50 Writing Prompts to Help You Decide If You Need a Massive Change in Your Life

Here’s the thing: making big life changes can feel like you’re standing at the edge of a cliff, unsure whether to take the leap or back away slowly. Whether you’re considering switching careers, transferring schools, leaving a relationship, or uprooting your entire life to move to a new country, decisions like these are never easy. I’ve been there—more than once—and every time, it felt both thrilling and terrifying. The trickiest part often isn’t making the change itself, but figuring out if you even need to make it in the first place.

I’ve faced some pretty big shifts in my life. I transferred schools after my sophomore year of college, and while it turned out to be one of the best decisions I ever made, it didn’t come without a lot of self-doubt. I constantly wondered if I was making the right choice or if I’d regret leaving. And in high school, I switched schools for a semester only to realize it wasn’t the right fit, so I went back. So yeah, sometimes we make a change and find out it wasn’t the right one—but that’s part of the process. You learn as you go.

Then there’s my husband, who walked away from a steady, secure job to start his own freelance creative business. That leap wasn’t easy either, but it taught me just how much courage it takes to step into the unknown. Now, we’re facing an even bigger life decision as a family, considering a move to another country. It’s exciting, nerve-wracking, and full of questions. And if you’re like us, you know these decisions impact more than just you—they shape your family, your future, everything.

The truth is, change is uncomfortable. It’s messy and full of uncertainty. But staying stuck can be just as unsettling. We all reach those moments where we question whether the path we’re on is still the right one or if it’s time to make a shift. The hard part is figuring out the answer. That’s where reflection comes in. Journaling has always been one of my go-to methods for working through big decisions. Writing helps me confront what’s really going on in my mind, and it can do the same for you.

So, if you’re standing at the edge of your own decision, wondering whether to leap or stay, these 50 writing prompts are designed to help you dig deep. They won’t make the decision for you, but they’ll help you uncover what’s driving your thoughts and feelings. Grab a pen, settle in, and start reflecting. You might just find the clarity you need to take the next step.

50 Writing Prompts for Deciding on a Massive Life Change

1. What is the biggest reason you’re considering making this change?
2. What are you hoping to gain from this change?
3. What is your biggest fear about staying where you are right now?
4. What is your biggest fear about making this change?
5. What does your gut tell you when you imagine making this decision?
6. Have you ever made a big decision like this before? How did it turn out?
7. What’s one thing that excites you about the possibility of making this change?
8. What do you think you might regret if you don’t make this change?
9. What will your life look like in five years if you don’t make this decision?
10. What will your life look like in five years if you do make this decision?
11. What are the potential risks of making this change, and how could you manage them?
12. Who are the people in your life whose opinions matter most to you regarding this decision, and why?
13. Are you more afraid of failure or of missing out on an opportunity? Why?
14. What is the best possible outcome if you make this change?
15. What is the worst possible outcome if you make this change?
16. What would you tell a close friend if they were considering a similar life change?
17. What emotions come up when you think about making this change?
18. Are you feeling pressured by external factors to make this decision? If so, what are they?
19. What are you willing to sacrifice to make this change happen?
20. What are the non-negotiables in your life that this change must support?
21. What are the current barriers that are stopping you from making this change?
22. How will this change impact your daily life, both positively and negatively?
23. What lessons did you learn from the last big decision you made?
24. How do you think making this change will affect your mental and emotional well-being?
25. What would your ideal day look like after you’ve made this change?
26. How will this decision impact your closest relationships?
27. How will you feel six months from now if you decide not to make this change?
28. Are you staying in your current situation out of comfort, fear, or something else?
29. What are you most afraid of losing if you make this change?
30. How does your current situation align with your long-term goals and values?
31. What would making this change teach you about yourself?
32. How do you handle uncertainty and risk, and how can you manage it if you move forward with this decision?
33. What are the best things about your current situation, and are you willing to leave them behind?
34. What is the worst thing that could happen if this change doesn’t go as planned?
35. How do you imagine your future self looking back on this decision?
36. What’s holding you back from fully committing to this change?
37. How does your past influence the way you’re approaching this decision now?
38. What resources (emotional, financial, or practical) do you need to make this change successfully?
39. What part of your current life will you miss the most if you make this change?
40. How do you handle big changes emotionally, and what strategies help you stay grounded?
41. How will making this decision align with your core values?
42. Is this change something you’ve been considering for a long time, or is it a recent thought?
43. How do you feel about the possibility of failing or facing setbacks after making this change?
44. What is the smallest step you could take today toward making this change?
45. How does this change impact your sense of purpose or personal fulfillment?
46. What would happen if you did nothing and stayed in your current situation? Would you be okay with that?
47. If you had no fear or doubts, would you make this change immediately? Why or why not?
48. How can you prepare yourself emotionally, mentally, and physically for this change?
49. How will you know when it’s the right time to make this change?
50. After reflecting on all these questions, do you feel more confident in your decision? Why or why not?

So, if you’re at a crossroads, wondering whether it’s time to make a big move, whether that’s in your career, your relationships, or even where you call home, these 50 writing prompts can help you get to the heart of things. They won’t give you all the answers (I wish it were that easy), but they can help you get honest with yourself about what’s really driving your thoughts and feelings. Grab your journal, find a quiet spot, and let yourself explore these questions. You might not figure it all out right away, but sometimes, just getting your thoughts on paper is the first step toward finding the clarity you need to make the decision that’s right for you.