The Journey from Comfort to Courage: 9 Questions to Move Forward.
There comes a time when staying in the comfort zone starts to feel more limiting than safe. You might sense that you’re meant for something more, but the idea of stepping into the unknown can feel overwhelming.
The journey from comfort to courage isn’t about making reckless leaps — it’s about making intentional, brave decisions that move you closer to the life and work you truly want. It’s about recognising when familiar patterns are holding you back and daring to take meaningful action anyway.
These nine questions are designed to help you check in with yourself, build clarity, and ignite the courage you need to move forward with purpose and confidence.
1. How can I make this more successful than I ever dreamed and have fun doing it?
When you find yourself procrastinating, examine the emotions behind your avoidance. Are you experiencing self-doubt? Fear of failure? Concern about imperfection or judgment? These accumulated feelings can prevent you from starting or cause you to play small.
This is precisely the time to ask yourself this question, as I borrowed from personal development expert Tony Robbins: "How can I make this more successful than I ever dreamed and have fun doing it?"
This question works on two levels. First, it shifts your focus from fear to excitement by reintroducing the possibility of success. Second, it adds the essential element of enjoyment. Who says meaningful work must be stressful? The energy you bring to a task largely determines how you show up for it.
Remaining stuck in fear prevents you from doing your best work. However, bringing lightness and enjoyment to the process not only makes it more pleasant but also creates space for your creativity and unique perspective to shine through.
2. What thought would you need to believe for change to happen?
If you've paused progress toward a goal, this question can help restart your momentum. Perhaps you need to believe that you've successfully navigated challenges before and always found a way forward. Maybe you need to reconnect with confidence in your abilities and track record.
Or you may need to believe more deeply that you deserve this goal and are worthy of achieving it.
You might need to remember that current difficulties aren't permanent, and circumstances will evolve.
Whatever it is for you, identify and embrace the thought that will serve your movement toward action.
3. What thought would you need to forget for change to happen?
For forward movement, what mental story might you need to release? Can you remind yourself that past experiences no longer define you and that you now possess the skills and wisdom to approach things differently?
Do you need to let go of disempowering emotions like anger or self-pity that keep you in a low-energy state?
Can you identify outdated habits and thought patterns that continually hold you back?
If this question feels challenging, return to question #2—what do you need to remember to move forward?
4. Will this decision create nostalgia?
When faced with uncertainty in decision-making, ask yourself: "Will this decision create nostalgia?"
Will you look back on this experience with contentment and joy? Think about past decisions regarding travel or experiences you initially debated but now wouldn't change for anything.
Are you remaining on the apathy bridge simply because it's familiar and predictable? What if crossing the action bridge is the only way to create more meaningful memories?
This isn't limited to leisure experiences. Consider decisions like stepping into a new role or speaking up in a meeting with an unpopular but necessary perspective. Such bold actions can become catalysts for positive change, not just for you but potentially for an entire team or organisation.
This creates a different kind of nostalgia—moments you'll always remember as testaments to your courage.
Some decisions simply can't be made through rational analysis alone. Your heart offers a vital perspective that complements your logical thinking.
5. If you could get 10% of a friend's happiness, who would you invest in and why?
This brilliant question, posed by Warren Buffett, reveals what you truly value. Once you identify the person, explore why you chose them.
This exercise unveils a set of traits and values you can incorporate into your own life. Does this person always recall meaningful details, such as birthdays? Do they consistently make time to connect with their team on a personal level? These observations highlight areas where you might enhance your own approach.
The qualities we admire in others often reflect aspects of ourselves that are either present or dormant. If this person's happiness stems from dedicating time to creative pursuits, hobbies, or passions, consider whether you've neglected similar elements in your life.
What adjustments might help you cultivate comparable levels of fulfilment and joy?
6. Imagine you get to the stage you are aiming for. What will that look like?
When feeling unmotivated or uncertain about next steps, use this question to clarify your destination. Its power lies in creating a compelling future vision. A vivid picture of your desired future energises and motivates you in the present moment.
Like Waze, it's hard to know you've reached your destination until you put in the end point. If you haven't decided what 'there' looks like, how will you know you've arrived? What if you're living your best life but have been so busy focusing on what you don't have that you missed the bigger picture?
Remember, there doesn’t have to be a new title or material goal. It could be the confidence you bring into a room, the energy you carry, or the relationships you nurture.
Who do you want to become as you achieve what you desire?
7. What would I tell my best friend to do?
This deceptively simple question removes you from the emotional centre of the situation and allows for a more objective perspective.
We typically see solutions to others' challenges with remarkable clarity; this question lets you access that same clarity for your own situation.
A powerful variation: Write a letter to your mentor asking for advice, then answer as if you were them. You'll likely be surprised by the wisdom that emerges from within you.
8. What do I want more of?
This question invites reflection on what works well for you and when you're at your best. Do you crave more variety, deeper connections, novel experiences, greater stability, or increased certainty?
If personal growth is your priority, consider how to integrate it seamlessly into your existing routine. Perhaps listening to podcasts or audiobooks during your commute or workout would satisfy this need.
If you value connection, could you identify three to five people you haven't spoken with recently and reach out to check on them?
If presence and mindfulness matter to you, what specific practices are you scheduling to strengthen these qualities?
Once you've clarified what you want more of, deliberately incorporate these elements to fuel your action.
9. What do I want less of?
Knowing what drains you is as powerful as knowing what energises you.
Do you want less rushing, negativity, or people-pleasing? Less distraction or overwhelm?
Identify your biggest energy drains, and commit to small changes to reduce them.
Moving From Questions to Action.
Often, the distance between apathy and action is bridged by asking better questions. While crossing over won't always be easy—you'll encounter fear and discomfort along the way—these emotions are actually your ticket to meaningful change.
To recap, here are your nine bridges to action:
How can I make this more successful than I ever dreamed and have fun doing it?
What thought would I need to believe for change to happen?
What thought would I need to forget for change to happen?
Will this decision create nostalgia?
If I could get 10% of a friend's happiness, who would I invest in and why?
Imagine I get to the stage I'm aiming for. What will that look like?
What would I tell my best friend to do?
What do I want more of?
What do I want less of?
Here's to crossing the bridge of action,
Warm wishes,
Lori