Questions to ask yourself when you'r ready to design your dream lifestyle
Location Independence, Musings, Remote Work, Travel

6 Questions You MUST Ask Yourself When You’re Ready to Create Your Dream Lifestyle

The life you’ve always dreamed of living–what does it look like?

Where are you in this fantasy and what are you doing on a day to day basis? Chances are, the things that come to mind are quite different from the way your life looks right now.

If you were really living the life of your dreams, you’d probably be doing work that fulfills you on an emotional level. You’d feel deeply connected to a sense of purpose as you move through each day. And you’d very likely have much more control over your time than you do at this moment.

In short, you wouldn’t be living the life that was expected of you, but the life that you had meticulously built from the ground up.

Perhaps you’re not entirely sure what your dream lifestyle looks like, you just know you are ready for a change.

The following questions are designed to help you understand what really moves you so you can set out to discover your best life. You can have this dream lifestyle, I assure you–but only once you find the courage to create it.6 Questions to Ask Yourself When You're Ready to Create Your Dream Lifestyle

Discover Your Dream Lifestyle by Asking Yourself These Questions

1. What gets you out of bed in the morning?

I vividly remember a time, about 7 years ago now, when a feeling of dread filled my stomach first thing each and every morning. I rolled over to look at my alarm clock, probably hissed at it, and then begrudgingly threw off my sheets to get my ass out of bed.

I didn’t know things could be any different. I didn’t know things SHOULD be different. I thought I was doing what was right because it was expected of me–following a career path that required years of schooling and would result in a string of letters after my name. It almost seemed irrelevant whether it actually made me happy or not.

A year went by, and by then I’d left that particular career path, thank God. I had a new job paying the bills, and it didn’t shoot fear into my heart every morning, but waking up still felt like a chore. There was nothing driving me to advance in this role, no feeling of excitement when I learned something new.

More years passed, as did more jobs. None of them stuck with me for too long, ultimately for the same reason every time: I just didn’t care enough.Questions to ask yourself when you'r ready to design your dream lifestyle

I know it’s become a cliché for a millennial like myself to seek purpose in the workplace, but I won’t let fear of intergenerational judgment stand in my way–I need to feel like my work is a part of something bigger than myself, and no, the bank account of my boss does not count. I need to feel as though I’m impacting those around me, as though I’m leaving the world a little bit better than it was before.

Chances are if you’re reading this, you need those things, too.

So if you’ve settled for the job you’ve got now because it pays the bills, I need you to ask yourself right here and right now…is the money really worth it? Do you wake up eager to get to work, or do you hiss at your alarm clock and scowl your way through your morning routine?

If the paycheck is the only thing keeping you there, then it’s time to stop lying to yourself. If you need motivation to get out of bed in the morning, whether in the form of coffee or the light at the end of the tunnel sometimes known as the weekend, your job is not fulfilling you and it’s time to figure out what will.

I always wanted to help people. That much I knew. What was less clear to me 7 years ago was that there were other requirements, too. I needed to create. I needed independence. I needed to be my own boss.

Once those things came into focus, it was easy to see that designing my own career as a freelancer and entrepreneur was the only path that made sense.

These days, mornings don’t scare me–I eagerly spring out of bed because I know that during the day that lies before me, I’ll be doing something I love with every fiber of my being.

2. What keeps you up late at night?

When I was a child, I had a pretty foolproof system for putting myself to sleep at night. I’d fantasize about something nice, typically a vision of how I wanted my life to look. More often than not, it involved whatever boy I happened to be crushing on at the time. Other times, I pictured how I wanted to cut my hair, what clothes I wanted to wear, or in what sports I wanted to excel.

What’s most obvious here is that I was rather shallow as a child, but that’s hardly my point. The point is, these fantasies–however superficial–gave me things to work toward in my real day to day life. They were the things my young mind naturally gravitated toward–the things I was most passionate about at the time (boys, duh).

As I grew older, these bedtime fantasies matured along with me. I envisioned what my life at college would look like. I conjured up opening paragraphs for essays I had to write. I imagined what a semester spent abroad would do for my language skills. Ideas swirled around in a constant flow, sometimes begging for my attention so feverishly, they couldn’t be ignored.Questions to ask yourself when you'r ready to design your dream lifestyle

Instead of putting me to sleep as my innocent childhood fantasies had, suddenly these visions of the future were keeping me up at night. I’d leap out of bed to write down my ideas before they faded into memory forever.

In hindsight, it’s easy to see that these were simply the ideas that lit a fire within me–the ones born of passion and purpose rather than reason and practicality–and now wish I had paid much closer attention.

I often wonder how many years I spent chasing the wrong dream because I listened to logic instead of my heart. The ideas that fill you with wonder and excitement have a habit of coming to you at night–I was foolish enough not to pursue them, but you don’t have to repeat my mistake.

3. What do you gravitate toward in your free time?

I have always, ALWAYS loved photography. My mom would probably be horrified to know how much money I wasted spent on disposable cameras and photo prints as a pre-teen. I wasn’t good at photography, mind you–I just enjoyed the hell out of it and picked up a camera whenever I got the chance.

In my college years, I shared a new photo album on Facebook every weekend, each one typically containing a hundred photos or more. Again, I wasn’t showcasing any special talent, I just enjoyed freezing a moment in time and looking back on that moment fondly at some point down the road.

Had I not been so laser-focused on the “right” path (that turned out to be very wrong), perhaps I’d have taken the time to pursue some actual photography training. Instead, I continued on as a hobbyist for many years, slowly learning and steadily improving, never thinking it would blossom into anything more.

Fast-forward to present day, and photography is an enormous part of my daily life as a content creator. It’s not my full-time job, but it plays a role–and the fact that something I love so much actually helps me pay the bills? It still floors me every day.

“Do what you love and you’ll never work a day in your life.” It’s fairly uncertain who spoke these words for the first time, but there’s no question that they’re true.

What is it that calls to you when you’re not at your day job? What could you do for days on end without getting bored? That activity that attracts you to it like a magnet might just be the thing you are meant to pursue.

We all have passions. Not all of them are suitable career paths, but I guarantee some of them are–and perhaps not in the most obvious way, but they are worth investigating nonetheless. I didn’t become a professional photographer in the traditional sense, but I still get to geek out over new photography gear and write it off as a business expense, so I call that a win.

Never let a lack of skills or expertise convince you that you’re not meant to do something, either. Everything in life can be learned so long as you have the patience.Questions to ask yourself when you'r ready to design your dream lifestyle

4. If you knew your life was going to end in 6 months, how would you spend your final days?

This question might seem a lot like the last, but it’s actually meant to suss out something slightly different. Thinking about how you’d spend your days if they were limited can help you discover your passions, but also what is most important to you in life.

With limited time, we are forced to prioritize. Suddenly, there is only room for the things that truly matter–the things that bring us joy and make us feel alive.

For me, few things compete with the feeling of touching down in a new city for the first time. Our world is impossibly beautiful and diverse, and seeing as much of it as I can has long been a top priority for me, hence why I felt compelled to create a career that could travel along with me.

The pyramids, the Amazon, the sprawling deserts of Africa; the canals of Venice, the Great Wall of China, the midnight sun of the Arctic. I want to see it all, or at the very least, try.

But travel is just one part of the equation. In the final six months of my life, I’d want to spend as much time as possible with the people I love–hence why I created a career that allows me to see my family whenever I want.

What would your priorities be if you knew you hadn’t long left to live? Would you finish writing your novel? Would you devote your time to helping others? Would you feel compelled to see the world like me?

This isn’t a trick question, and I imagine your answer will come to you without much effort.

5. What makes you feel proud?

Last week, I painted a chair. A CHAIR. And you know what? It felt good. For someone who typically cringes at the idea of accumulating material possessions, this feeling was strange and unwelcome at first. But the more I thought about it, the more it made sense.

It wasn’t the chair itself that made me so happy, it was the accomplishment of creating something beautiful that filled me with pride. As it turns out, I enjoy the creative process in all its forms. Whether I’m writing a powerful blog post, capturing a breathtaking image, or painting a chair is, apparently, irrelevant.

What matter most are the things I learn about myself along the way and the feeling I get when it’s all said and done. Creating something from nothing (or creating something new from something old) makes me feel proud, and that’s a feeling I want to have every day of my life.Questions to ask yourself when you'r ready to design your dream lifestyle

Perhaps your feeling of pride will come from creating. Perhaps it will come from connecting with people and helping them in some way. Perhaps you feel most proud when you’re learning.

Whatever gives you that deep sense of accomplishment, pursue it with your whole being. Don’t we all want to lead lives we are proud of?

6. What do people always tell you you’re good at?

My partner has an uncanny ability to get people to open up about their vulnerabilities. His calming nature makes them feel safe enough to talk about things they’d normally shy away from and his kind manner of questioning gently challenges them to think in new ways. It’s astonishing to watch.

He’s also an extraordinary singer and music is where his true passion lies, but I always tell him that if for whatever reason his music career came to an end, he’d make an incredible counselor.

Each of us has innate abilities that are the result of our unique life experiences, but they aren’t always obvious to us–we may need an outside observer to bring these abilities to our attention in order for us to recognize them. So the next time you are in the company of people who know you well, come right out and ask them.

“What am I good at? Do I have any secret strengths?”

Chances are, you will hear the same answer given time and time again, or your friends may even come to a consensus about the secret talent you are harboring.

Perhaps you never realized your paintings were good enough to sell (most artists have trouble seeing the value in their own work, after all). Maybe your organizational skills are unparalleled and you’d be great in a managerial role. Maybe you’ve never noticed that teaching people new concepts is one of your strengths.

The work we do for a living doesn’t have to come naturally to us for in order for it to be fulfilling, but it’s sure nice to do the work you feel you were meant for.

And of course, if it comes to us easily, it’s less likely to feel like work at all.

The Time to Make a Change is Now

Don’t wait for tomorrow, don’t wait for permission, don’t wait until you feel like you deserve it–your dream lifestyle can be yours once you make up your mind to go after it.

So ask yourself these questions and figure out what it is your heart truly beats for, because no one can steer you in the right direction but you.

Yes, it’ll be scary and yes, it’ll be hard. But what’s worth having is worth fighting for and once you start living your best life, you’ll wish you had gone after it even sooner.

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  • Reply Lynne Nieman August 2, 2017 at 4:40 pm

    Great post, Leah, with some good tips. I’m working on creating my dream lifestyle. Like you I tend to gravitate toward the creative pursuits. But I’m also planning travel for people since that’s one of my passions that I love to share. And even us GenXers like to do something with meaning and purpose!

    • Reply Leah Davis August 4, 2017 at 2:40 pm

      That’s wonderful that you love sharing your passion for travel with others! I do too, which is why this site is something I enjoy working on so much 🙂

  • Reply Gerardo August 4, 2017 at 9:07 am

    I ask myself these same questions all the time. Especially “What would I do if I only had a month to live” It’s puts more urgency. I always come up with travel and meeting girls. They have been enchanting to me since I was 5 years old. I know my soul wants to connect and make a difference in other people’s lives but I cannot get truly in touch with that. I certainly would if I was REALLY dying.

    • Reply Leah Davis August 4, 2017 at 2:45 pm

      Yes, the urgency! That part is important 🙂 It forces things into perspective for sure.

  • Reply Steph August 4, 2017 at 4:05 pm

    When I was a kid I used to make magazines and invent islands. I have a whole folder full of islands, they were awesome. Not too far off!

    Lately it’s been crossing my mind to just start saving for a boat. And interestingly that would be my answer to the 6 month question (so I could bring my loved ones with me on my travels).

    Maybe I’ll just go dust off a jar right now.
    Steph recently posted…The Ruins of Ancient CarthageMy Profile

    • Reply Leah Davis August 7, 2017 at 9:35 am

      Haha yes!! A good old-fashioned savings jar. We’ve got one going for our upcoming trips, works like a charm! I love that you want to take your loved ones with you on your travels 🙂

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