There are challenging crossroads in any career path of significance, from leaving a dead-end job to pivoting a product to pursing a risky idea. I've found this on my own journey from journalist to entrepreneur to coach. The best answers have to evolve from the best questions. Here are three great questions to ask when you are looking into the darkness of your journey.

How will my 80-year old self define success?

This is what founder Jeff Bezos asked himself when, in his early 30s, he considered leaving his Wall Street job to start Amazon. It quickly takes you out of the minutia: What will make the biggest impact in the long run? And what risks will change the course of my life for the better?

Inc. Contributing Editor John Brandon captured the ultimate quote: "It would be a 100 percent chance of regret if I didn't try and a 0 percent chance if I tried and failed."

Is it reversible?

As I talk about in The Ultimate Bite-Sized Entrepreneur, I asked myself this when my main business hemorrhaged and there was no clear pathway to actually bring in other income. I reminded myself, every day, that bills could be caught up and resources replenished, but only if I continued to focus on solutions rather than problems. The result was several new income paths, many of which fuel my business today - and they wouldn't have been discovered without that challenging period.

"It starts with acknowledging that the work you put in today doesn't go into an empty vacuum. It adds to your momentum and, like a slingshot, all that energy will propel you forward when the moment is right. You just don't know when that moment will be."

Is it figureoutable?

Hand-in-hand with my question, master life coach Marie Forleo's query shifts your mindset from one of a victim to one of a victor. The real magic here is confidence: There is a solution; I just don't see it yet.

"All of this is honestly figureoutable. It really, truly is. You just have to be willing to use your creativity and to think outside the box."

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Published on: Mar 29, 2018