Q: I like the people at work, the hours aren’t bad, the office is pretty nice, etc. But I hate my job and really resent going to work every day. My real passion is playwriting, and I can’t help but think that if I didn’t have this job, I’d get a lot more writing done. I feel embarrassed when I tell people what it is I do for a living and worry that they’ll think less of me and not “get” me. I know that’s stupid, but it’s wearing on my self-esteem.
How do you know when it’s time to quit your day job? Or: How do you keep up your day job and keep your head up at the same time? — P.B., San Francisco
A: Your worries are not stupid. Many people that you know and meet will think less of you, at least if you live in an absurdly competitive city like San Francisco. Any excuse to feel even a little bit better than someone else, right?
Because who knows what’s going on with them. Maybe they have sacrificed everything — even adequate dental care — to follow their dreams, and now their molars are falling out of their mouth and they can hardly eat yogurt, let alone subsist on all the writing they produce on a daily basis.
Or maybe they have a huge trust fund that they don’t tell anyone about, and they live in a hovel even though they could afford a mansion, and every week they complain to their expensive therapist about feeling like a fraud.
Maybe they have a professional partner who financially supports their work, and they write and they write, and they publish and publish, but it all sucks.
Maybe one day they meet you at a party. You say you have a day job, but instead of stating proudly that you work in a fine office with kind colleagues whom you actually like, you act like an impostor. After the party, they go home and gossip to friends that you’re a sellout and a fool. Their friends outwardly agree with them, even though they know inside your writing’s actually really good, day job or not.
In fact, everybody knows inside your writing’s actually really good, but no one will ever admit this to themselves, let alone each other, because this might jeopardize whatever sort of unstable hierarchy they have established in the gloomy bars and insular theaters that they frequent as a group in their ridiculous amounts of spare time.
Trust me, these people who despise you and talk about you behind your back would like nothing more than for you to actually stop writing. It would legitimize their choices, and it would also cull the field by one more body, which is more than none. But don’t give them what they want, OK? Just keep writing and, maybe more important, just keep putting yourself out there.
Bitter writing can be good. Angry writing can be really good. And writing about soul-crushing day jobs has produced some genuine theatrical masterpieces.
Don’t be a follower
Q: Should you follow your interviewer on Twitter after a (media) job interview? Or is that weird? — A., Boston
A: No, you should not. But it wouldn’t be that weird if you did, either.
Think upside and downside: The upside if you follow is … what? You read this person’s random hot take on whatever new pickle Jeff Bezos has gotten himself into? The downside is: There is a small but nonzero chance they think you’re creepy or annoying. If you think the interview went well, just leave it at that. Always leave them wanting more.
Q: As a freelance writer, I work from home. Many of my “work associates” are either (A) people who email me ideas, or (B) people I email ideas to. Multiple times a day, I receive follow-up emails from members of category A. Sometimes they’re checking in on something they sent mere hours ago. I get enough of these emails that I cannot respond to every one, otherwise my entire workday would be spent writing missives like “Sorry, not interested!” Of course, I find myself on the other end of this hellish pitch cycle when I send follow-up emails to members of category B, usually no sooner than three days after sending my last note.
All of which poses the question: What is a reasonable amount of time to wait before sending a follow-up email? — S.M., Los Angeles
A: I started off writing a long thing about how freelancers are like a pile of worms trapped in a Mason jar. They writhe around one another, unable to escape, because whenever one tries to climb up the disgusting, slippery wall, the others can’t help wriggling and pulling the almost-free one back into the heaving, moistened pile. But I stopped writing this because there is actually a simple answer to your question.
First, get a second email account. Give this new address to anyone who pitches you.
Second, write an out-of-office message: “Hello there. Thank you for your query. I do my best to respond to every pitch, but it can take me up to three days to do so. If your message is time-sensitive, please write ‘time-sensitive’ in the subject line and resend. If you have not heard from me within three days, you can assume that your pitch is not a fit for me right now.”
When it comes to your own pitches: three days seems a good interval to me, although you should certainly write “time-sensitive” in the subject line if three days will be too long to wait. Make sure it’s not a holiday or the editor hasn’t been fired since you first pitched.
As for escaping from the writhing Mason jar to actually get something of substance accomplished: During the day, go to a cafe and write from there. Don’t ask for the internet password. (When you do, you’re just begging for your computer to be hacked.) Get more work done and become rich and powerful.
Work Friend is a cheeky New York Times advice column to help with careers, money and the sometimes grim, sometimes hilarious maze that is the contemporary office, from a rotating cast of advice-givers.