How to know for sure it will work out

How do I know it will work out? In working with 1,000+ clients over the past 10 years, I’ve heard countless variations on this question.

How do I know …
… if I should start my own company.
… which job offer to take.
… if I should reach out to someone.
… if the guy/girl will stick around.
… if people will read what I write.

As a coach, my job isn’t to answer your questions. My job is to help you upgrade the quality of your questions. And any question that starts with some version of “How do I know if…” is not a high quality question.

Because that’s your primitive brain and ego personality talking, and their job is not to look for opportunities for you to have an exciting, fulfilling life. They want you to be SAFE, and they’re looking for guarantees: “Show me evidence this is going to work out and then I’ll do it.”

When we let them run our lives, we get so fixated on survival that we don’t give ourselves a chance to truly LIVE.

And most of the opportunities that make life interesting come out of the unknown and unexpected.

The musician who founded a tech startup when his iPhone died and he lost hundreds of valuable contacts (the Amos Winbush story).
The Japanese salaryman who invited the daughter of his American colleague to live with his family (my story).
The tongue-in-cheek article meant to be an inside joke for other chefs that gets published in The New Yorker (the Anthony Bourdain story).

Here’s the thing: the world is only going to get more uncertain and unpredictable. Instead of trying to control what happens, you would be better off deciding what you want — and then developing capabilities that would support your evolution towards it.

So, instead of trying to avoid disappointment and mistakes, what if you learned to bounce back quicker.

Instead of being afraid to make the wrong decision and getting caught up in analysis paralysis, what if you made the best decision you could and then committed to making it the right one.

Instead of trying to control external circumstances, what if you became more mentally agile and resourceful.

Because these skills — resilience, conviction, adaptability — are the ultimate survival kit. With them, you’re able to maintain a sense of safety and confidence no matter what happens, which fuels your ability to spot and take advantage of the next opportunity.