Chasing Your Dreams is Probably a Bad Idea

When it comes to jobs and careers, parents the world over tell their children more-or-less the same message: you can do anything you want in life. Follow your dreams, and the rest will work out in the end. Of course, those same parents leave early each morning to go to a job that — as statistics show — they probably don’t love.

Years later we find reality to be something a little bit different than a dream. Work is still work, we might have a boss with an ever-so-slightly different vision, and MY GOD why is that woman using the blender right now?!!

So, should we chase our dreams? Are we being misled by pages of digital content and feel-good aphorisms created by outliers? Let’s first begin with a true story.

2007

I’ve secretly scheduled a meeting with the dean of the College of Arts and Sciences at my university. Waiting in the drab lobby, I confidently go over my request again in my head. I think I’m being pretty damn reasonable, and surely he’ll see things from my 22-year-old point of view.

“Hi, there…Mr CC*?” (*he actually said my real name)

“Ah, yes sir, that’s me.”

“Come right in,” he says, shutting the door behind him. The reality of the moment hits. I’m in a closed-door meeting with a university executive. Maybe this is a bad idea.

“Umm. Well. I just wanted to talk to you about my, umm, graduation requirements.”

He suddenly stares at me like a dog being asked a question. His head is tilted sideways, propped by his hand, with a look of confusion, concern, and thinly veiled annoyance. Legs are tightly crossed and he’s tapping his desk with his free hand. “Go on,” he says.

“Well, umm, sir, I’m nearing completion on my geology degree, but I’ve decided that my best path forward is in the restaurant industry. So instead of spending additional money and time on the capstone field course requirement this summer, I was hoping that requirement could be waived. In this unique case, of course.”

“Right. I see. Have you spoken with the department chair about this unique request?”

“Umm, no sir, I have not.”

“Well, Mr. CC, you’ve given me much to consider. Let’s be in touch over this matter, shall we?”

“Oh, yes, excellent sir. I, umm, really thank you for your time.” Awkwardly getting up to shake his hand I do a weird little chuckle, immediately wonder why I just chuckled, and then give him a clammy dead-fish slide of the hand that instantly makes me want to crawl in a hole and die. I turn and leave, somewhat satisfied that my request just might have fallen on understanding ears.

The Verdict

It didn’t.

That evening I receive an email from my department advisor, a friend and mentor. She’s, well, a little pissed. The dean immediately reached out to the department chair, who, feeling slighted, reached out to my advisor to see what the hell is going on.

The verdict is simple. The department has set forth requirements for a degree in geology. For said degree to be granted, all requirements must be satisfied, and there shall be no exceptions.

An apology tour later, I’m back online registering for a 6-week capstone class I don’t want to take. I’ll have to use my summer to go out to dusty New Mexico to do more geology. I’d rather just cook and get ready for my move to Portland, OR, where I’ll one day be a chef. I’m running down my dreams.

Dreams In Flux

The truth is, I didn’t know what the hell I really wanted in life in 2007. I was 22 years young, and I assumed I would put geology in my past and go be a successful chef in Portland.

Here’s the greatly abbreviated story of what actually happened:

I attended the field course, loved it, and met my future wife, Mrs. CC-To-Be. I moved to Portland late that summer, and quickly burned out on the realities of professional cooking, despite having nearly a decade of kitchen experience. I also missed Mrs. CC-To-Be. The rain didn’t help my mood.

A year later I’m seated in a graduate geology class in sunny Arizona. I love my life here. It’s not my dream at all from a year prior, but life is really good. Mrs. CC-To-Be is moving to join me in Arizona. The new dream is to get a PhD and be a real scientist and lecturer at a university.

Today I live in Colorado and I’m still a geologist, but work is not a dream per se. I never pursued that PhD, and I ended up working for an oil company instead. I said I’d work in industry for 3-5 years, make some money, then go get that PhD. That never happened.

So, did I sacrifice my dreams for a paycheck? Yes and no. But I’m glad I did whatever it was I did.

Working Man’s Burden: Job Satisfaction

Statistics tell a stark reality. Most people aren’t passionate about their paid work. Yes, some are. But most aren’t. In fact, 87% of the US workforce are not passionate about their jobs.

So, many of us just take on one of two different stances on life. Let’s take a look…

“Work Sucks. I live for the Weekend”

This is the defeatist reality that says work is work and there’s nothing we can do about it. We only live after 5pm and on the weekends, and the rest of our time is devoted to a job that we simply don’t love. But whatever, we’re all in the same boat and that’s just life. The bills have to be paid and this is simply what the universe requires of us.

This is the mindset I carried for the first five or so years of my career. And then the catalyst changed it all.

“I don’t want to work in a cubicle my whole life, so I’ll do it differently”

This is where things get interesting. For many in this category, there’s the perception that traditional careers are a trade-off of passion for financial security. And no doubt, there are personality traits at play here. There are a handful of folks on my climbing partner list that wouldn’t last a single day in a downtown corporate office — it’s just not a good fit.

In the climbing world, this is where we find the climbing guides, the gym and gear shop employees, the coaches/trainers/healers, and of course…the dirtbags.

And believe me, I commend the entrepreneur. I have half-baked plans to pursue my own ventures one day. We’ve featured folks on this site like Kris Hampton, Dave MacLeod, and Justin Brown — all who have found ways to support their love of rock climbing through business creation.

From the outside looking in, these folks seem to have a dream life. They can have an entire existence built around a sport we all cherish so deeply, and deep roots within the community from which to grow.

But let’s not overlook the grueling level of work and grit that these paths require. These folks aren’t working bank hours. With few exceptions, I also suspect that revenue on these projects doesn’t far exceed living expenses (if at all), so there is a constant element of hustle to make ends meet.

(Related Post: Creative Craig and His Incredibly Captivating Career)

Life is Long and New Dreams May Come

And life is long. What if a career dedicated to being a climbing guide in one’s late 20s becomes dull and tedious by one’s mid 30s? What if you pursue a major in college that is well known to have limited and low-paying job prospects, only because you love the material?

Look, this is hard stuff to write.

I don’t want to crush anyone’s dreams, but I also hate to see folks bemoaning the hardships and realities of insufficient funds brought on by pursuing a path that almost certainly doesn’t provide.

So, hang with me here.

I’ve described above at least three examples where I thought I knew my dream path, only to find various forks in the road leading to new paths and new opportunities. I can’t tell you how many times I knew exactly what I wanted for a career.

One day I decided it was best to keep work and play separate for good.

Having Your Cake and Eating It Too

When I started this website a year ago, my first series of posts were titled Having Your Cake and Eating It Too. The original proverb goes something along the lines of “you can’t have your cake and eat it too,” meaning that two separate realities exist and we can’t have the best of both worlds.

For work/life balance, many folks believe you either must:

(1) Have a well-paying job and limit adventure/passion/craft, or…

(2) Fully pursue adventure/passion/craft and limit financial stability.

The crafty ones who are adept at time management or hustling can slide the scale a bit between these two end-members, but for most, those are the two realities. Ah, I have such good news for you: We can have the best of both worlds!

Financial Independence: Your Dreams Might Come True After All

Step 1: Find a Job That Pays Reasonably Well

My suggestion is simple. No matter where you are in life — but the younger the better — find a job that pays fairly decent, one that you don’t hate. It’s fine if you’re not racing out the door out of shear joy each morning, and we’ll discuss here in a moment why that’s okay. If you end up loving it, even better!

I’d try to find a job that yields at least $50,000 in post-tax income. You can piece together several sources of income, it doesn’t matter. And you don’t have to be there on day one, but try and ensure there’s a short line-of-sight to that income level.

Step 2: Increase Savings Rate

Why $50,000 you say?

A single person can live very comfortably for $25,000 per year in most places, which automatically secures a 50% savings rate. I really don’t care how much you make or what you spend, just make a goal to save at least 50% of your post-tax income. The more, the better. Again, this can be a process, marked with optimization and refinement over time.

Step 3: Invest Your Savings

What do you do with your savings? You invest it in one of three ways: passive index funds, real estate, or an entrepreneurial venture. We personally find passive index fund investing to be (by far) the easiest and least risky strategy, so here’s what we do.

Set up automatic systems with your paycheck and/or brokerage to regularly invest, and don’t screw with it. You will wake up years down the line quite pleased with yourself. Scout’s honor (although I was never a scout). Don’t worry about the news.

Step 4: Actually Begin Chasing Your Dreams While Enjoying the Journey

Remember when I said it’s fine if you don’t love your job? Well, with the income and savings rate described above, you’ll probably be financially independent in a decade or less. If you can increase your savings rate, being mindful to avoid indulging in unsustainable frugality, you can find work to be optional even sooner.

I’ve worked a decade in the oil and gas industry. There have been a handful of days when I truly enjoyed my work, but most have been somewhere in the range of acceptability. Some of have been downright terrible, and I’ve found myself more than once within minutes of drafting a letter of resignation. Sound familiar? Yep.

The key for me was to recognize that I could use this phase of my life as a stepping stone to where I want to be. It’s the ultimate delayed gratification.

Look for ways to optimize your work life, recognizing the impermanence of your position. Here are some aspects I’ve been implementing:

• Negotiate extra vacation and take it all.
• Ask about hour flexibility, remote work, etc. I rarely let meetings stand in the way of my climbing and/or training.
• Have an open mind, being mindful to recognize the good in your work, whatever that might be.
• Do good work and be a good person. There’s no need for hundreds of pages on career advice. If you do those two things, workplace privilege will come your way.
• Start working on your dreams on the side.

Financial Strength: It’s a Spectrum

It’s important to recognize that a savings rate of 50% is a buy-one-get-one-free deal. For every year worked, you can afford to take a year off.

We’ve decided to go for full financial independence, saving at least 30x our annual spending to create an income-optional life. And we’re almost there.

A position of financial strength for you may only require some percentage of this, allowing you to pursue a fully-funded lifestyle change.

Chasing Your Dreams with Stability

Maybe you want to be a teacher of impoverished youth, an artist, an actor, a musician, an artisan baker, a route setter, or any other career path that notoriously pays terribly. If you’ve amassed years of living expenses and now operate from a position of financial strength, you can afford to pursue your dreams.

You decide where you should fall on the spectrum of financial strength. Don’t let the idea of full-fledged financial independence discourage you from taking action in the first place. A few years of a slightly “okay” job could provide a solid foundation to build something that truly is your dream.

Summary

I’ll just say it: The “follow your dreams” aphorism leads folks to low-paying work and ultimately financial strain with no guarantees of fulfillment. There are exceptions, but many are outliers.

We also must ask ourselves an honest question: Are we young and overzealous for a career path now that won’t provide the same satisfaction over many years?

The solution to this dilemma is to first build a position of financial strength. This can mean full-on financial independence (25-30x yearly expenses), or it could be some small percentage of that.

From here, we are able to pursue truly gratifying careers with little concern about the pay. We can focus on doing deep and quality work, not spamming people in desperate attempts for gigs, ultimately being more content with life.

How ’bout them apples? What do you think?

Should we be chasing our dreams?

---

Remember, the best laid plans mean nothing if you can’t take action today. Have questions? Need some feedback? Hit us up on the Contact page.

---

We talk about investing and investment strategies here. Please remember, we are not financial professionals and only speak from our own experiences. We are not responsible for any decisions you make from information gathered on this site. More over at the Disclaimer Page.