The Sixty-Eight Question: Am I Missing Something?
Cracking open the shoulds that influence our behavior by trying to understand what motivates them.
Well, I feel lucky.
This community has grown by 10% since our last journal prompt. Wow! I want to thank and welcome all our new members. Given I haven’t sent out a prompt in about two weeks, I’m not sure how you all ended up here, but I hope you’ll stay. As a refresher, Asking the Question is a weekly series of journal prompts intended to help you build a journaling practice.
Journaling has been a key part of my #WellnessJourney, but it didn’t happen overnight. As someone who had dozens of false starts with journaling before I built a sustainable habit, I want to do what I can to help others get over the same hurdle. Asking the Question is my attempt at that. I send out a weekly prompt on Sundays, sometimes with my own reflection to the previous question, and then the rest is up to you. All you have to do is bring yourself to the page. Unsure what to write about? Think back to this week’s prompt and free associate. See where it takes you. Remember, there are no right or wrong answers, and nobody is watching you. Hope you’ll stick around.
I just turned 35! And my birthday week(end) was exactly what I could have wanted. Celebrated my birthday/the 40th anniversary of Purple Rain at an Alamo Drafthouse screening with friends, saw Sing Sing, had an intimate brunch with my girlfriend and a few close friends, and mostly stuck close to home. It was exactly what I wanted after a chaotic few months of travel. To be surrounded by those I love and to be still (by comparison to the rest of my life). Feeling grateful.
Let me also dwell on Sing Sing for a moment. You HAVE to go see this movie, especially if you’re a man. It has one of the most penetrating and nuanced looks at masculinity I’ve ever seen in a film. Offering a bit more of a review over on Instagram/TikTok.
But as beautiful as birthdays can be, they can also be a bit…uncomfortable. I revisited a previous journal prompt of ours to sit with that a bit. Specifically, my discomfort around being sung to. I explored it in more detail in this essay last year.

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And with that little recap of my joy, let me deliver this week’s prompt to you.
Question #68
I think we’ve covered this before, but I do believe that the “should” is one of the most dangerous ideas we tend to carry as people. I should do this, I should say that, I should wear that thing…(most) shoulds are what distract us from actually becoming the people we want to be (most because some of those shoulds are the things we do actually want for ourselves).
Shoulds can come from any number of different places. A sense of obligation to ourselves. A sense of duty and responsibility for others. A belief in some type of universal code of ethics or morality. They can also originate from our own ideas of our needs and wants.
To try to break open some of our shoulds, and everything else that comes with them, I want to try to back our way into understanding their origins.
What do you feel like you’re missing?
Think of a should like “I should go to the gym,” or “I should go out tonight.” Framed differently, they could be said as “I am missing a healthy fitness routine in my life and I need that,” or “Staying home tonight means I will miss a night out with my friends.” They’re clunky, but they work. My point is that our shoulds can sometimes come from a sense that we are missing out on something, whether an experience or developing a part of ourselves. That’s where I want us to try to dig in this week.
Why do you feel like you’re missing this?
Why do you believe you need it in the first place?
How do you think your life would be different if you weren’t missing this? What has informed that view?
Is this something you had before and lost, or something you never experienced before? If the former, how did you lose it? How might it be different now?
If you realized these things, what would it mean for you?
This Week’s Jam: Purple Rain
Not a song this week, but an entire album. THE album in fact. One of the few legitimate no skips to ever exist.
This weekend we mark the 40th anniversary of the release of the Purple Rain film.
How could I pick one song? It’s like picking your least favorite finger to cut off. Put it on. Bask in it. Bathe in it. Enjoy it.
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See you next week!