Lifestyle Design: 3 Steps to a Life of Freedom

Lifestyle Design: An Intro to Our Approach

In a recent post, we shared some insight into How We Fund Our Travels. But financial independence is just one piece of a larger puzzle we think of as ‘Freedom of Choice.’ Freedom of Choice is the label we put on our lifestyle design blueprint. A basic road map we set in place to help us live our ideal life.

In some ways, Freedom of Choice is similar to the current FIRE movement (financial independence / retire early). But we view Freedom of Choice as a more holistic approach to lifestyle design. It’s an approach that’s as much about conditioning our minds to follow our curiosities and overcome our ‘buts’ as it is a guide for tackling financial and other logistical barriers that stand between us and the life we want to live.

In this post, we elaborate on our lifestyle ambitions and share some insight into the 3-step process we used to build the lifestyle we live today. Consider it an introduction, which we look forward to exploring further in future posts.

 

A Lifestyle by Design

Before jumping into the steps we took to get here, let me briefly describe the lifestyle we set out to create through Freedom of Choice.

In short, our goal is a lifestyle that puts us in the driver’s seat and gives us control over how we use our time. We want a lifestyle that encourages and enables us to follow our curiosities, live our passions, and choose where we live and work. One that enables us to spend a summer in Tuscany, sail to the South Pacific, become bush pilots in Botswana, or devote time and energy to bettering ourselves.

I can remember catching up with a friend after we returned from our Africa overland trip back in 2008. On the phone, she said, “I don’t want to sound too direct, but shouldn’t you be thinking about your future?” The subtext was clear. Taking three years off from our corporate careers to travel struck her as irresponsible. Instead, we needed to be working, planning, and saving for retirement.

But living in the moment has never been at the expense of our future. We want a lifestyle that’s as much about living our best today as it is about planning for our best tomorrow. One that helps us get the most from every stage in life. If there’s anything we can do about it, we don’t want to be forced to choose between living our dreams today or tomorrow. We want every year to be the best it can be.

We want to live life intentionally, crafting a lifestyle that strikes a balance between work and play. We like to work and value the satisfaction that accompanies a productive life. Sheri and I both have ever-expanding bucket lists filled with interesting jobs we’d like to pursue. Recently Sheri said she’s inspired to pursue a career as a go-go dancer at one of those trendy bingo raves in South Florida. A wild job that’s likely to have her gyrating on card tables ‘til 5pm.

But work can be a double-edged sword. We enjoyed our corporate careers. The challenge was that our careers didn’t allow much time to pursue a life beyond our jobs. Everything else we wanted out of life – our interests and dreams – were forced to reside inside the confines of long commutes, demanding work schedules, and limited time off. Our goal is to integrate work into our lives rather than building our lives around our work. Living a life of freedom doesn’t mean retiring from work. It’s about being able to choose jobs that align with the life we want to lead.

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Our goal is to integrate work into our lives rather than building our lives around work

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To sum it up, going back to the beginning, if you asked our 23-year-old selves to define our ideal lifestyle, we probably would have said we want to live an intentional life that involves actively charting a course bound for somewhere extraordinary.

Fast forward to today. Five years into our current trip, it feels like we’ve achieved what we set out to do. As I write this post, from the sunny terrace of a mountain house above Lake Garda, Italy, Sheri and I are in control. We’re living a life of freedom and our ship is headed in a direction that was once just a dream.

 

Making it Happen

So how did we transform our lifestyle dream into reality? Freedom of Choice is based on three primary objectives:

• Cultivate our curiosities
• Overcome our ‘buts’
• Make the Pieces Line-up 

Our approach to lifestyle design is based on a series of steps we began working to achieve in our early 20’s, which we’re still employing and refining today. It’s an approach designed to benefit us throughout life, rather than only once we reach an end goal. It's been a lifelong evolution, which began yielding results early on, with steadily increasing benefits as more pieces of the puzzle fell into place.

Step 1: Cultivate Our Curiosities

Our approach to lifestyle design starts with finding our passions. It’s priority #1 – the foundation from which everything else is built. Passion energizes us and gives our lives purpose. It’s the thing that keeps us dreaming and motivates us to make the sacrifices required to realize those dreams.

But finding what truly inspires us - those things we’re so passionate about that they keep us up at night - isn’t always easy. Discovering our passions is a lifelong journey that demands time and investment in ourselves. It’s an investment we stamp 'high priority' and fiercely protect when threatened by the rat-race of life.

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Discovering our passions is a lifelong journey that demands time and investment in ourselves

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To find our passions, we’ve made it a priority to follow our curiosities. We aim to experience as much as possible - to touch, taste, smell, and listen to anything that interests us. Our idea is simple: follow our curiosities and we’ll discover new interests and passions.

Travel has played a central role in following our curiosities. It’s our shared passion, which has opened our eyes to new possibilities that extend beyond travel. Exploring new places – like Nepal and Ethiopia in our 20’s – proved transformative. Each new experience opened new doors.

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Finding our passions starts with following our curiosities

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Just before traveling to Ethiopia in 2002, I was talking to a friend from college. During our call, I mentioned our upcoming trip. “Why are you going to Ethiopia?” he said. “I haven’t been there, but I’m curious. I’ll let you know when I get back.” I replied. On the other end of the phone, I sensed disapproval. “I haven’t been either, and I don’t need to go to know I wouldn't want to visit that country,” he said. “Don’t you remember ‘We are the world’ and the famine in the 80’s?”

Step back a few years, before we started following our curiosities, and I may have said something similar. Back in college, Ethiopia was beyond our thinking. But by 2002, following our curiosities had taken us so far beyond what we thought we knew about ourselves, that we understood its' power to open new doors.

Ethiopia was another gateway experience that led to unforeseen opportunities. One that opened more doors, including our multi-year overland journey across Africa three years later. On our flight to Ethiopia, I couldn’t have predicted how our visit would lead us to drive over 80,000 kilometers across Africa. But it did. And that’s the point.

I suppose it’s like trying new foods. While you may not like everything you put in your mouth, get in the habit of tasting new things, and you’re guaranteed to discover unexpected culinary delights. With each new experience comes new revelations about ourselves and the world around us. Invariably, this expansion in our thinking leads to new (unforeseen) possibilities.

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Our approach to lifestyle design is about cultivating a mindset where it’s natural to follow our curiosities

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Our approach to lifestyle design is about cultivating a mindset where it’s natural - second nature really - to follow our curiosities. Whether it’s food, places, experiences, or anything else, if we’re curious, we're inclined to try it.

This approach gave birth to our bikepacking trip last summer. All we needed to go from never-done-it-before to bikepacking Europe was a routine trip to a local outdoor store. While paying for a couple of items for our upcoming trip to Indonesia,  I noticed a bikepacking bike was on display by the register. Something about that bike intrigued me. Enough so that within 24 hours, we up-ended our Indonesia trip and set out to source and outfit two bikes before heading for Ireland -  the start of a 5-month trip across Europe.

Cultivating our curiosities enabled our bikepacking trip. Another gateway experience that introduced us to a new way of traveling the world. Without cultivating the right mindset, our ‘buts’ would have cut down the idea before it could take root:

• BUT we leave for Bali next week
• BUT we’re not in shape to ride
• BUT we don’t have bikes
• BUT our camping gear is in Uruguay
• BUT we’ve never done it before
• BUT…

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But these days, our curiosity is more powerful than our ‘buts’

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The idea of following our curiosity is so ingrained that we didn’t think twice. Our curiosity is more powerful than ‘buts.’ Looking at that bike on display in the outdoor store, we only saw an opportunity to try something new - a chance to follow a curiosity and see where the road leads. This mindset is central to the lifestyle we live today.

Step 2: Overcome Our ‘Buts’

We all have them. ‘Buts’ are the mental roadblocks inhibiting us from doing the things we want to do. They’re obstacle #1, which we must confront before we’re able to get on with the business of making it happen.

“I’d love to spend a year living in Paris, BUT I just don’t have the money. Maybe when I have more money…”

 “I’ve always dreamed of sailing around the world, BUT I’ve got kids in school. Maybe we can do it after they go off to college…”

 “I’d love to bike across Europe, BUT I’m in no shape to be riding a fully loaded touring bike. Maybe once I’m in better shape…”

 “I’d love to kayak the Inside Passage, BUT I've never done it before. I wouldn’t even know where to start…”

The examples above highlight a fundamental challenge. These ‘buts’ equal real obstacles that must be overcome. But before we can tackle the problem, we need to get past our own mental barriers. If we don’t have the money, we can’t spend a year in Paris. And if we want to sail around-the-world, we can’t tell the kids we're running out for milk, and then sail off into the sunset (well, I suppose we could, but we’ll probably get blowback for being shitty parents. Good thing we only have hypothetical kids).

But the thing is, ‘buts’ are dangerous. Sheri and I call them dream-killers. It’s too easy, particularly when distracted by a busy life, to say “I’d love to [fill in the dream], BUT [fill in reason]. Translation: I’d love to do it but I can’t. ‘Buts’ are a convenient means of making ourselves feel better about deferring dreams in hopes that circumstances line-up better tomorrow.

But here’s the reality. If we strip ‘buts’ down to the bare metal, most ‘buts’ boil down to prioritization. How important is our dream of spending a year in Paris, or sailing around the world, or biking across Europe? Is it important enough to do what it’s going to take to make it happen? Are we willing to make the trade-offs and sacrifices required?

Overcoming our buts has gotten much easier over time. Before our Africa overland trip back in 2005, ‘buts’ were a significant barrier to achieving our dreams. But these days, ‘buts’ rarely hold us back.  Similar to how we trained ourselves to follow our curiosities, our approach to getting past our ‘but’s has been a slow evolution, focused on conditioning our minds to look past ‘buts’ and only see opportunities.

As I’m sure you’ve heard said: In a sentence, ignore anything that comes before the but.“He’s a really nice guy, but he can be such a jerk I can’t stand being around him.”

Our first step in tackling ‘buts’ starts with reorganizing the sentence. To refer back to our bikepacking trip last summer, here’s how I framed the ‘buts’ when pitching the idea to Sheri:

Instead of saying:

 “I’d love to go bikepacking across Europe this summer, BUT the timing isn’t right. We leave for Bali in a week.”

 I said:

“I know we’re scheduled to fly to Bali in a week and the timing isn’t ideal, BUT I’d really love to go bikepacking across Europe this summer. We haven’t paid for our airline tickets yet, so we won’t lose any money by changing plans…”

 AND

 Instead of saying:

“I’d love to go bikepacking across Europe this summer, BUT we’re totally out of shape.”

I said:

“I know we’re not in the best shape for cycling, BUT I’d love to go bikepacking across Europe this summer. We can take it slow and get in shape as we ride…”

Looking at the two examples above, I’m sure you get the idea. Rearranging the sentence doesn’t overcome the obstacle, but it does reframe the issue – placing priority on the dream rather than the objection.

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Overcoming ‘buts’ starts with prioritizing the dream rather than the objection

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Like most of the steps we’ve taken to craft our lifestyle, there’s no magic in our approach. At the end of the day, overcoming buts is about prioritizing the dream over the objection and then working to surmount any logistical hurdles – be it money, time, career, family, fitness, or whatever else.

The important question to ask: Is this a big enough priority to do what’s required to make it happen? Looking back, anytime our answer was yes, we found a way to overcome our obstacles and make it happen.

Step 3: Make the Pieces Line-up

When I was in high school, I worked part-time, running blueprints for an architectural firm. It was a job that involved feeding giant sheets of light-sensitive paper into a painfully slow machine for processing. It was the type of after-school job that came with lots of paper-cuts and plenty of time for contemplation.

One afternoon, I was working with Mark, a college student that worked at the firm part-time, and we got to contemplating life, travel, and dreams. Somewhere in the conversation, Mark said,

“You know, life’s a paradox. You’re either young, and you’ve got the health and the time but no money. Or you’re middle-aged, and you’ve got the health and the money but no time. Or you’re old, and you’ve got the time and the money, but you don’t have your health.”

Perhaps you’ve heard this quote before. It offers a simplified view of one of life’s big challenges. No matter what stage of life you’re in, lining up the piece of the puzzle – health, money, time, and everything else required to live your dreams – can be difficult. And when everything does line up, the pieces don’t stay aligned forever. Life’s opportunities are fleeting. This is one of life’s simple truths.

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If every life stage comes with challenges, why defer our dreams in hopes of a better tomorrow?

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We’ve always felt fortunate to have some of the most important pieces in place – our health, each other, the accident of birth, and a shared vision of the life we want to lead, among other things. We view our good fortunate as a gift, which could disappear without notice.

This reality motivates us to live with purpose and a sense of urgency. If opportunities are fleeting and every life stage comes with challenges, why defer our dreams in hopes of a better tomorrow?

We believe lifestyle design starts with being mindful of this gift and the opportunities it presents. It’s about picking up where our good fortune leaves off. Taking stock of the other pieces that need to be put in place and working proactively to make all the pieces line-up. No leaving life to chance.

There are so many potential pieces to the puzzle – family, money, career, time, health, etc. and everyone’s puzzle is unique. That said, I’ll try to highlight some of the key pieces to our puzzle. Each piece represents an obstacle, which we had to overcome for our lifestyle to take shape.

At a high level, we can group many of our obstacles into three areas of focus:

• Creating Financial Independence
• Freeing up Time
• Becoming location independent

I could probably write a book on each. But that’s not the point here. What follows is a quick and dirty introduction to some of the bigger obstacles we’ve faced.

Creating Financial Independence:

The Challenge: Secure the financial resource required to fund our desired lifestyle.

The Solution: Travel isn’t cheap, and building financial independence was an important focus in developing our travel-based lifestyle. I like to think of it in simple terms. The more control we have over our financial house, the more control we have over our time.

In our post How We Fund Our Travels, we explain how we overcame the financial obstacles standing in our way.

Freeing up Time

The Challenge: Carving out time to pursue our interest and passions.

One of the main lifestyle design challenges we faced was figuring out how to free up time to pursue our interests and passions. To accomplish our goal, we focused on two areas:

• Solve for time constraints inherent in corporate careers
• Minimize demands on our time

Solving for Career Constraints:

The Challenge: We enjoyed our corporate careers, but they didn’t leave much time for the rest of life.

The biggest lifestyle challenge we faced was overcoming the time constraints inherent in our corporate careers. Between demanding work schedules, long commutes, limited vacation, etc., there just wasn’t much time left for the rest of life. Solving for this was essential if we wanted a life of freedom.

Our Solution: There’s more than one potential solution to the problem. For example, we could have pursued jobs/careers that offered more free time and greater flexibility. We’ve met plenty of people who work jobs with ample time to pursue other interests – for example, working a three months on / three months off schedule.

As we discussed in How We Fund Our Life of Travel, our solution came in the form of financial independence. Being financially independent allows us to integrate work into our lifestyle rather than building our lifestyle around work.

The goal isn’t to retire, at least not in the traditional sense. It’s to be in control of when and where we work so that we have time and flexibility to travel and pursue other interests. Being in control means pursuing jobs because they seem interesting, not because we need a paycheck. I love the idea of piloting bush planes in the Okavango Delta or becoming a dive instructor in the Maldives. Jobs that may not pay well, but which fulfill us in other ways.

Minimize Demands on our Time:

The Challenge: It’s easy to get so bogged down with life’s to-do’s that there’s no free time left.

Freeing up time has always been a key focus, particularly when we were immersed in demanding corporate careers. When you think about how hectic life can be, it’s easy to understand the challenge. If you start with 168 total hours in a week, and then subtract for life’s to-do’s - like work, commute, family commitments, honey do’s, caring for pets, trips to the grocery store, and all the rest of it - it’s not long before there’s no free time left.

Our Solution: Starting when we graduated from college, we've waged a never-ending war to avoid/eliminate/minimize anything that infringes on our free time. One of the primary weapons we employee may seem counter-intuitive - we prioritize our wants over our needs. I don’t say this to suggest we're irresponsible. Everything in life that needs to get done, gets done. But, our approach is meant to reframe how we prioritize our time and how we define ‘need.’

For example, during our airline years, travel was a priority. If we wanted to go to Paris for the weekend, we went. For life’s to-do list, we took something of a triage approach. The truly important stuff always got done, and the rest of it didn’t. That’s the beauty of prioritizing wants vs. needs. By prioritizing ‘wants,’ we make time for them. And by not having all that extra time to work through a never-ending honey-do-list, the critical ‘needs’ rise to the top (and everything else drops off).

To help keep our list of ‘needs’ to a minimum, we leverage the art of avoidance. Specifically, we avoid anything that requires time to clean, maintain, repair, organize, tinker with, or keep alive. This includes everything from pets that need caring for, to lawns that need cutting. Whenever possible we’ve trimmed the fat – moving closer to work to reduce commutes, living in low maintenance condos to cut out maintenance, etc.

That’s why we travel in a Toyota Land Cruiser and don’t futz with multi-fuel stoves. I’d rather be out photographing lions than sitting in camp futzing with the clogged stove jet.

To be fair, I'm oversimplifying a bit. But only a little. We've always made time for our 'wants' and we've worked hard to minimize the demands placed on us by 'needs.' Most of this comes down to being mindful of how our decisions - no matter how small they may seem - impact our free time (and broader lifestyle goals).

Becoming Location Independent

The Challenge: We've always wanted to live and work in places like Colorado, Santa Barbara, and Cape Town, but our careers, house, and belongings  were obstacles that made it hard to just pickup and go.

Location independence is about eliminating obstacles that inhibit our ability to choose where we live and work. This is a major priority. A life of freedom starts with being able to pick-up and go wherever we want, whenever we want.

Location independence takes many forms. For some, being location independent is about living wherever they choose. Back in 2008, we traveled for three months through the western United States, British Columbia, and Alberta searching for the perfect mountain town. During our trip, many of the ‘locals’ we met turned out to be transplants from Los Angeles, New York, and other big cities. People seeking to improve their quality of life by moving to towns like Bend and Boseman. Many achieved location independence by working corporate jobs remotely.

For others, location independence is about spending part of the year at home and part on the road. It’s a compelling idea. Live a "normal" life back home for a few months and then travel for 2-3 months before returning home for another shot of normalcy. It’s the lifestyle our English friends Pat and Ness have lived for years – their location independence made possible by exceedingly flexible careers as doctors that allow them to take frequent time off to live and travel wherever they choose.

For still others, location independence is about being a true nomad. We meet more and more people who fall into this bucket. Vagabonds who are living, working, and traveling indefinitely. Some work remotely, some have portable careers, some work local jobs, and others don’t work at all.

For us, location independence is an ever-evolving concept. Simply put, we want to be completely free of any constraints on our ability to live, travel, or work anywhere we like. How we choose to use our location independence changes from year to year. Sometimes, it’s about traveling overland full time. Other times, it’s about picking an interesting place and settling down for awhile. Right now, we’re on a live – travel – live schedule. Over the last year we bikepacked 5 month in Europe, spent a month in Santa Barbara, traveled a month in Argentina and Uruguay, lived three months in Cape Town, lived and traveled three months in Turkey and Italy, and are now living in Croatia. It's been a year with a nice balance between living in interesting places and time on the road.

Our Solution: Our main obstacles to location independence were our corporate careers, which dictated where we lived. With a bit of effort, we were able to work remotely (although Sheri had better luck in this regard than I did). These days, location independence is a perk of financial independence, which eliminates the need for corporate jobs.

But, while work is often the biggest obstacle to overcome, achieving location independence often requires other lifestyle adjustments ranging from kids in school, to pets, real estate, and the anchoring effect of material possessions.

We’re very fortunate in this regard. We began working to build our current lifestyle in our early 20’s before planting roots. This gave us an advantage. Our ongoing focus on lifestyle design helps us avoid constraints instead of having to ‘unwind’ them later.

In our case, one big exception was downsizing. While we’ve never been ones to accumulate stuff, aligning our belongings with our location independent lifestyle still proved challenging.  Since we built our plans around living in many places and traveling often, our downsizing goal was to ensure our possessions fit into our location independent lifestyle, instead of working against it.

In many ways, downsizing - minimizing our stuff - was one of the more challenging projects required to achieve Freedom of Choice.

 

Closing Thoughts

While our passion for travel influenced our lifestyle, achieving Freedom of Choice isn’t solely about travel. Rather, it’s about taking control of how we spend our time and where we live and work. It’s about living an intentional life where we strive to be present and avoid putting off dreams until tomorrow. A lifestyle that’s focused on both today and tomorrow and on getting the most from every stage of life.

Importantly, our approach to lifestyle design has been as much about conditioning our minds to embrace life’s possibilities and overcome our self-inflicted ‘buts’, as it’s been about overcoming financial and other challenges.

Reflecting on the steps we took to get here, it all seems so straightforward. The countless questions we’ve had along the way answered. Our ‘buts’ overcome. The many financial obstacles and limits on our free time and ability to live where we want, surmounted.

But in truth, it’s been a challenging journey. Those answers, so obvious now, were anything but when we posed the questions.  Those ‘buts,’ now overcome, once seemed insurmountable. Those logistical obstacles, now viewed in the rearview mirror, were once our Everest.

As I write this post, our journey continues. As we evolve, our lifestyle evolves with us and with evolution comes new questions, ‘buts,’ and obstacles to overcome. It’s all part of a lifelong quest that’s been as exciting and rewarding as it’s been challenging.

We’re sharing some insight into our journey as food for thought. Perhaps it goes without saying, but our approach is only one of many. Hopefully, through our story, you’ll find something useful, which you can apply to the pursuit of your own unique lifestyle goals.

In the coming months, we look forward to expanding on many of the topics we hit on above. In our next lifestyle post, we’ll take a deep dive into one of our most painful goal – downsizing. Something we struggled with for years, before finally developing a simple and (relatively) painless, minimalist approach to reducing our belongings to only the things we truly love and need.