As we've learned from Singaporean singer-songwriter Nicholas Chim, there are several crucial factors that contribute to a well-executed tour overseas. By no means an easy endeavor for many Singaporean artists, especially ones with little to no support from a stable record label, it still remains as a viable route for artists to earn money, as the debate over the insufficient flow of streaming royalities rages on.

Singapore presents an unrealized bed of opportunities but the world out there is a monumentally vast playground of would-bes and should-bes, running around passing demos to the nearest gig-goer. It's already tough enough garnering devoted listeners in Singapore — even though it's only time before all of us can change that — how much more difficult would it be when you want to take on the world?

We got to ask two established musicians, both masters of the winding road and economy class seats, about their decade-long experience touring around the world and what they've learned so far.

If you've done midnight marathons of Grey's Anatomy or One Tree Hill over the years, chances are that you've heard at least one song by Joshua Radin. The singer-songwriter from Ohio in the US has hustled his way through more than 70 films and TV shows with his disarming brand of folk rock, both delightfully accessible and relatable.

His first break came in the form of a chance encounter with the acute ears of comedian Zac Braff, who brought Radin's first song "Winter" to his TV show Scrubs, forever cementing his place in the annals of TV soundtracks.

Radin has seen the world, met many people along the way and has been dedicated to his craft beyond being the "TV guy", releasing his last two albums on his own. He still remains recognizable for his contributions to several iconic TV shows, stating that "about 95% of fans" who attend his shows got to know about his music through TV or film.

JOSHUA RADIN — LIVE IN SINGAPORE

How was your first overseas tour experience?

It was incredible. I was supporting Tori Amos and I got to travel all over Europe, playing to audiences who would actually come to see the support act. 

What do you do to get you through mundane periods during long tours?

I am constantly trying to find the best coffee shops and restaurants in each city so when I return I sort of feel not so much like a tourist. 

What are your tour packing essentials?

Every tour I bring fewer and fewer items, especially when it comes to clothes. I basically wear the same few things all the time, ha. But a good hat helps, as does a worn in hoodie for the bus. Also, I like to bring a pillow from home so wherever I lay my head, I feel like I'm home.

What item/object has stuck with you since your first tour?

Maybe a pair of old brown work boots. They've been all over this planet for over a decade.

What's one lesson you've learnt while touring?

Always be as nice as humanly possible to every single person you meet.

Tell us your most memorable incident on tour.

There are just too many. Not one sticks out. 

What's your advice for touring musicians?

Try your best, even when you're exhausted, to remember that it's still the best job in the world and that every single person who even plays music as a hobby would cut off their leg to play to the audiences you're playing to.

How do you manage touring life with family responsibilities?

I don't have a wife nor kids so it's not too difficult.

What’s the most enriching thing about touring?

Hearing the stories from fans about how my songs have affected them. It's what gets me through the tough runs where I don't get to sleep so much.

How do you write new music on tour, if you do?

I rarely have time for that. 

Best known for fronting popular pop-rock bands Something Corporate and Jack's Mannequin, Andrew McMahon has been acclimatized to the touring life since 1999 — he won't let anything get in the way of spreading his music on the road, not even cancer.

With 2015 marking 10 years since his successful stem cell transplant, McMahon has continued to play shows around the world and put out records under different project names, his latest being Andrew McMahon and the Wilderness.

Before playing to an eager crowd at CHIJMES on August 28, the verbose musician sat down with us and shared many valuable lessons and experiences from many years of touring.

How was your first overseas tour experience?

We did a couple of canadian dates during our first real US tour as Something Corporate. It was the five members plus three or four crew members in a 15-passenger van, with a trailer on the back with all of our gear.

In those days, I was probably about 19 years old and we criss-crossed america which is like 500 miles and opening up for a band called lucky boys confusion. we made about $100 a night, that was barely enough to cover gas and we had this running joke where we had to sell at least 10 t-shirts or cds to be able to get a room or get to the next gig. we would sleep on the floors of fans if we had to, or just eight guys in one hotel room, you'd just eat fast food and just do your best to get the word out about your band.

What do you do to get you through mundane periods during long tours?

At that time, I think we were young enough that it was fun to us. It was like being at camp or something — we were getting to play shows every night and at that point, we were very passionate about the band and about sharing the music with people. We thought it was fun and it felt like an adventure.

I had a girlfriend at home, so there were a lot of calls home. I think I tried my hardest to make music while I was out there and I kept journals, documenting ideas whenever I could. Surprisingly there aren't many moments where I feel very homesick.

With Something Corporate, we pretty much travelled three years straight. So certainly there were days of being out of america and not having a phone that could make you feel lonely. I was a vegetarian and it was pretty hard to eat on tours so chips and falafels, it was. Lots of it. I had so many friends who were slaving away in college or university or doing jobs they didn't like, so for me to complain about travelling around the world in a rock band would be pretty silly. (laughs)

A ritual of mine before every show would be to play Billy Joel's Songs in the Attic and The Beach Boys' Pet Sounds, usually with a cocktail. Singing along with my favorite artists helps me a lot.

How did you think it managed to pick up for your band?

I think people were genuinely excited about the songs. A lot of the shows we did in those days were opening up for harder acts, so even though there was an element of having some people who were not into what we were doing, I think it was different enough for what was going on in music at the time, that it got people to pay attention. It turned enough heads that it got us fans quickly.

How long did you take to tour again after your transplant?

I didn't take that long of a break actually. I was very fortunate and motivated, so within a year of being diagnosed, I was cleared by my doctor to go back on tour in the US.

There was a period where it was a little bit more precarious and a bit scary for me. Because my health was compromised, just having a little cold, just little symptoms that would pop up would make me really nervous. I would regularly go to the doctor and even the emergency room just because things would come up and they would seem so scary.

So there was a fragile period in those couple years following my diagnosis. Thankfully, I had a great team around me. I had a lot of support. My band members were like brothers to me and my road crew looked after me so we just got through it together.

But those were some nerve-wrecking times, for sure.

Most nerve-wrecking?

I had an incident where something happened where it was pneumonia or some other kind of infection — this is kind of gross (laughs) — I ended up coughing up blood and had to be rushed to the emergency room.

Surprisingly it was nothing to worry about which is crazy. I had another time I felt really ill and checked into the hospital. Again, everything was fine. Your mind will play tricks on you when you get diagnoses like that so there would moments I would get myself worked up for nothing.

After a while, you can be afraid of the disease coming back and you can say "There's nothing I can do to change that" and live. And that's what I chose to do. That's what got me through most things.

McMahon's previous bands Something Corporate (left) and Jack's Mannequin (right).

Have you ever worried if people would turn up for your shows each night?

Absolutely.

Early on in my career, I'd get really upset. From experience, you just realize that you can't win every night. I just need to stay on top of my social media, get the word out about my project and work with great promoters and publicists. I won't have a horrible night if a show doesn't go great. 

Whether if it's a packed house of a half house, the best thing you can do is to give an amazing performance. Close your eyes and live inside the songs. I started these projects with five to ten people and those crowds grew because of these shows I give. So you have to think, if there's anyone in that room to play for, you give them everything you have and there will be more there next time.

"So I looked at my tour manager and asked him, "How do you feel about going to jail tonight?""

How do you make yourself feel comfortable in a foreign country?

I've travelled so much for most of my life that I feel comfortable in most places. But when I'm entering a non-English speaking country, it does gets a bit scarier because part of my show involves talking to the crowd. I have found that going to places like Japan, I generally will just tell stories anyway. I'll just hope that the energy and the feeling behind what the story is will be enough to communicate with them.

But I also will try to learn a couple of phrases out of respect, address the audience in their native language as best as I can. I'll still give a set that I've been doing in the rest of the world, but if I start feeling that they're picking up on this or that, maybe I'll change the set as we progress through the evening.

What's your most memorable story on tour?

It was a show in Massachusetts, at a college.

In the early days of Something Corporate, we'd play a lot with punk bands so like every punk show, there's a culture of moshing within packed audiences, where people would sweat or even pass out because it'd get hot. When this happens at regular concert venues, the staff present would know how to deal with that. But we were playing to 4000 people at this college and they weren't used to seeing that, even though it was very normal.

The chief of police came onto the stage and told our tour manager that we had to stop playing because he claimed we were fostering a dangerous environment, even though it definitely wasn't, but there were fans who passed out from exhaustion so that caused the police to overreact. Moreover, it would be more dangerous if you were to stop a show that would anger 4000 fans who'd pay good money to see us.

I'd have to tell my tour manager in-between songs that we won't stop the show, because it'll actually cause more of a problem if we stopped. So there was this back and forth and the police basically said, "if you don't stop the show, we're gonna arrest you and the band." It's funny, because many punk shows would have kids with bloody noses, so this was pretty tame in comparison. 

So I looked at my tour manager and asked him, "How do you feel about going to jail tonight?". We didn't stop the show and the police ended up pulling the power. Funnily, we got through the entire set until the last song then they pulled it. So the show ended, no power on the stage, turned on the lights to the crowd and cops were lined up like a barricade. Instead of rioting, all the kids were singing our song 'If You C Jordan' at the top of their lungs, so I just had to jump in and do a crazy stage dive.

We didn't even go to jail in the end.

How do you manage touring life with family responsibilities?

Usually during tours in the US, I'd have a crib at the back of my tour bus, with the wife and I on the bed next to the baby. We love to travel together, but I'll have to leave them behind during overseas shows across the world.

On these runs where I can't travel with them, I'd do a lot of Facetime sessions with them, for about one or two hours a day. My baby daughter's at that age where as long as she sees my face, she feels like I'm there so that's helpful.

Me and my wife built this together, I started dating her before the first Something Corporate tour actually. She's been there from the start.

"...even with the best people, if you're not paying attention, things can happen and you don't realize it."

What's the hardest part about travelling with a band?

The hardest part about this job is managing people, making sure that your crew are as happy as they can be, making sure is that your music is well-represented and that your people represent you to the rest of your world in a favorable way. It's something i'm really in tuned with.

There's no perfect combination, but I strive to keep communication open between my bandmates and my crew and management. I'd say right now, more than ever, we have a crew of people and a band and a team back home on the business side that's really locked and has a strong singular vision. Everyone looks after together.

It's hard to do, you'll have to be willing to do it. A lot of times, it's much easier in this job to not pay attention to that stuff and I've learned that that can blow up in your face, that even with the best people, if you're not paying attention, things can happen and you don't realize it. The next thing you know, resentment can build up quickly.

McMahon performing at CHIJMES Hall, in a show by Upsurge Productions.

For example?

I've had things happened like that in the past, with band members and with crew members — situations where you let things fester. It's the same thing with any relationship, where something happens and you don't talk about it and then six months down the line, you get fights about stuff that has nothing to do with what you're fighting about.

So when I see things pop up, I try to encourage people to talk about it and not let those little fights become wounds. 

What are your tour packing essentials?

My backpack is always with me, it travels with me on most days, along with my phone and a pair of rainbow sandals. That's about it.

I travel light almost everywhere, even in my house I don't have a lot of stuff. I try and not keep too many things because I'm really bad at losing things. Currently using my 10th pair of sunglasses within a year (laughs).

What's your advice for touring musicians?

Well, I have some...

Find a nurturing scene in your city.

Build a story somewhere before you start touring is the most important thing. With all of my bands, we always started by playing shows in our hometown and build as big of an audience as we can and grow it locally. That serves as evidence that you have something that you can start taking it elsewhere.

It's hard enough now as a band that already has records out and a fanbase, it's still hard to fill up a room on tour. So if you don't know people in a city and they don't have access to your music, the chances of them showing up and spending all the money that's gonna take to move forward is pretty slim.

During touring, you're gonna be in these scenarios that you'll never imagine where things don't work. We've had scenarios where we've had immigration problems. So at a drop of a hat, you can have dates where some of your band members may not be able to come along. You'll have to improvise and figure out how to play a different kind of show.

Play as many shows as you can in your hometown, win people locally.

If you can win people in your hometown, it's a sign that you can win people elsewhere. In a nurturing environment, let that be a place where you fall on your face or try out a song that doesn't work. Do all of that before you take it into this professional world, where promoters can refuse to work with you again if you leave them unimpressed with your working attitudes. Do all of that in an incubator then expand.

Communication is important in making a tour work together.

For our tours, we go out together and have meals as a group, so it's a very familial vibe and I try and keep it that way. It does have both of its benefits and downsides but I like to keep it that way. It's the only way I can operate because I'd like to know about the people that I travel with.

My goal is that, when I work together with people on tour — however long they stay — they would have a good experience when they leave. It's just like a part of life, but moreso unique when you're on tour.

In your opinion, how important is it to build a local scene?

I love the idea of building a local scene, and that doesn't mean it's fixated on one specific genre or anything. I think a city that supports its local musicians is an indicator of a thriving city.

You know when bands have places to express themselves and play music, I think that it's a sign that the city is embracing art and culture — bringing it to the people. I would have a hard time if that means there would be lesser places for me to see bands. Seeing local music is exciting for people in the city to be able to discover new talent and bring that to the rest of the world. I think it's a point of pride where I come from. There are a lot of bands that come out of my little county in California, and people from there feel proud.

If you can build a healthy conversation around music and art, wherever you are, I think those people will find each other and build something regardless of what people do to try and stop them.