The answer to the first question has three parts.
The thank you shout out
I like to highlight businesses that are pretty remarkable. When I visit them I like to give them a nice shout out as a way to say thank you for doing good work.
The next reason I use it is to share with others cool experiences I am enjoying. I like to hear about my friends experiencing interesting things so in kind I hope they like to hear about mine. I can’t remember who said it (and please leave a comment reminding me) but they said that today wealth is being gained more in experiences than money things.
The joy of unexpected meetup
The last reason is so that I can have chances for others to meetup with me or visa-versa me. Two weeks ago I was on a business trip, travelling to the Content Marketing Retreat held on Whidbey Island. My friend and business partner Chris Skaggs decided to tag along and go to the conference as well. About twenty minutes from the Seattle train station, I saw that our friend Jen Grant had checked into her client’s restaurant Art at the Seattle Four Seasons. Jen and I live only about 10 miles apart but it might as well be around the world due to our busy schedules. I showed the checkin to Chris and we both had the same idea. We decided to surprise her for lunch. Minutes before we had been talking about how we have not seen her in a while.
After getting off the train we walked up to Four Seasons and surprised her as she was walked out the front door. We ended up having a great lunch and caught a rare chance to catch up. All of it happened because we both use Gowalla.
Last, to answer the second question. How do you choose which tool to use? This comes down to convenience and utility. When I am trying to check-in someplace I want to be able to find the location easily. I don’t usually have time to add a place if it is not currently listed. This is very important if I am with others. I try to post discreetly since my experience I am posting on is with friends in meatspace. I want to focus on them and not technology. Second, it depends on what I want to do when checking in. Often I take a photo to or leave a useful tip to others that will follow. Whichever tool makes the easiest is the one I choose.
Jen Grant shared a great article on how diners are using location-based technology. It is a good read. Remember though that they are tools, and you the user are showing us all their real value.
*Both Whrrl and Gowalla are no longer in business.