Why I Sold My Stuff to Travel the World and the Questions I Ask(ed) Myself

Which is the greater risk? Leaving your job, your friends, your stuff, your routine, your life, to go on an adventure into the unknown because you feel it in your gut? Or staying put at your job, with your friends, surrounded by your stuff, ingrained in your routine, in your life, with no change in sight because it’s the “safe” and “acceptable” thing to do? It’s a thought that has crept up for me on many occasions in the past few years. And the more I opened myself to the understanding that change is good, all the time, every time, even/especially when I don’t want it, I realized that my staying stagnant, when in my heart I know I must seek change, made the decision to leave all the things listed above and embark on a round-the-world journey simple. Not easy, though. I just knew I had to do it and began to ask myself a truck load of difficult questions.

I went to Italy in 2014 with my cousins, aunt, and uncle after they suggested I tag along. I bought the plane ticket and met them in Cinque Terre a month later. On the front and back ends of the trip, I stopped into Rome for a pair of weeks to visit a couple of friends whom I had met in 2012 after a tour with my band and ended up having the time of my life. They introduced me to their friends, and they introduced me to their friends. We shared conversations, drinks, food, laughter, the whole nine. It was absolutely lovely. After that three-week trip I came back to LA and fell into a funk. But it wasn’t the standard “I wish I was still on vacation” funk that generally accompanies heading home after a beautiful experience abroad. It was deeper. And it lasted longer than any funk I’d been in in a while. As the months passed and I was unable to determine why I was down for so long, I started digging deep within myself. I busted out the magnifying glass and head lamp, cracked open the darkest parts of my soul, asked myself a zillion difficult questions, and forced myself to look in the proverbial mirror. I started assessing my life (What am I actually doing here?), my goals (What do I want to accomplish before I die?), and my purpose (Whom do I want to affect before the end?). So yeah, the easy stuff. Peeling off my skin and scratching my most vulnerable wounds was not a pleasant experience. But I did it. And I continue to do it. Unfortunately, this is one of those things that isn’t a one-time event. You have to constantly uncover the truth beneath the surface and face yourself and your demons on a regular basis. Sweet.

I read the Four-Hour Workweek among other books as part of that deep, uncomfortable dive. At the end of each chapter, the author poses a few action items, some in the form of questions. One of the questions that stuck out to me went something like this: How hard would it be for you to come back to where you are today — your job, your routine, your life — in 3 months, 6 months, 3 years? Not emotionally, per se, but practically. I knew the answer immediately: Easy. Wicked easy. I haven’t yet built an empire, eased my way into upper management, or gotten too committed to a lifestyle that would prevent me from pulling ties from a career which would bring my comfort crashing down. But executing this task of unplugging myself from my life is far from easy, it’s a chore. Physically and emotionally. How do I go from routine 9–5p, eat, sleep, band rehearsals, drinks with friends, all the way to the other side of the spectrum: sell it all, pack a bag, no obligations, nowhere to be, no one relies on you, and roam the earth? Is this even something I want to do?

I started by asking myself a series of questions similar to the one Tim Ferriss posed in his book. His was the one that pushed me to the edge and allowed me to move forward with my desire to see what was next despite not knowing what it was that I wanted or what the future would look like.

  • How hard would it be for me to come back to where I am today?
  • Do I have a support system in place? Friends, family, colleagues, etc.
  • Do I feel comfortable selling, donating, and/or storing all my stuff?
  • Do I really need all the stuff that I have?
  • What is the most important thing in my life?
  • Why do I work hard to obtain all sorts of stuff only to die with none of it?
  • What can I give back to the world?
  • What do I have to say with my life?
  • Do I love where I am in my life?
  • Will my friends support me? If not, are they really my friends?
  • Is my heart open and free?
  • How can I make this world a better place?
  • What is my purpose?
  • Am I special?

I continually asked myself these and myriad other questions and ruminated on them over the course of about a year and a half. I made adjustments in my life when some were answered, I pivoted when opportunity presented itself, and I changed my vision when change was necessary. I did not know where I was going, but I knew that the path being laid before me — by my own work and by the universe — was the right one.

I was on my way.

Each question I pondered yielded multiple iterations of answers. There was no point that I said to myself, “This is exactly what I will do!” It was more like, “I think this is a good idea for now, but who knows?” and I just stepped forward. Like in 2015, when I made the choice to use all my time off from work to live with my friends in Rome for a month instead of quitting my job and moving there. I had no idea what I was trying to accomplish outside of just enjoying time with friends and seeing if I could make a few professional connections. I didn’t set up meetings with anyone, but did question and probe the folks I met about their lives and what they do and why they do it. During that process, I didn’t find a tangible purpose for me to stay in Rome (i.e., a job/career, artistic opportunities, love), but I did further my knowledge of myself and my thoughts of this world based on my experiences, the experiences of others, and our shared connections. So I came back to Los Angeles to reassess. I knew I wanted a change — Rome was the first leaping pad — but I didn’t know what that change would look like. When I got on the plane in Rome to come home, I wasn’t sad to leave and come back to my “boring” life, I was invigorated and excited to see what I’d do next.

In reality though, Rome wasn’t the first leaping pad at all. As I continued to ask myself questions, I also pulled back my perspective from being deep in the weeds of my life and took a 30,000 foot view of what I was doing. I saw that my month in Rome was indeed way further from the beginning of my journey than I thought it was. I don’t know how long my journey will be, so I can’t say it was in the middle or near the end, but it certainly wasn’t in the beginning. This process started much further back than that year-and-a-half than I thought. Every choice, conscious or not, my own or forced by circumstance, has led me to this point. It’s easy for me to get lost in the “story” of my own personal journey, trying to pinpoint each plot change, and how exactly I got to this point, but that is a waste of my time. The “why” doesn’t matter yet. The “what do I do now?” does.

“So, like, what do I do now?”

Here’s my suggestion based on what I did: Think of every reason you shouldn’t do this thing and determine whether that reason is based in fear. DO NOT make decisions based in fear. That is not living. That is a prison. (And I’m not talking about survival fear — we all know to run away from a rabid dog, and not to hurl rocks into a swarming bees nest, that’s just common sense. I’m talking about ego-based fear: If I do this thing and it doesn’t work out like I want it to, what will people think? What will I do for money? How can I look at myself in the mirror? Etc, etc. That’s the fear we’re looking to avoid here.) I started asking myself even more questions about the things I fear the most as I started to consider this journey of relatively epic proportions.

  • What will people think?
    True friends will support you, or maybe even come with you. Forget the others.
  • What will I do for money?
    There are lots of online resources about saving money over short periods of time and making money on the road. Also, when you have no bills to pay or very few (which will happen when you forsake the routine of daily life in one place for travel), you don’t need a ton of money to maintain a life back home, which means you don’t have to work as much, which means you can travel more. Travel isn’t as expensive as people think and you really only need enough money to get to your next destination, eat healthy, and have a bit of fun. I understand this isn’t exactly an easy thought to get on board with. Lots of us want that sizable safety net “just in case.” But this is about relying on what skills and talents you already have, what support you have in place, and what is being laid out for you, too.
  • What about my stuff?
    You really don’t need all the stuff you have. It doesn’t bring you happiness. This is a fact.
  • What about my job?
    Again, how hard is it to get back to where you are? Do you love what you do? Can you live without it for a while? Is it a placeholder to maintain some sort of normalcy that the society in which you live has put on you?

During my trial-run month in Rome in August ’15, I recognized that I didn’t want to live there. Not because I didn’t love Rome, but because the thought of living there had the same weight as the thought of living in L.A. where I’d resided for the past twelve years. It just felt like a meh thing to do. Being in one place felt stagnant and stagnancy isn’t for me. I love both cities. And others, too. But L.A. lately hadn’t been working for me. It wasn’t the city, it was me. There’s something else out there that I needed to find, that I needed to give myself over to. That something is not in L.A. at the moment. It’s not in Rome either. Perhaps it’s in places I’ve never been or places I’d like to go back to. Long story short, I just don’t want to live anywhere right now. I want to experience everywhere. Or at least as much as I can before I run out of money/energy, find an awesome career, fall in love, or die. And those things won’t even necessarily prevent me from continuing on my travel experiences. Hell, I could find a career in travel. Or meet a woman who wants to work and live on the road with me for a while. Or I could change my mind and focus on something else entirely. Or I could die. But that could be the best journey of my life. Who really knows? (That’s definitely a topic for another time.)

The key to all of this is that having a very specific, clearly defined, OCD goal in mind is not the way I roll. I change my mind a lot. I’m human. Sometimes I see shiny things, go “Oooooooh!!!” and when I get close to them, they lose their luster. Sometimes the blemished things turn out to be the best, most rewarding things I’ve ever experienced. It’s tough to tell what result you’ll see when you’re in the heat of it. The emotional roller coaster of decision making can be wicked confusing and complicated.

It all comes down to this: You must do what you feel is right for you. Listen to that tiny voice that winces and sighs when you have to deal with an angry phone call from a client at work. Take note of the general emotional state during your days. Keep track of when you feel “down” or “uninspired”. Spend at least 10 minutes a day sitting quietly without interruptions (thoughts about what it all means count as interruptions). Do your best to recognize what you can control and what you can’t. (Hint: You can control wayyy less than you think you can, but you can absolutely control how you respond to situations.)

There are many different ways to succeed in life. New paths are laid out before us on a daily basis. To know which path is right before you choose it is impossible. But as long as you approach each path with eagerness and an open heart, you will make the right choice no matter which path you choose. Trust yourself. Trust those around you. Trust a higher power if you believe in one. None will let you down.

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