Award Travel Mistakes Business Owners Make (and How to Fix Them)
For many business owners, award travel feels like a bonus—an occasional free flight here, a discounted hotel there. But what if we told you that most small and mid-sized businesses (SMBs) are leaving tens of thousands of dollars in value on the table every year?
The truth is, while companies may be earning plenty of points through business spending, few are optimizing how those points are used. Worse yet, many are making costly mistakes that quietly drain their budgets and limit the potential of their hard-earned rewards.
At UpNonStop, we work with businesses every day to unlock hidden value in their credit card points and award programs. Let’s break down the most common award travel mistakes we see business owners make—and how you can avoid them.
Mistake #1: Treating Points Like Cash (They’re Not!)
It’s tempting to think of points as “currency” that you can easily apply to flights, hotels, or gift cards. But this mindset often leads to undervaluing points. For example, using points to book a $200 domestic flight might seem fine—but if you dig deeper, those same points could be worth $400 or more when applied strategically to an international business-class ticket or transferred to a partner airline.
Why this happens:
Many business owners default to using points through their credit card issuer’s travel portal, which may only give you a value of 1 cent per point (or less).
How to fix it:
Think of points as a dynamic asset, not a fixed one. Transferring points to travel partners (like airlines or hotel chains) can unlock far greater value. Partner programs often have sweet spots—hidden gem redemptions where your points go much further.
Mistake #2: Hoarding Points Indefinitely
Some businesses accumulate large balances of points and miles over time, waiting for the “perfect” trip or opportunity. However, this is risky for two reasons:
- Devaluation risk: Airlines and hotel chains frequently devalue their loyalty programs, meaning the same flight or stay will cost more points in the future.
- Missed cash flow optimization: Sitting on unused points means you’re not taking advantage of the travel savings they could provide right now.
Why this happens:
Business owners are busy running operations and don’t always have time to plan complex award travel or stay on top of program changes.
How to fix it:
Adopt a “earn and burn” mindset where you regularly use your points for high-value redemptions. This reduces exposure to devaluations and brings immediate value back to your business.
Mistake #3: Ignoring Transfer Partners
Many of the best credit cards offer transferable points (e.g., Amex Membership Rewards, Chase Ultimate Rewards, Capital One Miles). But some business owners never leverage transfer partners and instead opt for direct bookings at lower point values.
Why this happens:
The transfer process can seem complex or time-consuming, and many business owners don’t have time to study all the airline and hotel programs.
How to fix it:
Learn the basics of transfer partner networks, or better yet, partner with a service like UpNonStop to handle the process for you. Transfer partners often unlock international premium cabins, luxury hotels, and other “sweet spot” redemptions.
Mistake #4: Not Diversifying Point-Earning Strategies
Some businesses put 100% of their spending on a single card, thinking simplicity is king. But this approach can limit how many points you earn and which transfer partners you can access.
Why this happens:
Using one credit card simplifies bookkeeping, but you may be missing out on bonus categories or card-specific perks from other issuers.
How to fix it:
Diversify your card portfolio. Use multiple cards to take advantage of different spending bonuses. For example:
- Amex Business Gold: 4x points on the two categories you spend most in each month (e.g., advertising, shipping, etc.)
- Chase Ink Preferred: 3x points on travel, shipping, and advertising.
- Capital One Spark Cash Plus: 2% cash back on everything else.
Mistake #5: Overlooking Taxes and Fees on “Free” Flights
Many business owners think award flights are entirely free. Then they’re hit with high taxes and carrier-imposed surcharges (especially on international flights). Suddenly, that “free” ticket isn’t as free as it seemed.
Why this happens:
Not all award flights are created equal. Some airlines (looking at you, British Airways) charge hefty fuel surcharges, while others (like ANA or United) have minimal out-of-pocket costs.
How to fix it:
Be selective about which airlines you redeem with, and always price out taxes and fees before transferring points. You can also target low-surcharge routes or focus on U.S. domestic carriers with lower add-ons.
Mistake #6: Not Leveraging Companion Passes or Perks
Many business owners forget about valuable perks like companion passes, free hotel nights, or elite status fast tracks. These benefits can drastically reduce your total travel costs but often go unused.
Why this happens:
Perks are often buried in the fine print, or owners simply don’t have the bandwidth to track them all.
How to fix it:
Audit your existing credit card benefits and airline/hotel elite statuses regularly. Make sure you’re capitalizing on free night certificates, travel credits, or discounted companion fares.
Mistake #7: DIY Award Booking Without Expert Help
Award bookings can be notoriously complex. Between blackout dates, limited award availability, and ever-changing airline rules, many business owners waste hours searching for flights—only to settle for mediocre redemptions.
Why this happens:
Without expert tools or insider knowledge, it's difficult to find premium award availability, especially for business-class or first-class seats.
How to fix it:
Partner with a specialist who understands the ins and outs of loyalty programs and can secure the best possible redemptions for you.
Bonus: The Hidden Cost of Poor Award Strategy
Here’s the reality:
- Time loss: The average business owner might spend 5-10 hours searching for a decent award ticket. Multiply that by multiple trips per year, and that’s valuable time lost.
- Opportunity cost: Every point redeemed at poor value means less ROI for your business. For SMBs spending $50K+ per month on credit cards, this can easily add up to $10,000 - $30,000 in lost travel value per year.
How UpNonStop Solves These Problems for Business Owners
At UpNonStop, we specialize in optimizing your business travel strategy so you get the most out of every point you earn.
Here’s how we do it:
✅ Maximization Strategy:
We assess your spending, points portfolio, and travel needs to design a tailored strategy.
✅ Ongoing Monitoring:
We monitor airline and hotel program changes, devaluations, and promotional transfer bonuses so you’re always ahead of the curve.
✅ Award Booking Service:
Our team of booking specialists handles the heavy lifting, finding you the most valuable flight and hotel redemptions worldwide.
✅ End-to-End Support:
From recommending the right credit cards to booking award tickets to troubleshooting travel hiccups, we’ve got your back.
The Bottom Line
Award travel isn’t just a nice-to-have; it’s a hidden lever for cutting business costs and improving cash flow. Avoiding these common mistakes can unlock thousands of dollars in savings annually, boost your team’s morale with better travel experiences, and free up your time to focus on growing your business.
Ready to stop leaving points (and profits) on the table? Schedule Your Free Assessment Now 👇🏻
