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Daily Prompts for Deeper Reflection

How often do you check in with yourself? That is, how often do you really check in with yourself, beyond I’ve done X and Y today. I need to do Z. I need to run such and such errand. And I need to pay such and such bill. How often do you ask yourself meaty questions—questions that excavate and unearth versus simply skim the surface?

It’s hard to find time to genuinely self-reflect. And of course it’s hard to ask ourselves hard questions. But it’s vital. After all, we can’t find a solution if we don’t identify or admit the problem. We can’t create the lives we want if we don’t name what it is we want. We can’t move forward if we don’t know the direction we’d like to take.

The Daily Stoic Journal: 366 Days of Writing and Reflecting on the Art of Living by Ryan Holiday and Stephen Hanselman has a collection of probing prompts that can lead us to important answers. As they write in the introduction, “Think of this journal as a brush for your own soul, just like brushing your teeth each morning and each evening.” Below are some of my favorite daily prompts from the journal, which can spark deep self-reflection:

  • What things are truly in my control?
  • What inessential things can I eliminate from my life?
  • Which of my possessions own me?
  • Which of my pleasures are really punishments?
  • Where can I show other people kindness?
  • How can I refresh my mind today?
  • Where do I need help? Who can I ask for it?
  • Am I protecting my time and attention?
  • What painful things can I take responsibility for?
  • What can I learn from others—even the people I don’t like?
  • What do I feel when I look up at the sky?
  • Can I love everything that happens today?

After responding to these prompts, try to take action. It doesn’t have to be a grand, sweeping action. It can be a tiny step. Say no to a commitment or invitation that isn’t important to you. Unfollow the people on social media who don’t inspire you (and make you feel terrible about yourself)—since instead of refreshing your mind, it drains it, and highjacks your time and attention.

Make an appointment with a therapist. Do something sweet for a loved one or stranger. Recycle, donate or throw out anything that’s weighing you down. Start a creative project that is deeply meaningful to you. Look up at the sky every morning and night, and take along your journal. Spend tomorrow with the perspective that everything is lovable and lovely, including you.

Learn about stoicism, an ancient but very much applicable to today philosophy, at

Photo by Alexa Mazzarello on Unsplash.
Daily Prompts for Deeper Reflection

Margarita Tartakovsky, MS

Margarita is an associate editor at She writes about everything from taking compassionate care of yourself at any weight, shape, and size, to coping healthfully with difficult emotions. Her goal is to give readers practical, empowering tips to better their lives, and to remind you that whatever you're struggling with, you're never, ever alone.

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APA Reference
Tartakovsky, M. (2019). Daily Prompts for Deeper Reflection. Psych Central. Retrieved on October 31, 2020, from


Last updated: 27 Mar 2019
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