The Smart Way to Travel for Free Using Credit Cards & Memberships

I grew up watching my mom run businesses and squeeze every benefit from loyalty programs — she called it point stacking. In this post I walk you through why I still use that approach, how it actually works, the risks I learned the hard way, and the humane, practical systems (including a little AI help) that let me simplify to amplify.

1) Why Point Stacking Became My Default

My love for money systems started with a simple mission: help entrepreneurs simplify to amplify. When I remove extra steps from my finances, I get more time to talk to more people, meet more humans, and serve better. That mindset is what made Point stacking feel like the most natural “default” in our family.

Point stacking was a family system, not a hack

My mom ran points across all our businesses. She and my dad ran a consulting firm, and she treated rewards like an organized workflow: airlines, hotels, and even restaurants. The idea was simple—stack benefits in layers. If we stayed at a hotel, we’d put the bill on the hotel account to earn hotel points, then pay with a points credit card to earn card points too. Over time, travel stopped being a painful expense and became a lower-cost asset for the business.

Financial mastery 2026 starts with values and a family financial conversation

Before any rewards strategy works, I’ve learned you have to clarify what matters: more client time, more margin, more family experiences, or all three. That clarity makes decisions easy. It also makes a Family financial conversation powerful—when everyone knows the priorities, there’s less uncertainty and fewer “random” purchases that break the plan.

Why multi-generation entrepreneurs adopt it faster

We’re third-generation entrepreneurs, so we grew up watching cash flow decisions up close—my grandmother, my mom, even my Opa’s trade mindset. That background makes Financial Success Habits feel normal: track spending, choose tools once, and repeat the process.

• Use the same airlines/hotels consistently
• Pair loyalty accounts with a points card
• Reallocate saved travel cash flow into growth activities

A quick aside: homeschool entrepreneur travel

Some of my favorite “school days” happened at conferences. Points helped cover rooms for years at a time, which turned travel into affordable education—real people, real business, real life.

Jennifer: “I love empowering entrepreneurs to simplify to amplify.”
Jax Crider: “Welcome back to another episode of Financial Mastery Simplified.”

2) The Mechanics: How I Stack Points (Step‑by‑Step)

Step 1: Set up award accounts + one “main” card (Travel rewards strategies)

I start by opening award accounts everywhere I might spend: airlines, hotels, and even restaurant programs. Then I pick one primary points credit card and save all logins in one place. The goal is simple: every purchase should earn in at least one system, and often two.

Step 2: Charge to the merchant program, then pay with the points card

This is the core of point stacking. Jennifer explains it best:

Jennifer: "So every time they go somewhere... we will put the whole bill on the hotel and then we get the points from the hotel and then we also get the points from the credit card."

Example: if I’m staying at a hotel and eat at the hotel restaurant, I make sure the bill is tied to my hotel rewards profile, and I pay with my points card. With discipline, this can create major travel cost savings over time.

Step 3: Track each earning channel (Track Your Expenses + Business expense tracking)

I Track Your Expenses by labeling transactions in my budget tool and splitting business vs personal spend. I keep separate cards/accounts and clear names like HOTEL-BIZ or AIR-PERSONAL. This supports clean Business expense tracking and prevents missed points.

• Hotel points
• Airline miles
• Restaurant/merchant rewards
• Credit card points

Step 4: Use reimbursements carefully (Money flow automation)

If a client or employer reimburses travel, I pay first, submit an expense report, then collect reimbursement. This can accelerate points accrual, but only if documentation is exact (receipts, dates, project codes). I use Money flow automation—rules, reminders, and AI receipt scanning—to reduce mistakes and avoid surprise balances.

Step 5: Keep the card a points engine, not debt

Jennifer: "It is like a revolving door. I am constantly putting money down on it and then paying it down."

I pay the balance down frequently (sometimes weekly) to avoid interest and protect cash flow. I also watch application rules and bonus timing so I don’t miss eligibility.

3) The Tightrope: Debt, Discipline, and Self‑Awareness

I’m neither pro- nor anti-debt. As Jennifer put it, "I am not necessarily pro or anti- debt... debt is a vehicle that can be utilized for your gain, but you have to do it smartly." Points can fund real wins—sometimes even years of travel without paying for hotel rooms—especially when I’m fronting reimbursable work expenses or running business spend through one main card for miles. But the same system can wreck cash flow if I’m not self-aware.

Debt elimination strategy starts before I swipe

Before I chase rewards, I run two checkpoints that keep me making Informed Financial Decisions:

• Can I pay the balance within the billing cycles? If not, points aren’t worth it.
• Is this business-necessary or a want? As Jax Crider said, "You have to be cognizant of like one wants and needs as well too."

Red flags that signal Financial stress reduction is needed

The transcript warning is real: you can definitely get yourself into trouble. My biggest red flag is a surprise balance—like waking up to a $20,000 charge that I didn’t plan for. The second is when finance charges outweigh the reward value. A “free” flight is not free if interest and fees are piling up.

Rules: monthly review + Emergency fund building

Debt can be a lever for growth, but only with strict discipline and contingency planning. I do a monthly review to prevent runaway balances, and I follow a repeated pay-down pattern: I put spend on the card, then pay it down frequently (not just once a month).

1. Set hard limits per card and per category.
2. Model worst-case repayment scenarios in a simple note: If revenue drops 30%, can I still clear this?
3. Keep a cash buffer: 3–6 months of operating expenses for Emergency fund building.

Progress over perfection matters. I’ll make occasional mistakes, but aligning spending with my values lowers stress and keeps the points game sustainable.

4) Taxes, Bookkeeping, and the Fine Print

Separating Business Finances (so points don’t create a mess)

I grew up watching business owners run real spend through business cards to earn airline miles—like my mom with her holiday décor storefront, and friends in interior design and consulting. It works, but only if I’m strict about Separating Business Finances. Separate checking, separate credit cards, and clean expense reports make accounting faster and tax reporting simpler. As Jennifer put it:

“When you do that, if there's charges on there that are a business account, then they're not going to be able to take them off.”

Know what’s deductible (and what must be split)

Point stacking doesn’t change tax rules. I have to know what I can deduct and what I must report, or I risk surprise liabilities and audit exposure. Jax Crider said it best:

“You have to know what you can and can't do.”

One practical example: entertainment rules changed, and alcohol can’t be included the same way. For client dinners, I often ask for split checks so the alcohol is separated. That keeps Business expense tracking clean and protects the deductible portion.

Good Bookkeeping Practices that protect the value of points

Good Bookkeeping Practices increase the net value of point stacking because they preserve deductible status. I label every transaction with a simple note and mark reimbursements clearly.

• Use categories like Meals - client, Travel - hotel, Supplies
• Attach receipts and write the business purpose
• Tag reimbursed items as Reimbursed - do not deduct

Planning for Taxes when points cover travel

Even when points pay for hotels or flights, I still plan cash for taxes. If I’m charging business expenses to earn miles, I set aside a percentage weekly so I’m not squeezed at quarterly payments. Planning for Taxes is what keeps the strategy from putting me behind instead of ahead.

5) Family, Legacy, and the Values Behind the Numbers

Third-Generation Entrepreneurship and How I Learned to Think About Money

I’m a third-generation woman entrepreneur, and that history shaped how I view money, risk, and creative hacks like point stacking. My family story starts with grit and initiative. As I’ve shared before:

“My grandmother actually owned businesses before women actually could do that in the United States.”

That kind of legacy teaches you to look for options, not excuses. It also makes “numbers” feel personal—because behind every dollar is a decision, and behind every decision is a value.

Clarify Your Values Before You Optimize Your Points

Point stacking works best when it supports what matters most. For my family, that often means choosing experiences over status. We homeschool, and I routinely take my kids to events and conferences so they can meet people, learn, and build confidence. That’s a Family financial conversation we revisit often: what are we buying—impressions, or impact?

“We took almost most of our trips as a family through points.”

When I Clarify Your Values, spending trade-offs get easier. It reduces friction because we’re not debating every purchase from scratch—we’re measuring it against our legacy goals.

Family Systems That Multiply Financial Benefits

One reason this works is that we treat finances like a shared system, not a solo project. Family systems can multiply financial benefits when knowledge and habits are shared—especially across multiple businesses and roles. When one person tracks cards, categories, and redemptions, the whole household wins.

• One “points lead” manages rules and reminders
• Everyone learns simple habits (save receipts, tag expenses, pay on time)
• Kids absorb Financial literacy knowledge by watching real decisions

A Simple Principle for Lasting Financial Success

My quick prayer/principle is this: lasting financial success means our money serves our family, our calling, and the people we help—not just a bigger number on a screen.

6) A Practical Playbook: Tools, Habits, and a Few Wild Cards

Point stacking only works when my system stays simple. The goal is free meals, hotel stays, and airline miles—without drifting into finance charges that erase the win. As Jennifer put it,

"I'm going to say that... I firmly believe that people should be utilizing some of these things [AI]."

Money flow automation: my daily “cash-account engine” habit

I treat my main points-earning card like a checking account with rewards. Every day, I glance at the balance and recent merchant credits, then I make a quick payment. It’s a “revolving door” habit: charges go on, money goes down, and the balance stays controlled. Money flow automation matters here—autopay for at least the minimum, plus reminders for extra payments—so I don’t get hit with late fees or interest.

Review Regularly Monthly: the checklist that prevents surprises

Once a month, I do a deeper review because automation and monthly reviews drastically lower the risk of surprise balances. I reconcile points totals, confirm reimbursements posted, set aside estimated tax if needed, and update my emergency fund progress. I aim for a 3–6 month operating reserve so points stay a bonus, not a lifeline.

Automate Your Savings + small compounding moves

I also Automate Your Savings the same way I automate card payments. One small habit change I like is a 1% annual 401k increase; it feels tiny, but it compounds into long-term resilience. If I’m using Income increase methods (a new client, overtime, a side gig), I route part of that raise straight into savings before lifestyle creep shows up.

Wild cards: if programs devalue overnight

If a loyalty program cuts value, I don’t panic—I diversify points channels and keep a cash fallback plan. And I remind myself of Jax Crider’s line:

"Progress over perfection — you're going to just have to continue to move forward."