It’s nice to have someone knowledgeable to call whenever I have a travel question. Whether it’s a ticket schedule change, a missed connection, or having no idea how to book this award night, I get stressed out about what to do. Having someone to talk to that can help sort things out is a huge advantage.

Wait. I have things backwards. I’m supposed to be the encouraging voice on the other end of the phone helping sort out all the problems. At least that’s what I try to do. I can’t solve everything, but I’ll do what I can.

Being “The Travel Guy” of the Family

I’ve been “into this points and miles hobby” for a decade now. One learns things along the way. And when people figure out that you’re good at something, they come to you with questions.

I forget how daunting booking airfare is for some people. For those who rarely fly, it truly induces anxiety. At least that has been my takeaway after talking with more than a few friends. When you’re spending a large amount of money on one family vacation, you don’t want to screw anything up. It’s nerve wracking. This is one reason I’m happy to field questions from family and friends.

It can be as small as confirming that they’re getting the best deal they can on a flight. Or pointing them to an airline’s baggage policy. Or as large as walking them through booking award tickets. These might seem like “no brainer” items to many of us. But not everyone steeps themselves in miles, points, hotels, airlines, and travel like many of us do.

We take too much for granted. If you’ve been in this hobby a while, you may have gotten as laissez-faire as I have about booking flights and hotels on a whim. SkyMiles deal to Europe? Book it. Award on an airline that rarely releases seats? Book that, too. Ask questions later. With many programs offering free cancellation, there’s little downside. Either it’ll work or it won’t.

Both Pain and Gain

There have been facepalm moments. I once suggested to my parents that they use their annual Marriott free night during a trip to visit one of my siblings. My mom responded, “we get a free night?” Ugh. The pain. They’d had the card for a couple years at that point.

But there are great wins as well. I’ve helped one of my sisters book flights to the East Coast for their summer vacation. Given the difficulty and cost of summer travel the past couple years, I was glad to offer my expertise.

People have gotten into the hobby and later told me how much they’d saved. I have friends who have been able to visit family when they otherwise would not have been able to afford it, thanks to miles and points. I always love hearing the success stories. These are far better than hearing about expiring miles, forgetting to use free hotel nights, and redeeming miles for a toaster. Ok. No one I know has done that last one.

a man holding a cell phone to his ear

Helping My Parents with a Recent Missed Connection

Helping real-time is the biggest win. I will forever assert that being proactive is critical when you are facing a missed connection, delayed flight, or other travel stress. Don’t sit idly by and be at the mercy of the airline.

While my parents did do their best at the airport, my mom called me. She sounded stressed. They’d missed their connection in Denver due to weather. There were thunderstorms causing intermittent ground stops, and they deplaned late. Somehow, their connecting flight managed to pull away without them. They were only minutes late.

Since they were traveling to a regional airport, the next available seats were on a flight about 24 hours later. They don’t travel much, and losing a complete day of their visit to see my sister and family would hurt.

These are situations where miles can shine. While there was no way to make it to Missouri that night, I was able to rebook them on American Airlines via Dallas the following day. The kicker? It cost just 9,000 AAdvantage miles per person. They’d arrive midday rather than late in the evening. It would salvage a bit of the trip.

I encouraged mom to call United to see if they’d provide them a partial refund of the miles they used to book their trip. Amazingly, United did provide them with a hotel voucher and meal vouchers in Denver. She was also able to call Marriott and get her free night returned to her account, even though they were past the free cancellation window.

We accomplished all of this in about 30 minutes. No dithering, all action. They didn’t get a lot of sleep with a 6:00 AM departure, but it greatly reduced the stress.

Final Thoughts

It’s been over ten years since I first dipped my toe into the award travel world. I was in college, short on money. Miles and points sounded too good to be true. And yet they lived up to so much of my expectations. Soon, I was able to take vacations with my wife for a fraction of the cost. My kids have each been to somewhere between 5 and 12 states, and the older two have been out of the country multiple times. I enjoy traveling, and I enjoy the process that lets me do it inexpensively.

I also enjoy helping others. Writing about the best ways to use points and miles, family travel tips, or a hotel review is one way I can do this. But being able to help people I know is rewarding as well.

Are you the family travel agent? What success or failure stories do you have?