Bad Advice: How to disappoint your boss

The first of so much Bad Advice to come

Hey all! Bill here. Welcome to a new Worcester Sucks production: Bad Advice with Shaun Connolly.

If you were already a Bad Advice reader, the only thing that’s changing is the outlet. If you weren’t, well, now you can be! Hope you enjoy it. I think you will. 

As I explained in my last post, albeit a bit obnoxiously, Bad Advice belongs to this newsletter now. Shaun will be posting here weekly. Like my posts, they’ll go out via email to subscribers and also the website, where he has his own “Bad Advice” section under the header. (The website, btw, is no longer billshaner.substack.com. It’s WORCESTERSUCKS.EMAIL!!!)

In form, Bad Advice a standard advice column. You send him questions and he answers! Send questions to woocomedyweek@gmail.com with the subject line "Bad Advice."

Shaun has been at this advice column thing for years now, starting at Worcester Magazine, then on his own Substack, and now here, for the Worcester Sucks audience. It’s good stuff. I’ve been a fan since he started.

Before we get to Shaun’s first Worcester Sucks piece, I want to quickly explain my intentions with bringing his work on board.

Outside my own writing, the ultimate goal with Worcester Sucks is to cement it as its own institution, not just “my thing.” A bastion of scrappy and independent local journalism with its own brand and reputation. Really the dream is to re-establish a proper alt weekly newsroom covering Worcester, akin to the Worcester Magazine of the 1980s and 1990s, and similarly full of different personalities and perspectives. However, in 2023, the business model of an alt weekly is simply impractical. The media landscape does not support it. No one’s come up with an alternative that doesn’t amount to “ask your readers for money” and for the most part that only works for individual writers operating independently. 

Bringing Shaun’s column under the Worcester Sucks umbrella is an experiment. Can this newsletter model sustain two regular voices? Do people want to see this newsletter grow into a proper outlet? Can we eventually add a third voice? A fourth? A graphic designer? A photographer? A real life editor?

Instead of growing our own readerships independent of one another on separate platforms, me and Shaun are teaming up in service of the same audience, the same email list, and the same goal: independent local journalism in a world that’s trying to destroy it.  

Please consider a paid subscription so I can pay Shaun for his column. I’m currently running a half off deal for a whole year to celebrate this newsletter’s third anniversary.

Or send a tip! (Venmo / Paypal)

My posts on here are often long and winding. Stuffed with depressing observations and gloomy conclusions. Using Worcester as the petri dish to probe at some more universal themes. I like it that way. It’s a form I’m constantly trying to perfect. 

By contrast, Shaun’s column is refreshingly short, sweet and funny. Extremely Worcester, but in a markedly different way than my work. There could be sort of a good cop / bad cop thing dynamic here between my style and Shaun’s. Excited to see how that develops.  

(Sorry in advance for this next paragraph, Shaun! But we can’t assume every reader is familiar with you and what you do.)

Around these parts, Shaun Connolly’s sort of a big deal. He’s not “just some guy.” I mean... he is just some fuckin guy. But he’s also on the short list of people most personally responsible for Worcester’s special little creative community and the endearing weirdo vibe it exudes. He puts the work in. Has for years and years now. When other people want to put the work in, he’s supportive and encouraging. 

His main thing is WOOtenanny Comedy, and it’s the lifeblood of the local comedy scene. But that’s far from all he does. Looking at the things in this city that fall into the “I Love It” category, his fingerprints are everywhere. He also knows a lot more about Worcester politics than he lets on! I’d like to see my readers pry that out of him! Let’s all send Shaun some good juicy questions! Email woocomedyweek@gmail.com with the subject line "Bad Advice."

Ok Shaun, take it away. 

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How to disappoint your boss

By Shaun Connolly 

Dear Shaun,

First off, congrats on being acquired! Nothing like a little late stage capitalism to make it seem like you’ve made it. My question is fairly innocuous, however I feel like this could help a lot of folks. So here’s my thing, I’ve never had a boss before. I’ve always worked when I want to work and never had to worry about deadlines, or opinions or someone else’s manic episodes. But now, it seems in just a few short weeks I have to answer to someone. Truthfully, I’m losing sleep over it. It is less because I have a larger sense of responsibility, but more because my boss has to deal with me. I’m not easy to work with. I am not a good partner, I am not a good lover, I don’t listen fully, I cannot focus on a conversation, I leave people on “read.” Some have called me a narcissist, but I don’t think this is fair. It’s not as if I am focusing on myself while I’m being bad at those things, it is more that my brain triggers to other things based off what is in front of me. How can I start things on the right foot with my new boss?

-Underling

Dear Underling,

Thank you for the congratulations! I guess because of this acquisition I have a new boss now. (Hey Bill!) He won’t respond, he’s too busy filing another records request for the receipts of DPW workers to prove that their Dunkin’s purchases are actually 1/4 of the municipal budget, or some shit.

Yeah, adding new people to your life can be hard. Whether it be friends, in-laws, co-workers, lovers, neighbors, children. There is always a grace period where we are all super friendly to each other until we learn where the electric fence is. The electric fence, could be politics, or music taste, or how they interact with their pets or how they react to office birthday cake. I had this one co-worker, who would make a slurping sound if there was a treat in the office OR if there was mention of a meal that they liked they would make that slurping sound. As I type this anecdote I have chills going up my spine. It was so gross.

So you need to figure out your electric fence with your boss. Don’t wait for him to figure out yours. According to your own self-assessment you don’t want him to find out. You have to beat him to the punch and find out his and make him feel self-conscious about them. Think of yourself as a butcher and you are a knife master. Slice and dice their faults with precision. They will feel like their backs are against the wall. You will have the upper hand, and so whatever faults you may have, your boss will be too focused on their shortcomings. This is how you win.

Send any and all questions to woocomedyweek@gmail.com with the subject line "Bad Advice."

NEWS

This weekend I’ll be at Off Cabot Comedy Club in Beverly, MA with Erin Jackson. You can buy tickets here.

Next week on June 30th WOOtenanny will be hosting Kate Willett at Ralph’s. Kate has been on Stephen Colbert, Comedy Central, Netflix and more. Kate is truly so funny and we are very excited to have her come to Worcester. You can buy tickets for that show here.

I’m very excited to be a part of Worcester Sucks. Very happy to be able to stress out Bill for the foreseeable future.