Shades of Grey: How to Enjoy Life and Have Money

So many of us in the outdoor world choose a life and career path guided by a seemingly unavoidable fork in the road. Do we choose a safe path, paved with a steady paycheck and a retirement plan? Or do we cobble together whatever it takes to make it work, focusing on experience and patching the inevitable cracks as we go? Today we examine the completely accessible and exciting grey area between these two black and white choices. We can have money and still enjoy life.

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The Lifer Vs the Optimizer

One of the original posts on this website, written over three years ago, examines the binary existence of the lifer vs the optimizer.

The Lifer

The lifer, perhaps scarred from the financial failures of parents in pursuit of the American Dream—or the terrifying headlines of the 2008 financial crisis—choses a simple existence that places experience, passion, or recreation as the star of the show. Money is of distant concern, used only as a means for continued existence.

The Optimizer

Contrast that with the optimizer, who takes outward satisfaction in career, family, and a growing 401(k), using adjectives like “comfort” or “routine,” while living for the weekend. The desire for experience still exists. However, the reins of restraint and the desire for stability overpower the wanderlust or creative tendencies buried deep in the soul.

Money may also be seen as a vehicle for status; a way to fit in amongst a growing social class of the highly educated, highly paid, or at least well-spent. The optimizers aren’t prone to workaholism per se, eschewing the career-above-all-else mentality of some of their colleagues. Regardless, the margin between money in and money out might be shockingly slim despite all appearances.

The Grey Area Between Money and Life Experience

Meanwhile, there is a vastly underexplored grey area where the best of both worlds exists. Comfort and security coexist with exploration and freedom. Routine meshes with spontaneity. Well, at least some of the time. Let’s be real: life is still life.

Those who combine reasonably decent pay* with reasonably decent spending** profiles are the explorers of this grey area. As Diana Crabtree Green reminds us, those who routinely spend less than they earn have power not available to either the lifer or the optimizer. In all honesty, the salary or the spending profile is irrelevant; it’s all about the savings rate.

That said, we can be honest in stating the obvious: a higher salary makes saving easier, at least at the surface.

* My opinion: At least $50,000 per person in pre-tax salary.

** Anything that allows one to save greater than 30%, but ideally at least 50% of income. For more on how percent savings is calculated, check out this post.

The Expectations Around Money That Bind Us

What lurks below the surface of a high salary lies the realm of expectations, both external and internal.  Those who have spent years in the upper crust of society are normalized and well-adjusted to an existence of comfort, security, and privilege not available to the low-rung social and economic classes in developed societies.

Historically, the expectation of those deriving from the upper crust is of conspicuous consumption, inherited from bourgeois culture. Image and status are everything. For high income earners with a lineage in this social and economic class, to choose not to spend is swimming upstream in a stiff current of expectation and tradition. This might be at least one dilemma of the optimizer.

Meanwhile, the lifer often harbors resentment of money and views accumulation of such to be a tradeoff with happiness or life satisfaction. Perhaps they’ve seen the evil manifestations of careless consumption. The lifer may take comfortable aim at the nameless “1%” or look upon those building businesses (and especially promoting them) with cynical skepticism. And the cycle continues.

Forming Our Expectations Around Money

We are born innocent and wonderful, but time changes all that. We are hurt, and then sometimes we hurt back. And when we hurt back, that makes us hurt all the more still.

We look for things that make us feel better in the face of that hurt, and sometimes we turn to or away from money. The optimizer (or even FIRE enthusiast) might take comfort in financial security where other tangible forms of security remain elusive. Or the coworker that the optimizer despises might use a new truck, a set of golf clubs, or a round on me to replace the anger that follows him around every turn. The lifer seeks adventure and solace to replace the gaps in the heart. Trust me, I know.  

The Problem with Boxes and Money Mindsets

Wow, so that might have gotten interesting for you, huh? Isn’t that the problem with trying to put people in two, or four, or even six boxes? Our simple attempts at putting boundaries on behaviors and experiences that occur across broad spectrums is at least moderately effective though, isn’t it? It at least grabs our attention.

We’ve all heard the “there are two types of people…” quotes. I even found this series of clever illustrations to be a very effective way at communicating binary types of personalities. I’ve posted my favorite below.

Perhaps my favorite mic-drop quote on the subject comes from eccentric writer Tom Robbins, who says:

“There are two kinds of people in this world: those who believe there are two kinds of people in this world and those who are smart enough to know better.”

Tom Robbins

We take comfort in boxed identities. Democrat or Republican. Pro-freedom or pro-science. Hard worker or smart worker. Lifer or optimizer. But these boxes don’t capture everyone.

Life Outside the Box: Money and Life Enjoyment

The most interesting people are fluid in their identities and even their values, able to shift when presented new information or points of view.

For instance, recent interviewees such as Mike Tritt, writer Chris Mamula, or Mark Anderson probably once identified more with the optimizer description. They worked a standard job, but climbed or adventured as much as possible in the slim margins. Presented with new information—the ability to save and invest and achieve financial independence—they wisely shifted gears and created a third (and I’d argue more sustainable) new box: a fully-funded hybrid model of both lifer and optimizer.

But after three years of writing and recording on this website, I’ve come to find the hard way that I cannot apply my life experiences to others in some sort of dogmatic, faux-religious fervor. I can’t say, “hey buddy, if you just buy an index fund instead of that van, you can be done working in ten or so* years. Then you can have freedom and a van.” Believe me, I’ve tried.

Take for instance, the ever-thought-provoking Dave MacLeod. Dave, to my knowledge, is not in pursuit of financial independence. He has, however, found a highly effective balance between passionate and deep work which is compatible with his climbing. How well this model stands the test of time is yet to be seen, but I’m in admiration for now.

*This is a rough approximation. I know nothing about your savings and investing, and you may not hold my feet to that fire.

Exploring the Grey Area

I obviously find a life in pursuit of financial independence, if even a very slow pursuit, to be a near zero-cost game. Of course, anyone can go too far, become overzealous, and miss the forest for the trees. Folks are prone to suffer from unsustainable frugality or a scarcity mindset around money, even with plenty of it. But in lieu of that, the grey area of simply spending less than you earn (and ideally investing those savings), is simply a great way to go.

I can’t necessarily recommend retiring early, but I can without hesitation recommend achieving financial independence. Without question, it’s a good thing to do for those who can do it. And not everyone can or will.

So, the question then becomes how much we’ve identified with the boxes we’ve placed ourselves. In my experience, those most dubious of financial independence are of the “there’s two types of people” mentality, seeing themselves through a filter of limiting beliefs around consumption habits or income.

Breaking out of boxes is hard, weird, and terrifying. But regardless of finances, those we most admire have probably broken the mold of restrictive boxes repeatedly through their life and careers. Until we begin to live by our own nuanced talking points, how can we possibly break the frustrating cycle of binary choices?

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