An Unconventional Take on an Unconventional Life

Everyone has that one friend that is always in a cool location doing something awesome like climbing the tallest peak in a national park or visiting a new country. I’ve always wanted to be that friend. The person all of your other friends bring up at dinner when you aren’t there because you are going through class four rapids in a white water raft. So what’s holding me back? Rational thinking. The very thing that has helped me through many challenges in life also presents one of my greatest conundrums.

The typical adventure junky is also a dirt bag. I don’t mean that they’re an asshole, I mean that they live very cheaply, typically taking 6-8 months off in the year to go and have these thrilling experiences. Couch surfing or living in their old 1984 Volkswagen Vanagon and eating cans of beans. This lifestyle is so cheap that it can typically be funded by a single season of being a chairlift operator for a ski resort during the winter. So, if there are people doing that and I seem to be aware of how to make it work, whats the issue? Well like I said, rational thinking. Unfortunately, I suffer from something called overthinking. I know that most likely I won’t want to live the adventure dirt bag lifestyle my whole life. I’ll probably want a few kids and a decent house, all of which will cost a lot, especially with how the housing market has been the last few years. And I know what you are saying “Well, that doesn’t seem like an issue, just go do whatever you want until you are finally ready to settle down and then start working hard to afford the lifestyle you want.” That sounds great, other than I am not to optimistic that it will work. Let’s look at a few things:

  1. Moving up the Career Ladder (Salary)

Not only are entry level positions difficult to find currently as companies scale back their business and need to let people go, flooding the job market with applicants having more experience than is required for the position and out competing recent graduates, they don’t pay all that well, at least not to support buying a home and raising children. Therefor, it seems important for me to have some skills that I can leverage to be more competitive, meaning I need to work and get experience.

2. Planning for Retirement (Investing)

I have recently become very interested in investing, specifically with the goal to “retire” early. (AKA Financial Independence) Hopefully you know that the earlier you put money into the stock market, the greater returns you will see on that money, so long as you keep it for the long haul. This means that right now is the ideal time for me and everyone else to put any extra money you can spare into a brokerage account or retirement account. The sooner I get the money in the longer it has to compound (think of this like little miners, the more miners (dollars) you put to work (invest) and the longer you keep them working, the more diamonds (growth) you will get). This means I need to make disposable income now, not later in life when my money won’t be able to work as long for me. (If you are interested I currently have a Roth IRA and a retirement account similar to a 401k through my job; check out Mr. Money Mustache for information on Financial Independence and Early Retirement (F.I.R.E).

3. Spending time with my Kids

The whole point of having kids is to raise them as best you can (Or at least I think it should be). How can I raise my kids if I am working 80 hour weeks working overtime to be able to pay the mortgage? I’d actually like to do the opposite, work less hours than normal (somewhere around 4 hours a day) and have more time to spend with my kids. This means I’ll need a healthy retirement fund and/or investment portfolio to suppliment my income.

So, knowing that investing my money early will yield greater results (so long as you invest smart, EFT’s, Index Funds, Mutual Funds, etc.) and will also give me skills to be more competitive in my field and earn a higher salary, how can I possibly take 6 months off to go Thru-hike the Appalachian Trail?

Here lies the problem my friends: How to take an extended period of time off of work while still planning for the future, and not just one long trip, but many and frequent. Well, in truth, I have no fucking idea. If I did I would probably be hiking or biking across America right now. But here is what I do know, if I don’t figure it out I am going to go crazy. I got a taste of this adventurous, freedom filled lifestyle for two months in between my junior and senior year of college. I hiked roughly 1000 miles on the Appalachian Trail and have been chasing that high ever since. It was like I stumbled upon the pot of gold at the end of the rainbow, it opened my eyes to what my life could be, but I looked down to find I was standing on a speeding treadmill, unable to walk fast enough to reach that pot of gold. That treadmill happens to be many things including my brain and societal norms.

In other words, I will figure out how to have a successful career, make enough money to live comfortably (not keeping up with the Joneses), and have wild adventures. Here are some of my ideas on how to achieve this:

  • Start my own business: The idea would be to start and operate a business that can run with very limited interaction. For example, selling products online that can be packaged and shipped by a distribution company, who can handle any customer refunds or issues under a certain dollar amount, allowing you to work for less than an hour a day (See Tim Ferriss’ “4 Hour Work Week”). Or having a business that you can work seasonally, like freelancing, making enough money in the times when you are not adventuring and traveling. It is unlikely that you can make a business large enough to be bought for a high price or brought to public market (IPO) within a short period of time. Ideally, the business would take no more than 3 years of full time year round work to set up.
  • Take leave of absences: If your employer will allow you to take a leave of absence or multiple, this could be a good opportunity to test the waters on long-form adventures (multiple months) while still having a job when you get back. This does not solve the problem of income, as you won’t be getting paid while you are gone, but if you can save enough during the working period it could be an option.
  • Early Retirement / Financial Independence: As I mentioned before, with the right mentality, frugal living, saving and investing methods, it is not unreasonable to be able to retire by your early thirties (or ten years from your current age) (See Mr. Money Mustache, really). I am not a huge fan of this option however because it means I would need to work for 10-15 years before I have my nest egg saved up and ready to “retire”, meaning I will loose most of my peak physical performance years, which I find to be quite important for doing long distance hikes.
  • Digital Nomad / New Media: Many people have been able to make a living off of things like Youtube or other social medias. This can be very time intensive at the start of the process as there is a big learning curve. I like the though of this idea, as I am going to be doing cool shit, I might as well make a video about it because I am sure other people will like it. The execution of it is harder to do. The market is so saturated with outdoor influencers, what is going to set me apart? As I mentioned, the learning curve is high and requires some time at the start. It may also take away from your experience if you are now looking at it as a job instead of an escape.

How to live an adventurous life without being broke? That is the question, and unfortunately I do not have the answer, but I will keep you up to date on how my journey to reach the answer goes. Let me know if you have any ideas or if you know someone who has achieved this.


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