Winston Street : An Origin Story

We once mentioned on the metaphor of a normal and ordinary street that branches out to other streets. In any city you visit, you will always encounter this one street that you would always come back to because it is where you will find yourself bearing-corrected. Most of the times, this kind of street will be where you spend most times in during that trip because it is the most familiar place in that foreign city that you feel comfortable in (besides where you lodge, of course).

In this street, you will find a coffee shop or restaurant that you will keep visiting, the convenient shop that you would go into in the early morning before you start your exploration and also at the end of the day before you return to your Airbnb, just to stock up on snacks and bottled water.

Let's face it, almost 100% of the time when we say that we are going into an unknown territory or getting out of our comfort zone, we will always have a safe zone. So let's just call the act of going totally out of the comfort zone as a bullshit propaganda.

This idea of Winston Street is not new. It's just another method of representing our stories and thoughts on traveling, going places, vacationing and combating the possibilities of falling into the abyss of working life.

Who are we?

Winston Street (the blog) is a collaborative effort of many but founded and curated by two heads.

Sir Cheapskate is the most average person ever. Having a background in Architectural studies and still practicing has given him the chance to learn about places and cultures beyond his safe walls. Much like the pseudonym, Sir Cheapskate is indeed the cheap one, i.e doing things on bargains, visiting economical locations while being very particular on the expenditure. Sir Cheapskate stands for the believe that the funnest and most valuable of things and experience are not necessarily elaborate on the budget. Being cheap trains you to be smart and most importantly builds the self discipline.

But can one really get full experience on things with this budget issue that keeps limiting possibilities?

Count Extra on the other hand, enjoys proper and well-planned routine. Budget is not much of an issue as long as he gets that leisure and pampering experience. Despite comfort and safety being his numero uno, he is able (and on his way) to meet halfway to “rough it up” during his travels. Being in a routine puts his mind at ease, much like his days, being scheduled and organized is the way to go. A well-planned day will eliminate errors, with no errors, goals can be achieved. Count Extra wants only the best experience when going places, therefore believing that the limit does not really exist. So go extra on everything.

But does going extra really guarantee a good tripping experience?

We have nothing to prove. We have only the intention to share our travel stories on how working class people like us can manage to go places without abandoning our work life. These days, we see a lot of people and influencers that travel for a living. No shade to them, but we want to see more realistic examples.

Being 90's kids, we are exposed to the world before and after Internet and social media. Bare in mind that if you are born in 1995 onwards, you are not technically 90's kids because you pretty much are raised in the Internet era and probably think Bieber's music (and anything alike) is the best in the world. You probably don't know Spice Girls and Backstreet Boys prior to their reunion days. Yes, this is a shade to you. Because you know why? Kids raised after the Y2K grow up to think they deserve things and that they can do anything, that when they grow up, they become hipsters, claim to be self-employed (instead of unemployed) although one or two of their friends made it as young entrepreneur and become social culture oriented.

We think like this because we are in the forgotten part of the world. We are from South East Asia, where aliens and superheroes will never land onto (because aliens will always attack the States and London). In this part of the world, we are unknown, unmentioned and considered exotic because we aren't the global norm. Being out of the picture since forever does not give us the luxury to drop things and go for gap year (unless we are some super rich folks) like Americans and Europeans do. We can't afford traveling sans steady income, but fuck it, we are making it work anyways.

Winston Street is based in South East Asia which is mostly forgotten globally and exotic to those who came to know about this region.

There's a bitter origin to this Winston Street. So we will turn it all around now.

- Sir Cheapskate & Count Extra