June 25, 1918
You have a man in your employ that I have thought for a long time should be fired. I refer to Sherwood Anderson. He is a fellow of a good deal of ability, but for a long time I have been convinced that his heart is not in his work.
Once upon a time, author Sherwood Anderson worked as a copywriter for an advertising agency. And when he was 41, he decided to quit his job and work on his writing full-time. Anderson didn’t go up to his boss Bayard Barton and give notice, no—he wrote a clever resignation letter in which he let himself go. The letter was written about 100 years ago, but I think it’s just the greatest thing. But maybe I just think that because I wish I wrote it. And maybe I wish I wrote it because when I quit my job a few years ago, it felt super awkward, and a little humor would have made things so much better.
I find it difficult to ask for things, so when I felt like I deserved a raise, it took me a few months to actually build up the courage to ask for one. And when my boss said, “Well, maybe, I’ll think about it,” it took me about another month to follow-up with him about it. His answer was, laughably, “Oh yeah. Okay.”
I got to a point in my job where it became clear to me that there would not be another promotion coming my way nor another raise, so I pulled some strings through some connections I had and found a better job somewhere else. All I had to do was quit my job and move on. But for whatever neurotic reason I had, the thought of asking for a meeting with my boss to tell him that I was leaving terrified me. So I decided to talk around it until my boss figured it out on his own. This is what ended up happening:
Bob: Boss, do you have a minute to talk?
Boss: Oh god, Bob, what is it now, you want another raise? The answer is no.
Bob: No, it’s something else.
Boss: Okay, let’s go into the conference room. What is it?
Bob: I feel like I’m not feeling inspired here, that I’m not doing the work that I could be doing. I feel like I’m becoming a slacker.
Boss: Are you slacking off?
Bob: Am I slacking off? If I am, you deserve better than me.
Boss: You’re doing fine, Bob. Better than fine.
Bob: I don’t feel that way right now. Maybe I need to get another job.
Boss: I wouldn’t want that.
Bob: You should have someone who wants to be here.
Boss: What could I do to make things better for you?
Bob: Maybe a bigger budget?
[At this point I don’t know where I’m even taking this conversation anymore.]
Boss: We don’t have the money to give you a bigger budget.
Bob: Then nothing. There is nothing. Perhaps I should leave.
Boss: I don’t want you to leave.
Bob: You don’t want someone who doesn’t want to be here either.
Boss: Bob, do you want to leave?
Boss: What are you going to do? I’m worried about you.
Bob: I’ll be fine.
Boss: Okay, if you change your mind, just let me know. But if it makes you feel better to go, you should go.
Bob: You’re right, I’ll feel better if I go.
Boss: Don’t stay if you don’t want to stay, Bob. Go. We’ll miss you, but go.
I know it would have made a lot more sense to have marched into that conference room, tell my boss that I found a new job, and leave it at that, but the conversation I actually had made me feel more at ease about leaving. Because I am a CRAZY PERSON.
My boss said he was going to plan a goodbye party for me, but after two weeks he forgot to have one, and I’m glad he did. Now all I have to do is figure out how I’m going to ask for a raise and promotion and the company I’m at now.
B. Benson is an office drone.