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What travel advice would you give to the 25-30 year old version of yourself_

What travel advice would you give the 25-30 year old version of yourself?

by Jeremy B

Now that I am in my mid-forties, I’ve become a bit reflective on what is now more than a decade and a half of frequent business travel. If I knew then what I knew now would I travel any differently? You bet! Here’s what I would have changed.

What’d I do differently when starting to travel for work on a regular basis

Here is the travel advice I’d give the 25 – 30 year old version of myself.

Stick with one airline sooner

A common mistake travelers make (and I know I did) was switching airlines too frequently (in search of the absolute best and lowest price). As a result you build status much slower which delays benefits that may come from higher status (e.g. upgrades) or collecting meaningful amounts of points/miles.

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I did this early on in my business travelers bouncing from airline to airline. Now, I stick primarily with Southwest and United. Rarely do I ever fly anything else.

Sign for all frequent flyer / rewards programs – even ones I don’t use regularly

The 30-year-old me didn’t always sign up for the rewards / frequent flyer programs as I bounced around from airline to airline or hotel to hotel. Even if you plan to not stay or fly a specific company in any meaningful amounts it still might be worth signing up for their programs.

Sometimes they have special incentives for new accounts and even small amounts of points can accumulate over time. Lastly sometimes you can transfer points out of one program into another allowing you to pool your rewards for more substantive purposes.

Now, if I stay at a program, I am not signed up for I make sure to register before I use them–even if it’s just a likely onetime event.

Status matched earlier

The travel rookie me didn’t know anything about status matching and so while I thought I was getting a little more savvy by sticking a single airline or hotel I would still occasionally use other providers…but I’d do so with no status.

A few years in I found out that many travel companies offer status matching which is essentially where you use your current status with a company (e.g. Diamond on Delta) to get another airline (say United) to offer you status right out of the gates.

Companies do this to earn your business and in an attempt to yank a traveler away from a firm they’ve invested time and status in. Not everyone does it, and you don’t come in at the top usually, but it helps get you started. And there are some T&Cs about maintaining it you have to follow.

The younger me could have avoided a few middle seats if I’d exercised this option a time or two when flying an airline I wouldn’t normally be on!

Never picked a job where renting from Avis was required

This is a bit tongue in cheek, but I’ve really never had any great experiences with Avis and in fact have had several really bad ones. I don’t know what it is but they just suck. The older me would tell the younger me to ask what rental car company must be used by the travel program and if it’s Avis to run, run run! 🙂

Starting not checking a bag sooner

My second ever business trip was to Oklahoma (on Southwest) and I checked a bag. And it was immediately lost. Major hassle. This was years ago, but I learned a lesson about carrying bags on, traveling light, and never checking a bag. Now, I rarely check my bag – literally maybe only once a year under special circumstances (e.g. I have golf clubs or something).

Investing in higher quality luggage sooner

It wasn’t until about 2 years ago that I finally decided to invest in quality luggage. For years and years I always went with something cheap thinking it wasn’t that big of a deal. Boy, I was wrong. A nice quality piece of luggage can be a game changer.

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Quality luggage is often designed with features that are intentionally nicer and useful for frequent travelers (e.g., built in chargers are popular now) or special compartments for travel items. Heck, even the quality is better (e.g., better / smoother zippers, wheels, etc.). If you are just starting out into the world of frequent travel, make the investment and get some good luggage!

My luggage of choice these days is the TravelPro Crew 11 which is the best bag I’ve ever owned. You can read my product review here or check the price on Amazon here.

Dumping the rolling briefcase for a backpack much sooner!

For many years the younger me used a rolling Samsonite Briefcase. It seemed like the “professional” thing to do and a backpack seemed far too casual for the business world. So I would dutifully roll my two bags around on my trips (occasionally placing my case on top of my suitcase for easier-ish transport).

Yeah, that was dumb. It was some regular NYC travel that got me to change. Ever tried to roll anything on the streets of NYC or downstairs to take a subway? Insanity.

I started to look around and realized everyone is carrying a backpack. Doh! The light bulb clicked and I haven’t looked back.

For years I used the Ogio Metro Backpack which remains a wonderful backpack for business travelers. However, a few years back I switched to the Knack Pack which is now my absolute favorite business travel backpack.

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Chill the heck out

The older, more seasoned me would tell the younger me to chill out a bit more when traveling. Crap happens. Flights get delayed. You get sick. You miss connections, your client cancels, etc. etc. etc.

It’s not the end of the world. No need to get too stressed or irritated about things. Relax. A middle seat for 4 hours sucks but it doesn’t last forever so there’s no need to lose your mind over it.

Got more serious about my credit card game (both on and off the road)

Sure, I played the credit card game, but it I didn’t play with intention. As many fellow BoardingArea.com bloggers can teach you (including folks like the Frequent Miler), there is gold in them there hills!

Credit card games can turn this into a full-blown obsession, and we aren’t saying you should do that, but you should definitely make sure you aren’t missing any layups. For example, do your very best to use a credit card to pay for anything and everything (on and off the road!) to make sure you get some points / miles / cash back.

Amp that up a little by making sure you use the best card for that purchase. For example, if one card offers better points for gas purchases use that one. Use a different one that gives you better purchases for grocery. And so on.

You don’t have to go full into manufactured spender mode, but at least avoid leaving the easy points on the table. This will mean you can travel for fun more often and possibly re-earn status a lot easier each year.

Travel more (but for fun)

The older me would tell the younger version to travel more…not for work but for pleasure (or at least bleisure) and to bring the family! As a frequent business traveler, you get to see a lot of this world, but you often do it alone. I have brought family a few times but should do it more.

I also should use those points and miles I accrue to travel more as a family! Yolo, right?

Spend more time with my family when I am home

For the frequent traveler you are gone a lot and it can be tough on the home life. It means that while your job may be providing a nice life for your family you need to make sure YOU provide a meaningful presence in their life too.

That means BE HOME when you are home. Leave the work email alone if you can. Play some games with your kids. Kiss your wife. Take her on a date. Go to the beach. Whatever it is, be present and home with your kids.

The younger me didn’t do this so well all the time and while I still have a good relationship with my older kids, it could have gone south. With my two younger ones (who are still at home) I am FAR more intentional when I am home. I am present!

Final Thoughts

How about you? For those readers who’ve been traveling like crazy for years, what would you tell your younger self? We want to hear about it! Drop us a comment or tweet us!

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What travel advice would you give to the 25-30 year old version of yourself

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Arthur July 26, 2019 - 8:44 am

Agree with most of those. I’d add (1) never use an OTA, (2) pay a little less attention to just the price and more attention to the quality of an airline, their on-time performance, what plane is being used, and what the best seats are, and their ability to re-route you in the event of an IRROPs, and (3) keeping more of an eye open for cheap upgrades.

The C Boarding Group July 26, 2019 - 8:51 am

I like #2! Great advice right there!

Adam L July 26, 2019 - 9:17 am

I disagree with your first point. Picking an airline to rack up miles and status is a thing of yesteryear. I started off being loyal to an airline to get status, etc. but I found myself picking flights with worse timing and layovers just to be loyal. I’ve learned to just take the flights that cause me the least stress and if i want an upgrade to just pay for it and rack up points in transferable currencies. Unless you’re flying so much to get top-tier elite status with virtually guaranteed upgrades, you’re better off going with whoever is going to get you places with the least hassle.

The C Boarding Group July 26, 2019 - 9:25 am

We will have to agree to disagree 🙂

Stany V July 26, 2019 - 9:18 am

Take advantage of the “work and travel”/”working holiday” 1 year Visa that many countries offer, and go overseas for a couple of years, backpacking, and working odd jobs.

Majority of the countries do not offer this visa to people over the age of 30.

The C Boarding Group July 26, 2019 - 9:25 am

I like it!

John September 9, 2022 - 9:29 am

Don’t use your miles for domestic travel. Especially when you can get them for cheap by paying cash. Save your points for fancier international business/first class flights.

Christian September 9, 2022 - 10:39 am


DaninMCI September 9, 2022 - 10:57 am

Make sure to exploit the US airways Grandslam for more than I did. Make sure to buy more pudding cups and dumpster dive for Wendys cups. Buy more coins from the US mint. Don’t listen to Million Mile Secrets it was always about the money, sell my website to Red Ventures and retire early. Yell back at that one AA gate supervisor in PHL in 2016 instead of taking his crap because I wanted to board that plane to the UK. Don’t lock down due to Covid, go travel as much as possible. Buy bitcoin earlier and buy a private jet. Don’t buy any CRO crypto. Marry the same woman and don’t take TWA or the STL hub for granted.


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