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If you do a Google search for “self-development questions” you’ll find pages and pages of “top-30” or “top-100” lists that become overwhelming really, really fast. 

What if all you needed to ask yourself was one question? Can one question chart the course of your future? 

Would You Choose This Again?

Wherever you are in your life, you’re there because of the choices you made. After all, the only person or thing you can control is you—not your circumstances, environment, or other people.


Looking at your life as it stands, ask yourself: “Would I choose this again?”

Your answer determines what your self-development will look like in the future.

If Your Answer is “Yes”

You seem like you might be on top of things. Even if your past was full of difficult situations and choices, you recognize that those decisions shaped you into the person you are today—a person you enjoy being.

Answering “yes” means you are probably self-aware and sure of yourself and your ability to get through the hard parts of life. It means you have the ability and practice of extracting the lessons from any mistakes you made. That, in fact, is one of my 10 Guiding Principles of Life.

What does this answer mean for your future?

You probably know where you want to be, and you understand that there will be obstacles, setbacks, and pivots along the way. Those are normal. Because you know how to extract lessons from your experiences, you’re already well-prepared to keep chugging through life without the uncertainty that you’re on the “right” path.

You probably already regularly ask yourself self-development questions intending to better understand yourself and what you want out of life.

If Your Answer is “No”

Despite what you may think, you’re in an excellent position with this answer. You may have gotten to this point in your life thinking that if you could go back and change things, you’d jump at the chance.

I’ve thought about doing that. There were times that I wished I could go back and shake younger me by the shoulders, telling her to avoid such-and-such, do this-and-that, and reassure her that life is not supposed to be easy.

Knowing that you wouldn’t choose this again also means you have a measure of self-awareness. You recognize that you made choices that you perhaps now regret. For tips on how to let go of regret, check out this post.

What does this answer mean for your future?

Again, you’re in a great position. You know exactly the kinds of choices you regret making in the past, which means you’re primed to avoid making those same choices again. Answering “no” leads you to think about what you don’t like about your present. This leads you to think about what you want to change going forward. This simple progression ends up leading you onto the path you wish you’d started out on in the beginning.

If Your Answer is “Maybe” or “I Don’t Know”

Honestly, I think this is a cop-out answer. If you truly have no idea if you’d choose this life again, then you would benefit from some serious self-reflection beyond the original question. For you, those lists of 30 or 100 self-development questions might be worth the time investment to go through and honestly answer each one.

You might just be overwhelmed by shiny object syndrome, meaning you chase after things when they show up but suddenly switch paths because something shinier popped into your line of sight. The result is confusion, exhaustion, frustration, and the feeling of aimless drifting. 

What does this answer mean for your future?

That you need to do more self-searching! For this answer, I recommend picking up Simon Sinek’s book, Start With Why.

Find more books and resources in the Inspired Forward Shop.

Are you overwhelmed by long lists of self-development questions that will take ages to work through? Ask yourself this one question instead.

Bonus Questions, Because Why Not?

You didn’t really think I would keep this to just one question, did you?

Asking “would you choose this again” is probably the most important self-development question for you to ask, but if you’re hungry for more things to consider, consider these.

If Worry and Fear Didn’t Exist, What Would Be Different?

Humans seem to be natural worriers, but worry goes directly against God’s directions for us.

Brooke Castillo, the Master Coach Instructor at The Life Coach School, eliminated worry from her life. Every time she notices her mind going down the worry path, she redirects her thoughts to something else.

This sounds like an amazing change to make. I hate worrying. I hate having the feeling of fear that stems from my top fear archetypes of people pleaser, procrastinator, and rule follower.

Let’s do a thought exercise. If you want to write down your answer, grab a pen and paper now.

It’s okay, I’ll wait.

Got it?

Imagine the thing you fear most… Simply disappearing. Gone. Doesn’t exist. Never has, and never will. It does not affect you anymore. What does that feel like? Write it down. Did a weight lift from your chest? Can you suddenly breathe easier? Maybe your thoughts are a little confused about what to think about now?

Another way to identify and push specific fears away is to practice what Tim Ferriss calls “Fear Setting.”

It’s okay if the fear comes back. It will take practice to keep it on the sidelines.

Now I want you to do the same thing for worry. Everything you worry about—the worry is gone. Worry doesn’t serve you. It makes no difference in the outcome.

Worry pretends to be essential… So why do we treat it like it is?

Would Future You Be Proud of What You’re Doing Right Now?

This question is closely tied to our foundational question, “Would you choose this again?”.

Here’s why:

Current (or Present) You is “Future You” to your past self. As a thought exercise goes, this one is straightforward. If you’re not proud of what Past You did, and you have changed nothing to alter that opinion for the next iteration of Future You, then Future You will never be proud of what you’re doing.

You’re shooting yourself in the foot by paying attention only to the present.

Why are we all told relentlessly to save for retirement? To keep an eye on our health? Take care of ourselves? Invest in ourselves? To practice self-care?

Because all of these things, though some may be uncomfortable in the now, serve the interests and benefit of our future selves.

Future-focused people are the best-prepared people.

Will Future You be proud of what you’re doing now?

Are you going to let fear and worry hold you back?

Would you choose this life again?

The Next Step

Are you struggling to figure out the answer to this question, or the answers to any other self-development questions? Consider booking a free 1-hour consultation to discuss how life coaching could be the key to unlocking your future.

About the author 


Life & mindset coach, writer, host of podcast This is Type 1: Real Life with Type 1 Diabetes, and full-time analyst in the power industry. I'm passionate about showing people that how we think determines our realities.

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