Making the Blogfather: A (Cover) Letter to My Future

I’d like to say I left my law firm job amicably, but regrettably, and in what on hindsight now seems like a recurring trend in my abrupt life-changing moments, it began with a quarrel – with my sister, one of the firm’s partners. The day ended abruptly by lunchtime, with me saying I was quitting. As with many quarrels in my life, I cannot for the life of me remember what or why I got so angry. I could only remember thinking if I didn’t, things would have gone far worse.

But leave I did, and I found myself wandering around Fort Canning Hill, wondering what to do next. Over the blazing hot mid-afternoon, after I had taken enough deep breaths to calm down from the fight prior, I decided to whip out my phone and write a cover letter for myself. And this was a letter that would change the direction of my life; for better or worse, I can’t say.

And it went like this:

Dear Sir/Madam,

Seasoned socialites will tell you that “hello” is usually the most effective icebreaker, so here goes.


My name is Winston Tay, and I was wondering if you would perchance have a full-time opening for a struggling writer/editor/content manager/father of one who’s looking for a happier way to feed his family.

I am a wordsmith (not necessarily by trade, though most of my career endeavours do involve in large part a mastery of the English language) seeking a permanent position in the publishing industry to build up my writing career. My writing style is best described as fearless, friendly, and fun.

By fearless, I mean I am not afraid to broach controversial topics (of course, within Singapore’s OB marker range). I have a strong curiosity in my ways, which leads me to ask hard questions where hard questions are necessary.

By friendly, I mean I set myself to be highly approachable in conversation, and highly amenable to meeting and engaging people. I also make it a point to simplify my writing for common simplicity and readability, a skill I garnered from dealing with lawyers who pride themselves in complex legalese befitting of the 16th century lawmakers who authored the English common law system.

And by fun, I mean I have a sense of humour, and I’m not afraid to use it.

I’ve attached my resume for your kind attention and (hopefully) pleasurable reading. Samples of my work (commercial and non-commercial) are available on request, if not semi-permanently etched in the vast digital world which we would commonly term the World Wide Web.

Do let me know if you are interested to meet up for an interview. I’ll buy you coffee.


Winston Tay

I sent this letter as an introductory email to 6 magazine publishers, both print and online; 5 of them got back to me within a week – I think the last one got filtered into the addressee’s spam folder. And 2 of them never got to looking at my resume before calling me. I ended up having a lot of coffee that month; and as if I needed proof that decisions made in a huff are ultimately not the best decisions one can make, my last coffee session resulting from this over letter would end up tasting extremely bitter.

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