Lessons Learned from Playing Undercover Capture the Flag

This weekend I was part of a covert operation. Our mission? To infiltrate the Westfield Mall and play a secret game of Capture the Flag (CTF). Hosted by the awesome guys at Big New Ideas & some of their friends, this game involved custom blue/red CTF hand stamps, a ton of mass-texting to coordinate plans, 3 red and blue triangular stickers (the “flags”), jails and guards to watch prisoners and referees to watch for running or shouting.

The operation was a success.

Blue team was at one point ahead 2 flags to 0 but got greedy and mass rushed the last flag too early. Almost everyone got tagged out and had to wait in jail for next auto-jailbreak (which were every 30 mins). The remaining Blue team members couldn’t defend against the rest of the Red team and lost it. Everyone then went out for beers.

Besides being a fun activity, it was an educational one too. Here are a couple things to take from it.

Creation-based fun > Consumption-based fun

Playing undercover CTF cost me nothing – the only thing I had to pay for were all the texts we’d get from other team members. Organizing the whole thing and getting all the materials cost less than $50 total.

Using your imagination and creating a fun time for yourself is much more rewarding than just trading money for entertainment. It was ironic that we were at a mall as we were spending less money than everyone else there while likely having a much better time. Try to make your fun, and buy less of it.

Offbeat activities are great ways to meet new friends

This is a pretty random game, but it attracts the right people. It was marketed mostly online through social networking sites and so it got the attention of techie folks who loosely knew each other and were willing to try something new and perhaps slightly disruptive(as mall security is always something to watch out for). I didn’t know most of the people who played but they are all cool people that I’d want to be friends with.

When you bring a group of strangers together to do something a little off-beat, chances are they’re more likely to get along with each other than if the activity was generic. Firstly, because more people like “regular things” and that dilutes/broadens the group while weird things narrows the kind of people that come – in a good way. Secondly, the act of doing something off-beat brings people closer together because outsiders can’t really relate to those experiences.

Sometimes the best defense is no defense

This was the Blue team’s strategy this game. Last time we had people defending each flag and we realized that having guards actually tips off the other team on where to look. This year we only guarded one flag and let obscurity hide the other flags in plain sight.

Are you trying to protect something? Your ego, a new feature, a relationship? Sometimes the best way to protect something is to leave it alone and not draw any attention to it. It can slip right by any threats unharmed. Which brings me to my next point…

If you act like you know what you’re doing…

… people will often let you do your thing. There must have been security guards who saw us hovering over certain areas, texting like mad, “tagging out” people, and peeling flags of walls and walking really fast. But we didn’t act guilty or pretend we were sneaking around, so we weren’t questioned. This technique of looking totally sure of oneself was also frequently employed by successful flag stealers.

This advice applies to pretty much anything in life. I’m not saying that domain expertise isn’t important or that you can succeed in spite of poor judgement. But I am saying that once you decide to do something, acting very sure of yourself and carrying on like you know what you’re doing is a “force multiplier” (as Colin Powell would put it) for achieving your objectives.

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Jason Shen

Jason is a tech entrepreneur and talent expert. He is CEO of a performance hiring platform called Headlight, a Fast Company contributor, and an advocate for Asian American men. Follow him on Twitter at @jasonshen and subscribe to his private newsletter.

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