As much as you love traveling, there’s probably times when you’ve felt pretty lonely on the road or wished you could surround yourself with some of the amazing people instead of sitting at a diner by yourself or hanging out in your hotel. When I knew I’d be trekking out to San Francisco for CreativeLIVE, I decided to avoid this scenario by some pretty extreme measures. A friend of mine recently asked me how I ended up hanging out with so many near-strangers in a city where everyone’s really really busy all the time, so I thought I’d write up my strategy. Despite outward appearances, it really is more about putting in time to reach out to people than being naturally charming and charismatic.
Social media contacts
It’s really easy to go on Twitter and Facebook and say, “Hey San Francisco! I will be in you on October 16 through 18!” It’s much harder to ask people you don’t even know to try to hang out, but that’s exactly what I did.
Obviously I first contacted people I know well in town, but I decided to take it a step further. I happen to have a fairly robust LinkedIn and Facebook network of contacts, and I searched by location and emailed every single one of them to let them know I’d be in town and invite them to one of two meetups. These were personalized messages (though they did have an element of cut-and-paste) and I sent to literally everyone I knew, even peripherally.
This is obviously time-consuming (it took me about two or three hours), but I think I myself would love a warm, personalized invitation to hang out and be more inclined to show up than if I got a random Facebook event notification or Eventbrite notice in my inbox.
I didn’t discriminate. I emailed developers and writers, marketers and athletes, people I’ve worked for and who have worked for me, all ages, people who are well-connected and those who are not. Everyone.
Instead of asking 200 people to meet with me one-on-one, which would be a logistical nightmare for a three-day trip in which one day was completely booked, I also set up two events where people could come hang out at two different times (one was evening and one mid-day) and in two different locations. I put this on Eventbrite so people could actually register, which gave me a good idea of who was coming (and was easy to keep track of).
I did a meetup on a smaller scale, too, when I was in Seattle. I got together some online friends from various communities as well as old college classmates, and of course my brother and his friends. But since I had drawn from a wider net this time, one concern I had is that people from very different communities would show up, which could leave some people feeling left out. I worked hard in the wording of the invites and the Eventbrite page to emphasize that we’d be accessible and friendly, and it’s easy to help influence the tone of events when it’s a very small group.
Another way to meet people is to just show up. I decided I was dropping by the office of one of my favorite new startups, even though we didn’t exactly figure out the specific timing via email. I just stopped by anyway bearing gifts. The timing was bad, but it was still fun to visit… and I bet the next time I’m in town I’ll get that tour I wanted. Obviously dropping by somewhere big probably wouldn’t work out as well (some places even have warnings on their site asking people not to show up without an appointment), but I think if it feels right, it’s always worth a shot. It’s not like I was selling anything or trying to get a job.
I was lucky enough to find a place to crash the first night with a friend of a friend, which is always a good way to meet people as you’ll likely go out for dinner and spend time together. The next night I had to try out AirBNB, and really wanted to meet the other person staying at the same house but didn’t want to knock on his door and be creepy. However, I think housing is still a nice way I felt to meet people, and maybe get some insider tips on what’s cool to do in town without having to go to Yelp or FourSquare. I’d rather rent a room or crash on the floor of the house people are clustered around for an event, unless I’m feeling overwhelmed in which case I’ll hide out elsewhere. But where you stay is definitely a place to talk to strangers.
Bring people with you everywhere
I typically try deliberately to get people to meet others, and it works well when you’re traveling because things are sort of randomly thrown together anyway. And who knows when you’re connecting someone to a new friend in their city or wind up at a cafe or event in their area that they’d be interested in returning to.
Local friends are awesome
Also, that friend who lives in town who will show you which bus you need to go on or which street you want to take or walk you to the hipster donut shop and the BART station is the coolest person ever. I try to be that person for my friends who visit. As much as hanging out with strangers and organizing meetups is fun and interesting, nothing beats your really badass local friend.
But what happened when you sent out dozens of emails, you’re wondering. Emailing everybody you know in an area is not for the faint of heart. I got a lot of rejections. SO many rejections. The worst one was an editor for my dream magazine, who wrote, “Maybe. At the risk of sounding like a jerk, what would we be discussing?” My clever follow-up email about post-apocalyptic fiction was met with silence. I got rejections in various forms on every social media platform, as well as a lot of people who didn’t respond at all…because everyone has a different comfort level with random messages from near-strangers, right? In addition to the rejections and no-responses, I got a lot of cancellations. All at the last minute. Things come up; I don’t take these personally.
The trick for me with the rejections was to differentiate between people who really couldn’t make it, often for logistical reasons, but wanted to hang out… When they start talking about trying to take a taxi to skip out of work, that’s a sign, but in general it’s usually fairly obvious when someone really really wants to meet up and just can’t and when they just aren’t all that into the idea. When possible, I tried to make arrangements with people who really wanted to hang but couldn’t.
I also got a lot of positive responses, and the most interesting thing for me about this experiment is that they weren’t from the people I’d expected.
I had a really wonderful lunch with a writer who’d given me some much-needed tough love back in July 2008. If I had just picked out two or three people I’d want to hang out with, she wouldn’t have been on my list, but it really was lovely, lively conversation. She brought her coworker and I brought my badass local friend and we had some of the best conversation I’ve had in a while.
I had a small meetup with just 2 other people (my aforementioned friend and someone I know from How to Make Your First Dollar), and a larger meetup with a total of 7 people, including someone who’d done some web design work for me in the past (and who I knew through my friend), two fellow MMA writers, as well as this great personal trainer and his awesome wife (the strangers who put me up for a night). Again, these are mostly people I probably wouldn’t have expected to actually spend time with me but I am so glad they did…and I think we had enough ‘waves’ of conversation to keep everyone engaged at least part of the time.
Make your own luck
My event was amazing and I learned more than I ever thought possible about travel hacking, as well as meeting some great new people, but we’ve probably all traveled with excitement to something that ended up sucking. Then we wonder whether it was worth the time away from home, money on airfare, etc. I think arranging our own events while traveling helps with this. Even if the reason I was in town for didn’t work out well, I would’ve still hung out with so many great people who were only words on a screen, so it would’ve all been worth it. There is always the possibility nobody will show up, so pick a place you’d totally hang out at all by yourself if necessary. (I love cafes, for example, but could just as easily picked somewhere outdoors.)
Your mission, should you choose to accept it
I get that not all of you are crazy like me, and emailing every single contact in an area might be a bit out of your comfort zone…but the next time you’re visiting a new town, try contacting say 15 or 20 people to meet up and see what happens. The results may surprise you!