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Work

25 letters in this pile. Read each question, then open the reply when you're ready.

Work

Dear Toolsie,

I keep applying to jobs and getting ghosted, starting to think it's me

Toolsie wrote back.

Work

Dear Toolsie,

I've been offered a promotion that would require relocating my family for the third time in five years, and I don't know if I have the right to ask them to move again.

Toolsie wrote back.

Work

Dear Toolsie,

I found out my closest coworker makes significantly more than me for the same role. I don't know whether to say anything.

Toolsie wrote back.

Work

Dear Toolsie,

I've been putting off telling my business partner that I want to scale back my hours after having my second child.

Toolsie wrote back.

Work

Dear Toolsie,

My manager presented my idea to leadership as her own and I don't know whether to say something or let it go.

Toolsie wrote back.

Work

Dear Toolsie,

I've been in the same role for 12 years and I'm starting to wonder if I've just stopped growing.

Toolsie wrote back.

Work

Dear Toolsie,

I was passed over for a promotion I was told I was a lock for and I don't know how to face my team.

Toolsie wrote back.

Work

Dear Toolsie,

I signed an NDA at my old job and I want to tell a reporter what really happened there, will I get sued?

Toolsie wrote back.

Work

Dear Toolsie,

My business partner has been moving money between accounts and won't show me the books, is that embezzlement?

Toolsie wrote back.

Work

Dear Toolsie,

My manager keeps making comments about my body and invited me to his hotel room during a work trip, I said no but I'm scared this will affect my job, what should I actually do.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, my manager keeps scheduling 'quick check-ins' that turn into hour-long meetings with no agenda, and I'm losing entire afternoons to them.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I got passed over for a promotion I was basically promised, and now I have to keep working under the person who got it instead.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I've been ghost-applying to other jobs during work hours and I'm starting to feel guilty, but I also don't see another way to job search while employed.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, a coworker I mentor just got hired at a company I've been trying to get into for two years, and part of me is happy for her and part of me is furious.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, my company announced layoffs are coming 'sometime next quarter' and I can't tell if I should start looking now or if that's overreacting.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I accidentally sent a complaint about my boss to the whole team instead of just one coworker. It's been three hours and nobody has said anything.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I'm the only one on my team who actually enforces the deadlines, and I'm starting to feel like the office villain instead of just doing my job.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I want to ask for a raise but my company just did a round of layoffs and everyone says now is the worst possible time.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I've been at my job for eight years and I'm comfortable, but a friend keeps telling me I'm 'wasting my potential' and now I can't stop thinking about it.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, my new hire is clearly more qualified than me on paper, and I'm nervous he's going to make my own gaps obvious to our manager.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I'm 34 and thinking about going back to school for a completely different career, and everyone around me thinks it's too late to start over.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, I dropped out of college fifteen years ago and never went back, and a recruiter just told me the degree requirement is non-negotiable for a job I really want.

Toolsie wrote back.

Work

Dear Toolsie,

I'm 34 and thinking about going back to school for a career change, but it means taking on debt and my spouse thinks it's reckless timing with two young kids.

Toolsie wrote back.

Work

Dear Toolsie,

I was passed over for a promotion I was told I was the top candidate for, and the person who got it is someone I trained myself.

Toolsie wrote back.

Work

Dear Toolsie,

Dear Toolsie, my coworker has named the office printer 'Steve' and apologizes to it out loud every time it jams, and now half the department also apologizes to Steve, and I think I might be the last person in this office who still calls it 'the printer.'

Toolsie wrote back.

Done here? Read a letter at random