“Be loyal to yourself,” the Chicago Seminars

Each attendee should have been given five minutes on the stage to share their niche expertise. The Rapid Traveler attempted to meet each of the 500 attendees at the Chicago Seminars but fell woefully short because each encounter engrossed him as he learned and laughed. As Pudding Guy said, “There is probably no more diverse group of like-minded people, from millionaires to unemployed college students.”

The roster of superb speakers imparted practical information and madcap capers to achieve travel dreams. Pudding Guy capped the event by stressing the importance of determining a personal philosophy and setting written goals.

For some, collecting miles and points is the thrill itself, the end not the means, for others it is an expedient to achieve travel beyond their budget. Some fall into rapture at the sight of a hotel suite upgrade, while others just want to hunch over in a cheap economy seat until the flight is over and their trip can really begin. And that is the genius of the event: each person has their own angle.

This was not a hot deals pony show because those come and go by the moment. For those, the presenters already provide invaluable service by relentlessly sniffing out deals and techniques, sharing on their blogs or FlyerTalk posts. Each is an online professor to study:

The presenters instead focused on concepts, strategies and techniques, beginner to advanced, to equip attendees to maximize their earnings in the constantly changing miles and points world.

Frugal Travel Guy refers to miles and points as a “crack-like substance,” because the illusion of ‘free’ can induce madness worthy of an entry by Mackay. The advice from the speakers could appear on a Berkshire Hathaway shareholder letter: determine goals, rigorously research, have a plan, be prepared to act, be bold but prudent. Card churners just don’t find as much value in Bank of America credit cards as Mr. Buffet hopes to find in Bank of America itself.Some lessons that resonated with The Rapid Traveler, many themes of which ran through all speakers (note: being unable to clone himself, The Rapid Traveler could not attend all sessions):
  • Set goals. Answer the what, who, where, when, and how of travel goals before chasing miles. (everyone)
  • Set a philosophy and moral compass. One person’s great deal is another’s sleaze and each has to make their own determination. In some cases the law may draw the line before the moral compass. (almost everyone)
  • ‘Be loyal to yourself’. None of these companies are loyal to customers. Pick the programs that work for you: no limit on partners in these relationships and one-night stands can be great. (beaubo)
  • If you have a family, set goals and tolerances together. Award tickets for several people may only be available on separate flights. Will your spouse be at the other end with divorce papers? And how do immediate (and distant) family members react when you ask for their social security number or when you say “AmEx is calling about this card I got in your name, just tell them you approved.” (Pudding Guy and beaubo)
  • Be ready to be promiscuous at a moment’s notice: build up points in programs like American Express Membership Rewards, Chase Ultimate Rewards and Starwood SPG that have flexible, generous ability to move points to multiple programs as the need arises, such as a great redemption like Air France Promo Awards (beaubo and The Points Guy).
  • Calculate the real cost of ‘free,’ from time invested to taxes, fees, etc. (Pudding Guy and beaubo)
  • Seek out people who are expert: network, network, network. (everyone, especially bikeguy)
  • Credit cards are the best current earning opportunity. (everyone)
  • Elite status is less and less valuable unless at the top-tier. There are so many competing members for quantity-restricted benefits like upgrades, while there are more and more ways to match benefits like checked luggage and lounge access with credit card features or fees. Low and mid-tier elite status can be hard to justify in a cost-benefit analysis. (beaubo and One Mile at a Time)
  • There are ways to make timeshares work through exchange programs but you better do your research first, and do it really well. Timeshares are a sucker’s game for 99% of the people, so be the smart 1% (gomike)
  • There is no shame in using priceline, even among rabid point collectors, but use it well with rebid techniques outlined on sites like Bidding Traveler. (gomike)
  • Hotels programs have all kind of promotions for most everyone. And crazy benefits for elites. Learn them and be prepared to have to remind hotels to get credit to post to accounts. (One Mile at a Time)
  • Document everything, using technology like screenshots. No proof can mean no points. (dlouise37, Pudding Guy, mrpickles)
  • Delta can actually work for awards, a bit, if you try really hard and know what your are doing. Conveniently, the most hard-core travelers shun Delta, leaving space for everyone else! (fti)
  • Read the fine print (Pudding Guy and mrpickles)
  • Give back. milepoint Kiva Lending Team is a great way to give back and earn miles. In eight months the teams 458 members are the #7 all-time Kiva team and #1 the past two months. More here.

These only scratch the surface, fortunately each presenter’s body of work is online at the above links. Anyone who wants to travel smart, fast or slow, should be on the lookout for details on next April’s Frequent Traveler University in New York and next September’s Chicago Seminars.

Thanks to the organizers and attendees for a superb weekend. Belize and Guatemala are on tap for The Rapid Traveler next weekend (more BA miles burn!) and may not be able to compete for fun.

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