of course, such idiosyncrasies are not endearing to those they have to deal with … But personalizing patterns of action helps to free the mind from the expectations that make demands on attention and allows intense concentration on matters that count.”

It’s not just creative individuals either. Abraham Maslow described something similar for self-actualizers:

• “People selected as self-actualizing subjects, people who fit the criteria, go about it in these little ways: They listen to their own voices; they take responsibility; they are honest; and they work hard. They find out who they are and what they are, not only in terms of their mission in life, but also in terms of the way their feet hurt when they wear such and such a pair of shoes and whether they do or do not like eggplant or stay up all night if they drink too much beer. All this is what the real self means. They find their own biological natures, their congenital natures, which are irreversible or difficult to change.”

So, in theory, lifestyle design covers everything in your life. According to Peter Drucker, we have an unprecedented amount of choice today:

• “In a few hundred years, when the history of our time will be written from a long-term perspective, it is likely that the most important event historians will see is not technology, not the Internet, not e-commerce. It is an unprecedented change in the human condition. For the first time—literally—substantial and rapidly growing numbers of people have choices. For the first time, they will have to manage themselves. And society is totally unprepared for it.”

If you are someone who is prepared to take responsibility for all this newfound choice, there are tangible and intangible factors to consider:

• Tangible factors of lifestyle design may include demographic aspects like work, location, and home environment.
• Intangible factors of lifestyle design may include psychological aspects like values, beliefs, interests, and preferences.

There are a few similar concepts to be aware of:

• Intentional Living: The act of consciously taking responsibility for your life and attempting to align all aspects of your lifestyle (beliefs, behaviors, environment, etc) is often referred to as “intentional living.”
• Alternative Lifestyle: When you intentionally design your life, you may end up with something that looks different from the mainstream cultural norms—often referred to as an “alternative lifestyle.”
• Lifestyle Business: It’s not uncommon for those pursuing intentional living and lifestyle design to run a “lifestyle business”—sustaining a level of income that allows for the desired and designed lifestyle.

35+ Lifestyle Design Questions to Ask Yourself

When you answer these questions, consider both your current situation and aspirations. You will likely be able to more intentionally design your current lifestyle while also planning for your ideal future.

Lifestyle Design & Yourself:

• Do you know what’s most important to you in life (see essentialism)? What is it?

• Do you know your life purpose? Do you want to design your life around it?

• What does your personality type say about your preferences and how you interact with the world?

• What are your life roles that you need to consider?

• What is your life stage (e.g. just starting work, retiring, having your first kid, empty nester, etc)? Are you planning for the short-term or long-term?

• What’s your relationship situation? Are you on your own, dating, have a family, looking for communal living, etc?

• If you have kids, what kind of schooling is important (private, public, homeschooling/unschooling, etc)?

• If you have pets, what do you need to consider for their quality of life?

Lifestyle Design & Your Day:

• What does an ideal 24-hour day look like to you? How does a normal weekday look? What about a weekend?

• What is your preferred way of using your daily energy (in work, leisure, etc)?

• Are you someone who prefers spontaneity or routine (timeboxing)?

• Do you prefer an active or sedentary lifestyle?

• Are you designing around MEDS (Meditation, Exercise, Diet, Sleep)? What kind of diet is important (e.g. vegan, vegetarian, etc)? How much sleep? What kind of exercise?

• How much daily time is spent with family and friends?

• Are you incorporating “life philosophies” like downshifting, slow living, simple living, or minimalism?

• Are there other lifestyle considerations around ethical or sustainable living or other personal priorities?

• Are there other physical, mental, or spiritual daily considerations?

Lifestyle Design & Work / Leisure:

• Do you need to work for money? If so, what kind of work do you want to do?

• Can you utilize the internet for leverage to disconnect your work inputs and outputs (see Naval Ravikant’s “How to Get Rich”)?

• Are you pursuing FIRE (Financial Independence Retire Early)?

• What other work considerations do you have (e.g. commute, grooming/dress code, etc)?

• How important is it for you to design hobbies into your life (e.g. lifelong learning, reading, athletics, music, arts, volunteering, etc)?

• Can you combine hobbies with work (avocation + vocation)?

Lifestyle Design & Location:

• Are you locked into a specific location due to work, family, hobbies, or other reasons?

• If not, do you prefer city, country, beach or something else?

• Do you want to live in (or close to) nature?

• Are you part of a subculture that requires a certain type of location (e.g. surf culture, ski culture, etc)?

• Do you want to live domestically or abroad?

• If living abroad, are you interested in geographic arbitrage to make your money go further?

• How important is self-sufficiency / self-reliance (e.g. back-to-the-land, off-the-grid, homesteading, etc)?

• What about intentional communities or eco/smart villages?

Lifestyle Design & Home:

• What kind of home do you want (e.g. big house, a tiny house, apartment, boat, van, RV, etc)?

• What’s your minimum viable home (in square footage) based on your possessions, needs, and desires?

• How much time, energy, and money do you want to spend cleaning, maintaining, and shopping for your home?

• What interior aesthetic do you prefer?

• Do you want to be settled or nomadic?

• Do you want to travel domestically (e.g. van/RV)? Full-time or occasionally?

• Do you want to travel internationally (e.g. global nomad)? Full-time or occasionally?

Have more questions you want to add? Please share them in the comments.

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