37. Paying Off Debt: How He Flipped $114K of Consumer Debt into Financial Freedom with Kyle Fowler
- Brittany Miller
- Dec 12, 2023
- 13 min read
Updated: 5 days ago
If you're reading this because the idea of paying off debt feels overwhelming, welcome — you’re in the right place. This article breaks down a real-life, step-by-step story of paying off debt (a total of $114,000 in consumer obligations) and turns it into practical strategies you can use today. We’ll cover the mindset shifts, the exact method Kyle and his wife used, tools to stabilize unpredictable income, ways to survive expensive seasons, and journal prompts to keep you motivated while paying off debt.
If we haven't met yet, I’m Brittany, an online marketing strategist for female entrepreneurs. I teach women how to make their entrepreneurial dreams a reality through smart, actionable marketing strategies that get them seen, loved, and paid. Whether you’re eager to DIY your way to success or hire professionals to help you along the way–my goal is to make sure you walk away with the clarity you need to see the results you desire and build a life you love.
Meet Kyle
When I decided to be an artist at a very young age, I thought I was also choosing to be a starving artist. I adopted my financial instability as a truth and came to see myself as a victim of my financial situation, forever limited by the career I loved. By the time I was 32, I had traveled the world performing, was married to the love of my life (also an artist), had just moved into a brand new home, and was working at the most magical place on Earth - Disney World. Life was good. But we were broke. After seeing my wife's reaction to splitting bedsheets and pillows over multiple credit cards at Macy's, I knew something needed to change.
And so, in January of 2018, we decided to take action, created our very first budget, and started focusing on paying off our debt. It took 26 months, but we had achieved something we never thought possible. We had paid off all $114,000 of our personal debt, a number that still doesn't feel real. The following month, Covid hit. But because of the work we had done paying things off and learning how to manage our money, we were blessed to not have those financial worries that so many others had. And each time life would throw us another curve ball (because it always will), the financial worries that had once loomed over us were no longer there. It was clear that our lives had been changed.
We live in a society obsessed with consumption. And we live in a society that treats money as a taboo topic; one where if you ask a simple question, it's viewed as a weakness. So I grew up never asking questions which meant I never got answers. During the process of paying off our debts, I quickly found that I was not the only one struggling to make sense out of my finances. It's overwhelming all of the financial information we have access to, but people need to ask questions. So I began helping those around me as a financial coach. I enjoyed it so much that I went on to get multiple certifications, and am now on a mission to help creatives, like you, change their lives forever and pursue their passions.
Table of Contents
Why this story matters
Paying off debt is often framed as a math problem — pay down the highest interest rate, refinance, cut expenses. Those tactics matter, but there’s a deeper layer: how you talk to yourself about money, how you set boundaries, and how you create systems that let you make consistent progress. Kyle’s journey from creative performer to debt-free financial coach shows how practical tools and emotional work combine to turn a mountain of debt into options, security, and freedom.
Quick snapshot: What Kyle and his wife paid off
When they started, their consumer debt (not including mortgage) totalled about $114,300 (rounded to $114,000 in many tells). That included:
Multiple credit cards (individual and joint)
Furniture and lifestyle purchases tied to a new home
Car loans
One personal loan used to consolidate a card (and later re-maxed)
Student loans
Other consumer items: phones, store cards, interest and tax-related balances
They paid this off in 26 months. The timeline and the dollar figure are impressive, but the most instructive parts are the decisions they made along the way — the system they picked, how they handled irregular income, and how they protected their mental health while paying off debt. Kyle's story is powerful and he shares it best in our conversation which you can listen to here 👇🏻
The approach they chose: paying off debt snowball
There are several ways to attack debt: highest-interest-first (debt avalanche), highest-payment-first, or lowest-balance-first (debt snowball). Kyle and his wife chose the debt snowball, and this is why it mattered:
They prioritized momentum and emotional wins over a strictly optimal dollars-and-cents outcome.
Paying smaller balances first created quick wins that kept them motivated to continue.
They accepted that paying off debt faster in math terms (interest saved) might be slightly different than maximizing psychological momentum — and that was a conscious choice.
The phrase paying off debt snowball captures both a technique and a mindset. You concentrate on one debt, extinguish it, and roll that payment into the next balance like a snowball gaining size and speed.
How to decide which debt-payoff method is right for you
Choosing the strategy is part technical, part personal. Ask yourself:
Are you motivated by psychological wins or strict math? (Snowball vs. avalanche)
Is cash flow a bigger issue than interest rate? Then prioritize high monthly payment reductions.
Do you have unpredictable income? Then a method you can flex around makes sense.
There’s no universal "best" — only the best for your personality and the life you’re living while paying off debt.
Make the plan concrete: Get payment-specific
One of Kyle’s core teachings is “get payment specific.” This means:
List every debt with its exact balance, minimum payment, and interest rate.
Decide which single debt you will attack first.
Lock in how much extra you’ll contribute each month to that debt.
When it’s paid, roll that entire payment amount into attacking the next debt.
The act of getting specific turns vague intentions into mechanical actions. It short-circuits the “I’ll do it next month” loop and gives you a measurable target to hit while paying off debt.
Tools you can use right now
Kyle notes that you don’t need fancy software to start paying off debt, but useful tools make it easier:
Debt payoff calculator or “thermometer” — visually track progress.
Debt GPS (Kyle’s Get Payment Specific tool) — a simple worksheet that lists debts and shows the order and payment flow.
Budget app or spreadsheet — record your inflows and outflows, then allocate toward debts.
Automations for bill payments — avoid late fees and reduce mental load.
Taking one afternoon to set up a sheet and a “thermometer” is often the tipping point — it makes paying off debt feel real, not abstract.
Handling inconsistent income: Hills and valleys
If you’re an entrepreneur, freelancer, or have gig-based work like me, irregular income can make paying off debt feel impossible. Kyle recommends a Hills and Valleys account — a business-oriented smoothing account for variable income.
Here’s how to structure it:
Determine your baseline monthly needs (the lowest month you can operate on).
Save enough into the Hills and Valleys account to cover that baseline for one to three months (your comfort level).
In high-earning months (hills), top up the account. In low months (valleys), pull from it to cover minimums.
This creates stability and prevents emergency spending that derails progress while paying off debt. It’s essentially an income buffer that turns jagged cash flows into a predictable financial rhythm.
Architect your finances with Profit First principles
Another framework Kyle recommends for business owners is Profit First. The core idea: allocate percentages of incoming revenue to different buckets (profit, owner pay, taxes, operating expenses). When you see money designated for specific purposes, it becomes harder to spend inadvertently and easier to budget for paying off debt.
Using both Profit First allocations and a Hills and Valleys buffer can transform how you manage irregular income while paying off debt.
Emergency fund vs. debt payoff — how to balance both
You’ll hear two schools of thought: pay every dollar to debt, or keep an emergency fund. Kyle’s lived experience supports a balanced approach:
Keep a small emergency fund (three hundred to one thousand dollars) to prevent tiny surprises from creating new debt.
Build a Hills and Valleys buffer for business income variability.
When unexpected large costs happen (like medical, car repairs, or urgent pet surgery), having those savings turns emergencies into inconveniences instead of financial crises.
The goal is to avoid debt from new emergencies while maintaining momentum for paying off debt.
Real-life pressure test: The dog surgery during COVID
A powerful moment from Kyle’s story: two months after they paid off their debt, their dog needed emergency surgery that cost about $6,400. Because they had prioritized paying off debt and built financial skills, they were able to make that choice without catastrophic worry. That surgery also highlighted a core truth: paying off debt isn’t just about toys and travel. It’s about options — the ability to say yes to life when important moments happen.
Holiday spending, relationships, and love languages
The holidays and gift-giving seasons are emotionally charged and can threaten progress when paying off debt. Kyle offers practical, empathetic guidance:
Set boundaries early. Saying “no” or “this year we’re doing small gifts” is not mean — it’s protecting your financial future.
Shift how you express love. Gifts are just one love language; acts of service, time, and written words can be equally meaningful.
Plan intentional, budgeted ways to celebrate so you don’t get knocked off track while paying off debt.
Protecting your financial goals does not equal withholding love — it means being clear about what you can sustainably give.
The emotional work: Rewriting your money story
Kyle and his wife both grew up in homes where money wasn’t talked about. That silence creates a lot of assumptions about worth, spending, and scarcity. Rewriting a money story is a long-term project; it includes:
Journaling about money, gratitude, and priorities
Asking questions instead of assuming (curiosity beats anger)
Discussing money openly with your partner in non-judgmental ways
Recognizing that money is neutral — it’s how you use it that creates outcomes
One phrase Kyle keeps close: “Don’t get furious — get curious.” When money decisions trigger emotion, curiosity helps you discover the root cause rather than reacting from it. That shift alone can accelerate paying off debt because it replaces shame and blame with understanding and action.
"Don't get furious — get curious."
Journaling prompts to move your finances forward
Journaling can flip fears into plans. Kyle suggests repurposing standard writing prompts into financial prompts. A few to try:
If you learned you had 365 days left, what would you spend money on — and why? (Then budget one small piece of that into your life now.)
What’s the most unfair thing about capitalism? How does that belief influence your financial choices?
Describe a future where you’ve finished paying off debt. What’s the first choice you make with your time and money?
List three non-monetary ways you can show love this holiday season.
These prompts help you explore values. When your budget reflects values, paying off debt stops being punishment and starts being a path to what you truly want.
Small rituals that sustain you while paying off debt
Momentum is built from tiny, repeatable actions. Try these rituals:
Create a visible debt thermometer and update it monthly.
Schedule a monthly money date with your partner to review progress (no blaming — only facts and next steps).
Celebrate micro-wins: paid off a card? Buy a small treat from a preset “fun fund.”
Automate payments so you don’t miss minimums and incur late fees.
Rituals reframe the process. They make paying off debt feel like a team sport instead of a lonely slog.
Practical month-by-month blueprint to start paying off debt
Use this simple blueprint as a launchpad for the next 6 months. Adjust based on your income and chosen method (snowball or avalanche).
Month 1: Inventory and baseline
List all debts with balances, minimums, interest.
Create a basic budget that covers essentials and minimums.
Build a $500–$1,000 emergency buffer.
Month 2: Choose your method and systemize
Pick debt snowball or avalanche — write the order and commit.
Set up automatic minimum payments and one automated extra payment to the target debt.
Create your debt thermometer and hang it somewhere visible.
Months 3–6: Increase momentum
Look for 1–3 ways to free up cash: subscriptions to cancel, meals to plan, a temporary side gig.
Apply saved cash to the focused debt. Keep the rest of the budget steady to avoid burnout.
Hold monthly money dates to reassess and celebrate progress.
After six months, you’ll have traction. The goal is to build systems that outlast short-term discipline so paying off debt becomes an inevitable outcome of your routines.
What paying off debt really feels like — the emotional payoff
When Kyle and his wife paid off their debts, the day itself wasn’t fireworks. They’d already practiced the financial skills for 26 months. But what changed afterward was profound:
Less anxiety — money conversations stopped triggering panic.
More options — they could choose care for a sick pet, pivot careers during COVID, and plan moves without immediate fear.
A different relationship with money — it became a tool to create options rather than a constant stressor.
That’s the promise of paying off debt: not instant happiness, but expanded choices and calmer decision-making when life happens.
How entertainment and travel taught financial lessons
Kyle’s background as a performer for cruise lines and Disney shaped his approach to money. Touring taught him about front-loaded work, unpredictable schedules, and the value of perks and experiences over hoarding cash. Working at Disney taught him discipline, teamwork, and how to find joy while living in unusual conditions.
These experiences also informed his empathy as a coach: he knows variable income, life interruptions, and the emotional ups and downs that come with creative careers — and he crafts tools that fit those realities while paying off debt.
Common traps to avoid while paying off debt
A few pitfalls show up again and again:
Fuzzy math: assuming a balance in your account without checking. Track actual numbers.
All-or-nothing: extreme deprivation leads to burnout. Build small rewards into your plan.
Using savings to pay small debts without fixing the spending leak that caused them.
Comparing your timeline to others. Everyone’s context and income differ.
Being aware of these traps helps you stay on course without guilt when life throws curveballs.
How to talk about money with your partner (without fighting)
Money triggers are real. Kyle recommends:
Set a recurring, neutral “money date.” Keep emotions low and facts high.
Use “curiosity” language: ask “why” instead of accusing “you.”
Define roles: who manages the day-to-day, who organizes bills, and how to escalate decisions.
Make a shared vision board or simple list of priorities so your budget matches what you both value.
This approach protects relationships and makes paying off debt a shared mission rather than a blame game.
Practical checklist to start today
Use this checklist to move from thinking to acting on paying off debt right now:
Write down every debt (balance, minimum, interest).
Pick your strategy (debt snowball or avalanche) and commit to an order.
Create a simple debt thermometer and hang it up.
Open a Hills and Valleys account or designate a business buffer.
Automate minimum payments and one extra payment to the target debt.
Schedule a monthly money date to update progress and plan for the next month.
Frequently Asked Questions
How does the debt snowball differ from the debt avalanche and which should I pick?
The debt snowball focuses on smallest balances first to build momentum; the debt avalanche focuses on highest interest first to save more money over time. Choose snowball if you need psychological wins and risk burning out; choose avalanche if you’re disciplined and focused on minimizing interest costs. Both are valid systems for paying off debt.
Can I still save while paying off debt?
Yes. Keep a small emergency fund to avoid adding new debt, and build a Hills and Valleys buffer if your income is irregular. After that, funnel extra money into your chosen debt strategy and re-evaluate once major balances are cleared.
My income is variable. How can I reliably pay off debt?
Build a Hills and Valleys account to smooth income, establish minimums, automate payments, and use Profit First allocations to assign revenue to priorities. In low months draw from your buffer; in high months replenish it and send extra toward the debt you’re targeting.
What if I get a windfall — should I invest it or pay off debt?
It depends on your interest rates, buffers, and goals. If you have high-interest consumer debt, applying a windfall to debt often yields the best financial return. If you’re lower-interest or student loans, consider splitting a windfall between debt, an emergency fund, and a small celebration.
Is it worth consolidating credit card debt into a personal loan?
Consolidation can reduce interest and simplify payments, but it only helps if you don’t re-accumulate balances. Treat consolidation as a structural change — continue the discipline that got you onto the debt-payoff path in the first place.
Final thoughts: Stay curious, not furious
Paying off debt is a marathon, not a sprint. The numbers matter, but the emotional and behavioural work determines whether you finish the race. Kyle’s experience shows that choosing a method that fits your temperament, building systems for variable income, and creating rituals to celebrate progress are the things that convert a plan into reality.
If you take anything away, let it be this: paying off debt creates options. It doesn’t promise instant glamour or entitlement; it promises the freedom to choose when crises occur and the capacity to lean into life on your terms. You don’t have to be perfect. When you combine a paying off debt snowball approach with buffers, automation, and curiosity-driven conversations, you set yourself up not just to erase balances, but to rebuild a healthier relationship with money.
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00:00 Intro
4:30 Our upbringing with money
8:00 Kyle's debt repayment story
11:40 What it feels like to pay off your debt
17:00 Audio issues (lasts 6 minutes, can skip ahead)
17:20 Strategies for paying off debt
23:50: Audio issues resolved
24:00 Tips for managing expensive seasons
30:00 Working on cruises & at Disney
33:00 Vision boards
40:00 Journal prompts for financial awareness
42:00 Wrap up & stay curious
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