It’s funny how ideas seem to recur in the things I read. It’s probably just my mind making spurious connections, but the things I read often seem to be linked in some way. Probably from my curiosity about a certain idea leading me down the rabbit hole to another related one and so on.

This summer, one of the recurring themes has been optionality. It’s a fancy term that just means “not being locked into a given program, so one can change his mind as he goes along based on discovery or new information” (Antiragile, Nassim Taleb 431). It pops up all the time in discussions of decision making, business, and entrepreneurship.

I first encountered the term in some blog post whose title I can’t recall, but this summer I discovered the most rigorous definition/discussion of it in Nassim Taleb’s Antifragile: Things That Gain from Disorder. Summarizing this book in one sentence is futile, but the essence of it is, in Taleb’s own words “decision making under opacity.” Or, put another way, “how we should live in a world we don’t understand” (Taleb 521).

You needn’t have read the book, though, to understand (and appreciate the value of) optionality.

Throughout the book, Taleb repeats the phrase “exercising an option” to describe taking advantage of a favorable set of (random) circumstances by making the right choice.

Choice. That’s another theme in the book. Having choices is powerful. Making the optimal choice is transformative.

But to make any choice (let alone the right one), you first need options. As I’ve come to realize through my reading and reflection this summer, options are inextricably bound with one of the messiest and most uncomfortable of all subjects: money.

This post is an exploration of why the two subjects are so closely linked, along with some thoughts on how to manipulate your finances to increase your number of options and, more importantly, your ability to exercise them.

Your Money or Your Life

old clock

I’ll be the first to admit that I’ve never read the book of the same title, but the notion that your money and life are bound up together is one that, according to what I’ve read, seems to be true.

We could debate endlessly about the philosophical “value” of money economies/capitalism and the transactionalization of human relationships, but like it or not, most of us have to deal with money day to day. There are exceptional people who manage to live (mostly) without money, but the majority of people in the world have to deal with money in some form or another. Since it’s such a part of our daily lives, we would do ourselves a favor to respect and understand it.

Worry about money plagues us.

We worry about not being able to pay our bills. To put food on the table. To pay our medical expenses in an emergency. To fix our car if it breaks. To fund our retirement. To afford to send our kids (even if yet unborn) to a good college.

This worry stems not so much from the money or external circumstances themselves, but from the chaotic, helpless feeling they give us. It feels like the widening gyre of Yeats, or like the water as it runs down the drain. Inevitable yet unpredictable.

Money worries can make you feel like these guys.

Money worries can make you feel kind of like these guys.

Luckily, as I’ve learned, much of this is in our control. The fear comes from the unknown, from confusion, maybe even from ignorance. But these our curable problems. Most of these worries about money, it turns out, come from poor decisions we make regarding the money we have available, as opposed to an inherent lack of money.

How to increase the money available to you is a complex topic that others have already covered, and is once again beyond the scope of this article. In some cases, increasing your income can help solve your financial worries, particularly if your income is very, very low.

But beyond that point, only using your available funds wisely will help you make any change. After all, it’s just as easy to make stupid decisions with $100,000 a year as it is with $30,000. The decisions just increase a couple decimal places in amount; the stupidity remains the same.

Just because you have more money, doesn’t mean you know how to use it more wisely. Indeed, I would venture that you stand to do a lot more damage with lots of money than a more modest amount if you lack the financial acumen.

Let’s dig more deeply in how to be less stupid with our money. To do that, I’m going to introduce you to one of my idols and mentors.

Enter Mr. Money Mustache

hipster beard wall

Whenever I need a good hard dose of reality, I read Mr. Money Mustache. If you’re not familiar, he’s the author of a blog that’s part personal finance, part life advice. He retired at age 30, and his blog is (ostensibly) about showing you how to do the same through saving, savvy investing, and good old-fashioned hard work.

The critical thing MMM made me realize is that while you can’t always increase how much you earn, you always have control over what you spend (and consequently, what you save). He lays out the mathematics behind early retirement, making you realize that it’s purely a factor of how much you save each year.

The more of your income you save, the faster you can retire. The more you can make small sacrifices now, the faster you’ll get to the big, satisfying payoff of never having to work again.

Far from extolling laziness, however, MMM argues that once you’ve retired you’re not done with all work – just mandatory work. You’ll be able to fill your time with more worthwhile pursuits that interest you. For MMM, this ranges from renovating houses to raising his son to writing his blog.

All of this is transformative, unconventional advice, rather contrary to the typical “work hard till you’re 65 (more like 75 for my generation) and then spend the rest of your days slowly wasting away on some beach (or more likely in a home hooked up to tubes).”

hunter s thompson quote

But that’s not what I want to focus on here. Rather, I want to examine crucial insight from MMM in an essay of his called “Get Rich With: The Position of Strength.”

The essay defines The Position of Strength thusly:

Looking back at my list of all the articles, I am starting to realize that this isn’t a personal finance blog or even a lifestyle design blog. It’s a never ending sermon on the joy of strength. Strength, also known affectionately as Badassity, is at the root of most of the joy in a human life.”

There are different kinds of strength, of course. Moral, physical, financial, etc.

In MMM’s view,

Money is the most acknowledged source of strength in modern society, for it gives you the power to get other people to serve you, and to do so with a smile.”

And he goes on to say that, consequently,

An Abundance of Money is even more powerful, because you no longer find yourself feeling the need to act like a weenie in the pursuit of more of it. With this Abundance power, you can properly align your earning and your spending with your values, rather than just seeking out the cheapest option or trying to squeeze more money out of your customers, employees, or fellow citizens.”

And how do we achieve this enviable position of strength? It’s simple, but not sexy:

Voluntary Discomfort is the secret cornerstone of strength. We build our whole lives around increasing comfort and avoiding discomfort, and yet by doing so we are drinking a can of Weakness Tonic with every morning’s breakfast.”

When it comes to money, Voluntary Discomfort means sacrifices. It means forgoing fine clothes, fancy cars, expensive coffee, and rare books. It means cooking your own food even when it would be more convenient to order takeout. Biking when you could drive. Using your hands to fix things when you could afford to hire someone.


Far from “wasting time,” forgoing a certain amount of convenience makes you wealthier not only in the short-term, financial sense, but also in the higher-return areas of new skills, increased resourcefulness, and greater mental toughness.

It has been so transformative to find someone not just preaching, but validating, this way of living. Since I began my journey of personal development back in 2014, much of the advice I’ve read goes like this:

“You can be healthy, in great shape, successful, and wealthy without having to sacrifice anything.”

Bullshit. I always smelled a rat when reading this advice, but I put my gut feelings aside and tried to realize this doctrine. It’s not complete bs, but much of it is.

You want to do great things? Sacrifices are necessary.

The key thing to understand, I’ve realized, is that you just need to know what kinds of sacrifices are acceptable. Sacrificing your health (except over very short periods of time)? Absolutely unacceptable. Love and friendship? Rarely (what else do we have, after all?). Your values? Think thrice.

But sacrificing material comfort in the short term for true wealth in the long term? Hell yes! Particularly when such sacrifices pay off in ways beyond your bank balance.

The surefire formula for financial health then becomes this:

Financial health = saving more than you make

Simple. Hard, but simple.

How does all of this translate into optionality? That’s up next.

Leveraging the Position of Strength


Let’s look at an example of how you could leverage a financial position of strength. We’ll start with a dramatic (and, admittedly, overused) example:

Present day, your apartment. You’re tired of living where you do. You want a change of scene. Under ordinary circumstances, it would be irresponsible to just pack up everything and leave. What about your steady job, your good house, your safety? Only an idiot would throw that all away.

Well, only an idiot with no savings. With your war chest adequately stocked, you can say “fuck it” and just do it. So long as you know your financial burn rate and live below your means, you can do such things with no worries.

But this is just one example, and a fairly wild one at that. I’m not advocating erratic, irresponsible behavior (although the whole point is that such behavior is neither with adequate savings).

You can leverage the position of strength in mundane, everyday ways. It let’s you jump on exciting, spontaneous opportunities without fear of “wasting your time.” If you get an idea for a product, the position of strength can help you make it a reality. Want to take some time off to work on a project? Easy if you’ve the money saved.

bicycle gear

I should make it clear, of course, that you should have a separate savings account for these sorts of things. I personally use Capital One 360 for this, since it allows you to have multiple savings accounts with custom names/purposes, but you can do it whatever way makes the most sense to you.

In general, you should be responsibly saving and investing the majority of your money, keeping spending to a minimum and essential level.

It’s a balance, for sure, and for more info I’d recommend Nat Eliason’s excellent articles on Personal Investing for 20 Somethings and Entrepreneurial Personal Finance (to both of which this article is considerably indebted).


man on hill open space

Getting back to the original notion of “your money or your life,” much of the discussion around money is really a discussion of freedom. That’s what controlling your finances gives you. The progression is basic:

  1. Get Out of Debt
  2. Avoid Future Debt
  3. Save a Reasonable Amount of Monthly Expenses/Create an Emergency Fund
  4. Begin to Invest
  5. Optimize by Cutting Expenses or Increasing Income

Once again, it’s not complicated. Just hard.

But you can make it easier (paradoxically) by embracing discomfort. It doesn’t mean that you can never have nice things. It just means that the majority of the time you forgo luxury in favor of the simple pleasures.

fancy car

Of course, there is a balance. So much of life is. So much of money is especially. If you’re stingy and cheap, you can end up being miserable. Particularly if it gets to the point that it’s embarrassing or unpleasant for others around you. And you could die tomorrow, after all, so you ought to live a little.

But you don’t need to spend lots of money to have fun. That’s easy to forget in a capitalist economy predicated on consumption. It’s worth remembering, though.

Indeed, when I look back on the most fun things I’ve ever done, few of them cost more than $25:

  • Rappelling down a 30 m (~100 ft) cave – $25 (which covered the cost of getting there – the trip itself was free)
  • Hiking Cave Hill in Belfast – $5 (the cost of the bus ticket to get there)
  • Catching up with friends at a cheap restaurant – $10 (the cost of a meal)
  • Reading masterpieces like Pilgrim at Tinker Creek and Walden – Free (library books)
  • Listening to some of the best music ever created by humans – $4.99/month (cost of a student Spotify subscription)

Those are just off the top of my head. No doubt there are many more. Having enumerated them that way, few were completely “free,” and through mental gymnastics you can attach a dollar value to almost anything, but the point is that fun requires little extra expenditure. Certainly less than advertisements lead us to believe.

Mind you, sometimes it’s worth it to splurge a bit. I certainly did while traveling in Europe. But you don’t have to. Remember that.

The Path to Freedom

path to freedom

To sum up, this is what I’ve learned this summer:

  1. Flexibility and optionality (properly exercised) lead to freedom.
  2. The best way to have flexibility and optionality in modern society is to be financially secure.
  3. Financial security comes from saving (and properly investing) more than you earn.
  4. Earning more money can increase your financial security, but only if you us the extra money wisely.
  5. If you upgrade your lifestyle every time your income increases, you’re just creating a fancier cage.
  6. To save more money, you have to spend less money.
  7. Spending less is hard, but it’s not complicated.
  8. Forgo nice/superfluous things now so you can have more freedom later.

Pretty cool, right? I found it inspiring, anyway.

What are your thoughts on money and freedom? How are you manipulating one to increase the other? I’d love you to share in the comments section below!

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