Why I Stopped Chasing Money and What I Now Know About Happiness

“Money is numbers. And numbers never end. If it takes money to be happy, your search for happiness will never end.” ~Bob Marley

On January 17^th, 2020, I lugged the last remaining boxes from my office and sat in my frozen car, stunned at what had come to fruition. The “be careful what you wish for” adage poked me in my tear-filled eyes. I didn’t even try to hold them back… Months of stiff-upper-lipping-it meant the floodgates were now safe to open. Whoosh! 

No more client meetings. 
No more financial plans to construct. 
No more market-fluctuation counseling sessions. 
No more copious notetaking, proving I had a client’s best interest at heart. 
No more rigorous compliance audits. No more pleading with underwriters. 
No more feeling like an imposter.
And, I hoped, no more stomach-aches.

It had been a ten-year financial slog to re-acquire my client base in exchange for majority share ownership in the family business. And that decade of payments ended the day I chose to exit stage left. The “house”—if you will—was finally paid for. But it was too late. I was done.

Guys, who does this?! I mean, who puts in all that time and abandons the rewards right when they’re finally accessible?

Apparently, I do! As the reality of my situation took hold, I continued to sit in the car like a statue, staring at the door I would never walk through again at will. I had surrendered my key, my clients, and my livelihood. At forty-six years old, I walked away from that little goldmine.

Some thought I had gone completely bonkers—a midlife crisis unfolding before their curious eyes. “Don’t you still have bills to pay?” “The girls are so young!” “You’re throwing away sixteen years!” But my reasons for leaving will become clear as I outline a few life lessons I’m taking with me on my new path. Most of these insights have come directly from helping my clients.

Lesson #1: Life is precious. And, short. 

Insert eye-rolling, and yawn! Yes, we all know this. But do we really? 

The gift of life is a miracle. That you exist defies all odds—about 1 in 400 trillion, according to Google. While you let that sink in, know that your life also matters. Greatly. And whether you feel the magnitude of that statement yet is immaterial. One day it’ll tap you on the shoulder when you least expect it.

You were put on this earth to have an impact that only you can have. Because, there is no other you.

But what if I told you that vast potential could all be wiped away in one catastrophic, single-engine plane crash? You might say, “Nah, I don’t make it a habit of getting in those things!” Or that you’d soon find out you have an inoperable tumor that will rob you of the chance to see your daughter walk down the aisle next year? “Dude. I’m a vegetarian with no family history of Cancer, so stop with the Debbie Downer sh*t.” 

If this sounds dramatic, I get it. Realistically, we all face life and death at any given moment. The above are the kinds of situations I dealt with all the time in my practice… Walloping, unexpected curveballs that changed everything.

None of us has sorted out the business of living forever. (Except maybe that Wolverine guy. My twelve-year-old says he kicks ass at immortality!) Yet, some bank on the illusion that if we work tirelessly now, we’ll get to enjoy the good times down the road. You know, like, in retirement.

This is fool’s thinking!

My clients showed me the fragility of life. The idea that tomorrow is promised has set us up to live as though we’re in rehearsal, just practicing for the grand event that will eventually be our life. It plays into the “I’ll be happy when” mantra, where we chase an elusive carrot on an ever-turning treadmill. (Only to find we’re going nowhere but around in circles.) We magically expect that once we hit that golden age of retirement, we’ll have made it! Phew! Now, I can really live!

One time, I delivered a life insurance cheque to a young widow whose husband was taken from her at the precise moment she was on the phone with him. Can you even imagine? His truck literally exploded while they shared a routine conversation. Thanks to this level of extreme perspective, I’ve come to a place where I’m not interested in practicing at life.

I’m going to live it. Every day, and on my terms. Not on the assumption that tomorrow will stick around and wait for me. Note: even in saying this, I recognize the privilege and know that many people are just trying to survive, let alone thrive.

Life Lesson #2: You can’t take it with you.

Some of my clients had more money than they could spend in three lifetimes, but they wouldn’t spend any. The truth is, it gave them a sense of security. Most of these people grew up in a time of austerity or came from parents who served in one of the World Wars. They fought hard for every nickel, and their values around money were simple: accumulate and save. I’m not judging, and I understand where the mentality comes from.

But added to this was often a desire to leave a legacy to their children and grandchildren. “When I die, I want to leave all this to the kids.” I found it fascinating that these clients were sacrificing so much of themselves, even though they didn’t see it that way. I always believed that money doesn’t mean anything until you trade it for something. Their altruism for the future generation touched me.

It also bewildered me. I wondered if there wasn’t an opportunity to impact their next-gen-kin while these folks were still young and impressionable? Parcel out bits of that nest egg and play a role in teaching them how to handle money? Or, relieve some of their financial pressure while they duke it out with education, finding jobs, and getting established. It’s not easy being twenty-something today.

And yet, forget that! What about spending some of it on yourself? Get out there and make a bucket load of memories with the people you love! Put it into the world and watch it come back ten-fold, especially when it’s invested in more than just funds. Which brings me to my next life lesson…

Life Lesson #3: Diversify your investment portfolio. Make deposits into your Memory Bank. These will pay dividends that can last a lifetime.

I confess I had a slightly unconventional style when it came to dispensing advice in my financial practice. Sure, I subscribed to the importance of shoring up risk and planning for tomorrow. (None of us wants to eat cat food in retirement!) But you’d never hear me tell a client not to take that trip with their kids just so they could max out retirement contributions.

Screw. That. Noise.

Investing is an interesting phenomenon. You dump the energy you’ve earned (that’s money) into something you hope will make it grow. There’s a headache of upfront homework required, including assessing your risk tolerance, understanding what it is you’re investing in, and then paying attention along the way through the ups and downs of market performance. It takes discipline and patience.

What I think we can all agree on is the end-goal of our investing: to make money on our money. (Let’s not split hairs about feeling good for supporting young entrepreneurs and other social enterprise start-ups. This isn’t about that.)

But what about investing in your Memory Bank? Is that even a thing? Because if it is, boy does it sound hokey!

Guys, it’s a real thing. Four years ago, my husband and I came into a bit of money, giving us the privileged opportunity to get thoughtful about what we should do with it. The options were endless— including, but not limited to, fixing our roof (not sexy), topping up our girls’ education funds (boring), or paring our lives down to one backpack each and hitting the road for a South American adventure. Winner, winner; chicken dinner!

We called ourselves The Traveling Gong Show, because, quite frankly, we were a disaster at the best of times. A family of four: set to bicker and bumble their way through Ecuador and Peru! Our only goals? Slow our lives down, bond hard with the kids, and show them a piece of the world that offers a new cultural perspective. (They were thirteen and eight at the time.) Again, peeps thought we were a little crazy—“Wait, you’re going to be on a bus for fifty-two hours? Are you nuts?!”—but that didn’t stop us.

I’ll admit that we even wound up taking on a bit of debt by the time the three months were up. See, when you don’t work there’s no income (go figure), and, we didn’t know if we’d ever have another chance like this, so we embraced as many opportunities within reasonable proximity as we could.

But the money spent was a fair trade-off for all the memories we made… Hiking the Salkantay Trail to Machu Picchu. Dune-buggying in the Peruvian desert. Swimming with sharks in the Galapagos. These investments were far more epic than reading the Fund Facts for a medium-risk growth portfolio! And while it’s true we short-changed an opportunity to save more for their educational future, we actually wound up shaping their lives in ways I couldn’t have dreamed possible.

Thanks to this experience, my eldest daughter’s goals for her future now include how she could make a difference on a global scale for some of the inequities in the world. Who knew that our bebopping around on a shoestring adventure would inform her budding ideology about life, culture, and social responsibility?

Life Lesson #4:  A job/career that you don’t like—but one that offers a great pension plan—could equal years of misery.

I counseled dozens of clients who were hanging on by a loosely woven thread at their jobs. They were miserable, but the carrot at the end of the treadmill was a guaranteed pension. And that does count for something. A lot, these days, in fact.

As far as lessons go, this one is sensitive. Job security is important. Planning for our futures and self-reliance is important. But churning out eight to twelve hours a day, five to seven days a week at something that kills your soul is not a fair trade for a future life that isn’t guaranteed. At least, not in this girl’s honest opinion.

Even as I type this, I can think of a number of people I know who are virtually miserable in their places of employment, but they’re banking on that guaranteed pension once they hit the age-factor of retirement.

And I can speak with some authority on this. These pensions are called Defined Benefit plans. The employer takes on all risk and future income is a combination of years of service, your top five years of earnings, and their own market investment performance. You just have to show up and work. Every day. Until you hit that magic number.

But pensions like this are concerningly underfunded today, and thus going the way of the dodo bird. People who have access to them (usually those in some sort of civil service) are told over and over how blessed they are.

And, they are.

Only, guess what? If you are literally TOILING and only living for tomorrow, you’re not really living now, are you? I know some people in this situation. Fabulous skills. Talent wasted in a job they loathe, but it offers them a better financial tomorrow than they could likely get anywhere else. So, it’s the age-old today, or tomorrow?

Look, I’m not here to convince you to leave your job. That’s not it. I do believe in challenging the status quo, however. And I believe in remembering that today matters. Today deserves a shot.

Speaking for myself, after sixteen years as a financial advisor, I could have easily stayed in the career and metaphorically cleaned up. Most established practitioners do extremely well if they have the stick-to-it-iveness for the long game.

But the trade-off of all this future money, for me, was control. So much of what I thought, valued, and wanted to pursue in my personal life was distilled down to regulatory policies of what was and was not acceptable. And I’m all for regulation –geez, there are crooks and *ssholes out there! The honest guy pays a price, however. Incessant scrutiny. A feeling of Big Brother watching you. It all became a little too much for my free-spirited, ethical self.

And? There was something else, too. Which leads conveniently into my final life lesson for today.

Life Lesson #5: Being true to yourself is critical to (genuine) happiness.

I consider my time as a financial advisor a massive blessing, but it began to feel disingenuous with my soul. I had poured myself into the career through my thirties and early forties, but along the way lost a bit of who I really was.

There is a much bigger problem at play when you feel like a square peg in a round hole. It can manifest physically, showing up in the form of stomach aches and a chronically watering left eye. (Had this for two years). It’s also a quiet erosion of your spirit—but this is only noticeable when you step completely away from your situation.

Thankfully, I decided to do something about the growing unease I felt in an industry that had been mostly good to me. Once again, I distilled my belongings down to a backpack and set out on a pilgrimage to gain some clarity.

For thirty-three days, I put one foot in front of another, following the famed Camino de Santiago trail in Spain, walking a total of 800 km. With each step, I tuned closer into the frequency of my soul, until it was no longer garbled static, but a loud, booming voice: Samantha! You need to make a change in your life! This career is killing you!

What I discovered was that being true to myself was vital to my growth, my purpose, and the peace I craved. I didn’t want to waste another moment not being the woman I had found on that trail.

So, what now? There’s a pandemic—cue another curveball—and mass global uncertainty. But I’m choosing to plug away at a new dream, one fueled by passion, not wealth. I remain grateful for all of life’s blessings, and even the struggles. For they have taught me that chasing money and status does not ultimately fill a person’s happiness bucket. And that’s gold to me.