In every job I’ve ever held I’ve always written a letter. If I stay a year, it’s delivered on my anniversary date. If I don’t, it’s part of my letter of resignation.

The letter basically has 3 components: a huge thanks for the opportunity, some of the things I’m looking forward to for the future (kind of a “here’s what’s possible” section) and finally things that really need looked at.

It’s a really ballsy / foolish / egotistical thing to do, and I know that. Upon leaving my one and only dot-com position, Iwrote something to the effect of (boiled down) “this place is okay, but has no business strategy and in spite of serious funding will flounder until it finds just such a strategy”.

That was the only negative letter I’ve written though. Every other one (I’m at 5 so far) have all been overwhelmingly positive and encouraging because, ultimately, I believed in the place I was working.

Embarrassingly, and probably sadly, each one of my letters has been bang on. Maybe it’s because I never write them lightly or in a cocky manner. I often spend more than 10 hours agonizing over them. Sometimes they are self obvious. One time it served as a wakeup call. Every other time it’s effectively been ignored with a “sure young’un, whatever” shrug and a smile. But, again, each time they’ve been right.

I don’t say that pompously. It’s just my string of luck so far.

I’m approaching my 1-Year anniversary here at HSC. Sure it’s not until February, but with a baby, 3 weeks of holidays and Christmas coming up it might as well be right around the corner.

And I’m starting to think about this letter.

I’m seriously debating not doing it. Not because I’m afraid I’ll be wrong, but because I’m afraid I’ll be right.

Earlier today I mentioned that I was “walk the tightrope between honesty and losing my job“. That’s exactly how I feel. HSC’s been good to me. They hired me for a job that I wasn’t actually qualified for, gave me time to learn the ropes and have given me the freedom to practice my unique blend of skills fairly well.

But I am still left questionning the point of these letters. Is it to leave a big “I told you so” behind? Is it actually to encourage change? Is it to satisfy my own ego?

It’s always difficult to feel like you’re being heard. But when your director tells you “I see you as a mowing the lawn type of guy” (ie: doing the grunt work) it’s hard not to feel… Pigeonholed.

But HSC, healthcare and public sector work in general excites me. The politics, the lack of opportunity for advancement and hte lack of communication annoy me, but those are things I know I can live with (having been in several similar situations in the past).

What do you think? Is there a point to such a letter, even a well intentioned one? Or am I just spinning my wheels and ultimately wasting my breath?