7 Journal Questions for a more Intentional Life

Living On Autopilot

I’m sure you have heard that one of the most common regrets people have at the end of their life is not living out their dreams. Why do you think this happens? Could it happen to you?

I think the reason it happens is a little sneaky. People slip into autopilot mode. Have you ever been there? Are you there now?

I remember once years ago, I was driving into my office in downtown Cincinnati and watching all the cars crossing over the bridge and those on the interstate below it and thinking that we all looked like a bunch of ants headed into the main hive. Day in and day out we do this work thing, and somewhere along the way trying to manage this, family and our health, we lose track of what we are working so hard for in the first place. Our dreams fade. We forget about them. We lose them. Do you have a clear vision of the dreams you are working on today?

I can’t tell you how many people have told me they don’t have dreams anymore. Or that they are too old to dream, which is just not true. As a life coach, I’ve helped countless people go from feeling like this, to being excited about their life again. Sometimes we just lose our way.  

What if I told you that asking yourself specific questions can shake you out of the autopilot routine and unlock a future so compelling, you’ll actually want to jump out of bed in the morning? If you’re ready for a positive shift and are open to getting real with yourself, that’s what these journal prompts will help you do.

Before we dig in, let’s talk about that autopilot feeling. It isn't just a slump; it’s kind of a quiet warning. It’s what happens when you begin to feel like life is happening *to* you, instead of you intentionally creating your life. You get so buried in the daily grind, and what people expect from you that you miss asking yourself, "Is this actually the life I want?"

The problem with autopilot isn't just boredom. It’s that you are missing out– on the little joys, opportunities for growth, and your bigger purpose. On autopilot, years later you’ll be in the exact same spot.

Now please don’t take this as a reason to beat yourself up. This is more about realizing you have the power to grab the steering wheel of your life again. It all starts with asking yourself better questions. This is because we learn from more than just experience; we learn from *reflecting* on those experiences.

Question #1 No Fear

Not surprisingly the first question has to do with fear. 

If I had nothing at all to fear, what would I do?

Seriously, think about this. If the fear of failing, being judged, of the unknown—all disappears, what would you go for? What would you allow yourself to consider? This question has so much power because it instantly whispers to what you *really* want, deep down, under any self-doubt.

Fear helps us stay safe, but you have to get outside your comfort zone for growth and cool things to happen. So, what would you do? Write that book? Learn a new language? Maybe even move to a new country? 

And don’t get caught in the trap of making excuses for why it’s not possible. If there’s one thing I’ve learned in my lifetime, it’s that so much of what we think is impossible for us, just isn’t true. Time and again,I find that life surprises you.  Time, money, connections–I know these feel like real roadblocks, but most of the time, if you set those aside for a moment, you'll find a layer of fear holding you back.

Write down everything that pops into your head, no matter how wild it sounds. This helps get your brain unstuck and open to more possibilities than what you can currently see.

Question #2 The Lottery

You’ve heard it before, but it’s a classic for a reason:

If you won the lottery tomorrow–millions of dollars–what is the first thing you would change about your life?

Notice I didn’t ask what you would buy. This is about what you would do. How would your day-to-day life look different? This is a smart question because it removes the financial roadblocks in your mind. It’s how you can see what truly lights you up when you have more than enough money to do whatever you want. 

Would you quit your job? If the answer is an immediate "yes," what does that tell you about your career? Would you travel somewhere? Would you pour your time into a cause? Or maybe you would spend your days learning, or creating, or hanging out with the people you love? There is no wrong answer here.

The point is to figure out what you truly value. If your first thought is, "I'd finally have time to paint," the lesson isn't that you need millions so you no longer have to work. It’s that you need to make time for painting in your life *right now*. The lottery is just a trick to help you figure this out.

Question #3 - The Regret Test

This one delivers a huge dose of perspective:

When you look back on your life now, what would you regret *not* doing?

This is one of the most clarifying questions you can ask yourself. It slices through all the trivial stuff you worry about and forces you to focus on what is truly important to you.

Nobody’s last thoughts are "I wish I'd worked more," or "I wish I had a fancier car." They say they wish they had spent more time with the people they love, or took a big risk, or were more true to themselves.

So, what about you? What experiences would you regret if you missed out on them? Is it forgiving someone? Reconnecting with someone? Running a marathon? Seeing the Northern Lights? Again, no wrong answers.

When you answer this on paper it creates a sense of urgency—not that you have to do something right away, but to begin doing the things need to do to make this happen. It helps you figure out the difference between what you feel you "should" do and what you know you "must" do to make this one precious life truly complete. 

Question #4 - The Inner Child

Let's lighten things up a bit now and think about rediscovering a part of you that’s probably been ignored for a while: What did you love doing as a kid that you've completely forgotten about?

Go back in time–before you were making smart career choices and taking care of other people. What did you love to do just for the fun of it? What did you dream about being? A writer? An artist? A detective?

Our childhood passions are often the purest reflection of what we find really fascinating. That part of you can get buried under responsibilities. Maybe you loved building elaborate LEGO cities—that could hint at a hidden passion for creation or design. Maybe you were always writing stories in a notebook–a sign that there's a storyteller in you waiting to come back out.

This isn't about quitting your job to do something entirely different. It's about finding the *essence* of those childhood dreams. What were they really about? Adventure? Helping people? Creativity? Freedom? Once you figure that out, you can figure out how to bring that into your life today. Maybe you don’t fly to the moon, but you could easily take up stargazing. Those childhood passions that still linger can be given new ways to be explored.

Question #5 - The Growth Filter

This next one is a good gut check for future goals.

Will this choice help me grow stronger, more capable, or more confident?

This shifts your focus from just being about what makes you happy to being about purpose. Think about the things you've already written down—and run them through this filter.

Traveling to a new country as an example would be fun, but it could also make you more confident and independent. Starting a side hustle might make you some extra cash, but it also will teach you new skills and boost your confidence.

This question pushes you to choose the challenges that help you evolve into your best version of you. It turns a bucket list into a roadmap for actually being the person you aspire to be. Lasting fulfillment doesn't come from just achieving goals; it comes from who you become along the way.

Question #6 - The Perfect Day

This next one is more like a visualization exercise.

What does your perfect *average* day look like?

Not when you are on vacation or doing something special. I’m talking about your ideal weekday. From the time you wake up until your head hits the pillow at night, what does that day look and feel like?

Are you up early in the morning, or do you sleep in? What's the first thing you do? What activities fill your day? What do you do for lunch? Who do you share your evening with? How do  you unwind? What brings you peace?

Try to get really specific. This process is so powerful because it helps you zero in on the small, daily habits that actually create your happy life. You might realize that your perfect day involves a quiet morning walk, an hour of reading, or a home-cooked dinner with family.

Once you see these things, you can start asking, "Okay, how can I sprinkle a little more of that into my life *right now*? You may not be able to quit your job tomorrow, but perhaps you can start making time for these little things that will bring you joy. This is how you build a life you love—one perfectly average day at a time.

Question 7 - The Legacy

Our last question zooms all the way out:

What impact do you want to leave behind?

This beckons you to think beyond your own happiness and consider how your life touches other people. How do you want to be remembered? What mark do you want to leave on your family, your community, or even the world?

This isn’t about being someone famous. It's more about the impact you have on others. Maybe your legacy is in the kindness you show to strangers every day. Maybe it's raising kids who are compassionate and resilient. Maybe it’s knowledge you share, art you create, or the community garden you help with.

Thinking about this gives you a strong "why" for how you live. It connects your small, daily efforts to a bigger purpose and allows you to feel the satisfaction of being involved in something that’s bigger than you.

Reframing Your Future

So, there you have it. Seven questions to completely reframe your future. Make an intention to ask yourself these maybe once a year or whenever you feel that autopilot mode creeping in. 

And if you want to go deeper and give yourself even more ideas for things that you want to experience in this lifetime, you’ll want to check out the free downloadable I made to help with this, “The Ultimate Guide to Creating Your Dream Bucket List”. This guide will help you create a robust list personalized to you–that will help you create a roadmap that will help you truly thrive throughout your lifetime.

I want to reiterate that It’s smart to ask yourself these questions from time to time, as over the years we all change and our dreams change too. That’s part of what makes life beautiful. And that’s why I created this channel. In sharing the ways that I am striving to live more intentionally it helps keep me living more intentionally too, because without doing this kind of work, it’s easy to get stuck in a rut.

And if that’s where you feel like you are now, let me remind you that you too can change things by living with intention. Your future is something you create by the little things you do each day.

Don't let this just be another interesting blog post. I challenge you to pick one insight you gained—just one—and then take one tiny step toward it this week.

If you’ve enjoyed these questions and plan to keep going with my bucket list guide, you also may want to consider creating a little solo retreat for yourself to help you find the mental and physical space needed to really connect with your heart. If you decide to do this, I have a great video on how to go about creating a solo retreat that you may want to watch as well.

Thank you so much for reading this and taking the time to work on being your best version of you. I hope this video has inspired you to take that one tiny step, because if you do it, I know you’re going to take another and another.