10 “GPS” Questions to Ask Yourself to Ensure Your Life’s On the Right Track

Questions to ask yourself about life when you’re unsure which way to take it—or just to double-check you’re not going the wrong way.

Finding Your GPS Signal

For much of my life’s journey, I’ve felt like the GPS of my Google Maps wasn’t working, like this:

Google maps screen lost and no GPS
Oh crap. Where do I go now?

Not knowing which direction to go, I played it safe. I followed others. I figured they—or at least whomever they’re following—must have a better signal than me.

This worked out ok for a while. But eventually, I got bored. I started wondering if I was headed in the direction that would make the most of my trip through life.

And that’s when my GPS signal started kicking in.

It turns out that asking the right questions is the trick. Doing so refreshes your map and double-checks if you are on the best route. And the better the question, the clearer the direction.

These are the 10 that have been working best for me so far.

Maybe asking yourself one or two of these questions will help you find your signal, too.

Google maps with full signal and a sense of direction thanks to asking myself the right thought provoking questions.

1. The Value Finder

“By describing what they can’t stand, people unintentionally divulge what they stand for,” writes Tony Schwartz. And knowing what you stand for indicates where you should direct your energy.

Working in that direction fuels the fire under your ass. And any progress you make will feel extra fulfilling.

How I’m Answering It

I can’t stand snobs who excel at fitting in rather than standing out then look down on anyone who acts differently. But I only stopped griping and started doing something about it when I began writing here on The Unconventional Route. Now that I’m working on values that I stand for—and against those I can’t stand—I feel like I’ve found my calling.

Related Question to Ask Yourself

2. The Problem Solver

A great life tells a great story. And every great story needs conflict.3Check out one of my favorite books that change your thinking, A Million Miles in a Thousand Years for more on this idea.

How I’m Answering It

Rather than let conflict find me, I’m better off finding a problem I’m eager to spend my life trying to solve.

As I’ve made clear in my corny but practical personal mission statement, my problem is the force of complacency. It holds us back from making the most of our trips through life, so I’m trying to find ways to overcome it.

Related Question to Ask Yourself

  • What’s your personal mission statement? Successful corporations all have them to guide their decisions and actions, and you’re the CEO of Your Life, Inc, so why do you think you can succeed without one?
Cover image for how to become a winner at life by defining it.
Time-out. How do I know if I’m “winning”?

3. The Strategy Setter

Good luck winning at anything if you don’t even know what “winning” means. Yet we tend to race around the game of life, shooting toward goals and hoping it’ll magically happen.

It may be worth taking a strategic time-out.

How I’m Answering It

By asking myself some more thought-provoking questions, I defined what “winning at life” means to me. For what it’s worth, here’s what I came up with:

Winning at life is putting on the best performance I can given my situation so that when my show’s over I feel like I had a blast, others are grateful for it, and my output continues to echo and inspire.

What’s your definition?

4. The Habit Starter

Your subconscious immediately answers this question for you.

Listen quickly because your conscious catches up soon after, makes excuses and rationalizations, and tries to convince you of something more comfortable but less impactful.

How I’m Answering It

My subconscious tells me, “Be more social.” I ought to work with other people more on my mission rather than hack away at it from behind a computer screen.

My conscious doesn’t like the sound of that. It invents excuses not to do so—e.g., “It’s such a pain in the butt to get people to commit these days.” Then it suggests alternatives closer to my comfort zone, like “Go for more walks” or “Take naps.” But those aren’t as impactful as my subconscious’ answer.

Related Questions to Ask Yourself

Your future self cover image of me and future me smiling and high-fiving
Earn a high-five, not a slap in the face, from your future self.

5. The Regret Minimizer

Anyone who says they don’t have any regrets in life is lying to themselves. They’ve painted or plastered over poor decisions from their past so they don’t have to feel bad looking at them.7Mistakes Were Made, But Not By Me, is an eye-opening read on how we delude ourselves. It’s also one of the top “sledgehammer” books that changed my thinking.

There’s nothing wrong with doing so. Rationalizing our mistakes keeps us from losing our minds to what-if-itis.

But it’s better to avoid making such irreversible missteps in the first place.

Consulting with your future self can help you do so.

How I’m Answering It

Old man Chris has tons of advice for me. Train for the “Centenarian Olympics.” Don’t fuss over anything he won’t remember. Focus on, amplify, and record the moments he will want to remember. The list goes on.

PS: Check out my post on how to be less selfish and more socially responsible with your future self for more on this.

Related Questions to Ask Yourself:

6. The Legacy Beginner

I don’t even know my great-great-grandparents’ names.

Some people do. That’s because their great-great-grandparents did something that left a legacy. They came to the New World, started a family business, created timeless artwork, wrote books, or whatever.9Or they have a descendent who ventured deep into the genealogy wormhole to recreate their family tree. But that’s beside the point.

How I’m Answering It

I want to be remembered as the crazy old ancestor who cracked the code for getting the most out of his life.

Whether I actually leave a legacy is beside the point. As long as I’m striving to do things that echo after I’m gone, I’m winning at life.10See again Question #3: The Strategy Setter.

Related Question to Ask Yourself

  • What do you hope people say about you at your wake?
  • If you’re younger and don’t want to be morbid, what do you want people to say about you at your wedding?
My 20-year-old self, whose opinion I should ask for perspective on my current life.
Would 20-year-old me be so excited about where I am today?

7. The Un-Settler

What our 20-year-old selves lack in wisdom, they make up for in optimism and ambition. They shudder at the thought of settling for a “comfortable” life that isn’t the best they can do. Asking for their input reminds us not to fall into ruts.

How I’m Answering It

“You work by yourself, sometimes with your wife, writing random ideas online?!?!?” is what he’d say. “WTF. And you haven’t come close to visiting 100 countries, bedding 100 chicks, having a few kids, and founding a huge company. You were supposed to have done that by age 30. Now you’re 35. Ouch.”

This wouldn’t bother me. His goals were misguided.11Or I’ve successfully brainwashed myself into believing so.

But I’m listening when he says, “You can do better than just a couple hundred thousand readers a month. Think bigger. Do more, cooler sh*t. Please.”

Related Question to Ask Yourself

  • If you could rebuild your life from scratch, what would be different?
  • If you were given three years paid leave to do whatever you want and guaranteed to get your current job back afterward, how likely is it you would take it rather than do something different?12From the story of my pretirement.

8. The Mind-Opener

Most of us have a hard time coming up with examples. This proves we’re not as open-minded as we think.

It’s easier on our egos to settle on “proof” that confirms our beliefs than look for and listen to evidence that indicates we’re wrong.13Check out one of my favorite books that change your thinking, Mistakes Were Made But Not By Me, for more on this. But doing so puts us on a slippery slope toward becoming a stuck-in-their-ways old person who life has passed by.

This brings to mind one of my favorite quotes:

“The man who views the world at fifty the same as he did at twenty has wasted thirty years of his life.”

Muhammed Ali

How I’m Answering It

I wrote a whole list of things I’ve changed my mind on in the comments of 9 Exercises to Try Today to Be More Open-Minded.

More recently, I’ve changed my mind about how I breathe. I used to think my broken nose was useless and breathing through my mouth was fine. Two books, Breath and The Oxygen Advantage, have convinced me otherwise.

Related Question to Ask Yourself

Trying to live the 100-millionaire lifestyle without the big bank account.
How can Kim and I live the $100-millionaire life without the big bucks?

9. The Priceless Life-er

You’ve probably heard some version of this question before. It’s a classic. A cliché, even.

And your answers are probably cliché, too:

  • Spend more time with loved ones.
  • Get healthy.
  • Quit my job to do something I love doing.
  • Blah, blah, blah.

But not blah, blah, blah.

Whatever your answers to this question are, and however cliché they may be, you can and should be working toward them. Money’s a shortcut. With patience and the right approach you can do it—even without $100 million.

How I’m Answering It

I’d find a way to get my close friends and family all living in the same neighborhood. This is something I have to get to work on.

Related Question to Ask Yourself

  • What could you remove from life to make it better?
Chris, Kim, and family
Future Me is going to long for moments like these.

10. The Gratitude Giver

I’d say this is the most important of all the questions to ask yourself.

These things won’t last forever. Relish them while you still can.

How I’m Answering It

Kim and I have complete freedom to do whatever we want every single day. My parents are healthy. I can dunk a basketball. The weather’s not so bad. And the list goes on.

Life’s great, even if I don’t really know where I’m going with it!

Related Question to Ask Yourself

  • What would someone who is much less fortunate than you think if they saw you and how you are (or, more likely, aren’t) making the most of your more fortunate situation?

Wrong Is Better Than Lost

For all I know, all my answers to these questions I ask myself about life could be wrong.

But they seem to be helping me find a better direction in life than when I was blindly following along with no GPS signal at all. So all I can do to make the most of my trip through life is keep asking, refreshing my answers, and adjusting course accordingly.

Whatever questions you ask yourself, and whatever your answers may be, hopefully they give you the perspective you need to find your way, too.

Keep Asking Questions

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Kim and Chris are fighting the status quo to win at life, then sharing their best tactics on The Unconventional Route. If you want to join, subscribe to Consider This for a fresh dose of ideas every 10 days.

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