The hardest part is the first sentence.

Letters to the ones who didn’t get the letter. Usually because they’re gone.

• Write to someone who died before you could apologize.

  “I’ve been rehearsing this for a long time. Of all the things I never said, the one that won’t leave is…”

  to someone who is goneUse this opener

• A eulogy for a friendship that ended without one.

  “We didn’t fight. That’s almost the worst part. You slowly stopped and I slowly stopped and now I don’t know how to call you.…”

  to my old friendUse this opener

The email you cannot send because it would end the career.

• The resignation you’d send if you didn’t need the reference.

  “I’m not writing to give two weeks. I’m writing to tell you why.…”

  to my bossUse this opener

• Answer an HOA memo with the energy it deserves.

  “Regarding your memo: I have read it four times. Each read removed a year from my life.…”

  to the HOAUse this opener

• Quit the group chat with a speech instead of just leaving.

  “Before I go: I like you all individually. It’s the combined draft of us that I can’t be in anymore.…”

  to the group chatUse this opener

Giving up a thing without asking for permission.

• To the person you’re tired of apologizing to.

  “I’ve been apologizing to you since I was old enough to know the word. I’m still trying to figure out what I did.…”

  to the one I keep apologizing toUse this opener

• To the place (or person) you’ve decided to leave for good.

  “I’m not coming back. I keep telling you that and I keep coming back. This one is different because…”

  to the one I keep going back toUse this opener

Not to them, exactly. More to the part of you that hasn’t yet.

• To someone you want to forgive but haven’t.

  “This isn’t forgiveness. This is the letter I have to write before forgiveness is possible. Here is what you did.…”

  to the one I’m trying to forgiveUse this opener

• To the version of you who did the thing you can’t forgive yourself for.

  “You thought you were protecting yourself. I want to tell you something I wish someone had told you then.…”

  to me, thenUse this opener

To a past or future version of yourself. The postman isn’t picky.

• To the you who reads this a year from now.

  “One year from today, if you’re still at the same job, still with the same person, still making the same excuses about the same thing —…”

  to me, a year from nowUse this opener

• To the oldest version of yourself. Ask the question you’re afraid to answer.

  “Old person. I hope you exist. I hope you can read this without flinching. Here is the thing I’m deciding right now, and I need to know if you think I got it right.…”

  to me, at the endUse this opener

• To yourself at 22, the version before the mistake.

  “You haven’t made it yet. You’re going to make it in about six months. I’m not going to tell you not to — it turns out the mistake is the one that…”

  to me at 22Use this opener