6 Bootstrapping Travel Hacks for Maximum Flexibility

By Stuart Blitz — find me on Twitter @StuartBlitz

I admit that I’m a travel freak. I know too many airport codes, too many routes (thank you Airline Route), and know too many airplane types. That said, I’m still always surprised by friends in tech and entrepreneurship that know very little about traveling smart — booking cheap trips for maximum flexibility. Saving $50 here or there is preferred, but nothing compared to missing out on key meetings or making it back to the office with your team.

There are always many issues to consider when booking a trip. But I think the most important are optionality and cost. Everything else is secondary.

These rules have served me well:

1. Book one-way tickets, not round trips.

Maximum flexibility for the same price. Here’s an example:

• I booked 2 one-way tickets BOS-SFO and SFO-BOS.
• Oops, I need to go to Chicago first.
• Now I book a cheap one-way ticket to Chicago and one-way ticket to San Francisco.
• Still have my return flight as planned.

I can’t tell you how many times this scenario has happened to me. Then my plans change. I’ve saved thousands of dollars in change fees.

If you book a round-trip and anything changes, there’s a 100% change you’ll need to shell out money.

For international travel, this doesn’t apply as much and you may be forced to buy round trips. But it’s worth checking anyways.

2. Get status with an airline — no, not for the free booze.

Upgrades? Priority boarding? Free luggage tag? Yes, you get all of that. It’s nice, but frankly I don’t care about these things much. Being a United 1K for many years, I only really value 2 things:

• I can book as many mileage tickets as I want and then cancel them at the last minute. No fees.

So, how do I use this to my advantage? Whenever I think I may need to go somewhere when flights could be expensive, I book a ticket. Simple. Many times I get the exact flights I want too. I can decide later if I should instead a) buy a ticket, b) go or not go, or c) take another form of transportation, e.g. the train.

• I’m at the top of the list should any weather or mechanical issues arise.

Enough said. You want to get on the next possible flight ASAP. Also, there’s a new service called Freebird. Their intent is for travelers to be able to buy an option in case of a severely delayed flight. They book you on the next flight, even if it’s on a different alliance.

3. Accumulate points and big credit card sign up bonuses.

It sounds obvious, but I’ve found this is key mainly to use them in case you need to travel at high demand times, on monopoly routes, or expensive, out-of-the-way destinations. At my last company, we had a customer in Montreal so would have to fly from Boston periodically. A 45 minute flight shouldn’t be expesnive, right? Well, Air Canada has a monopoly on that route, so it was never below $500 and could be as much as $1,200 for a last minute trip. Screw that. I just used 10,000 miles.

4. Consider how likely you are to be screwed when booking certain flights.

If your flight gets cancelled, will you miss a key meeting with a potential customer or customer? Or a speaking engagement? Or valuable time with your team in the office?

Thus, be smart about when you leave and what airlines you take. It’s well known that early morning departures are much more likely to arrive on time than ones at the end of the day. Also, certain airlines have miserable reputations. For example, Norwegian Air made a splash when they offered $300 round-trip US to Europe flights. Amazing, right? Well, flights were often delayed a ton, some for days — so you get what you pay for.

5. Do Not Check.

My wife reminds me it’s easier for men than for women to go all carry-on, but I still can’t see any reason to check a bag when traveling on business. What happens if you need to catch a different flight to make your meeting? Your bag won’t make it. What happens if they offer you free money to switch flights (this happened to me a few months ago — $500 for a flight 1 hour later)? You need to have optionality when traveling and a checked bag kills you. Do laundry if you need to. Just don’t check.

A number of years ago, I flew from Florence to Dusseldorf, stopped for 2 days, then flew onto Beijing. Lufthansa lost my bag in Frankfurt and it sucked — luckily my flight to Beijing happened to connect in Frankfurt and I had just enough time to grab it from their found luggage room. I vowed never to check again after this.

6. Choose your layover city wisely, if possible.

At my last company, I had to fly to Grand Rapids, Michigan regularly. It’s a snowy, cold place. As a United flyer, I could change planes in Newark, Washington, or Chicago. If it’s all the same, I’d choose Chicago — odds are you’d make it there, but if my connecting flight was cancelled I could easily rent a car. In Newark or Washington? Screwed.

Traveling is simply a part of life for any entrepreneur and keeping as much flexibility as possible is critical. Traveling cheaply is a given, but just consider these hacks on your next trip. Hopefully they pay off.

Enjoy!

Find me on Twitter @StuartBlitz