There have been weeks when I was so swamped that I didn't do a single painting. However, those weeks tend to be the exception rather than the rule. Instead, on most days, no matter how hectic the schedule, I'll sit down after breakfast and paint for about 30-45 minutes.

Every painting is almost always done in stages

I'll often do a whole bunch of pencil sketches. For me, the pencil sketch is what takes the most time. It involves the entire scene, the font I'm going to choose and the layout. I may start, get a lot of the scene done, then erase it all and make it better, or I may go at it from conception to a final looking draft. Either way, it's important to get the pencil sketch done really well. If I do something shoddily in pencil, the painting will almost always be a compromise. Hence the pencil work is the one that takes a fair bit of time.

When people see my work, they think I paint mostly on vacation

They assume (and assume wrongly) that the books are about my trips. We do take three months off every year, so admittedly there's a lot of travel, but the books are about my every day life, no matter whether I'm in Rome or just down at the local cafe. I do tend to get more art done when I'm travelling, often an entire book, but it can be a bit of a juggle. When travelling, we tend to spend a lot of time just resting, eating and doing the tiniest bit of sightseeing. Trying to fit the painting in between it all, isn't easy. Even so, a lot gets done—often 45-50 pages of the Moleskine book.

You can see some of the Moleskine samples below. Or if you'd prefer a slightly orderly format, it's at www.theotherseandsouza.com. On the other hand, if you're more of an Instagram fan, I post almost daily at https://www.instagram.com/seandsouza

You know how it feels when you're the second last person to join some social media movement? We took years to get on Facebook, really never did much with Twitter, and then ignored Instagram for the longest time. However, that was before I got the iPad Pro (no, there's no commission or affiliate link on this page, in case you're wondering). Once I got drawing, I didn't want to stop.

But we need some cartooning history here as well

When I lived in Mumbai, India, I pretty much cartooned my way through university. While everyone else went to the movies, I went and sat in the offices of newspapers. I figured if I showed up almost every day, they'd feel sorry for me. I did that with magazines too. I'd drop in and ask if they had any articles I could illustrate.

The funny thing is that if you're persistent enough, things start to happen. At first it was slow. An illustration here and there, but over time I had enough to buy my own motorcycle and pay my university fees (they're sensibly priced in India). However, my big dream was to do a daily cartoon strip like all the big cartooning heroes of mine. I kept bugging the editors of two newspapers, hoping that at least one of them would say yes.

Have you heard the saying, “when it rains, it pours”?

I'd been trying to hedge my bets with the two newspapers, namely Midday and The Daily. And in a single week, both the editors decided to give me a space to run a comic strip, five days a week. Whoah! That meant I had to turn out ten comic strips a week!

That's when I got my first surprise

I always thought it was better to do a little bit here and there, but when I had this overwhelming deadline, things didn't get worse. They got better. My ears were tuned in to every possible scrap of news and turning out all of those comic strips per week wasn't hard.

The hardest part, if you ask me, was getting the comic strip across. This was before the days of e-mail and the internet, or “computers” for that matter. I literally had to get on a train and deliver the cartoons to the newspaper office, or find someone who worked at the office who could take it across as a favour.

On days when I couldn't go across, I literally couriered a single cartoon across. And then when faxes came along, I could fax the cartoon—because the print quality of newspapers was still pretty iffy.

Which is why five days a week on Instagram doesn't faze me that much

It's a big ask to get back to drawing one every weekday especially after I get back from a vacation (and I refuse to have anything to do with work when on vacation). But by and large, you'll enjoy the zany sense of humour. When you get to Instagram, you may as well “follow” along. And if you have any ideas, send them across as well.

At one point, I decided I wanted to learn to draw animals a lot better. Which is why I started drawing them on an envelope and sending it to friends family and to clients. But others got the postcards too, like my masseuse for example (she was thrilled to bits).

At first I used only a fountain pen. I have this beautiful cigar-shaped, bright orange Nakaya. And I like to use it to draw, but there's so much of a battle between the iPad, Photoshop, and the watercolours, that the fountain pen never got any usage at all.

Out came the envelopes and so did the fountain pen
I think I ended up doing a heck of a lot of envelopes first with animals (which would take well over an hour each) and then started doing watercolour cartoons as well (but without the fountain pen). I switched back and forth between fountain pen and Rotring Isographs, but the Rotring ones are so temperamental, aren't they? Anyway, here are some of the fountain pen illustrations.