What keeps you up at night?

What keeps you up at night?

This is a question commonly asked when entrepreneurs get together (especially in my experience with other founders.) It's a way to quickly get past surface-level "How's everything going?" chit chat and get to the good stuff. It's the place where magic can happen if we allow ourselves to be honest (with ourselves) and vulnerable (with each other).

I've heard a variety of answers from my fellow goal-getters, the heaviest of which include "how am I going to make payroll if we don't make our numbers?" or "do we take on private equity or continue to bootstrap?" and lately from some of my female founders-who-are-also-moms friends:

"How am I going to lead my company while also leading my family?" 

And by female founder friends, I also mean me. That question keeps me up at night too.

The enormity of this what-keeps-me-up-at-night-question is compounded when I also start to count sheep subtasks under each of these big check boxes (in between random ADHD-inspired thought bubbles).

☐ Raise solid, happy humans who grow up thinking I'm a good mom.

Did I lock my car doors? Hey that waiter never brought our extra ketchup.

☐ Grow company that becomes a global household name. 

So here's the thing. Lean in real close. What keeps you up at night should also be your "what gets you up in the morning" and "what keeps you going during the day."

I want you to be so obsessed with your Wildly Important Goals that you sometimes lose sleep about it and sometimes you sleep like a baby knowing you are trusting the process. If you don't have clarity around your vision and goals, let this be your wake up call.