I’ve been told in the past, “enjoy your adventures before you have kids because once they arrive you certainly won’t be traveling full-time ” and now that I’m a parent I’d be delusional to suggest that life hasn’t changed dramatically. That said, I believe in the the almighty workaround enough to try and defy the skeptics–most notably the one that lives between my own ears. In this post I want to share the 10 questions I asked myself that enabled me to commit to traveling full-time and climbing with my family. As you read this, please keep in mind the following:

  • There is no such thing as “living the dream” –only choices aligned with our priorities.
  • I’m not writing about my goals and obstacles because they’re uniquely worthy–everyone has their own.
  • My system of self inquiry isn’t better than yours but it’s better than no system at all.

I’ve been wanting to write this post for a while–and I’ve put it off because it’s hard to share this without feeling like I’m dangerously close to giving life advice. Perhaps that’s just my ruthless self-editor speaking. I recorded a couple of podcast episodes that deal with this subject matter and I decided that with the launch date of the LivingVertical roadshow looming, I’m going to speak my piece. I think that having a system to assess risk surrounding major decisions is more than a little useful. I’ve seen the micro-application of this within diabetes and it extends to basically everything else, including this next big move.

  1.  Can this actually work? It’s always been intimidating to take this first step. If you don’t have to actually implement an idea, it can live safely forever in the purgatory of “maybe”. Once you put your idea under the microscope with actual intent, it will either fail or succeed. Trying to spare our dreams from the harsh light of day has undoubtedly caused many of us to love our ideas beyond the hope of becoming reality. Once I knew that the answer was ‘yes’, and that it was actually possible for our family to live on the road full-time, it meant that I had no good reason not to try. The question now became how can this work, leaving me with the responsibility to unlock that puzzle.
  2. Will my wife leave me? Relationships are fragile. When taking on a big project like this you have to know that you’re exposing your relationships to risk. In my case, I have to prioritize a relationship with my daughter and my wife–but for others it may be friends or parents. The strain of living in a small space with less consistency and comfort for the foreseeable future is a decision that could make or break these relationships. Looking back, I feel like there is a decent body of evidence to suggest that we have enough durability to thrive on the road.  Stefanie and I eloped in 2008 at the end of a 6 month road trip. We had just driven down to San Diego from Alaska in my Honda Civic–which had doubled as our home–and I realized that the most important thing was being with someone who understood the life I wanted to live and who would hold me accountable to not give up on that dream. Having confidence in support from the people closest to you can be the difference between a dream and reality. Choosing who to keep closest to you based on their willingness to support is a long term approach to enabling achievements.traveling with your family full time rving
  3. Who cares? I am aware that this upcoming project is going to be a huge amount of work and not a vacation. There needs to be a good reason to take on this kind of hare-brained idea. It’s important to know if anyone will actually care about this–will we be able to impact someone through this venture? When Stefanie and I announced that we were buying camera gear, selling all our stuff and going to live on the road and start LivingVertical in 2011, an amazing thing happened. Friends, relatives and in some cases acquaintances mobilized to get behind our work. No one accomplishes anything great without someone, somewhere supporting them and caring. It’s incredibly important to know who actually cares and who will support your goals. On the other hand, it’s impossible to know who cares and who will be impacted without taking that first step–and committing. Even if we only have one (more) free meetup that helps one person, it will be worth the effort.camping in joshua tree national park
  4. Downward social mobility? People laughed at me when I used this term, but since I was in college I asked myself if I could actually do more with less. I joke about being like the post apocalyptic cockroach who can survive in the most austere conditions. Rather than seeking to climb a corporate ladder that leads to more financial wealth and and less free time, I chose to hone my “inner cockroach” and take my dividends in time. It’s not necessarily the right approach for everyone, but it’s my answer to how I can live this way: simply need less. camping in yosemite national park
  5. Do you really need that? It’s way easier to hone in on a priority if I am not occupied with competing tasks or possessions.  Turns out I can save a lot of money when I have fewer things to maintain and pay for. I’ve gotten rid of most everything that I don’t use frequently enough to consider it essential to my life and well being–and I keep checking in to see if “I need that” each time I make a purchase so that I don’t regress. I feared taking that step for so long–but the less I have the less I feel like I have to worry about. It’s basically impossible to recommend what is objectively necessary and what is not–but being willing to experiment can reveal opportunities to downsize where you may not have expected them. For example, I loved my iMac for editing–that big screen offered such wonderful real estate for photos and video projects. When I considered this move into a tiny trailer, I decided to replace my big computer with a laptop. It’s about 15-20% less fun to edit on, but it’s 100% more portable and it can perform all the same tasks. This is just one decision that has simplified my life a great deal.
  6. Can we afford this? Having a low overhead is all well and good, but I still have to provide for my family. That’s hard enough if you devote your life to work. My answer? Think less about developing a career (dependent on an employer) than developing skills which I control and can leverage to my advantage across a broad spectrum of the business world. Knowing my value gives me confidence that I can provide what I need for myself and my family. Skill development has everything to do with practice, not perfection. Want to see how I learned to shoot video or photos? Look at our Films and Projects. Want to hear how I learned to produce audio? Listen to the AdventureRx podcast. Having a low overhead allows me to invest time into my skill development. That’s why I felt free to leave a good job and take a 50% cut in pay and no health insurance. This arrangement gives me enough work to survive and enough time to develop my professional skills in media production.
  7. Is this a healthy decision? Diabetes motivates me to live fully while I can–for myself first of all and my family–but also for the sake of pushing back against the fear and the negativity that surrounds this condition in the public. I believe that the fear of diabetes is more damaging than the diabetes itself. Conversely, I have had to ask myself if my fear of leaving a good job was due more to insurance worries than financial concern. It may sound odd to hear those two concerns separated, but there is something really comforting about insurance that income alone can’t provide. I’d love to have that comfort, but I won’t put my life on hold for the sake of it. I need insulin and strips to survive–and I can get enough of that on my own if it comes to it. If health insurance costs more than buying insulin and strips on my own, then that eliminates my attachment to it. Of course this doesn’t change the fact that I have to make sure Stefanie and Lilo are covered–which is why we chose to base ourselves out of Massachusetts. Not all states have good (affordable and useful) health insurance options. Massachusetts actually has a great system that offers very good insurance options which are scaled according to income, so we are able to pay a reasonable price to have some coverage even without a massive income. I will go on record as saying that personally, I would be willing to go without any sort of insurance if not for my child.rock climbing with a gopro red rock nevada las vegas
  8. Can I become debt free while living this way? I believe that freedom from debt lies at the heart of self determinism. I also think that accepting debt is something my generation has unfortunately been made to embrace as normal. I was cheap from the time I was a little kid. My dad used to joke that I was as “tight as the skin on a hotdog”. I literally refused to spend the money I’d get for birthdays or Christmas. Maybe that’s why I believe that I can enjoy freedom with very little money. Having lots more money offset by lots of debt seems like a thinly veiled guise for servitude. Despite this approach to managing money, I still have some debt, which I am paying off aggressively.
  9. When do you bail? I decided that I’ll pull the rip cord when it’s financially impossible or when it stops being fun, whichever comes first. Financially impossible: taking on additional debt to live this lifestyle–I’m ok with investing in a skill or business opportunity, but if we are having to put bare essentials on credit, then it’s not viable. No longer fun: If I have to choose between my family and this lifestyle. If I have more than 14 consecutive days where I go to bed thinking ‘This is not worth it. Give me back my sofa and Netflix’. Having a good exit strategy and knowing when it’s time to deploy it can give you the ability to really focus in the moment, because there are clearly defined parameters for failure and until you cross those predetermined lines, you have no reason not to keep fighting to make it work.
  10. Is this the right risk to take?  It’s easy to view risk as “bad” or at least undesirable–something to be avoided. To me, risk signifies an opportunity for dividends of some kind. Risk requires mindful attention in order to determine if it’s an appropriate risk or an irresponsible one. Taking the time to thoroughly assess the risk of this proposition is how I know it’s the right risk to take. I like to borrow from Tim Ferriss on risk management. Roughly paraphrased, risk is an irreversible negative outcome. If the downside of your choice can be reversed in a year or so, then what’s the harm in trying? If I don’t make any creative progress or this journey is a total buzzkill, I bet that within a year of bailing, I can get back to approximately where I am right now.

One of the reasons that I insist that diabetes has played a positive role in my life is that it forced risk into my life–and I am a timid person by nature. Learning that I had to embrace risk to deal with it has opened my life up to so many amazing things that I literally would not trade for a million dollars. My system of self inquiry basically comes down to looking at risk from a variety of challenging angles and separating the risks that I can’t manage and the ones that I can mitigate–which leaves me with two “piles” to weigh against each other. I think that while this may not be relevant to everyone and every goal, it’s a general framework that allows normal people to take big dreams and whittle them down into achievable steps.


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