You can’t afford to carry around regret, shame, or guilt, it’s debilitating.  If you’ve done something that you regret, learn what you can from it and move on.  The lesson you learned was costly, so go find a way to make it worth the investment.

That’s what I told a person I met recently.  She had asked me to lunch to get some advice about a particularly unpleasant year with her team.  The basics of the story were that she had joined a new team and very quickly become an outcast.  As she flashed back on the details, it was clear that things had started to go wrong the very first time her teammates asked for feedback.  She gave the feedback, but likely in a way that touched a nerve and created resistance to what she was offering as help. The whole thing soured quite dramatically.  Very unhappy ending for all involved.

Listening to her story and really empathizing with how stuck she was in her regret over how it all played out, I recommended that she do something I’ve never recommended before.  But in the weeks following, I’ve found several other situations where I thought the same advice would be useful, so here it is.

The Letter

Letter writing is a lost art and one that we’d be wise to pick back up when we need an antidote to the superficial, staccato communication that’s so prevalent today.  There is something wonderful about communicating with someone in your own handwriting.  It’s so intimate and personal.  And because you can’t simply delete errant text, it causes you to be thoughtful and reflective as you write.  So my advice is if you’re wrestling with something important, try writing a letter.

  1. Pick the stationery. It sounds silly but I think it’s a really important part of the exercise. Go stand in a card store and look around. They are like little art galleries. Which card speaks to you? Which one perfectly represents how you feel or who you are? Which one is just right for the person you’re sending it to or the situation? Just this step will get the creative juices flowing and get you thinking about how you feel and the message you want to convey.
  2. Get the opening right. The first line sets the tone. If the person you are sending the letter to holds a grudge, it’s important to get the first line right or they might read no further. Tell them why you’re writing. “I have been thinking so much about our experience this year and wanted to share with you what I’ve learned.” “I have realized now that I did so many things that set us on a bad course.” “I value our relationship and hope that we can reconnect.”
  3. Share your reflections. As much as possible, write about yourself and your own actions and reflections. A letter that lays blame at the feet of the recipient is going into the trash in a hurry. With the benefit of time, what have you realized? “I have thought about it a million times and what I could have done differently was…” “I spoke out of turn and as I try to imagine how this felt for you, I feel terribly.” “I know now that my version of honesty is too blunt and rather than opening up a conversation, only shuts it down.”
  4. Ask for a remedy. It’s possible that the only remedy you’re looking for is just the peace of mind of sharing your perspective. But if you’re looking for more than that, be explicit. “I am really hoping that you would be willing to give me some feedback that would help me avoid a similar situation in the future.” “Will you be my guest for lunch so we can have a chance to move forward.” “Please accept my apology and know that I am truly sorry for what happened.”
  5. Mail it. It’s really important that you finish the exercise by addressing the envelope, affixing the stamp, and sticking the letter in the mail. What you get to decide is whether you send it to the person to whom you wrote it, or whether you send it to yourself. I think it’s fine if you decide once the letter is done that it’s not one you want anyone else to read. It might be too personal, too damaging, too…whatever. This exercise was about you and laying to rest the regret that was plaguing you. It’s up to you how you do that.


Relationships are really hard work. When you make a mistake or do something with unintended consequences, it can be costly.  But wallowing in regret isn’t going to help anyone.  If there is an issue that is troubling you, try writing a letter as a way of collecting your thoughts and figuring out what you can do to repair the situation.  Even if you never send it or the other person doesn’t come around, at least you’ll have come to terms with the episode for yourself.

Further Reading

Exercise: Exposing Reactions to Change

Dealing with a Hold Out

Curtailing your Need for Detail