Are you a box checker?

Michelle Obama is a box checker. 

Or at least, she used to be. 

In her #1 bestselling book (now a brilliant Netflix documentary), Becoming, Michelle describes herself as a box checker. 

She explains why this personality trait (which might seem like really a good thing) actually chokes your potential and keeps you exhausted and unfulfilled.

As a box checker:

  • You follow instructions to the letter, and you avoid taking risks.
  • You want to please your parents and mentors, so you strictly adhere to their vision of what your life “should” be: Ivy League education, six-figure corporate salary, nice house with a white picket fence, sensible minivan, 2.5 kids, etc.
  • You’re on a never-ending treadmill of achievement. You acquire accolade after accolade. Yet, for mysterious reasons you feel empty, or feel like something is “off.”
  • You pursue goal after goal after goal, relentlessly checking things off, but without pausing to consider, “Why am I doing this?” “Does this feel right?” “Am I passionate about this?” “Does this light me up?” 

Box checkers blast right past those kinds of introspective questions. It’s all about checking the next box, not pondering if it’s actually the right box to check. 

Box checkers get things done. But there’s a high price to pay. 

The price is joy. 

I have quite a few clients who are box checkers. Not only does this suck joy from your life, but also, if you’re running a business? Box checking keeps you broke.

As a box-checker-preneur: 

  • You diligently send your weekly e-newsletter, but you play it safe. You never share vulnerable stories or take creative risks. (Outcome: your writing is boring and forgettable. People tune out.)
  • You reply promptly to emails and your inbox is empty. But that big, audacious project you’ve been dreaming about doing for years? You still haven’t started. It feels too risky. (Outcome: your million dollar offer is still…sitting there. A huge missed opportunity.)
  • You feel like you’re working incredibly hard (you’re so busy!), yet something isn’t “clicking” with your audience. People just don’t seem inspired by you, or interested in what you have to say. (Outcome: Low engagement. Slow sales.)

Perhaps you see other entrepreneurs building massive audiences and making tons of money, and you can’t figure out why this isn’t happening for you. After all, you are checking all the right boxes!!!

But that’s your mistake. 

Because to capture people’s attention, build a global fan base, and make millions, you can’t just be a box checker. 

You have to be an inspiring leader. 

You have to take risks, fall down, get up, and bring your audience along for the journey. 

You have to bring your whole heart into everything you do. 

Look, there’s a big difference between sending out a bland, neutral, safe announcement to promote your new offer (aka: box checking) versus delivering a heartfelt sermon with a bold (and possibly controversial) message that lights your heart on fire. 

Box checking leads to *crickets*. 

Taking a risk leads to an explosion of applause and sales. 

What’s one area of your life where you’ve been behaving like a box checker? Being safe? Playing small? Staying busy, accomplishing tasks, but without stopping to ask, “Does this actually feel right?”

This week, do something radical. Swerve away from what’s expected of you. Do the bold, risky thing instead of the safe thing. Burn your usual checklist. Leave boxes unchecked. 

Fuck the boxes. 

Watch what happens next.


PS. This week I’m celebrating my bestfriend Robert Hartwell who did something COMPLETELY out of the box when he bossed up and purchased a house that was built when slavery was still legal in this country in cash with his own money. And now he and his inspiring story are featured in Pharrell Williams’s new video- RUN to watch this right now and look for him at the end! I can’t help but cry every time I watch it!!

PPS. Recovering box checkers, unite! Join the We Should All Be Millionares: The Club. If you are so *done* with box checking, and ready to become the wealthy badass you were born to be, this is your club, and these are your people. Come hang with us.

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