Two Absolutely Key Questions for Achieving Prosperity

Last week, I talked about WHY you should embrace your own prosperity … this week, I want to help you get clarity about the path to prosperity.

Prosperity is a journey. And as with any journey, getting focus and clarity is a key to success. And I want you to succeed.

In the WProsper survey we sent to you, I asked these questions, because if I am clear about them, I can better help you. (The responses have been amazingly helpful, by the way.)

Here they are:

  • Where do you want to go?
  • What’s holding you back?

Getting crystal clear answers to these questions multiply your chances for success greatly.

Our time, talent and treasure are limited resources. We need to be laser focused and use them wisely to get to the place we want to be.

And if you are taking off on a journey, but don’t have course direction to follow, or a compass to guide you, you’ll end up lost, wandering aimlessly in the wilderness.

So let’s unpack them … so you can get get clear and focused.

Where do you want to go?

What is your summit, the destination you’re heading toward? What is the journey you on are?

Where do you want to go? Today, this week, this month, this year … and beyond?

It’s essentially asking: What do you want out of life?

And I’ve found the best place to start is actually at the end. 

Specifically, at the end of your life. Then we’ll start working back from there. Yeah, it seems morbid at first. But to make the most of your time on earth, asking yourself where you want to end up, what you want to have achieved and done, who you want to have loved, and how you want to have lived … all these inform the journey.

Otherwise, we will zealously chase things that don’t mean anything. And we’ll end up empty and possibly alone.

So, I ask, at the end of your life, what do you want to be true about you and your life?

Take some time and answer that deeply, thoroughly. The answer won’t come in an instant, so spend enough time thinking, dreaming, pondering this big question.

These exercise will inevitably lead you to ask: Who you are and who do you want to be?

This is one of the reasons I’m always seeking to learn more about myself and asking me these questions continually.

It’s not self-absorption, but more self-awareness. And why I’m always taking discovery tools like StrengthsFinder, or 5 Love Languages and encouraging others to do the same.

I want to make the most of my life. And knowing more about myself helps me understand my unique contribution to the world (or my little corner of it).

Then asking yourself: Knowing who I am (at least at this point), what do I want? And of course if you have a significant other, what do WE want?

The next part of this question is: WHY?

Why do you want those things?

Knowing why gives me inspiration, motivation and encouragement to stay the course. And if a Why doesn’t match up with my values, I correct it because the wrong Why will lead me off course and into trouble. (It always does!)

So I’ll admit … I also ask these questions regularly because I’ve found they change and drift at each stage of life.

My goals and ambitions in my 20s, as a single guy living in an apartment working insane hours, are different now as a 37-year-old father of two. And they should. I have more people to think about than just me!

And let’s face it—life doesn’t always turn out the way we planned it … and I’m actually VERY thankful for that. Every day is a surprise. Typically a pleasant one. But it’s full of twists and turns. And each day that I’ve simply savored the journey and the view, I’ve loved the ride.

So here are some reminders and thoughts as you struggle with this question:

  • Knowing the end informs the beginning and middle. It’s the summit we strive for. And all roads should lead to it.
  • Find the why and be lead, motivated and inspired by it.
  • Know yourself deeply. We don’t spend enough time in thoughtful self-awareness. But it can save us from detours that waste time and energy.
  • Don’t expect clarity even in a moment of thoughtful reflection. It’s ok if the summit is a general direction. But as you move you should see the clouds dissipate and have more and more clarity.
  • Sometimes you have to walk down a path simply to see if it’s the one you really want to be on. As long as you’re learning and clarifying, chalk it up to progress.
  • Things change. And that’s OK. Let me repeat that. Things change. And again, that’s OK. In my professional life, I’ve wanted to be a truck driver, newspaper journalist, church planter … and now I’m an entrepreneur. The journey is mine. If it changes, it changes, and as long as I’m pursuing something bigger that gives me purpose and passion, using my talents and strengths, and making progress on that, making a difference, then that’s the journey I ALWAYS want to be on. Even if it’s changed 50 times. I’m sure mine will.

What’s holding you back?

Now once you’ve gotten a sense of clarity in where you’re heading … what’s in your way?

I know we’ve spent some time on positive things … and this seems almost counterproductive. But in my experience it’s absolutely key to achieving success.

Although I’ve been using forms of this idea for years, when I read The Obstacle Is the Way last year, it fortified the idea that whatever is in my way of success is actually the keys to my success.

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” –Zen parable found in The Obstacle is the Way book

This philosophy is similar to the question I ask often now — How can this fail? But I like this focus even more. It’s an epic formula for achievement and success.

Focusing on the challenges and obstacles that stand in my way and then blowing them up (or using them productively) has been life-changing. And I don’t say that quickly, or without thought and value.

(Here’s a slideshow titled 10 Strategies For Turning Obstacles Into Opportunities from the author Ryan Holiday.)

Now as I list my goals (from question one) and I’ve fully identified and clarified the big things I want to achieve in my life, I instantly started a new list called Obstacles and Challenges. From this list, I began to see what blocks our path … so we can attack, minimize, blow it up, use it against itself.

Let me give you an example.

One of my goals this year is to help you prosper. In order to help you do that, you have to WANT to prosper and you may need help on WHERE to start.

I realized one of the limiting beliefs for myself could also be one reason you don’t commit to WProsper with us. So I wrote last week’s post to tell you WHY you should embrace prosperity. And why I wrote today’s post … to give you ideas on how to get started.

These all came about because I asked myself … in the pursuit of our goal, what are the obstacles for people truly committing to it?

The obstacle is the way. Get clear on what, who, where they are … and use them.

Again, it’s why we asked in the WProsper survey — What is holding you back?

Your responses have been so helpful. And exciting, honestly. Why? Because I know we can help you and I’m thrilled to be able to do so.


Your Homework / Challenge

Get clear(er) on these two questions … take some today, this week, to answer:

  • Where do you want to go this year?
  • What’s holding you back?

Write your answers out. Then print them off and post to your mirror or desk. Send them to someone you trust to support you (my wife is my biggest supporter and when I commit to something she’s the first person I tell about it). Or  … if you want others to see, post them in the comments here. (And of course you can always email them to me at cory at ithemes dot com).


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