18 Really Good Questions to Ask Yourself When You’re Feeling Stuck

Keep them handy and refer to them often

Catherine Andrews
Published in
2 min readApr 26, 2021


Photo: Jon Tyson/Unsplash

As a writer and coach, I think a lot of people like my work because I ask really good questions. I once heard the concept of “asking high-quality questions to determine high-quality answers” and I dismissed it as self-help fluff, but I’ve found through my work with myself and others that honestly, it’s true.

So whenever I am facing sticky situations, or fearful ones, or when I find myself caught in a shame loop that threatens to take over, I return to this list of questions to remind myself, over and over again, that if I ask the right questions, I’ll find the right answers.

I offer these up to you today. Print them out, put them on a Post-it by your desk or bed, or stick it in your Notes app. Because sometimes, to get a different perspective on a situation that feels hopeless, a simple reframe from the right question can get you moving again.

  • Am I attempting to mind-read somebody else’s intentions in this situation?
  • How could I give myself what I’m hoping this other person will give me?
  • Is this thought arising from shame or fear? What is a thought I can have from self-compassion or hope instead?
  • Can I name three things I need right now?
  • Can I name three things I could let go of right now?
  • Can I figure out a way to make this 5% easier on myself?
  • What answer feels easiest to me?
  • What if what felt right to me was actually right?
  • Who may be benefiting from how I am thinking or feeling right now?
  • Is there a way I am protecting myself by continuing to believe or act this way?
  • Where is this situation reflecting some hurt inside of me, and how can I tend to that hurt?
  • Where am I feeling this in my body? What wisdom does that sensation have to tell me?
  • If nobody was watching or judging me, what decision would I make?
  • What would five-years-down-the-road-me tell me to do?
  • What would it look like to trust?
  • Would this decision make my life bigger or smaller?
  • Is it true? (hat-tip to the great Byron Katie)
  • Do I want to keep thinking this thing? Why or why not?



Catherine Andrews
Writer for

Teaching awakening + healing through vulnerability + self-compassion. Finding hope in a messy world. Author of the Sunday Soother. http://catherinedandrews.com