How Did I Miss That?!

Has a simple, random interaction ever completely changed your perspective?

It happened to me last Tuesday night as I was heading back to my hotel in NYC. I was in the checkout line at a pharmacy near 42nd and 6th when the person behind me asked, “Do you have a sick kid?”

I was confused until they followed up with “Why all the Pedialyte?” I let this person in on my 'long days with no sleep' travel hack: “Pedialyte is how I stay hydrated on a grueling travel schedule. Plus, black coffee, aspirin and zero sugar!” The response: “I’m glad I asked, I would never have thought of that.”

“I’m glad I asked, I would never have thought of that.”

I’m glad they asked because I would have never would have thought of this either: what do the smartest, most successful people I know have in common?

Before I hit up that Walgreens, I met up with a pal of mine who happens to own a billion-dollar business (yes, with a “b”). I love this guy – he’s one of the biggest positive influences in my life. We have a Jay-Z/Kanye dynamic… that big brother thing. He’s only a few years older than me and abso-fucking-lutely killing it. Way beyond “startup crushin’ it,” he’s a legitimate global business mogul. #Goals, as the kids say. ;)

So, what is he doing that I’m not?

I started to think about the most impactful meetings I’ve had since starting a business and came up with five interactions. Whether it was a 10-minute car ride or a 2-hour meeting with a large group from all over the country, what did these five people, five key interactions have that nothing else had? That random person in Walgreens sparked the answer!

Damn good questions.

This is the common thread between the smartest and most successful people I know: they ask the right questions at the right time and dig deeper with better questions.

The next day, I woke up and wrote this out…

  • What exactly am I trying to accomplish before I die? 
  • How do I want Helo (my son) to remember me?
  • Am I the best husband I can be?
  • Can I be a better CEO?
  • Am I doing the best I can at this point in my life?
  • Is anything holding me back from being a better version of myself?

I woke up with more questions than answers and I feel better than I ever have… So, are you asking yourself the right questions?

Can you be a better version of yourself?

[Does this post excite you or does it feel like bullshit? ;) Leave me a comment either way.]