20 Questions for a New Season of You

Reflective prompts for self-discovery, emotional growth, and gentle transformation.

by Roslyn Ashford, LPC

The Season Is Changing — Are You?

Hi! I'm Dr. Roz

You have the power to make an impact in your life, career, and relationships. My goal is to help you unlock the path.

There’s something about Spring.
Maybe it’s the way everything slowly comes back to life — the trees, the light, even our own sense of possibility. April, especially, feels like a sacred threshold: not quite the beginning, not quite the end — but definitely a turning point.

For me, this time of year always stirs something deeper.
A quiet invitation to release what no longer fits, and reconnect with who I’m becoming.

If you’re feeling the same — maybe a little restless, stuck, or simply not as connected to yourself as you once were — you’re not broken.
You’re just in a new season of you.

And you don’t need to rush to change everything.
You just need a moment to pause… and ask the right questions.

Why Questions Help Us Grow

In seasons of personal change — whether subtle or seismic — we often look for the next right step.
But true transformation rarely begins with answers.
It begins with curiosity.

The right questions don’t pressure you. They soften you.
They open space for truth, compassion, and clarity.
They help you hear the voice you’ve been too busy (or too afraid) to listen to.

Below are 20 carefully chosen questions to guide your growth in this season. Let them meet you where you are. Take your time. There’s no rush to bloom.

20 Questions for a New Season of You

🔍 Identity & Alignment

Who are you underneath the roles you’ve outgrown?

Reinvention often begins with a subtle misalignment — a feeling that the version of you the world sees isn’t quite the full picture anymore.
Maybe you’ve been the strong one, the responsible one, the one who keeps going. But now? You’re wondering if there’s more to you than what you’ve had to be.

Peel back the layers and ask:
What parts of me are still true — and what am I ready to release?

When I’m not performing or proving, who am I?
What do I no longer want to pretend to be okay with?
Where in my life am I shrinking or settling?
What version of me have I outgrown, even if I’m still attached to her?

🌱 Vision & Intention

What is your soul craving more of?

This is the season to ask not just “What do I want?” — but “What truly nourishes me?”

Sometimes our goals are inherited, our plans outdated, or our energy pulled toward things we never chose. These questions will help you clear the noise and get honest about what you want more of in your life — not just on the outside, but in how you feel on the inside.

This section invites clarity. Calm. And courage to name your deepest desires.

What kind of woman am I becoming — when no one is watching?
What do I want to feel more often in my everyday life?
What needs to be released for the real me to rise?
What does the most honest version of me crave right now?

🔁 Patterns

What cycles are asking to be broken?

Sometimes we don’t even realize we’re living on repeat.
These questions help you gently notice the loops — the thoughts, habits, and emotional reactions that may have served a purpose in the past but now keep you stuck.

This isn’t about blame. It’s about awareness. Because once you see a pattern, you can shift it.

What old stories or patterns am I still carrying that no longer reflect who I am?
What have I learned from the parts of my story I used to hide?
Where do I feel most disconnected from myself — and what might help me return?
What am I still doing out of habit, not alignment?

🔥Power

Where are you being invited to rise?

Personal growth isn’t just about healing wounds — it’s also about reclaiming your power.
Notice where you’ve been waiting — for permission, for clarity, for a perfect moment — and instead ask: What am I being called to step into now?

You don’t need to feel fully ready. You just need to say yes to what’s already rising within you.

Where am I being called to rise, even if I don’t feel ready?
What would change if I stopped waiting for permission?
What would I love to look back and thank myself for one year from now?
What’s one truth I’m ready to live out loud?

💖 Compassion & Becoming

What if softness is your superpower?

We often try to force our way into growth. But becoming doesn’t always come from hustle or fixing — sometimes, it comes from tenderness.

This is your permission to slow down, offer yourself grace, and recognize that you’re already transforming — not by doing more, but by being more present with yourself.

What do I want to be known for in this next season of my life?
How do I define success in this season — emotionally, spiritually, relationally?
What would it look like to meet myself with more grace and curiosity this month?
If I believed healing was possible for me, what would I do next?

Ready to Go Deeper?

You’ve opened the door with reflection — now it’s time to take your next step with clarity and care.

The 7 Steps to Start Your Healing Journey is a free guide I created to help you move from emotional overwhelm to grounded, supported healing. It’s not about rushing or fixing. It’s about gently reconnecting with yourself and creating a path forward that actually feels aligned.

Download the guide now and begin your healing journey with purpose, presence, and support.

A Powerful Start On Your Journey

Healing is often thought of as this big, complicated process that feels impossible to start — but it doesn’t have to be overwhelming.

The 7 Steps to Start Your Healing Journey is a simple, clear guide to help you begin, whether you’re taking the first step toward therapy or need guidance on how to heal on your own.

Manageable Steps toward Healing and Healthy Relationships

This free guide is a gentle, empowering starting point for anyone ready to move out of survival mode and into healing — but unsure where to begin.

Through 7 reflective, soul-honoring steps, you’ll learn how to reconnect with your emotional world, release what’s been weighing you down, and take the first aligned steps toward lasting change. By the end of this guide, you’ll feel:

More grounded and emotionally aware
Clearer about what’s been holding you back
Encouraged to take action — with support, not pressure
Empowered to begin healing on your own terms

Begin Your Transformation in three steps

Download the Guide

Start with a free, gentle guide that helps you reflect, reset, and move forward with clarity.

Reflect and Journal

Use the reflection prompts to tune into your needs and begin the healing process — one small shift at a time.

Walk Away with a Strategy

You’ll have a clear, personal roadmap to help you take action that fits your life.

You’re not alone on this journey

We understand how isolating it can feel to face life’s challenges. This workshop offers a compassionate space where you can explore self-discovery and healing with others who understand your struggles. Trust us to guide you with wisdom and care. Our approach combines empathy with expert guidance, ensuring that you feel supported every step of the way. With nearly two decades of experience, we know how to empower you to reclaim your emotional well-being.