9 Deep Questions To Help You Figure Out What To Do With Your Life

Changing your life is a big step. Here's how to find the best path.

Last updated on Mar 29, 2023

woman with red hair and glasses standing against wall Mladen Mitrinovic / Shutterstock

If you're asking yourself, "What should I do with my life?" then you might be wondering how to change your life completely — but don't know where to start.

Maybe something is not right, maybe even downright toxic in your life. And you’re finally going to do something about it.

Or maybe you just know deep inside that it’s time to make a decision to “park it or drive it." To stay where you are or get moving in a new direction.


In order to figure out how to turn your life around, read on to find some deep questions to ask yourself. Your answers just might shine a light on the best path forward.

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Here are nine deep questions to help you figure out what you want to do with your life:

1. Am I making this change because I want to, or because I feel like I should?

This can be a biggie if you’ve had the voice of your parents or your high school counselor or (fill in the blank) in your head telling you what they believe your best prospects are.

Do you want to lead your life according to someone else’s expectations, or embrace your own unique path?

Make sure you’re not “should-ing” on yourself here.

2. How does my body feel when I envision this new life/work/direction?

Sometimes your brain can work overtime when you’re faced with a big decision. Considering the practical issues is certainly important, but don’t succumb to “analysis paralysis.”


Step back and listen to your body’s wisdom. Do you feel “sick" in the gut when you consider this next move? Or do you feel a spontaneous smile breaking out, and your heart expanding? Your body knows, even if your mind is muddled!

3. Is this change in alignment with my long-term goals?

If you’ve never sat down and come up with a five-year or ten-year plan, now would be a good time. There are plenty of books and websites that can take you through a process to help you articulate your future vision.

But really, just try tapping into your own imagination and ask yourself where you’d like to be in five, ten, or even twenty years from now. You’re certainly allowed to switch your direction at any point as life unfolds, but it helps to start with some idea of the destination, with milestones along the way.

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4. Does this change match my core values?

Your values are your fundamental beliefs, your deeply held ideas about how you want to be in the world. They guide your behavior and, like defining your goals, are a key factor when you’re faced with making a big life decision.

You can find lots of value listings online and use your intuition to pick the ones that most resonate with you.

5. How long have I been wanting to make this change?

If you’ve just read an amazing book or finished a life-altering self-discovery workshop last weekend that revealed your “true self,” that’s terrific. Just take time to consider all these other deep questions to be sure you’re not operating out of a temporary high.

Another good exercise is to look at what you wanted to do when you were younger but put it on a shelf because it wasn’t practical or convenient. In her book, Now What: 90 Days to a New Life Direction, Laura Berman Fortgang calls these “interrupted dreams” and they can be powerful indicators of your core values.


6. What will be different in my life?

Another way to think about this question is to ask what you’d gain or lose if you take this step. Take time to consider what you’ll be leaving behind, both what you’d be happy about and what you’d miss.

Doing this assessment before you make your change so you can be prepared for the “Holy crap … what have I done?!” moments on the other side is incredibly important.

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7. Do the benefits of making this change outweigh the risks?

This is the logical next question. It’s where the pros and cons checklist comes in. Get specific and realistic — you’ll have a fabulous new job, but the pay may be lower. You’ll finally be out of your unsatisfying relationship but have to negotiate the singles scene again.


Then widen your perspective and tune into your body again. Is there a sparkle of anticipation or excitement as you consider the risks? Or is the overwhelming feeling one of dread and heaviness in the pit of your stomach? You’ll have a better chance of success on your new path if your whole system — body, mind, and spirit — are all on board.

8. Will I be happy I made this change 10 years from now?

Here’s where you really want to call on your “wise self.” Life balance expert Renee Trudeau describes this as “Your soul, your intuition, or a higher power that’s always waiting and ready to respond with wisdom and deep compassion.”

Imagine that older, wiser self is writing a letter to you. Where might you be at that future point in your life as a result of the decisions you’re making now? What would she/he say to you about your choices? Really let go and write down whatever comes to you, without judgment or self-criticism.


9. What happens if I do nothing?

After all of this, there’s a real possibility that staying right where you are is the best decision you can make in this moment. Maybe it’s just not the right time, but you have more clarity about the things you can do to prepare for when you do get moving.

Or maybe you’ve discovered through this process that an attitude adjustment is in order. What could you do differently to make your present situation more manageable, even enjoyable? Do you need to set stronger boundaries or make some specific requests of your boss or partner? Sometimes you can turn your life around by staying in the same place and shifting your inner conversation and intentions.

Whether you decide to completely change your life, or just make a course correction, you’ll definitely want to take time to ask these deep questions before you take the leap. Carve out a quiet space for yourself and ask your wise self to join you … remember that voice is always there, it just needs an invitation and a little less noise to be heard.

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Deborah Roth is a career/life transition coach, relationship coach, and interfaith minister with over 35 years of experience coaching, training, and speaking.