The Hardest Question to Answer

Back when I was listening to Serial for the first time, I scoured the internet for more information about Serial and Adnan Syed’s case. This post isn’t about Serial (although I’ve listened to it twice now so if you want to talk about it, we definitely can).

Deep in the threads of Reddit, I came across a comment which has stuck with me. It read

A man is never as bad as the worst thing he has ever done.

I read it again. So simple and strangely beautiful. I googled it to determine if someone actually famous said this and came up with nothing, though there is a quote attributed to producer and screenwriter Billy Wilder which reads, “You’re only as good as the best thing you’ve ever done.”

Then I sat back and thought a minute. What’s the worst thing I’ve ever done? What’s the best? And for me, these were both incredibly difficult questions to answer.

The fact that I can’t answer the first perhaps means that I haven’t done too much bad. Maybe that’s a good thing. But when I couldn’t answer the second – What is the best thing I’ve ever done? Well, that made me a little sad. Shouldn’t something pop out at me? If I’m only as good as that thing, and I don’t even know what that thing is? I walk around each day believing that I am a good person at my core. How true could that be if I couldn’t think of an example?

I don’t have any glaring acts of good or bad in my life. In my story. I asked a few other people if they could think of anything and no one really could. Realistically I guess you may not share the worst thing you’ve ever done (or the best, out of modesty), but still, people seemed genuinely perplexed.

I guess I’ve concluded that most negative and positive acts aren’t these big, life changing events. It’s everyday kindness and accidental slips of mean.

But what this led me to recognize is that I feel this desire to make my life mean something more by doing more acts of good. That someday I may sleep at night knowing that I can answer the question “what’s the best thing you’ve ever done?” with absolute ease.

Ask yourself these questions and tell me if you can easily think of your examples (you don’t have to share them). I’d be so curious if this is a challenge for others as well.


  • I’m definitely struggling to think of the worst thing I’ve ever done, but honestly, my career change (and the impact that I’m able to have on underserved communities is the best thing I’ve ever done. I kind of feel like a jerk when I say it, but I absolutely know that my job, my role, and my organization make a difference for SO many people every day. That does help me sleep a little bit, but the truth is, there’s still so many starfish we aren’t getting… so I can’t stop trying to do more, if that makes sense. It’s a double-edged sword to recognize both of these things, honestly.

  • Brittany Grogan

    LOVE THIS. The first thing that comes to my mind is that the best and worst thing are the same thing for me: letting go of people. Worst in the sense that, it felt like it was almost TOO easy – like flipping a switch. It probably caused hurt and confusion to the other person. I hate to imagine causing strife for another. However, it is also the best thing in the sense that I let go of toxic relationships/friendships. Releasing myself of that burden has provided so much clarity and relief.

  • I LOVE this, so thought provoking. I am in the same boat as you, I can’t really think of anything that stands out. And I too, would love to do more GOOD so that I can clearly know what the best thing I’ve done is. This is great, thank you for sharing!

    • I think we have to remember that the good we do is mostly in the little things. I’m working to make sure that I add more of the big things but also more of those little acts of good to my life. I’m sure you do plenty of good already!

  • So good! 🙌🏾 I have a hard time coming up with one thing for each (I feel like I’ve done a lot of bad things and a lot of good things). I’m loving this thought and aiming to do more good things.

  • Beautiful post!!

  • Hmm, so (doing the psych major in me justice) I way overanalyzed the question – what is the best thing you’ve ever done?

    In terms of experiences that have resulted in all of the best parts of my own life? Easy. The traveling, the education, the moment when I’ve begun or strengthened the relationships I have with my loved ones.

    But I think you were taking this to a more literal place – what is the single act of GOODNESS you’ve ever done? And you’re right – I think it’s less one concrete example and more – how do you lead your life? What are the choices you make in the day to day? What values do you hold close to your heart, and how do your actions prove that?

    And you know what, through the many years of reading your blog, I know you to be someone who carries out your life in a genuine, kind, and meaningful way. From what I know about your job and your honesty, and the way that you treat your loved ones (and Archie!!) – I think this is what exemplifies goodness best of all rather than, “that one time” I or you did this or that or the other! (I mean, both would be ideal, I guess!)

    • I definitely was being more literal but perhaps I shouldn’t have been. I just worry sometimes that I live my life and assume that I’m a good person but am not actually doing enough good. That last paragraph though got me right in the feels. It makes me so happy that my life comes across that way on my blog because I do feel that I live my life in a good way and I’m glad that shows. Your comment completely made my week. Thank you, Caroline.

  • Pollybug

    I can sadly answer the worst thing. I left my husband after 12 years of marriage (and 6 years together prior to marriage) right after he was diagnosed as bi-polar. While I know in my heart that I did not leave him BECAUSE he was sick, but because of his truly erratic and scary behavior in the years prior to his diagnosis, I will never really be able to forgive myself for leaving when my long-time best friend needed me most. I think I will probably carry the guilt forever (even though he is happily remarried today and has told me repeatedly that I did the right thing at the time).

    • Thank you for sharing this. I do think the fact that he believes you did the right thing speaks worlds about your decision. If he believes it was right, and theoretically he was the one wronged, than I hope you are able to forgive yourself at some point.

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