Self-Assessment Questions
Gentle, thought-provoking questions to help you understand your relationship with writing and discover what feels right for your journey.
There Are No Wrong Answers
These questions aren't a quiz — they're a quiet check-in. No pressure. Just honesty. Take your time, and remember that your answers might change as you grow. Some questions might not apply to you right now, and that's perfectly okay.
Am I Ready to Start Writing?
Exploring your readiness and motivation
What draws you to the idea of writing?
Common responses include:
- "I have stories in my head that feel like they need to come out"
- "I want to process my experiences and emotions"
- "I've always loved reading and want to create something myself"
- "I want to help or inspire others through my words"
- "It feels like something I'm meant to do, even if I can't explain why"
- "I want to preserve family stories or memories"
Reflect:
Your reason doesn't have to be grand or noble. Even "I'm curious" or "it sounds fun" are perfectly valid motivations.
What does "being ready" mean to you?
Many people think they need:
- More time (the perfect schedule)
- Better writing skills or education
- A clear plan or detailed outline
- The "right" equipment or software
- Permission from someone else
- Certainty about where it's leading
Consider:
What if readiness isn't about having everything figured out, but simply about having curiosity and a willingness to begin?
When you imagine yourself writing, what do you see?
People often envision:
- Writing in a cozy café with a cup of coffee
- Having a dedicated writing space at home
- Working on a laptop in bed or on the couch
- Handwriting in a beautiful journal
- Writing late at night when the house is quiet
- Stealing moments throughout a busy day
Remember:
Your ideal writing environment might be different from what you see in movies or on social media—and that's perfectly fine.
What's My Writing Why?
Understanding your deeper motivations
If you never shared your writing with anyone, would you still want to write?
This reveals whether you write for:
- Internal satisfaction and personal growth
- The joy of creating something
- Processing thoughts and emotions
- External validation and recognition
- Connection with others
- Professional or financial goals
Both are valid:
Writing for yourself and writing to share both have value. Understanding your primary motivation helps guide your approach.
What would you regret more: trying to write and "failing," or never trying at all?
This often reveals:
- How important writing feels to your sense of self
- Whether fear of failure is holding you back
- If you're more motivated by possibility or security
- Whether perfectionism is a barrier
- How much you're willing to risk for growth
Remember:
"Failure" in writing is often just learning in disguise. Every published author has a drawer full of imperfect early work.
When you read something that moves you, what do you think?
Common reactions:
- "I wish I could write like that"
- "I have a different perspective on this topic"
- "I want to create something that affects people this way"
- "I could never write something this good"
- "This inspires me to try writing myself"
- "I have stories like this to tell"
Notice:
Do you feel inspired or intimidated by good writing? Both reactions are normal, but inspiration tends to be more helpful for getting started.
What's Holding Me Back?
Identifying and understanding your barriers
What thoughts come up when you imagine sharing your writing with others?
Many people worry about:
- "What if it's terrible and people judge me?"
- "What if no one cares about what I have to say?"
- "What if I'm not as good as I think I am?"
- "What if people think I'm being pretentious?"
- "What if it reveals too much about me?"
- "What if I fail publicly?"
Consider:
You don't have to share anything until you're ready. Writing can be private for as long as you need it to be.
Complete this sentence: "I'd write more if only..."
Common completions:
- "I had more time"
- "I knew what to write about"
- "I was better at it"
- "I had the right environment/tools"
- "I felt more confident"
- "I knew where to start"
Explore:
Which of these barriers are real constraints, and which might be fears dressed up as practical concerns?
What messages about writing did you receive growing up?
People often internalized messages like:
- "Only special/talented people become writers"
- "You need perfect grammar to write well"
- "Writing isn't a 'real' career"
- "You should focus on practical skills instead"
- "Creative pursuits are selfish or indulgent"
- "You need formal education to write seriously"
Question:
Are these beliefs still serving you, or might it be time to examine and possibly release some of them?
Where Am I in My Journey?
Assessing your current position and experience
What's your relationship with writing been like so far?
Common experiences:
- "I wrote as a child but stopped when life got busy"
- "I've always journaled but never tried 'real' writing"
- "I write occasionally but lack consistency"
- "I've never written creatively but want to try"
- "I write for work but want to explore personal writing"
- "I started and stopped many times"
Remember:
Every writer's journey is unique. Starting and stopping doesn't mean you're not "meant" to write—it means you're human.
What do you already know about yourself as a creator?
You might recognize that you:
- Work better in the morning/evening
- Need structure or prefer flexibility
- Thrive with deadlines or feel pressured by them
- Like to plan thoroughly or dive in spontaneously
- Need quiet or can work with background noise
- Process better by talking it out or thinking internally
Apply this:
How can you use what you already know about yourself to set up your writing practice for success?
If you've written before, what made you stop? If you haven't, what's kept you from starting?
Common reasons for stopping/not starting:
- Life transitions (school, job, family changes)
- Negative feedback or criticism
- Perfectionism and self-doubt
- Feeling like you "should" focus on other priorities
- Overwhelm about where to begin
- Comparison with other writers
Consider:
Are those same factors still present now? If so, how might you approach them differently this time?
What Support Do I Need?
Understanding your learning style and support preferences
How do you prefer to learn new things?
Different learning styles:
- Reading books and articles at your own pace
- Taking structured courses or workshops
- Learning from videos and tutorials
- Getting hands-on practice and feedback
- Learning through community and discussion
- Working with a mentor or coach
Apply this:
What kind of writing resources and support would align with how you naturally like to learn?
Do you work better with accountability or complete freedom?
Signs you might benefit from accountability:
- You procrastinate on things you care about
- You work better with deadlines
- You like sharing progress with others
- External structure helps you stay motivated
- Pressure makes you freeze up or rebel
- You prefer to work at your own pace
- You're self-motivated once you get started
- External expectations feel restrictive
Consider:
You might need different levels of accountability at different times. Start with what feels comfortable and adjust as needed.
What kind of community, if any, appeals to you?
Community preferences vary:
- Large, active online groups with lots of discussion
- Small, intimate groups where you can get to know people
- Local, in-person writing groups or meetups
- Quiet communities where you can observe more than participate
- Professional networks focused on craft and career
- No community—you prefer to work independently
Remember:
You can always start with lurking or minimal participation and increase involvement as you feel comfortable.