Gang by Roy

I‘ve been part of many gangs in the past. Not your traditional type of gang, mind you. I tend to avoid wearing all black, even though I hear it’s slimming. And my gangs don’t run around selling drugs or looting businesses, but we do often run amok.

  • Story/illustration Roy
  • Soundtrack of the report
  • Born to Be Wild
  • Steppenwolf

No, the gangs I’m referring to are the type which go traveling together. It’s a happy gang, sort of like the Brady Bunch except that we aren’t related.

In most situations in life, if I was given the choice of whether I could be a loner or part of a gang, I would choose to be part of a gang. When you are part of a gang you have companionship, safety in numbers and playing board games is so much more fun. It’s also more exciting to embark on random adventures like Free Hugging, dumpster diving or playing in a school playground at night. Unfortunately, whenever you’re part of a gang, there is always a risk of conflict.

Gang History

I used to be part of a gang in Toronto. We would embark on Couchsurfing City Invasions in Canada and USA. Our first adventure happened mostly by accident. The couchsurfers in Niagara were hosting an event and an acquaintance invited me and 4 others to join him to go on that invasion. Our gang leader chose well. Even though we were all only acquaintances at the time, we quickly meshed like old friends. In fact, we got along too well. The five of us were boisterous extroverts, but our host was shy and polite. We had lots of fun that weekend but ended up deciding to leave a day earlier after we made our host cry!

The second adventure with this gang was much more positive. We headed to Pittsburgh this time and we made sure to pick a host who could handle our rowdiness. We were almost like a swarm of locusts descending on our unsuspecting host. But he was very easy-going and didn’t seem to mind.

“How could I say no to adventure?”

That summer, yet another friend decided to form a gang to couchsurf across Canada in an RV. How could I say no to adventure? There were 7 of us, mostly strangers, whom had agreed to spend the next 3 weeks together. There were great times and times of frustration. Not only did we not know each other beforehand, we didn’t make any firm plans other than a commitment to couchsurf all the way. Considering this, it was a very successful journey. We were lucky to have great hosts all the way. And our gang of 7 was mostly easy-going and self-organizing. There was occasionally some bickering but that’s to be expected when you have people in close quarters for an extended period of time. One of the 7 did however decide to leave the gang halfway through as she felt her expectations had not been met.

“ In fact the only thing we could probably agree upon was that we should never travel again together.”

Last summer, my old flatmates and I decided to go on a similar roadtrip across Canada. We had lived together in a house for many months, so we assumed that this qualified us to be great travel partners. This couldn’t have been further from the truth. There was major conflict all the way through from whether to couchsurf or camp, about how long to stay in each place, even when buying food. In fact the only thing we could probably agree upon was that we should never travel again together. After being part of three distinct gangs, I was surprised that it could go so horribly wrong. So after that, I decided to dissect what happened and to find out what are the key ingredients of successful gang travel.

sea of expectations


8 Key Ingredients To Successful Gang Travel.

1. Communicate

Clear communication is critical well before and during travel. Some conflict is natural when a gang spends a large proportion of time in close quarters. However, how you deal with that conflict is the difference between a positive experience and a negative one. E.g. Non-violent communication is ideal. Being passive aggressive is not.

2. Expectations

People often say the best way to travel is to have no expectations. However, when you’re in a gang you should have some expectations. You should expect that the gang can get along most of the time. You should expect that the gang can communicate in a healthy way. You should expect to have a good time and enjoy the trip. If these expectations aren’t met you should expect that you can leave the gang and do your own thing.

3. Time-frame

What is the time-frame? Gang travel for a weekend is easy. But gang travel for weeks or months requires much more planning and communication. It’s good to set a time-frame so you know what you are working with. On the other hand, if you are just joining some travelers for a leg of their journey, you aren’t really part of the gang. You are a temporary companion.

4. Goals

What are your goals? Surely it’s not just to reach the other side? Do you want to spend most of your time in nature or do you want to spend most of your time in cities? Do you only want quality time with your gang or do you want to meet new people. Do you want to take lots of pictures or do you want to spend your time going out? Should you share food/expenses or do your own thing? Spend some time to reflect on what would make an ideal experience and communicate that.

5. Needs and Deal-breakers

Everyone sees the world differently. You have to discuss your needs and deal-breakers honestly before going traveling.

For me, I need to shower everyday if I can. Illegal camping and bathing in lakes are not my idea of fun. Couchsurfing is my ideal way to travel but I’d tolerate camping sites and hostels. Remember, this is not a negotiation and shouldn’t be dismissed. If you can’t wholeheartedly agree on similar needs beforehand, it’s going to be a disaster during the trip.

6. Personalities

Group dynamics is a very unpredictable animal. You need to find a way to be compatible – and to best adapt and encourage synergy within the gang. There needs to be compromise, patience and empathy from all gang members. And there also needs to be time reserved for “me time” – where gang members are free to go do their own thing.

7. Leadership & Teamwork

All successful gangs have gang leaders with a strong vision. They need to also have charisma to bring out the best in the team. No one in the gang is a tourist; they all have a part to play to ensure the gang operates smoothly.

8. Planning

Often travelers will boast that their plan is to have no plan. Being free-spirited like this may be liberating, when you’re traveling solo but when you are in a gang this can quickly cause frustration and disillusionment. You don’t have to have firm plans but if there is no plan then little gets done. Like it or not, when you are part of a gang you need to be much more organized.

Being part of a gang of travelers can be one of your best travel experiences. But don’t just join any gang fool-heartedly. Take careful consideration before committing to one. Remember to make a concerted effort to ensure the success of the gang. And along the way if you experience an irresolvable personality clash, take the initiative to leave. Because you should be allowed to travel as you are and never have to make apologizes otherwise.

Have you ever been part of a gang?


Roy is a perpetual traveler. He’s lived in 7 countries, traveled to 40+ more and right now works on a cruise ship. He also likes to contradict and talk about himself in the third-person. You can follow his travels on