Every once in a while, something happens to remind us that we only get one go around on this merry-go-round called life. Regrets are something nobody wants.

I decided I wasn't going to have any when I made the move to leave a robust, profitable corporate life behind to broaden my platform for making a difference as a keynote speaker and writer. People often ask how I went about finally making the call to make the bold leap in pursuit of the life I truly wanted.

So today I'll share a bit of my story, as told through a series of powerful questions I asked myself once upon a time. They helped guide me down a path to joy. Whatever that path looks like for you and whatever your career endpoint is, I hope these questions help you start the journey.

1. At what point is enough money enough?

My wife and I came to grips with how big a lifestyle we really needed to make us happy and how much money that would require. It wasn't nearly as much as we would have thought in years past, and lowering the expectations raised the bravery for setting a post-corporate path that might not lead to as much wealth-creation.

But, admittedly, I was locked into the "golden handcuffs" of option grants and big annual bonuses for far too long. Walking away from big chunks of money each year seemed hard to imagine.

Until it wasn't.

2. Am I ready to let go of what others think of me and expect from me?

For years I felt like continuing to climb the corporate ladder was what I was expected to do. Work hard. Make your people a priority. Deliver results. Get promoted. Repeat. The expected progression came to define me, if I'm honest.

Until it didn't.

It wasn't until I realized that I decide who gets to criticize me, that I decide what value I'll place on the words spoken to me, that I decide how much I'll let others expectations and opinions of me influence my life, that it clicked.

It was like someone whispered in my ear, "It's time to stop worrying about the universe (what everyone thinks) and start worrying about the you-niverse (what matters to you)." That came when I was confident enough that the life I was choosing to lead was viable and valuable--i.e. more than doable and the best thing I could be doing with my time left on this planet.

3. Am I ready to stop comparing myself to others?

This one will always be a challenge for me. I was constantly comparing myself to others, getting caught up in a race I didn't even want to run. Comparing to others is an elusive pursuit at best, and an unquenchable, soul-crushing one at worst. And still I kept comparing to others around me in corporate.

Until I couldn't.

I just couldn't do it anymore because I finally realized how debilitating it was. I finally woke up and understood that the only comparison that mattered is to who I was yesterday and whether or not I was becoming a better version of myself. I finally realized that my differences are what make me greater than, not lesser than. And while I'm still not perfect at it (now four years in to living the life I truly want) the amount of comparing I do doesn't compare to what I used to do.

4. Have I shed all the anchors weighing me down?

I used to just accept that the presence of negative ion personalities in my life and the constant companion of negative thought patterns was just how it was. Such it is to be human. So I'd continue letting toxic points of view from unhelpful people infiltrate my life. I'd continue letting my disempowering inner monologue wail on me and chase away self-confidence and distort reality.

Until I wouldn't.

It wasn't until I came to understand that to rise up I had to cut ties to everything weighing me down.

5. What threads running through my life connect to when I was most happy, fulfilled, and energized?

It's critical that before you make any moves to migrate to the life you want that you apply a simple acid test: Are you running to something or from something? You want the former, and know that the latter can be disguised as the former.

And stepping back to examine the threads running through my life that connected to my greatest moments of joy was an incredibly powerful confirmation that the life I thought I wanted would indeed deliver the joy I deserved.

I hope these introspective questions introduce you to a new vein of courage buried within.

Published on: Sep 22, 2019
Like this column? Sign up to subscribe to email alerts and you'll never miss a post.
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.