The Ultimate Guide to Lifestyle Design (& 100+ Questions To Ask)

If you’re like me, your journey to financial freedom began with a desire to enjoy a lifestyle design curated by, and specifically for, you.

You want your daily schedule and work to align with your unique rhythms, intentions, passions, goals, and dreams. 

And you want your finances to support this lifestyle. 

So, let’s make that wish a reality. In the following sections, you’ll design your target lifestyle, learn how to bankroll your plans, and make an action plan to implement your blueprint’s components.

Let’s find your bread and butter.

Lifestyle Design Defined

Lifestyle design is curating your actions, community, experiences, and possessions to align with your values, dreams, passions, energy, and nature. 

This means erasing the “shoulds” from your behavior and decisions, often implanted into your subconscious by friends, family, co-workers, school, and society. 

As a lifestyle designer, you define where you want to live, who you want to live with, your house, car, profession, routine, reading list, wardrobe, hobbies, weekend plans, etc. Your choices may fall within the traditional ways of living life, or they may not. 

All that matters is that they work for you

In essence, when you live according to your individually crafted lifestyle design, you, and only you, make the rules over where you spend your time, energy, and money.

Why You Should Consider A Cultivated Life

Lifestyle design allows you to live authentically. To show up fully as yourself. 

Doing so creates a waterfall effect over every aspect of your life. You’ll find meaningful, fulfilling work, enjoy independence, and have greater control over your income streams.

And if you’re looking for concrete evidence before embracing your own lifestyle design, or else are concerned that the concept of lifestyle design is selfish, ponder this:

A study published in the 2019 book, Authentic: How To Be Yourself And Why It Matters found that a person engaged in living authentically is not only more likely to…

  • feel more gratitude
  • have a sense of purpose
  • engage in challenging activities

…but is also more likely to contribute to their community through…

  • volunteering
  • donations
  • supporting charitable causes

All in all, living your ideal life according to your authentic design is good for you and your community. 

In the next section, I will walk you through designing your ideal, authentic lifestyle.


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    The Ultimate Guide to Designing Your Ideal Life

    There are four steps to developing your lifestyle design:

    1. Define
    2. Explore
    3. Implement
    4. Reflect

    And then repeat. Monthly, quarterly, annually – whatever you need to feel aligned.

    Let’s explore each in more detail.

    Step One: What Lifestyle Do You Crave?

    To design your ideal lifestyle, you first need to separate who you are and what you want from the demands/expectations/rules of your family, friends, partner, community, society, employer, etc. 

    To get you started, I pulled together the following questions. Consider addressing the questions by journaling and meditating or creating a spoken-word voice memo.

    You’ll find that the questions are categorized into the various departments of our lives (i.e., childhood, work, future, etc.) to make the reflection process more manageable. However, make sure to expand your answer beyond a specific category. 


    Just like we bring childhood mannerisms into adulthood, our interests as a child reflect our interests as adults. 

    For example, I spent summer days reading in a tree as a kid. Today, I read two books at a time, have over 50 houseplants, and my view from my desk is an urban forest.

    So, if you’re looking for guidance on potential a new career path, skill, or hobby to champion, look no further than what you gravitated towards as a child (and the questions below!).

    1. What activities did I gravitate towards as a kid?
    2. What was I good at as a kid?
    3. What activities did I avoid as a kid?
    4. What was I bad at as a kid?
    5. When I was a kid, what did I want to be when I grew up?
    6. Who did I most look up to?
    7. Was I a loner, or was I always with my friends?
    8. What feedback did my teachers give my parents during conferences?
    9. What was my favorite subject in school?
    10. What did I major in college? Why?

    Tip: It may help to ask your family the above questions for additional insights or else scrounge up old-school papers or diaries. 


    Studies suggest that the average person will spend a whopping 90,000 hours working. That’s a mammoth portion of our lives, time, and energy. 

    This is why it’s essential to find a profession, working style, and schedule that makes you feel vibrant and animated.

    Examine the following questions to bottom out what you need from a vocation: 

    1. During what hours do I work best? 
    2. Do I enjoy working with others? Or independently?
    3. Do I enjoy working in an office?  
    4. Do I want to work 100% remotely?
    5. When do I like to work out?
    6. What do I enjoy about my current job?
    7. What do I not enjoy about my current job?
    8. Why am I doing what I chose as a profession?
    9. What motivates me to work? Money, free time, learning, competition, challenge, recognition?
    10. Do I want a commute? 
    11. If yes – how long?
    12. If yes – what type? Car, rail, bike, walk, carpool, bus?
    13. Do I enjoy dressing up?
    14. Do I need to make more or less income than I do today?
    15. What job title do I want?
    16. What awards do I dream of receiving?
    17. Who are my mentors? 
    18. What technical skills am I good at?
    19. What skills come to me naturally?
    20. When I procrastinate, what do I do instead?
    21. What made me leave my previous jobs?

    Tip: Be careful; it’s easy to “should” yourself here. Go with the first answer that pops into your head. No one will see your answers but you. 


    Knowing your innate personality is a powerful tool. 

    For example, I prefer to work independently. So those “group essays” we had to do in college? The worst.

    I used to think that this preference suggested a character flaw, that I was “anti-social.” But after learning about my natural tendencies, I now know I am just naturally inclined to work alone. Plain and simple.

    This gave me much-needed peace of mind.

    At the end of the day, knowing your personality helps you identify what you can and can’t control about yourself and your life and design your lifestyle accordingly. 

    So ask yourself:

    1. What are my positive habits?
    2. What are my negative habits?
    3. Am I an introvert or an extrovert?
    4. When do I feel most confident?
    5. What’s my love language?
    6. What am I afraid of?
    7. What’s my tolerance for risk?
    8. Do I like spontaneity or routines?
    9. Do I prefer a busy lifestyle or a slow one?
    10. Do I enjoy cleaning?
    11. Do I like having scheduled commitments? 
    12. What boundaries do I want to set?
    13. What bothers me about other people?
    14. What do I talk about the most?
    15. What exhausts me?
    16. What is the most beautiful thing in the world?

    Tip: To keep yourself honest here, consider taking a personality test, like Myers Briggs, explore a system such as human design or astrology, or check out apps like Dimensional and The Pattern.

    Current Lifestyle 

    Completing an inventory of where you are today helps you get to the heart of your day-to-day lifestyle and to make quick changes if needed.

    The inventory:

    1. What’s my relationship status?
    2. Am I happy with this status?
    3. What’s my ideal relationship?
    4. Do I want children?
    5. What type of life do I want for my children?
    6. Do I want pets?
    7. What type of life do I want for my pets?
    8. Do I enjoy my current diet?
    9. Do I want to be more sustainable? 
    10. How much sleep do I get?
    11. Do I need to sleep more?
    12. If I sleep too little or too much, why do I think that is?
    13. Am I spiritual?
    14. If not, do I want to be? 
    15. If yes, does my current practice satisfy me? 
    16. If yes, what about my current practice do I not like?
    17. If yes, what about my current practice do I enjoy?
    18. Is there a moment I would like to relive?
    19. How do I relax?
    20. What’s my favorite movie, book, show, song, or play?
    21. What’s my favorite word, phrase, or quote?
    22. What do I daydream about?
    23. What makes me lose track of time?
    24. What are my favorite things about my culture?
    25. What are my least favorite things about my culture?
    26. What countries/cultures, besides my own, have always intrigued my
    27. What’s my favorite part of my daily routine? Why?

    Tip: This set of questions is almost like having a first date with yourself. So have fun with these!


    In a Harvard T.H. Chan School of Public Health study, Joe Allen, head of the Healthy Buildings Program, notes:

    “The home influences heart health, brain health, hormone health, mental health, all these factors. We know what a healthy meal looks like. We know that exercise is good for you and that pollution is bad for you. But we know a lot less about the places where we spend all of our time.”

    It’s clear from the statement above, and the simple knowledge that we spend over 60% of our time in our homes, that living in a home you love is crucial to well-being. 

    The question below will help you define the what and where of your ideal home.

    1. Does my current geographic location fulfill me?
    2. What about it do I enjoy?
    3. What about it don’t I enjoy?
    4. What’s my ideal living environment? Beach, rural, suburban, urban, mountains, farm?
    5. What type of home do I want? Traditional, tiny, van, communal. Why?
    6. How big of a home do I want? Why?
    7. What aesthetic would I like my house to have?

    Tip: Check out PinterestApartment Therapy,  HouzzArchitectural Digest, and The Spruce for inspiration on homes of all sizes, shapes, styles, and colors.


    Just as planning for retirement decades down the road impacts your financial decisions today, designing future you’s lifestyle heavily influences your choices and actions in the present. 

    An article published by the BBC in early 2022 summarized various studies that confirmed this theory, highlighting that people capable of connecting with and visualizing their future selves were more likely to:

    On the other hand, those unable to connect with their future selves often fail to contemplate the long-term consequences of their decisions and actions today on their lives tomorrow.

    Do your future self a favor and answer these questions: 

    1. Where do I want to retire? 
    2. How do I want to look and feel physically?
    3. How do I want to feel mentally?
    4. What would I regret not doing?
    5. How do I want to be remembered? 
    6. When I pass, do I want to leave any money behind? For whom?

    Tip: Remember, these questions are not based on where you are now. But where you want to be. Don’t restrain yourself.

    Without Limits

    One of my favorite Tim Ferris (author of the 4-Hour Workweek) quotes is:

    “The fishing is best where the fewest go, and the collective insecurity of the world makes it easy for people to hit home runs while everyone else is aiming for base hits. There is just less competition for bigger goals.” 

    What would you do if you didn’t limit yourself?

    1. If I could travel anywhere, where would I visit or live?
    2. If I could use any means of transportation to travel the world, what would I use? Airplane, boat, train, chauffeur, self-powered?
    3. What world problem do I want to help fix?
    4. What services would I invest in if money wasn’t an issue? Personal chef? Laundry service? Cleaning? Personal assistant?

    Tip: Dream big. Write down the first thing that comes to your mind – and then go bigger.

    The Big Ones

    You’ve probably started to notice themes in your answers to the questions above. Themes that hint at who you are, who you want to be, and what you value. The foundation of your lifestyle design.

    The questions below will help to further distill these themes down into the essence of you. 

    1. What is most important to me?
    2. What do I want to be free from?
    3. What do I want to be free to do?
    4. What do I want to be free to be?
    5. How do you want to feel?
    6. What does an ideal day look like to me?
    7. In what areas am I “shoulding”?
    8. What is missing from my life? 

    Tip: Meditation and journaling will be big here. Try using applications like Insight Timer or books like The Presence Process if you need help finding answers.

    Step Two: Time to Design

    Now for the fun part! It’s time to develop your lifestyle design.

    To do so, review your answers from step 1 and flesh out what your ideal life looks like. 

    Areas to design include:

    • Daily Life
    • Vocation
    • Family/Relationships
    • Health
    • Home
    • Travel
    • Skills
    • Hobbies
    • Philanthropy
    • Spiritual
    • Achievements

    When laying out your vision, keep in mind that the following are myths about lifestyle designs:

    • You have to live a nomadic lifestyle
    • You have to be a multi-millionaire
    • You have to be self-employed
    • You have to work remote
    • You have to live on a beach or in a major city

    For some inspiration, check out a few of the components of my own lifestyle design:

    • Flexibility to wake up naturally and without an alarm clock
    • Autonomy over my daily schedule
    • Autonomy over my location
    • A home within 30 minutes of hiking trails
    • Access to calm waters for paddle boarding, kayaking, and swimming
    • An at-home sauna and heated saltwater wading pool

    Step Three: Putting Your Lifestyle Design into Action

    Your next step as a lifestyle designer is to plot how to make your vision come alive. 

    This entails identifying your umbrella life goals (your ultimate lifestyle design) and the cash/income you need to support your designed lifestyle. Next, you’ll need to develop a plan to fulfill identified monetary requirements.

    Next, you will distill your design into manageable timelines, including 1 year, 6 months, monthly, weekly, tomorrow, and today. 


    If your goal is to retire and live off passive income within the next 10 years. You will need to calculate what you need in savings/investments/other fixed income streams to retire and assess where said wealth will come from

    With a lifestyle goal of retiring and living on passive income, your action plan may look like this:

    Milestone Tracker- Lifestyle Design

    And then….get started on your plan!

    Tip:  I limit my actionable step plan to one year since a lot can happen in 12 months, including your dream life! But feel free to expand to 2,3, 4, or 5 years if that suits your process. 

    Step Four: Does This Design Still Work For You?

    You’ve answered a thesis worth of questions, you’ve put your lifestyle design into play, and you’re taking action.

    Now it’s time to sit back and relax, right?!


    Yes and no.

    If you’ve designed your lifestyle according to your authentic passion, values, patterns, etc., your life should steadily become more and more enjoyable.

    But as I said before, things change. We change. Dreams change. 

    So to continue feeling ease and enjoyment, it’s important to check in and reflect on whether our lifestyle design still accurately depicts the life we want. The good news is – this round of reflection is far less extensive than Step One.

    Every quarter, evaluate the following:

    1. What have I learned about what works and doesn’t work for me?
    2. What were my most significant achievements? Did these bring me joy, pride, and excitement?
    3. What do I want to continue cultivating? 
    4. What do I want to remove from my design?
    5. Is there anything I want to add to my lifestyle design?

    Level Up Your Life (& Finances) With Lifestyle Design

    To rehash – if you want your daily schedule, work, and finances to align with your unique rhythm and dreams, your own path, you’ll need to become a lifestyle designer.

    Here’s how:

    1. Define what you want to be, do, experience, and give
    2. Explore what these visions would look like holistically 
    3. Implement an action plan to bring your lifestyle design to fruition
    4. Reflect on design and identify opportunities for improvement

    Looking for additional tools to support you through this process?

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