Following suit, persona non grata and sucking up

Dear Rachel,

Let’s suppose that I choose not to wear a suit anymore and instead opt to wear the same clothes as my peers and colleagues. And then, I have a meeting with a couple big bully windbags who mock me for not wearing a suit. Which is worse: wearing something in solidarity with my people or wearing something that fits as poorly as a Spirit Halloween costume?

– Dressed Down

Dear Working Attire,

Don’t worry about wearing a suit. Wear what suits you – and wear what suits the circumstances. Plenty of people in history have changed the world while wearing clothes that didn’t fit. The important thing is that you are true to yourself, so long as you are a good person. Maybe the other people should consider changing their clothes and maybe everything about themselves.

– Thoroughly fatigued, Rachel

Dear Rachel,

I recently tried to go skiing on a break from work. Yet, when I got to the slopes, I wasn’t welcomed at all. In fact, people yelled at me and wrote hurtful things on signs. I had to cancel my trip, and it sucks because the skiing was on national forest land, which might not even exist by next winter. How can I reclaim my needed getaways?

– Out in the Cold

Dear Frozen Out,

Did anyone accuse you of skiing in jeans? Because that right there is one of the classic slope-adjacent jabs. I really can’t think of anything worse than that when you’re trying to catch a fresh powder day. I mean, unless you’re trying to make yourself responsible for the downfall of civilization or something like that. Then you deserve much worse. But that can’t be you, right?

– Cold shouldered, Rachel

Dear Rachel,

I’m in a pickle at work. I don’t like my boss. In addition, I think my boss is wrecking the whole company. But he recently gave me a big promotion, and the job has only two requirements: 1) Do whatever he says, and 2) Pretend he is the best person who ever lived. I gave him a “World’s Best Boss” mug, but he has this other friend who bought him a whole country. I can’t compete with that. Should I stick this out until retirement? 

– “Yes” Man

Dear Sycophant,

Retirement isn’t all it’s cracked up to be. Especially the way things are looking now. Like, why save dollars if dollars won’t be worth anything by the time you finish working? I recommend you ditch the boss and take the secret files with you on the way out. Go find yourself a better cause to work for. An actual Best Boss doesn’t demand you to say so – and you can tell by the way he acts, more than the way he dresses.

– Boss babe, Rachel