DECISION DIARY

Don Lemon’s Message of Courage

Last week, I attended a comedy show in NYC that unexpectedly rebuilt my belief in humanity.

Not typically where you’d go looking for hope, given the trope of comedians as despairing, sharp-tongued sh*t-talkers. But this wasn’t a typical show.

I went to see DL+DL Anything Goes, hosted by Don Lemon and DL Hughley, an unlikely pairing with genuine chemistry and mutual respect. Think Martha and Snoop, but on the right side of history.

The timing made it even more poignant. It was the first week of Black History Month, just days after Don Lemon’s arrest while reporting on protests in Minnesota, a jarring development in a country that claims freedom of speech and the press as core values.

Both men were born during the height of the civil rights movement, raised by matriarchs who instilled in them a deep sense of patriotism… and a clear-eyed understanding of how fragile the American project really is.

“Comfort is poison right now. It may feel good, but it’s corrosive.”

Don Lemon

Listening to them felt less like entertainment and more like recovering the wisdom of elders.

While recounting his arrest, Don said something that stopped me:

“Comfort is poison right now. It may feel good, but it’s corrosive.”

What does that have to do with you, me, or this note?

The opposite of comfort isn’t discomfort. It’s courage.

Don’s story is a reminder of the futility of trying to craft a clean narrative or a perfect journey. Here is someone who “did it the right way,” worked his way through a stringent corporate media environment, and still got fired. Still got arrested.

So why are we still enamored with the fantasy of the perfect arc when reality keeps disproving it?

After his arrest, I saw another quote circulating again. In 2024, rapper and activist Killer Mike said:

“All my heroes have been in handcuffs.”

He was referencing Martin Luther King Jr., Malcolm X, Nelson Mandela, Rosa Parks.

No one we celebrate had a tidy journey. Many faced exile, imprisonment, public condemnation, or worse.

And yet.

We still hold ourselves to impossible standards of safety, likability, and perfection. The need to be “twice as good”.

Why? Fear, guilt, shame, the system — a.k.a the usual suspects.

But we don’t have to give fear all the power. At a talk promoting his book, How to Be Bold: The Science of Everyday Courage, Harvard Business School professor Ranjay Gulati said:

“Fear is a reaction, but courage is a decision.”

That distinction matters.

Fear happens to us. Courage is chosen.

Comfort may feel protective. But it also quietly shrinks us. It diminishes what we think is possible.

So maybe the real question isn’t whether fear shows up… It will!

The question is what we decide to do in response. What do you decide?

Hey there!

You’re reading Unpopular Decisions— a biweekly newsletter for people navigating life’s toughest decisions. Every issue brings personal stories and interviews from our growing community of people choosing differently. Let’s get into it.

— Jameelah
DECISION DIALOGUES

Protection vs. Projection

What if moving in silence is actually just fear?

Jovonne Cameron, the software engineer powerhouse behind @jovitalkstech on TikTok and Instagram, joined me on the couch in this week’s episode of Unpopular Decisions podcast. We talked about the advice we get as Black women that often keeps us stuck, isolated, and playing small…

“Fail in private”

Growing up in Caribbean households, we both felt the pressure to keep appearances up and not to show our struggle. So when Jovonne decided she was not going back to her role as a Special Education teacher during the pandemic and wanted to finally pursue her dream of being a software engineer, she had a choice to make:

Was she ready to defend a version of herself she hadn’t met yet? Or would she lie to her community to keep the questioning eyes at bay?

She chose secrecy. What stays with me was the cost of that choice.

Jovonne recognizes now that silence ultimately disconnects us from community. What felt like protection is really isolation. Now she wishes she had given herself permission to take up more space.

DECISION DIALOGUES

Motherhood by Any Means Necessary

There are so many paths to motherhood —and so many ways that your motherhood can be questioned.

We had a special double header this week! Connie Rutherford, a wall street maven turned tech executive and now author, also joined me on the couch in this week’s episode of Unpopular Decisions podcast.

Motherhood is truly a “profound destination,” but one thing we can’t get around is the need to have a village. But, what do you do when your family or a partner are not going to be there to carry you through?

Connie’s honest new memoir, Searching for Tadpoles, on her journey to becoming a single mother by choice unveils her realization that asking for help is a strength, but asking for permission is recipe for regret.

After a few failed relationships, she dove headlong at 39 into trying to fulfill her dream since she was 16-years-old to become a mom. At 41, she fulfilled that dream and became a mom to twin girls (surprise!).

I was struck by how much we undervalue the platonic love of friendship compared to romantic love. When she reached a low in her post-partum healing in the middle of COVID, it was her friends who held her and her babies, not a partner.

Now, Connie’s only regret is that she didn’t start her fertility journey and didn’t ask for help sooner.

Watch or Listen to the Episode Now!

THE UNPOPULAR TABLE

Welcome to The Unpopular Table

“Where stories are shared and scripts are rewritten.”

Authenticity is courageous and intentional. But, choosing differently can feel isolating, especially for people navigating cultural, familial, and professional expectations.

At The Unpopular Table, we transform individual acts of bravery into collective belonging. It’s a shared space where courage seekers and courage practitioners see their experiences reflected and normalized. After all, courage multiplies when it’s witnessed, shared, and held in community.

The Unpopular Table will continue to grow its footprint over time, including events, forums, and more. But for now, just know that you’ve got a seat at the table.

In this regular newsletter segment, we will highlight voices from throughout this community. Your vulnerability in email replies, comments, survey responses, and more are seen, witnessed, and appreciated.

Since this week was our first official episode launch, I thought I’d bring you words from recent comments and reviews.

I think we often hold ourselves to impossible standards because we’re far more aware of the weight of our own failures than we are of those behind the success stories we admire.
Our experiences are personal. We feel every ache and setback as we move through them, while the failures of others register only as distant facts.

Charlotte

Thank you Charlotte!

THE SHIFT

Where in your life are you choosing comfort over courage — and calling it wisdom?

Reply to this email to share your thoughts. I read every one.

Until next time, I’m glad you’re here.

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