Pillar Talk ft. Jamal Robinson!

Conversations inspiration, play, and pushing yourself through fear

Welcome to Oh, Please!, Welcome to Pillar Talk! (a play on words from the phrase “pillow talk” - get it?!) A new interview series featuring honest, emotionally intelligent conversations with people who are learning to live with emotional clarity instead of emotional compromise. It’s the evolved version of my “Oh, Please” series, less about performing politeness, more about practicing self-trust. Each conversation explores what it means to live with emotional intelligence after a lifetime of people-pleasing, and how we can build lives rooted in truth, not approval. Please consider subscribing to follow along with our guests!

In the spirit of my favorite season of the year, AND to celebrate the birth of The Fifth Pillar, I’m offering a SUMMER SPECIAL!!

50% OFF paid subscriptions- FOREVER! *To all new paying subscribers*

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“Playing is my biggest act of self-care. Whether it's pickleball, basketball or board games with my friends, I make time to let my inner child do his thing.”

-Jamal Robinson

Welcome back to our Interview series, newly re-named, Pillar-Talk! (read above to learn the context)

I am so excited to introduce you/reconnect you to someone whose emails I NEVER miss. His creativity always inspires and gives me fresh perspective. He’s a poet, a photographer, his prose is perfection and…he’s an extrovert!! (Try not to gasp too loudly). His latest series is on the poetry of finding stories in strangers and is the perfect way for any introverts (like me) out there who like to learn about other humans - from a cozy distance.

In this conversation, he shares some personal favorites from reading, to play time, and how to push through fear.

Get ready for an honest, energizing, and heart-opening chat with a man who embodies what it means to show up fully.

Jamal Robinson

Welcome to Pillar Talk, Jamal! Can you please share when you realized your "yes reflex" was becoming a problem? Where were you, and what was the incident thatmade you think, “Wait...why am I baking 100 cupcakes for Karen's third cousin's cat’s birthday?”

I kind of chuckle at this now, but it seriously took my marriage almost ending to realize I had a problem with saying “yes”. The root of the problem wasn’t that I was saying yes too often, or to a bunch of people. It was that I didn’t say it to my own needs. When I discovered boundaries, it felt like I’d unlocked a superpower. Hell, it still does.

Do you have any Mentors/Gurus/Greek Philosophers who have supported you on your journey? Tell us about them.

I didn’t intentionally surround myself with emotionally healthy people until I began pursuing it myself. So, a lot of my initial influences have been writers like Khalil Gibran whose book The Prophet explored the nuanced aspects of being human so beautifully. It’s also the only book I’ve ever read all the way through more than twice. Another immensely important influence in my journey is the great bell hooks who led me to question if I knew what love was and if I loved myself. It turns out I didn’t fully.

When you feel yourself slipping back into people-pleasing tendencies, what do you do to reset, besides searching Zillow for the cheapest deserted island?

As an extrovert, I couldn’t imagine living on an island alone lol. But, anytime I fail to set or uphold my boundaries, I tend to feel a bit of regret. This often leads me to sit with the experience and double down on the ways of being that authentic and loving to myself.

Since you stopped being an expert “yes-person,” what’s been your biggest self-care indulgence (and how much do you love it)?

Playing is my biggest act of self-care. Whether it's pickleball, basketball or board games with my friends, I make time to let my inner child do his thing.

If you could give one piece of advice to fellow recovering people pleasers, what would it be (besides faking bad cell reception)?

The best and most life-changing experiences I’ve enjoyed have all stemmed from moments of pushing through my fear (i.e. asking my now wife to be my girlfriend, taking a part-time job in a school even though I had limited experience, trying out for the basketball team in middle school, etc.).

If saying no is that type of obstacle for you, then it’s a good sign you should continue doing it. It might be one of the most transformative things you ever do.

RAPID FIRE ROUND

Kryptonite. What (or who) is yours when it comes to pleasing?

I honestly don’t know if there’s something or someone that pulls that out of me anymore. My wife would have been my answer in the past, but because our relationship was the catalyst for my growth, its probably the area I most vigilant about.

Do you have a favorite Book or TV Show/Film?

I LOVE anime! Solo Leveling is one of my favorites from this year but Attack on Titan is one I’d suggest for people who are looking for an introduction to the genre that is heavy on plot.

Do you have a Motto? A Mantra? A guiding belief to return to about creating a life you don't hate? Would you share it with us?

What I do matters, but not more than who I am.

Where can we find you and your work from here?

I recently started a new series called Talking to Strangers where I take street portraits of strangers while they share their stories with me. My hope in sharing my reflections on these moments is to reveal the beauty of our shared humanity and the way it continues to connect us in an increasingly disconnected world.

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Jamal, thank you SO STINKING MUCH for taking the time to participate in this interview series and kick off the face-lifted version of “Oh, Please!”! I have admired your writing, and now portraits + writing for almost as long as I have been on Substack and to share your personal insights on my own publication feels surreal.

Readers, if you don’t already subscribe, be sure to check out

Jamal Robinson

for consistent doses of joy and connection.

Before I let you go reader, I want to acknowledge that there has been a hefty amount of change around here, DPP transitioning to The Fifth Pillar, and Oh, Please morphing into Pillar Talk…it’s a lot to keep up with. As Jamal was working on our interview throughout the update to my publication name, the questions he answered above are from “Oh, Please!”. Future interview questions will be slightly updated to reflect living more in alignment with emotional intelligence, and less about people-pleasing tendencies, which he has HEALED from! 👏

I want to thank you, so very much dear reader, for sticking around through this evolution, and also gently remind you that this newsletter has always been based in emotional intelligence. I hope that my essays and interviews continue to bring you something worthwhile, but if they don’t, or you no longer relate, this is me, setting you free. 🕊️

I’m off to re-read The Prophet, and start some anime, join us?

xX kaylen alexandra Xx

If you are feeling lost: Dear People Pleasers is now The Fifth Pillar! Read all about it here:

What Happens After the Four Pillars?

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P.S. I believe that we can learn something from everyone: If you have walked through fire and have tips to share on living emotionally intelligent lives, I would LOVE to interview you! Please submit your contact information (safely) here: Interview Me! 🐞

There are 5 ladybugs now…did you notice? ;)