Normalizing stupid


“This might be a silly question, but…”

“That’s not a silly question at all”

A profoundly compassionate and subtle thing we can do for each other in conversations is to gently puncture notions of shame and fear that arise.

An example we often see is the “This might be a silly question, but…” preface to a question. It’s so commonplace that we rarely acknowledge it, but noticing it might be worth your time.

When we create a space for the underlying fears that direct the flow of our emotions to be seen for what they are—psychological suffering that can be overcome—we free ourselves to show up more fully and honestly in the moments when we’re fearful.

A quick “That’s not a silly question at all” before responding might be all that’s needed.


When I was a bright-eyed and clueless freshman at Florida State University, I used to correct friends of mine when they made mistakes around me. Typographical error? Not on my watch. Factual error, however trivial? I’m on the job—thank me later!

For me, the motivation to correct them was obvious: how could someone not want to know when they’re wrong about something? I wished more people pointed out my mistakes when I made them. I asked them to!

Sadly, this is not actually how humans work.

I learned that my habit of correcting people made them extremely uncomfortable. I was blind to the effects of my “goodwill” until some generous souls pointed out how the corrections made them feel. I hadn’t for a moment considered the possibility that there weren’t people who didn’t want to aggressively participate in their own personal development.

I was so naive.

What I was actually exhibiting was an act of breathtaking self-absorption. Not only did I assume that everyone thought about things like me, I proceeded with the solutions without their approval or consent. I did not, as it turns out, have all the answers.


Over time (and many re-readings of good books), I’ve learned how to better communicate with and relate to humans. I’ve noticed the ways in which fear and shame are baked into my own mental models and patterns of thought. I’ve observed how varying degrees of anxiety is crippling generations of leaders and thinkers and world-changers.

It’s sobering, and puts many of our perceived struggles in perspective: the suffering most people reading this post experience is psychological.

This realization—coming alive to me in ways that it never did before—helps me better understand a host of other things more clearly. Perhaps most closest to home, it helps me understand why so much of Seth’s writing is about fear and the lizard brain and the emotional component of business.

This is curious because Seth is one of the most frighteningly adept business minds I’ve ever encountered. I’m not into hero worship, but the man is a monster. And this mental dexterity is wrapped in an immense and unwavering kindness and generosity.

And contrasting this with my juvenile intentions as a 22 year-old undergrad crystallizes nearly a decade of learning that will continue to pay dividends as I continue to evolve.

Here’s to stupid questions.

Grand Opening


There’s a Chinese restaurant near my apartment that recently printed new menus. I noticed this because the menus were a different color than the others I’ve seen in the past.

[Whether this reflects a great memory on my part or an addiction to MSG is beyond the scope of this post.]

But what stuck out to me was the “Grand Opening” announcement on the new menus—this was not a new restaurant. Sure enough, I later found an old menu at home I grabbed when I moved here about a year ago. “Grand Opening” it read as well.

I won’t be filing a lawsuit against the restaurant for its misleading menu, but this is as good a time as any to think about the things we do and say that have become meaningless with overuse.

A trend I’ve noticed in people who exhibit a high level of mastery in a given domain is the ability to distill knowledge into digestible chunks for others. This is often accomplished though the use of relevant metaphors.

To be effective at this, a deep understanding is required — not only of an area of expertise like software engineering or theoretical physics — but also of the complexity inherent in everyday things.

If you can help me understand your point of view through a metaphor relevant to my life experience, it’s possible that I’ll immediately understand you. If you articulate the point of view in a way that’s relevant and accessible to the people you’re trying to reach, it’s possible that you will win.

Shonda Rhimes is a boss.

I particularly enjoyed the style and delivery of her talk.

Shouts out to all my spoken word artists (active and retired).

My rules


Yesterday, I had a great call with my dear friend and board member Andre Blackman about leveling up and creating healthy professional boundaries in the interest of productivity.

This is particularly relevant for ‘Dre because he’s a super-connector. And during our call, I realized that I hadn’t shouted him out in my post with the other great folks I mentioned.

I was mortified and almost lost my train of thought mid-sentence. I knew he probably saw the piece when it went live—what if he felt slighted by the omission? It felt lame to try and justify the mistake to myself, so I certainly wasn’t going to invest thinking cycles in “making it up” to him.

Because I remembered that this is my blog and I can do whatever I want.

So this post is for Andre.

Connect with Andre on LinkedIn, Twitter, and his site. I can’t promise that he’ll connect with you in return, of course — Andre is busy leveling up right now.

If the question you think you’re asking yourself is, “how can I begin now?” but it really feels like, “how much shame should I feel for not having done this already?” — don’t despair.

The dissonance you detect between what you think and what you feel is a part of the human experience, and how you deal with this dissonance is up to you.

I’m not being glib, I literally mean that you can decide how to act rather than acting reflexively. If you’re ready to be the kind of person who sticks with tasks until they’re done, you’re allowed.

Sounds like freedom to me.

Having a good answer to this question is more important that you might think.

Compassion for all


You included.

If you wrote down the things that you say to yourself in your head—the critical, judgmental, harsh things you say reflexively—you would be horrified.

What if you countered those hash statements with ones of compassion and understanding? What if you trained yourself to show compassion proactively?

How would that make you feel after 30 days?

Don’t be selfish


Why would you keep your gifts from the world?

I know it’s scary, I know it’s hard, and yes, you might fail.

But that’s kind of the point.

The bad news is you’re falling through the air, nothing to hang on to, no parachute. The good news is there’s no ground.

— Chögyam Trungpa Rinpoche

Introduce two people who need to know each other.

Then two more, and keep going until you remember how dope your network is, how fortunate you are to know so many amazing people, and how great it is to have such abundance in your proverbial rolodex.

[This post is inspired by Ivo Philbert, Nkrumah Pierre, Michael Roderick, Pam Slim, and the other generous and thoughtful connectors in my life.]