Determining when to retire is one of life’s biggest decisions, and the right time depends on your personal vision for the future. Have you considered what your retirement will look like, how long your money needs to last and what your expenses will be? Answering these questions is the first step toward building a successful retirement plan.

Our guide, When to Retire: A Quick and Easy Planning Guide, walks you through these critical steps. Learn ways to define your goals and align your investment strategy to meet them. If you have $1,000,000 or more saved, download your free guide to start planning for the retirement you’ve worked for.

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Let me tell you about two people I know.

One drives a brand-new **Chevrolet Silverado every couple of years.

Out-of-pocket cost to him: zero dollars.

The other takes his family to Hawaii every year.

Out-of-pocket cost: also zero.

Neither of them is running a scam. Neither is gaming the system. They’re just doing something painfully boring and wildly effective: running every legitimate business expense through a rewards credit card—and paying it off every month like adults.

Same spending. Same bills. Different outcome.

If you’re actively investing—materials, contractors, insurance, utilities, property management, marketing—you’re almost certainly spending $20,000–$40,000 a month. During renovation-heavy periods, it’s usually more.

If you’re writing checks or using ACH for all of that, congratulations: you are voluntarily declining free money.

Run that same spend through a boring 2% cash-back card:

That’s a used truck. Or a decent vacation. Or seed money for your next deal.

Now run it through a card with accelerated rewards.

All of a sudden, you’re not just paying expenses—you’re manufacturing assets.

One of my friends uses a GM business rewards card.

Everything goes on it:

During active flipping periods, he runs $30K–$40K a month through that card.

Every 18–24 months, he redeems the points for a new Silverado or Tahoe.

Registered to the business.

Used for business.

Expenses written off like any other company vehicle.

Annual fee? Sure.

Material to the outcome? Not even close.

He drives it for a couple of years, trades it in, and the next truck shows up right on schedule—paid for by expenses he was going to incur anyway.

This isn’t clever. It’s just disciplined.

Another friend prefers sand to tailgates.

He runs his business spend through a premium travel card—think American Express or Chase—earning 2–3 points per dollar. Then he redeems through the card’s travel portal, where points are worth 1.25–1.5 cents each.

Do the math:

That’s not “a weekend getaway.” That’s real vacations, every year, paid for by drywall and insurance premiums.

I can hear the gears turning.

Generally speaking, rewards and cash back tied to business spending are not taxable income. The Internal Revenue Service treats them as rebates or discounts on purchases you were already making.

There is a gray area if you use business-earned points for personal travel. Technically, that could be considered taxable income. Practically, it’s rarely enforced and poorly defined.

Using rewards for a company vehicle that’s actually used for business? Cleaner. Simpler. Easier to explain to your CPA.

Which brings us to the mandatory disclaimer:

I am not your tax professional. Ask yours. The risk is low, but pretending it doesn’t exist is how adults get surprised.

This strategy only works if you follow three boring rules:

1. Pay the balance in full. Every month.

If you’re carrying balances at 18–24% interest, stop reading. Rewards don’t matter when you’re lighting money on fire.

2. Don’t pay surcharges bigger than your rewards.

If a contractor adds 3% to take cards and your rewards are 2%, write a check. This is math, not loyalty.

3. Keep business spending clean.

One card. Business expenses only. No groceries. No date nights. No “I’ll sort it out later.”

Clean books = easier taxes and fewer headaches.

Vehicles:

Cash Back:

Travel:

Annual fees range from $0 to eye-watering. If you’re spending $300K+ a year, even a $695 fee disappears into rounding error.

If that’s you, just use a simple 2% cash-back card and move on with your life.

You’re spending the money anyway.

You can let it vanish quietly into the void…

or you can make it buy you something useful.

A truck.

A vacation.

Or at the very least, the satisfaction of knowing your expenses are finally pulling their weight.

Your move.

The best HR advice comes from those in the trenches. That’s what this is: real-world HR insights delivered in a newsletter from Hebba Youssef, a Chief People Officer who’s been there. Practical, real strategies with a dash of humor. Because HR shouldn’t be thankless—and you shouldn’t be alone in it.

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Knowing when to retire starts with understanding your goals. When to Retire: A Quick and Easy Planning Guide can help you define your objectives, how long you’ll need your money to last and your financial needs. If you have $1 million or more, download it now.

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