On Work and Wealth, or Why I Quit

Jobs, money and the courage to bet on yourself

Hi,

I mentioned last week a reason why I’d be posting more frequently. This is why. I hope it resonates with anyone who’s in the same boat. And if so, please like, subscribe, share or send some feedback – I’d be grateful!

In this edition:

• Quit math: what happens to money and health when you walk.

• Choice drivers: the tug-of-war between salary and meaning.

• Risk > regret: why rolling the dice can beat staying put.

Author and financial blogger Nick Maguilli wrote that there were two kinds of emergency funds:

Your first emergency fund is the money you have set aside for a rainy day.

But your second emergency fund is your skill set, your network, and your ability to deal with hardship.

Everyone focuses on the first one, few focus on the second.

Well, I’m happy to say I’m tapping emergency fund number two. Releasing the strategic reserve of skill. Firing rocket two of self-sufficiency.

That’s because I recently quit my job.

Long(ish) story short, I was told I wouldn’t be allowed to write publicly in my full-time role – including this very Substack.

Basically, it came down to a choice: the job or my passion for writing. Do I keep treating work as a career to climb and just stay somewhere long enough to retire? Or do I take it as a sign – God saying, “now or never” – to give the work I truly value my full attention?

Financially, the choice was between a steady paycheck, benefits and… well, I don’t know what… whatever I can make of myself.

The artist Paul Gauguin abandoned a successful career as a stockbroker to start painting. Susan Cain quit a corporate law job to become a writer, even as people told her she was nuts. And of course, the Mount Rushmore of Silicon Valley, featuring the likes of Bill Gates and Mark Zuckerberg, famously dropped out of elite colleges to bet on themselves.

Succeeding after a leap might be the exception, but among those we admire, the leap is the common denominator.

So, job or writing?

I knew what was behind door one, and chose to see what’s behind door two. I took the red pill, to find out the truth of what I can do. All in – I’m betting on myself.

If success depends on timing, I could’ve picked better. This might not be the best era to experiment with life without a solid job. Just the other week, U.S. companies announced the most October job cuts in more than 20 years.

Not looking good…

What’s more, as companies take a GLP-1 approach to slimming down, the gauntlet to get a job has never been tougher. You fight through hundreds of applicants and an algorithmic sorting hat before a real interview even starts. That brings up the supergenius elephant in the room, AI, which could irreversibly upend the job market.

Amid all this uncertainty, you could convincingly argue that a steady paycheck is at a premium.

And yet, I quit.

As I contemplated that decision, I wondered about the relationship between money and work.

What happens when you leave a job, financially and emotionally? How much does money matter in choosing work? Are people happier when they love what they do or when they earn more?

Ultimately, how risky is this bet I’m making?

Of course, I only started digging into the research after I made it official. If you’re weighing a big change yourself, or curious what happens to people who do, here’s what studies say about how leaving work can shape your money, health and happiness.

The impact of leaving the workforce on wealth and health

• Leaving a job without another lined up can dent your earnings. One study found that men displaced in mass-layoff events lose the equivalent of 1.4 years of prior pay if the national unemployment rate is below 6%. That loss nearly doubles to 2.8 years of pay when unemployment is above 8%.

Okay, well, I guess I’ll have to work back up the income ladder a little bit. What about my long-term wealth?

• Leaving a job could take a bite out of your wealth, too. A report looking at older workers found household wealth remains about 8% lower six years after a job loss.

That’s not encouraging. But at least I’ll still have my health, right?

• A shaky work situation can also hit your health. Research shows mortality risk rises sharply after displacement, along with higher anxiety and depression. Not surprising, given the financial stress.

But it’s not all doom.

Sometimes, quitting to pursue new opportunities can pay off. In strong job markets, job-switchers often see real pay gains, as they did in 2021–22, versus those who stay put.

Full disclosure: I didn’t leave for total unemployment. I’ll be writing for various publications and offering freelance content, copywriting and ghostwriting for small businesses and founders (shameless plug: if you’re in need of content help, let’s connect).

Nonetheless, doesn’t everyone want something more from their work than just money?

Money versus meaning in work

Turns out, most people still choose money over meaning – by a wide margin.

Research from the University of Illinois found “most people overwhelmingly prefer higher-paying jobs with low meaningfulness over low-salary jobs with high meaningfulness.” Researchers say that’s because many assume higher income will lead to a happier, more meaningful life.

Of course, that assumption is tenuous. The link between money and happiness is more complicated than people think.

As one researcher put it:

“Figure out what kind of work you’ll enjoy doing, and how that work is going to make you feel about your life and about the impact you’re going to have on others, because so much of our motivation at work is really about whether that work feels meaningful and purposeful to us.”

While it may not be the deciding factor, meaning ultimately does matter. Consider one survey found nine out of ten American workers would trade a portion of their lifetime earnings for greater meaning at work.

That said, it’s easy to romanticize. It’s one thing to believe you’d take a pay cut while filling out a survey; it’s another to live with the real consequences, like vacations closer to home and fewer holiday presents.

In the end, whether taking a pay cut for a more meaningful job is worth it or not, is personal. As this Fast Company article shows, the results vary from person to person.

But what rarely gets measured is the cost of not trying.

Life is short – burn the bridges, burn the boats

Over a lifetime, it’s been estimated you might spend about 90,000 hours working – roughly a third of your life.

That’s more than you’ll spend with your spouse, your kids, your friends, reading, learning, exercising – just about everything except sleep.

Maybe it pays to find something you love. In fact, a Business Insider review of Deloitte data found that those who love their jobs earn more, build more wealth and are happier than those who don’t.

Sure, money matters. But when you’re giving up a third of your life, and who knows how many f***s, there’s more to consider.

One important thing I’ve learned in life is to do things in the rain. Go hiking, hit the beach, visit the zoo, explore even when the forecast looks bad. Often, everyone else stays home and you end up with the world to yourself. When it pours can be the best time to do anything.

We underestimate the value of taking risks. A study on adventure sports (mountain climbing, hang gliding, etc.) found participants were motivated by things like achieving goals, testing personal abilities and overcoming fear – all key ingredients to what we’d likely label a fulfilling life.

It’s not the times we slipped off the cliff we regret; it’s the times we’ve walked ourselves to the edge and backed away.

As Daniel Pink notes in The Power of Regret, inaction regrets outnumber action regrets nearly two to one. Simply put: We regret what we didn’t do more than what we did.

The writer and thinker Kevin Kelly wrote:

“Your goal is to say on your deathbed that you’ve become fully yourself.”

I wonder how many of us die unfulfilled, or worse, someone else? Hospice nurse Bonnie Ware, who wrote about the biggest regrets of her patients, found the top one was this: “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Of course, you shouldn’t chase every whim. Impulsivity is shown to be the enemy of both wealth and happiness. But when something keeps calling to you, it can hurt more to keep the dice tucked away in your pocket rather than letting them roll.

Maybe things won’t work out as I hope. But staying somewhere that muzzles me guarantees they won’t.

Richard Branson, the Virgin founder known for bold bets, risk-taking and personal conviction, once said:

“If your dreams don’t scare you, they are too small.”

Brandon: never one to shy away from risk

That’s why I quit. I was ready to try for something bigger, despite the fear.

Speaking about our innate fear of change, athlete and wellness podcaster Rich Roll put it this way:

“People change when the pain of their circumstances exceeds the fear of doing something different.”

For me, the pain of not writing outweighed the fear of the unknown. I may make less money. But at least I won’t lose my voice.

That’s why I quit.

When it comes to making such bold, lofty decisions, the author Oliver Burkeman wrote:

“Don’t worry about burning bridges: irreversible decisions tend to be more satisfying, because now there’s only one direction to travel – forward into whatever choice you made.”

There’s a companion phrase I like better, also involving fire: burn the boats. It means to cut off all possibility of retreat by committing completely to a course of action, leaving no option but to fight to survive.

That’s why I quit. It leaves me no choice but onward.

Maybe “follow your passion” is bad advice. But starving your life of meaning for money isn’t much better. If you make every decision a financial decision, you might end up poorer in other ways.

Steve Jobs, another college dropout, offered timeless advice on where to find guidance in moments like these:

“Have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”

The pursuit of an audacious dream is as worthy a lifestyle as I can imagine.

So, I quit.

I quit because I didn’t want to stop writing.

I quit because I wanted to bet on myself.

I quit because I want to tell my kids — and myself — that I at least tried.

Maybe I would have been better off financially if I stayed.

Well, I guess we’ll never know.

Burn the bridges. Burn the boats.

It might be worth betting on yourself – at least once in your life.

Notes to my future self:

• We regret what we didn’t do more than what we did.

• If you make every decision a financial decision, you might end up poorer in other ways.

• Burn the bridges. Burn the boats. Bet on yourself – at least once in your life.

Until next time,

• J.S.