By Wendy Watson
People often ask how I remain so confident, even when life is unpredictable. One of the things people find both inspiring and occasionally frustrating about me is just how deep my sense of confidence runs. But what they don’t always see is the road I took to get here. My confidence isn’t arrogance or blind optimism—it’s the result of having been tested time and time again and still choosing to rise. I’ve had everything fall apart more than once, and each time, I built it back with more wisdom, more faith, and more clarity than before.
My story with money began early. I started working for my parents when I was just 11 years old. My mom ran a financial mortgage office, and my dad was in construction. From a young age, I was exposed to spreadsheets, budgets, invoices, and blueprints. The day I turned 16, I got my first official job at the local bowling alley. By 18, I had bought my first brand-new truck (with my mom as my co-signer), had savings in the bank, and could comfortably support myself. Understanding the importance of credit, budgeting, and living within my means was second nature—my parents made sure of that.
Then came my first real financial curveball: marriage.
I married a man I was convinced was “the one,” despite everyone else’s warnings. Emotionally and psychologically, the relationship was deeply unhealthy, but he helped me come out of my shell in many ways. Financially, though, we were a disaster. He didn’t believe in budgets. If a debit card worked, that meant there must be money, right? DSF fees stacked up like a second rent payment, and no matter what system I tried—credit limits, cash budgets—he’d revert back to overspending. Add in college debt, unstable job situations, and constant financial juggling, and you’ve got a recipe for bankruptcy.
When we moved from San Diego to Phoenix in 2003 to escape California’s high cost of living, I thought I’d done my homework. I found him a job transfer with equal pay and assumed I’d find work at the same rate. But I was wrong. I had to take a pay cut, and four months later, he had a seizure while driving a big rig—causing a massive accident that his work insurance wouldn’t cover. Months of medical bills and lost income followed. We filed Chapter 13 bankruptcy and tried to dig our way out.
By 2004, the emotional and financial stress reached a breaking point. I was not only navigating a failing marriage but trying to stay afloat in a system that felt impossible to win at. I remember the sleepless nights after his suicidal threats, the anxiety that clung to me every time the phone rang or another bill showed up. I had to work just to convince myself I wasn’t a failure. I worked 70 hours a week to still have cold water at times. That period tested me emotionally, mentally, and spiritually. The straw that broke the camels back was when he threatened my life. When I finally made the decision to file for divorce, it wasn’t with a sense of defeat—it was with a sense of reclaiming. Even though my credit was wrecked and my heart broken, I knew I had to bet on myself.
I went from a financially independent young woman to a divorcee with two bankruptcies on her record—in just 5 years.
And yet, I knew I was doing the right thing.
A friend let me move in rent-free while I paid off my debts—including money I owed to my mom—and started rebuilding. I paid back every dime. Four years later, I hit a major milestone: I bought my first home, just two months after my 30th birthday in 2008. That same friend eventually became my partner, and though he had no credit score at all, we made it work. We got creative with proof of reliability—letters from landlords and utility accounts—to get approved.
But just a year later, I was laid off during the Great Recession. I had been in a middle position that was no longer available. I pivoted. I enrolled in massage therapy school and launched a new career in 2011 while working side jobs to stay afloat. The next year he lost his job months before our wedding and fell into a depression. I helped him build a handyman business while also growing my massage practice. We hustled.
In 2015, after another painful divorce, I found myself living alone for the first time ever and down to 1 income. I went into overdrive with my massage business, booking nearly 150 hours in a single month to make ends meet (80 is average). It nearly broke me physically. My body gave up. I sat down, ran the numbers, and realized something shocking: I could afford my lifestyle. In fact, my ex had been costing me more than he contributed. I not only had enough—I had room to hire a house cleaner so I could finally rest.
In 2017, when my roommate moved out, I realized I didn’t use half the house. My business brain kicked in. “This is wasted space. Find a use for it or monetize it.” So I rented it out, downsized, and moved into a condo. Every penny I had went into making that transition. In April 2018, my tenants moved in, and I settled into my new place.
Two months later, right before my 40th birthday trip to Israel, both AC units in the rental and condo failed. I still remember sitting with my renters and falling into tears and feeling like the universe had sucker punched me. They tried to tell me it was ok not to replace the a/c unit but by law and my own morals (June in Phoenix, come on!), I knew it was what needed to be done. I had to finance $12,000 worth of replacements within 24 hours—and just like that, my debt was higher than my savings again. It was one of those moments where you just stare at the ceiling, sigh deeply, and remind yourself that you’ve survived worse. I was maxed out—mentally, emotionally, and financially.
A month later—while I was literally on the other side of the world—I woke up to dozens of missed calls and texts. My rental house had caught on fire! My tenants were safe, but it was devastating. I couldn’t fly home. I could only make calls and hope for the best. The house was eventually rebuilt, but those six months tested every ounce of my endurance. Contractors, insurance, pushy tenants—it was chaos. But I survived it.
By the end of 2018, the house was repaired. In 2019, after my tenants violated their lease, I was able to evict them and sell the newly remodeled house for a six-figure profit. Finally—finally—I could breathe. I joined my HOA, started enjoying some spare time, and then… COVID hit.
And I was okay. Because I had prepared. That sale saved me! I wasn’t financially trapped during the pandemic like so many others. I was safe, comfortable, and grounded.
In 2021, I wanted to reinvest. I bought an RV to rent out and it did great in Arizona—until I moved to Denver in 2022. That year, I sold my condo, closed my massage business, moved the RV to Colorado Springs, and went on a month-long vacation before starting from scratch in a brand-new city.
I knew no one. I had no business plan. But I trusted myself.
In 2023, I began building my next venture. I knew I wanted to help others find their own power and create authentic lives, but I didn’t yet know how. I invested in coaching, systems, branding, and business development—every move fueled by trust in myself. I had to learn how to sell, how to pitch, how to stand out in a saturated market. There were weeks where I questioned everything, and weeks where I soared. I leaned into my intuition, asked better questions, and stayed open to change.
Now, in 2025, I’m in year two of my newest business while working a 2nd job to make ends meet. Some days feel abundant, others feel tight—but every day, I lead with clarity and confidence.
So what have I learned through two bankruptcies, multiple reinventions, and the rollercoaster of being a self-made woman?
Here’s What It Really Takes to Be Financially Free:
- Talk About Money—With Everyone. One of the most overlooked pieces of financial freedom is communication. We’re often taught not to talk about money, but that silence leads to confusion, mismatched expectations, and sometimes even disaster. I’ve learned that it’s vital to talk openly about finances with your kids, your romantic partner, and your business collaborators. Kids need to learn early. Partners need to be aligned. And in business, money must be part of the vision, not just the result. Financial maturity means you can talk about the hard stuff with clarity and respect.
- Reevaluate Often. Your relationship with money isn’t static—it’s alive. I’ve had to reinvent my financial habits, beliefs, and strategies every time my life changed. After every marriage, job loss, career shift, and cross-country move, I took stock. I asked myself: What does financial alignment look like now? What tools do I need? Who do I want to be financially in this next chapter? Don’t assume what worked before will always work again. Revisit your relationship with money like you would any important relationship—check in, ask questions, and be willing to grow.
- Confidence in the Unknown. You don’t need all the answers to move forward—you just need a clear “yes” in your gut. I’ve made huge moves, literally and financially, based on nothing more than a deep inner knowing. When you trust that kind of clarity, you build a foundation that money can’t buy.
- Resilience Over Perfection. I’ve filed for bankruptcy, twice. I’ve had relationships fail, twice. I’ve had to start over more than once. But perfection was never the goal—resilience was. The ability to bounce back, to keep learning, to stay open to new ways of doing things—that’s what builds wealth over time.
- Resourcefulness Is Wealth. When I bought my first house with a partner who had zero credit, I didn’t give up—we got creative. Letters from landlords, utility records—whatever it took. That mindset of “we’ll find a way” has been my saving grace more times than I can count.
- Your Relationships Impact Your Finances. It’s not just about what you earn—it’s about who’s around you. Some people add chaos. Some add clarity. I’ve learned the hard way that the wrong partnership can drain your energy, your bank account, and your peace. Choose people who are aligned with your values.
- Trust Yourself First. I’ve had well-meaning people try to steer me “off the ledge” of big decisions. But only I know what’s right for me. I’ve trusted my intuition when it made no sense on paper—and it’s always led me somewhere important.
- Flexibility Is a Superpower. If I had clung to one job, one plan, one identity—I would’ve missed out on some of the best chapters of my life. Financial freedom isn’t about rigidity. It’s about options. It’s about being able to shift gears without falling apart. You can change careers, change cities, change plans. Freedom isn’t rigidity—it’s adaptability.
Financial freedom, for me, is not about never having debt. It’s not about being rich. It’s about knowing that I can rebuild anything. That I trust myself to weather any storm. That I have a deep relationship with my money, my values, and my vision.
I’ve had it all—and lost it twice. And still, I rise.
That, my friends, is real financial freedom.
