10 Strategic Questions that Change Your Life



“Most people fail in life because they major in minor things.” – Tony Robbins

This is going to be a fast post, but hopefully insightful.  I’m challenging myself, by giving myself exactly 10 minutes to see if I can come up with something that might just help you for the rest of your life.

Let’s roll …

Here are 10 questions that I think if you strive to answer these well in thought and action, they will pay you back over your life-time, and multiply your results.

1. Who do you want to be and what experiences do you want to create?

You are not who you see in the mirror.  And, you are not your job title.  The better you can answer this question, and the better you can root your identity in who you truly are, the better off you will be, in dealing with the ever-changing world.

Long ago, I asked one of my colleagues how he managed his career.  He said, “Simple:  I figure out what experiences I want to have for this next year.”

Several years ago, one of my managers asked me one day, “Who do you want to show up as?”  I didn’t want to show up like a chicken with it’s head cut off.  I wanted to show up more like James Bond.   Related, another manager asked me the question, “How do you want people to experience you?”

When you put it all together, it’s such a simple question that we can guide us on a daily basis:

Who are you, and what experiences do you want to create?

2.  Why do you do what you do?

When you know “WHY” you do what you do, you are unstoppable.   Why?   Because your purpose gives you power.  It fuels your body, mind, and spirit in powerful ways.

It’s your simplest way to become a relentless force of power.

It’s your fastest way to renew on a regular basis.

It’s your best way to get on path and to get back on path after you’ve fallen off.

Why do I do what I do?  I want to improve the quality of life for as many people as I can, as long as I can.  It’s that simple.  But here is an elaboration on why do I do what I do, for you.

3. What are your values?

Your values light up your life.  They really do.  The problem is, most of us don’t walk around with awareness of what our most important values actually are.

Here are a few of mine:




At one of my leadership trainings, we did a deep dive on finding our values.  Once I figured out that Adventure was important to me, I baked it into work and life.  At work, instead of driving projects, I started leading epic adventures.  I would have the team draw the movie poster of our future victory to inspire our quest.   And I made it a point to take at least one amazing cross-country road trip each year.

All in the spirit of baking more Adventure into my life.

Need help find your values?  Here’s a simple exercise to help you find your values.

4. What are your strengths?

Your strengths are your natural talents that you can do all day.   You get better and better in them, and they come naturally to you.  In fact, they come so easily to you, that you might not even realize that they are strengths.

They are easy for you.

But hard for other people.

And that’s the twist that makes them so valuable.

Do you know what your unique strengths are?   Are you able to describe them in a way where other people know what you bring to the table?

I was blind to my strengths for years.   Luckily I had a manager and mentor who taught me to spend more time in my strengths.  One of my strengths is information architecture.  It’s easy for me to manage and simplify complex information.  I’ve used that special ability to shape my impact time and again, in any job that I’ve take on.  It always helps me find new ways to generate more value, for myself, for my team, for the business, and beyond.

Here’s what makes it worth it.  You can change the world, or at least your world, in the most fantastical way by playing to your strengths.

Need help finding your strengths?  Here’s a simple exercise to help you find your strengths.

5. What do you spend your time on?

You know what they say, “First we make our habits, then our habits make us.”  It’s so true.  And, if you want to easily get more out of life, then find a way to spend more time in your values, and find ways to connect everything you do, back to your values.  For example, if you like to learn, then make your next task all about mastering your craft.  If you value productivity, then find a way to do it better, faster, cheaper.

But there’s a little more to spending our time well.

You need to know the three paths of happiness according to Martin Seligman: the Pleasant Life (having as many pleasures as possible), the Good Life (spending time in your values), and the Meaningful Life (using your strengths in the service of others). Related, the key is taking a parallel approach vs. serial approach (the most common mistake) to balance and blend the 4 needs (happiness, achievement, significance, and legacy), which become a source of our renewable fulfillment in a dynamic and expanding way.

6. Who do you spend your time with?

As a friend told me, we’re the average of the 10 people we spend time with.  Are you spending your time with catalysts or drains.   Do the people you surround yourself inspire you on a regular basis?  Do they lift you up or tear you down?

It’s always been true that it’s “what” you know and “who” you know.  Now, more than ever, it really is about “who” you know.   Your network helps you find jobs, and helps you navigate the world of information overload.  Your network can help you compound your capabilities and unleash your potential.

7. What projects do you take on?

Long ago I heard that Leonardo DiCaprio was very selective about the work that he takes on.  He wanted to build a portfolio that would guarantee him future work, as well as be a legacy he could look back on and be proud of.

I adopted this pattern at work and soon realized that work can be the ultimate form of self-expression.  I found ways to negotiate taking on bigger and better things.  I quickly became known as “the director of blockbusters” because I took on the big challenges and change the game in significant ways.

8. What do you eat?

While eating at one of the healthier restaurants recently, the waitress quickly rattled off things that she learned helped her to be healthier over the years.  Her short-list was: “No dairy, no soy, no gluten, no GMOs, and organic when possible.”

Your body gives you feedback on a regular basis.  It’s been said that, “you are what you eat.”  And, Tony Robbins long ago said, that people spend a lifetime building wealth, only later to be paying for their health.  There are a lot of strategies around how to eat healthy, but also a lot of confusing and conflicting advice.   One strategy I see show up time and again in various ways is Dr. Joel Furhman and his approach of nutritional density.

9.  What do you spend your money on?

Or, maybe more importantly, what do you avoid spending your money on.   A fast way to build wealth is to save more than you make.  One of the most important ways to save more than you make, is to reduce spending money on the non-essentials and to live well below your means.

But there’s more to it.

In order to amplify your wealth, you need to get very good at generating extreme value.  Sure there are exceptions, but if you want to build extreme wealth, you need to generate extreme value.  Oh, but there is a little more to this, too.  There’s a big difference between those that generate extreme value who are wealthy, and those who aren’t:

Those that are wealthy know how to capture the value.

10.  Are you asking the right questions?

If you want better answers to life, then ask better questions.    You can quickly start asking better questions can directing your attention.   What’s the fastest way to change your focus?

Change the question.

What are the right questions you should be asking?  Now that is a great question to ask.

Here is a starter set you can draw from:

101 Questions that Empower You

Well, I’m out of time, but I hope that this little exercise gives you food for thought for the years to come, or at least today.

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Image by Derek Bridges.