Money makes the world go round. So, it’s been said. But, how would our lives look if we had a different relationship with money?

Welcome to the new year and the first day of the rest of your life. There’s not much we can do about the past, except think upon it, learn from it, and use those lessons learned to optimize our future.

I would consider myself a student of the world and life. I’m not trying to find it’s meaning but rather just observe, and take note. I would also consider myself a student of human behavior.

As a writer, I think my apprenticeship of the world and other people have been a tremendous help. It’s allowed me to build real connections with real people and share my ideas and thoughts in ways that encourages others to think differently or deeper about certain subjects.


As the calendar turns to a new year and a new decade, you may find yourself setting some goals for 2020. I have done the same. Truth be told, I’m still ironing them out a bit. But, as is life.

One portion of your yearly goals may be “financial.” A great idea given the importance of managing your money. You may have even picked up a book to help you get your finances in line.

I’m sure there are many books out there that help in this regard. I have not read many books, as it relates to finances. Rather, I’ve gathered my financial habits from philosophy.


“Spending of the best part of one’s life earning money in order to enjoy a questionable liberty during the least valuable part of it, reminds me of the Englishman who went to India to make a fortune first, in order that he might return to England and live the life of a poet. He should have gone up garret at once.”

 – Henry D. Thoreau 

I’ve pondered on this quote often over the last few years. I first heard it in a book called “Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel.” I’ve read / listened to this book just about every quarter of the last 3 years.

What Thoreau was alluding to was retirement. I’ve been hearing the “R” word since I was in high school. I’m sure you’ve heard it to. Hell, when you turn 22, this is something you’re suppose make a priority.


Retirement – the action of leaving one’s job and ceasing to work


Personally, I’ve never really put much of a focus on retirement. It may surprise some of you to hear that I haven’t really saved money for retirement. I’m getting closer to 30 and most might say that I should get my “shit together.”

In many ways, I agree but I must remain true to my intuitions; they’ve not let me down yet. And, I still feel as young as ever. Today’s age, 30 years old isn’t as old as it use to be.

I’ll have to save the “age” conversation for another time. For now, let’s get back to our friend Henry.

Thoreau is concerned with wasting our best, youthful years focusing on making money to save for retirement, which he argues is the least valuable part of our lives.

We all know that youth doesn’t last forever. Each day brings us closer to our inevitable death. For those fortunate enough to experience old age, I think they could confirm that their not able to do everything they once could.

That’s just a fact of life. It may be sad or disheartening but it’s a fact and facts don’t care about your feelings.

Even though there’s millions of dollars being spent trying to reverse aging there’s nothing we can really do about it. Except, change our thoughts around it.

Should we really spend our best, youthful years optimizing our financial income instead of pursuing our passions?

I can’t really answer that question for you. It is a question we all must answer for ourselves. There are certainly major pros and cons to either side. But, I think this is a question we must ask ourselves, as early as possible.

What good is all that retirement money if you’re not able to use it to do things you’ve always wanted to do?

Dropping in on the South America Boulder Field on the Grand Mesa (CO).

Recently, I’ve discovered my second passion: snowboarding. The combination of climbing mountains, experiencing first-hand the rugged beauty, and getting to slide down them on a snowboard is something I’ll never fully be able to explain, but I love it.

My whole life revolves around snowboarding, or splitboarding to be more specific. (Google it) If I was living by the traditional model of saving for retirement, I’d probably have a decent 9-5 job that allowed me to get out on the weekends and snowboard.

With my frugal means, I’d probably be able to stack some serious cash and possibly be able to retire in my early 50’s. However, I don’t think many would argue that my 20’s, 30’s, and even my 40’s may offer better days on the mountain than in my 50’s.

[Side Note: I most certainly expect to be splitboarding as long as I am able to do so. I plan on taking great care of myself and with any luck, I could certainly be snowboarding, in some extent, well into my 70’s.]

I would be missing out on some awesome days in the mountains, if I took the normal route. There will always be time to settle in one location, get a good a job, and save money.

The second portion of Thoreau’s quote talks about the Englishman who desired to be a poet but thought he must have a lot of money in order to live as such. Thoreau was convinced that he didn’t need to go off and make a bunch of money before devoting his life to being a poet; he should’ve just became a poet.

As it turns out, you don’t have to be filthy rich to become a poet. Likewise, you don’t have to be rich to be a ski bum.

I think we, humans, have a natural tendency to over-estimate how expensive something is, especially when it comes to the amount of money one needs to survive or even just enjoy their life.


“Money is like gas during a road trip.

You don’t want to run out of gas on your trip,

but you’re not doing a tour of gas stations.”

– Tim O’Reilly

Don’t get me wrong here, money is an important aspect of life. We need it for obvious reasons that I won’t mention here. It is so important that we need to figure out our best ways of utilizing it for us personally.

Money is a tool, a resource that we use to live on our terms. We need to optimize this tool to work for us. Not allow us to work for it.

I think O’Reilly really nails the concept of money in this quote. Money is simply a means to an end. You decide on the end. And, ironically enough, I think it’s best to start with the end in mind.

What do you want your life to look like? Do you want a mansion in the Hollywood Hills with views of the Pacific Ocean? In that case, you’ll probably need to start working your ass off.

But if it’s a mansion that you want, I would have a few questions for you. The first being, why?

I’m not trying to be nosey; I’m generally interested. I think it would be cool to have a sweet crib overlooking the ocean but I don’t think I would truly be as happy as I am now, living in a small mountain town. But, I digress.

Having an end goal in mind, will be tremendously helpful in determining what the costs are for your desired lifestyle. I don’t think most people want huge mansions. I believe that most people just want to do what they love with the people they love.

For most people, their ideal lifestyle is much more affordable than one might think. You may have to make a few difficult decisions (i.e. move thousands of miles away from where you grew up) and / or sacrifice some wants now for a much better tomorrow (i.e. save money by not going out on the weekends, etc).

LaToof’s Key Lessons

Despite not putting much stock into retirement, I do have a mind for the big picture. I feel comfortable operating under these constraints, as over the years I have developed a keen sense of self-awareness. Below, please find my “key lessons” to potentially implement in your own life!

1. Work Should Serve Your Interests 

Don’t mistake my alternative thinking to not liking work. I enjoy working hard and the satisfaction it brings. However, work should have it’s place and you should put it there!

I’ve had many jobs in my short life. Some of them high paying and might even be considered “dream jobs.” I’ve also worked jobs for minimum wage. I’m not too proud to work any job if it’s serving my interests.

Most people will find that they’ll be much happier making a little less money as long as they get to do the things they enjoy doing.


2. Get Out of Debt ASAP

Debt can be crippling. The world really opens up to you once your don’t owe anybody anything. So, before doing something drastic like quitting your drop, dumping your girlfriend, or moving across the country, maybe have a few dollars in your pocket and minimize your expenses as much as possible.

Currently, I have a bit of debt. But, it’s debt that I consider: strategic debt. What I consider strategic debt, is debt that I’m not currently paying interest on. Over the years, I’ve taken advantage of promotional deferred debt that many credit cards offer.

These offer periods give you many months to pay off the full balance before being charged any interests. I’ve used these to my advantage by 1. never paying any interest and 2. allowing me to make purchases on equipment that will be immediately valuable to my content creation, that I couldn’t buy outright.

3. Don’t Wait to Reverse Engineer the Life you Want

Time is a non-renewable resource. We’ll never get any of it back. Strive to make every day count. Yes, you’ll have some bad days and possibly even miserable days but if you take control of your own life and start living on your terms, the good days will more than make up for the bad.


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