In the summer of 1992, as a sophomore in high school, I went to Germany for our school trip. Aside from being a great 3-4 weeks, my German teacher insisted that we each sign up for Northwest FF miles accounts. I'm pretty sure I've still got that card filed away...
I didn't travel much before and didn't travel much immediately after but I definitely wanted to and held on to that card. Upon turning 18, I got an apartment and had to select a long-distance carrier and get my first credit card. It didn't take long to realize that Sprint and another carrier (perhaps MCI) would routinely give me Northwest miles for signing up for LD. I probably switched 5-6 times... I also started taking US Bank up on their CC offers, canceling after a year or so.
Somehow I ended up generally keeping 60-100k worldperks points in the bank. I'd only redeem at a comparable ticket value of $400=25k ($.016/mile) or better. Oddly, I NEVER looked around online for other like minded people.
Along the way, I did some things with miles that I just wouldn't have done otherwise including a cheap trip to London with a friend that had never left the country, taking a girlfriend to San Francisco at the last minute, a miles+points fare to Montreal with my eventual wife, doing a great miles+points fare to Bangkok for my honeymoon.
It's amazing to me how savvy I was elsewhere in my financial life, how much I recognized the value of those points, how much I wanted to travel more, and yet just never, ever looked online.
Moreso when I think back to a friend of mine telling me about a deal in the late 90's early 2000's where you signed up for LOTS of Inside Flyer mags. He redeemed for 2 tickets on the Concorde. He told me about it and I just thought it was too good to be true and didn't go in with him on it. When he pulled it off, I was sure it was a one-off and I missed it. Bummer. In retrospect, that was flyertalk related. I don't think I ever looked...
When I got married, we immediately signed my wife up for one of the last Northwest CC offers, an AA visa, and a Delta Amex. I was pretty excited about those offers I received in the mail.
Then we moved to New Orleans and away from family. I know my wife (better than she does sometimes I think and probably vice versa) and know the only way she'd be sustainably happy was the ability to travel home. A lot.
As I watched our FF balance dwindle from ~250k to ~130k and our budget remained tight, I started to get a bit nervous.
I still can't remember how, but last January I stumbled onto FrugalTravelGuy.com and the expired BA deal. I was bummed. But it came back and we got in on the 2nd to last round of 100k BA deals. Both of us. And so it started.
As of 1/2010, I had ~135k miles left. Today, if all our pending miles were counted, we'll end the year at ~1.4m hotel, FF, and Amex MR points (or equivalent value) with another 150k or so scheduled for early next year ($10k AA cards for 100k take a while to finish). We've also redeemed ~250-300k this year. Needless to say, I'm hooked.
A greatly increased amount of business travel helped but honestly, this was mostly by working programs found on this site. One person earlier in this thread called this his 2nd job. Next year, I'm looking to scale back a bit but that's an apt description.
My wife remained skeptical until late this year. This past weekend, we were talking about whether it would be good to gift her Delta FO (silver) when I hit Platinum or take another gift. I noted that I wanted to do something special for her but that frankly, silver wouldn't get her upgrades since she flys almost all awards, it wouldn't get her security line access, she's small and so doesn't really care about exit row seating, and she already gets free luggage by her Delta Amex. I'd like to do something for her but gifting silver just doesn't do much... She replied, in a distinctly different tone than before about FF, that she was just really happy to be able to travel for free. It used to be one-offs for her. This year, we paid for 1.5 RT's and got 5 free for her. The 1.5 were just too inexpensive to use the miles for (E.g. $109 one-way from MSY to MSP).
She still thinks what I do is nutty but has moved from skeptical to appreciative.
I'm really not sure when to say I started... Was it with my trip to German? Those phone sign ups? Those trips and my early calculations of value of miles? Of signing up for those BA cards? Or the flurry of activity in May-August this year?
Thanks to everyone in the community and especially Rick @ FrugalTravelGuy.com.