12 Questions to Help You Design the Life of Your Dreams


It’s time to live life on your terms. These questions can help.


^one thing that’s part of my dream life- lots of time at national parks with my hubby!

I know firsthand what it’s like to dream of living a different life… only to find out that I’m not exactly sure what *I* want out of life.

It’s easy to look around at what other people are doing and think, “Yes! I want that, too!”

As Gretchen Rubin says in Life in Five Senses, “We can build a happy life only on the foundation of self-knowledge.”

It takes a lot of courage to get to know yourself well enough to live a life that other people might not understand, but that brings you great joy.

So if you need some help getting clarity on what kind of life you want to live, I have some questions that can help! (And by the way… They should work whatever stage of life you’re in.)

If you like to journal, now’s the time to grab your writing elements of choice (I’m partial to my sketchbook or a bullet journal, but you might prefer your phone, a legal pad, sticky notes, or the wall of a cave- who am I to decide for you?).

In any case, ask yourself any of these questions you like (different ones will be helpful depending on what you’re trying to decide):

What Drives Me?

Another (slightly problematic) way to say this: what would I willingly skip a meal or sleep for if I meant I got to do more of it?

And please don’t say “Taylor Swift tickets.” I love Taylor, but nobody has a meaningful life if the only thing they’re passionate about is a fleeting event.

Now, please hear me loud and clear- I don’t want to encourage you to lose sleep or food.

But, what’s something that keeps you going? Something that makes you wake up most mornings with a smile on your face?

If you’re driven to do it, and you would be even if you weren’t getting praise or attention from anyone else, chances are it’s something that needs to be part of the life of your dreams.

When Do I Feel Most Alive?

The last question forced you to focus on something that is part of your daily life (or that you wish was!). This one could very easily be the opposite. After all, one can’t go around feeling “the most alive” every second of the day.

But… I think most of us could stand to feel really, truly alive a little more often than we do.

What are the things that make you catch your breath with wonder?

What are the things that leave you feeling exhilarated?

Once you know the answers to these questions, brainstorm some ideas for how you can incorporate more moments like that into your life.

Do I Like What Success Looks Like Here?

I first heard this question from Sahil Bloom in his newsletter, who learned about it from Cory Wilks.

It’s a great question to help you determine if something that’s currently part of your life needs to be there long-term. It’s also helpful in determining how much effort, attention, and energy you should give something.

If you achieve all the success your job has to offer, does the idea of that make you happy?

If that side hustle you’re running explodes, do you want to go full-time?

If you married your current s/o, do you think that’d be a good marriage?

If the answer is yes, then by all means work the extra hours or invest more time in that relationship, or whatever it is you’re doing.

But if it’s no… Make appropriate decisions on how to allocate time based on that.

(And, in the case of relationships, it’s probably best to make sure your partner is on the same page)

What Kinds of Relationships Do I Wish I Had?

This can be any kind: romantic, platonic, professional…

Where do you see gaps, and what steps can you take to fill those gaps?

For me, personally, I see a couple of gaps.

One is a big one professionally: I need to find a mentor. Thankfully, there are gov agencies in my state that provide coaching for entrepreneurs, so I’m going to check that out. There are also a lot of amazing coaches and courses out there on professional development topics, so I can use some of those to fill in the knowledge gaps… But I would really like to have someone with experience in my corner.

Another: I’d like to meet more local friends. Our church family is amazing, but we don’t really have a ton of friends outside of church. I’d love to join a club or do something on a regular basis that gets me out of the house and making new friends. My husband is ahead of me on this: he’s already made some new friends by playing basketball every week and going to local board game meetups.

What Words Would I Want People to Use to Describe Me?

I got this idea from Andy Stanley’s talk on Winning at life. Can you think of 3-7 words that you’d like people to think of when they think of you?

Once you can, think this part through: what are some small things I can do, today, to live according to those values?

What’s Currently Holding Me Back?

If you feel stuck on what changes you want to make in your life, this can be a helpful question. It can also be a hard question if, like me, you tend to assume that either nothing is your fault or everything is your fault. That kind of thinking isn’t very helpful, and it’s also just plain wrong.

When I find myself in these situations, it’s usually best if I use the 50/50 rule (which is a name for it that I just made up). It goes like this:

When trying to assess something that’s gone wrong in my life, I’ll start out by assuming that I’m 50% responsible for it. For the other 50%, I’ll assume other forces are at play.

The 50/50 Rule

This helps me take a balanced view:

How was I at fault?

What other things contributed to this?

And then, only once I’ve considered the possibilities, can I decide if I want to shift the percentages.

When you’re trying to figure out what’s holding you back in life, this can be a really helpful tool.

To truly become the person you want to be, you’re going to have to look inside sometimes and face the things you don’t like.

But, you’re also not the commander of the universe. Chances are, there are circumstances in your life that are holding you back right now. What are they, and what can you do to eliminate or change them?

Who Can I Ask for Help?

*Gulp* This is a hard one for me.

I hate asking people for anything. Maybe it’s because I’m an older sister. Maybe it’s because I’m from the Midwestern United States. Maybe it’s because I drink a lot of tea and spend too much time pondering how powerfully I’d have to feel about freedom in order to dump a bunch of it into the Boston Harbor when asked. Whatever it is, I have a strong sense of independence and the desire to not need anything from anyone, ever, to match.

But, that’s not really how life works, is it?

If you have some ideas about what the life of your dreams might look like, who can you ask to help you get there?

You don’t need to (and probably shouldn’t) ask them to hand your dreams to you on the silver platter.

But you could ask them questions like:

  • How did you get your job?
  • I’m interested in going into the same field as you- could you give me some advice?
  • How have you kept your marriage strong?
  • What’s something you wish you’d known when you started your business?
  • I’m trying to get some experience in [a skill]. How did you first learn?
  • Do you know if your company has any internships coming up?
  • What kind of books would you recommend I read if I’d like to grow in this area?

What Kind of Friend/Spouse/Parent Do I Want to Be?

This question can help you set your priorities.

If you don’t know how you want to show up in the most important relationships of your life, chances are you won’t show up much at all.

I’m not criticizing- I struggle with this as much as anyone. We all live busy lives. We all have different levels of energy.

But it helps to know who you want to be so that you can decide when and what you want to do for the people you love.

If Money and Schedule Weren’t Considerations, What Would I Want to Do Tomorrow? Next Month? Next Year?

This is a spin on a question that set me on my entrepreneurial journey, which I read in Amy Porterfield’s book Two Weeks Notice.

It’s so helpful, and here’s why:

A lot of times, we let practical considerations dull our dreams.

It seems silly, because aren’t dreams supposed to be a little far-fetched?

Well… yes. But we’re so quick to turn them into goals. As a result, we limit ourselves. We dream small dreams and wake up feeling just the same as we did before we chased them.

No more.

Let your imagination run wild for a little bit.

Give yourself permission to dream things you think are impossible.

They might not come true, but you’ll have a better vision than ever before.

What’s Something I’ve Never Tried but Always Wanted to?

Trying new things does two things: it gives you a chance to grow, and it helps you rediscover what’s fun for you.

Both of these elements are crucial to living a fulfilling, joyful life.

So every once in a while, it’s helpful to dig deep into your memory bank, then get out there and try something new.

What Did I Dream of as a Kid?

This will help you get in touch with yourself a little bit more. There are probably plenty of things that you loved as a child that you no longer love- but there are also probably plenty of things you’ve forgotten or abandoned along the way that you would still enjoy.

Here are some things I’ve remembered, that I still LOVE as an adult:

  • Curling up with a captivating book
  • Collecting colorful little trinkets
  • Painting, drawing
  • Most crafts, really
  • Cuddling something fluffy (pets, stuffed animals)
  • Putting around in the garden
  • Learning things about plants and animals
  • Calming myself down by singing

I could go on. Are all of these things part of my dream life? Maybe not. But knowing they exist can help me think of ways to spend my days that are proven to bring me a lot of joy.

What Would I Do if I Were Brave?

I’m partial to this question because seeing it in my Full Focus Planner is actually what inspired me to tell Andrew that I liked him, setting off a chain reaction that’s resulted in being married to the man of my dreams.

It might not work out that way for you- but that’s okay.

The important thing is that you know what you’d do if you were brave. And then, you decide if it’s the proper time to muster your courage & DO IT! (If it’s not, ask yourself this follow-up question: what would it take for me to get there?)


These questions are designed to help you imagine the life of your dreams. It’s okay if you don’t know how you’ll get there yet- the first step is knowing what’s truly important to you.

Now, if you’re ready, let’s take little steps toward making that a reality. ❤️

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