The Fallacy of Happiness and Meaningful Work

We all want to live the best life. Today we examine the paradox of how attempting to do just that can result in less happiness after all. For all of us that dream of the greener grass on the other side⏤a full-freedom lifestyle or a better job⏤why do so few find a life of contentment once they’ve hopped the fence?

What Is Happiness?

Is happiness really something that exists after our brain is developed enough to recognize the world for what it really is?

I mean, seriously. When we are children, armed with the mental capacity of a golden retriever, it is easy to flail wildly in a playground, piss our pants, faceplant, and somehow end up with a smile six minutes later.

But as the years pass, and we begin to understand death, injustice, love, and then the crushing defeat of a broken heart, does happiness just become a word that we should just shrug off as silly and unattainable?

In the traditional sense, yes, I think we should shrug it off. The puppies-and-cinnamon vision of happiness is not attainable, nor should it be. Furthermore, in the pursuit of happiness, some paradoxically find deeper troubles.

For instance, poorly constructed ideas for an income stream that seemingly support a more full-freedom lifestyle might not pan out. How many adventure blogs last and provide a livable income? We’ll examine this idea of meaningful work further.

Paradise Can’t Bring Happiness

Have you ever been to a tropical beach? The photos look amazing right? The blue sky, the even bluer water, the palm trees, no crowds. Paradise, they say.

But once you get there, you realize it’s, like, REALLY hot. It’s humid too, unbelievably so. The view is nice and all, but there are really a lot of people here. How did anyone get a photo framed without 86 people in it?? I’m covered in some sort of sticky substance which attracts grains of sand. And no thanks, I don’t want a $5 palm leaf grasshopper origami from the local with the hard-luck story. Mosquitoes.

So, in the end, paradise isn’t always as it seems. But perhaps the disappointment comes in expecting too much without giving enough in return.

If there is any fountain of youth, any magic elixir, it’s effort.

Money Can’t Bring Happiness

Even though the subject has been discussed at length, some folks still seem to think that attaining financial independence will somehow bring about a new level of heightened happiness.

It won’t.

As a “recent achiever,” there are elements of this new existence that I really like. I’m carrying less low-level stress related to work, I’m sleeping more and I’m sleeping better. I’m starting to see options where I once saw barriers. But still, as they say, money still doesn’t bring happiness.

We need other important elements: we still need to really put forth effort. If there is any fountain of youth, any magic elixir, it’s effort.

Effort to Find Happiness

We have to put forth effort to push ourselves physically, whether it’s long walks or training to achieve our climbing goals.

Effort is required to build valuable skills necessary for meaningful work.

Effort is required to get off the couch and foster important relationships. Let’s face it: most of our friends and family aren’t automatically enamored with financial independence. Most people in society are going to conjure up reasons for why they can’t achieve something similar, leaning on limiting beliefs like a pool table in a Friday night dive.

I’ve long ago accepted that most of my friends and family will never share a strong desire to optimize their finances, but that’s okay. We have so many more other experiences in common and items to discuss, that it’s hardly even appropriate to bring up the subject of money. If asked, I will most certainly froth at the mouth, but it’s rarely a subject I broach unprovoked. Well, except of course that I write about it every week on the internet.

What financial independence does provide is the time to put effort toward things that matter most to each of us. It’s on us to make the effort to get there, and then it’s on us to make the best of this gift.

Chasing Your Dreams: The Fallacy of Happiness

I wrote a post back in the fall of 2019, titled Chasing Your Dreams is Probably a Bad Idea. That post was widely circulated, and as such, I braced for a barrage of negative reader feedback. If there was going to be an article to get under someone’s skin, it would be this one.

Or actually, maybe this one: “Financial Freedom Is Only Possible With Your Soul-Sucking, High-Income Career”

Much to my surprise, the negative comments never came. Not one.

In that post, I argue that following your dreams is bad advice. And my opinion hasn’t changed. I give the example of how I nearly left behind my degree in geology to be a chef. After moving across the country with no money, I took a job that paid $10/hour cooking in a good restaurant in Portland’s trendy Nob Hill neighborhood. I was burnt out in three months, loathing my existence and regretting such a major life decision. It took years to rectify that situation.

I wanted too much too soon.

Be So Good They Can’t Ignore You

I’ve been reading Cal Newport’s So Good They Can’t Ignore You, which is truly a must-read for anyone who is considering quitting their job for a better life, or wanting to improve the careers they already have. Just like in my post above, Newport argues that chasing a passion is bad advice.

Only by building what Newport describes as “career capital” —time spent mastering a set of skills or a craft (usually years of work and effort)—can we begin to experience the joys of mastery or workplace freedoms brought on by being someone with invaluable and rare skills.

Here is a great summary of key steps to develop career capital based on Newport’s work.

The Allure of Chasing the Dream in the Climbing World

I get emails from a good number of young climbers at a crossroads in their life. They really love climbing, but they are also aware that they may have a college education (and associated debt), or good job prospects. Folks fear trading the joy of life for a paycheck. And I can identify with that notion entirely.

Those early emails were the motivation behind this post, which was one of my first widely-circulated articles: Reader Case Study: Maximize Adventure or Career?

But Yvon Chouinard Did It!

The climbing world glamorizes the stories of decades-past vagabonds and dirtbags who turned a passion into a business. Examples include Yvon Chouinard (founder of Patagonia—the company, not the region), Douglas Tompkins (founder of The North Face and Esprit), or Royal Robbins (founder of Royal Robbins Clothing). The allure is strong to taste that sense of freedom, and then find some way to monetize that life indefinitely.

All of these characters—and there are a number of others—went from enjoying the sport of rock climbing to making it a very lucrative career. But what is either forgotten or overlooked in these stories is the amount of time and effort that was required to first hone the craft of rock climbing, but then understand that sport well enough to custom-tailor products that someone was willing to buy. These individuals recognized gaps in technical gear during a time when the sport was rapidly evolving.

The product was so good it couldn’t be ignored.

Quitting Your Job to Build a Life Around Happiness

Today, hordes of young climbers increasingly leave behind reasonable job prospects to pursue passion. For many, unfortunately, there isn’t a clear line-of-sight to financial stability. Most of these folks are young, and as such have spent maybe only a couple of years in a more traditional job.

Newport argues, and I would completely agree, that job satisfaction increases with time and with the acquisition of a skill set that makes them valuable. With value comes increased work/life balance, more vacation, higher pay, and the leverage to design a job that suits one’s lifestyle.

Lifer climbers unsurprisingly often turn to income streams where passion already exists: climbing. Many of the jobs in the outdoor industry are bolstered by a strong economy, dependent on the abundant discretionary spending of a population well-paid and employed.

While the outdoor industry in general showed resiliency to the Great Recession, some elements of the climbing industry exhibited attributes of a bubble long before the coronavirus pandemic. This 2019 article highlights the ballooning climbing gym bubble in particular, questioning the long-term viability of the big-gym business model. That post feels particularly poignant now; nearly all gyms have been closed for a month and counting. As with most things, time will tell.

I’m hardly here to say that a job in the climbing industry isn’t sustainable. But to be recession-proof, you might want to be so good (and unique) that they can’t ignore you.

(Related Post: Five Ways to Recession-Proof Your Life)

Examples

This makes me think of my recent interviewee, Mike Doyle. Mike used his well-crafted skills as a software engineer to design a remote work life that allows him to travel often for climbing, yet still maintain a good and well-paying career.

Other former interviewees Kris Hampton and Justin Brown created successful grassroots businesses around the sport they love. However, Kris and Justin worked tirelessly during the off-time from their traditional paid work to develop their product and skill set. Kris wrote a blog and offered free training plans for many years until word of his training ethos got out in a bigger way. Justin started tinkering with skin care products on the side of his full-time job as a chef. His friends enjoyed the product, and eventually there was a line of sight for making it a full-time gig.

Another interviewee and friend Mark Anderson, along with his brother Mike, published a book on climbing training that arguably kick-started the golden era of training in the last five to six years, The Rock Climber’s Training Manual. They didn’t quit their job and hope for riches. They meticulously researched and self-experimented for years, while juggling the responsibilities of full-time work, full-family obligations, and a thirst for high-level climbing on the margins.

But this took time. Good things come to those who wait. But not only wait, but also those who put in the effort required to build a set of skills worth someone opening up their wallet.

In Mike’s case, it’s his company that is opening the wallet. In your case, or like Kris or Justin, you might want to be a coach, sell a product, or have a company sponsor your climbing life.

What sets of highly-polished and rare skills can you offer that aren’t already in abundant supply? Getting someone to open up their wallet is surprisingly difficult!

My recommendation is to put in the work before putting in your notice.

But Didn’t You Quit Your Job, Mr. CC?

Yes indeed, Mrs. CC and I decided that we were suitably financially independent. We’ve put in the time to design the next phase of our life. This post describes the bigger (and much better) story, but the key distinction here is that I did not quit while needing to make an income in another way.

We worked out a plan many years in advance, and we put systems in place to achieve our goals. I also put in enough time in my industry (10 years) to know that the job was probably never going to be fulfilling. That said, over 10 years, the job did get better as I became a more valuable employee. Way more free lunches.

And now the cycle of skill creation begins again.

There Will Always Be “Exceptions”

Certainly, we can always find stories of folks who have seemingly “made it,” chasing the dream against all odds. Perhaps the story of someone like interviewee Jonathan Siegrist is inspiring. Siegrist has created a fully-funded career around climbing, traveling, and inspiring others to do the same. His infectious psyche pays the bills!

However, few people are willing to put in the grind that Siegrist happily enjoys. And again, he’s spent years upon years building and honing his craft to become one of the world’s best climbers. And hell, he seems like a pretty great guy, too.

How Unconformable Are You Willing to Get for Happiness?

Behind every “exception” is usually a story of hard work, grit, and perseverance to a set of goals that stretch the individual out of their comfort zone.

How uncomfortable are we willing to get for a better life? They say that to be exceptional, you have to be willing to do what others are not. But far too often, we take comfort in being amongst the herd. We don’t believe much in luck around here.

How soon are you willing to start honing your craft? Don’t let it be the day you walk out of the office.

We undoubtedly live in a world of immediate gratification. How long are you willing to stumble on building something, when success is never remotely guaranteed? For most, expect years, not weeks or months.

If you can read these questions and feel confident that you are ready and willing for the long haul, then you will find success. 

For those that have created fulfilling work and have actionable suggestions, tell me about it!

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