Unpopular Decisions: Real Stories of Bold Career & Life Decisions for People Who Were Taught to Play It Safe
Unpopular Decisions: the ones nobody claps for in the moment, but feel like they could cost you everything. Unpopular Decisions is a narrative interview podcast hosted by Jameelah Calhoun — an eldest daughter of a Haitian immigrant who spent 20 years building the business school-approved marketing executive career she was taught to want, and is now living her truth one unpopular decision at a time. Each episode is about the moment everything changes. Not the highlight reel. The actual decision — the doubt, the financial fear, the people who stayed and the ones who quietly disappeared when you chose differently. Every person felt the pull between the life they had been taught to seek and the life their heart craved. For some of them, that pull came loaded with extra weight. The burnt out executive walking away from the prestige and identity they spent years building. Eldest daughters taught to chase someone else's definition of success. First-generation professionals caught between honoring others' sacrifices and honoring themselves. Women told to cling to the relationship your culture said would bring you stability and status.And anyone who has ever had to choose between who they're becoming and where they come from. Some lost friends over it. Some lost income. Some lost versions of themselves they'd become attached to. All of them did it anyway. This show is for anyone questioning the responsible choices they were told would make them safer or more accepted before they fully understood what it would really cost. Guests include corporate executives who walked away from the ladder, creatives who stopped waiting for permission, athletes who refused their diagnoses, and everyday people who chose meaning over safety when the safer thing would have been to stay. Topics include leaving corporate to build something of your own, the career pivot that didn't make sense on paper, the six-figure salary you walked away from, the relationship you left when it still technically worked, the belief system you quietly outgrew while everyone around you stayed the same, and the quiet work of figuring out who you are when the script runs out. This isn't a success podcast. It's a human one. New episodes every Tuesday If you've ever felt the pull between the life you were taught to live and the one you actually want — you're in the right place. ✨ Follow and subscribe wherever you get your podcasts ✨ Watch episodes on Youtube (@unpopulardecisions) ✨ Follow on Instagram (@unpopulardecisionspod) ✨ Subscribe to our biweekly newsletter
Episodes
Note: This episode is part of our Summer Rewind Series, featuring unreleased scenes and deleted clips from our episode in Season 1.
Working 12-hour days, taking pay cuts for startup equity that ends up worth zero, and mistaking toxic endurance for career ambition.
When Megumi Calver joined an early-stage startup as an early employee and Head of Marketing, she thou...
Sometimes the hardest part of leaving isn't the other person. It's admitting you got something out of staying.
In this season finale of Unpopular Decisions, Jameelah Calhoun explores a type of shame we rarely talk about: the shame of realizing you weren't just hurt by a situation, you also participated in it.
Maybe you stayed because the job made you feel important.
Maybe the relationship ...
Note: This episode discusses pregnancy loss, severe medical complications, and second-trimester abortion care.
Two second-trimester abortions, a high-control religious upbringing, and a public decision to stop telling people she had a "stillbirth".
You follow every rule in the script. You abstain from sex, get married in the church...
Note: This episode discusses abortion care, pregnancy loss, and reproductive healthcare.
We don't talk enough about abortion in professional settings, losing long-term clients over personal values, and why a D&C for an unwanted pregnancy at 17 is the exact same medical procedure as a D&C for a miscarriage at 40.
One in fo...
Note: This episode discusses veteran re-entry, mental health, suicide attempts, and homelessness.
From homeless Navy veteran sleeping in his car to founding a logistics movement featured in the Obama Presidential Center, Dion Dawson joins Unpopular Decisions podcast to share why real impact requires building better infrastructure, not asking for permission.
Some people tell you to build in public. Others tell you to move in silence.
Jovonne Cameron did the latter.
She told her friends and family she was going back to school for a degree in English. She was not.
Everyone is talking about reinventing themselves and identity shifting…
As if the person you need to become is a stranger. Someone you have to manufacture out of thin air.
But, it is not an identity shift. It is an identity recovery.
In this solo episode of Unpopular Decisions, Jameelah Calhoun talks about the golden child she spent most of her life being and the scapegoat she became the moment a project went sideways at wor...
Everyone told Temika Cage to be realistic.
She was the golden child in a religious household, who was now 15 and pregnant. She had just shattered every expectation her family had for her.
Her community assumed she would be another statistic and give up on her college dreams. Her parents assumed she would stay close to home and let them care for their granddaughter.
Temika said no.
She packed up her daughter and left for Mich...
Troy Anthony's own choir petitioned to remove him as minister of music.
Not strangers. The people who raised him. The woman he called Auntie. His grandfather sitting right next to him as the votes were cast four to three.
She was the eldest daughter of six children in a family that could not afford nannies.
So she became one.
Molly Gazay spent her childhood as Militant Molly, the one in charge, the one who kept everyone in line, and even the one her parents came to when their marriage was falling apart. She spent her twenties and thirties doing the same thing professionally as a beloved nanny and caregiver. She was so good at taking care of everyone...
But, she was missing the thing she wanted most. She wanted to be a mother, ever since she was 16 when she was caught doodling baby names in her diary.
Sometimes growth doesn’t feel exciting. Sometimes it feels like your entire nervous system filing a complaint.
In this solo episode of Unpopular Decisions, Jameelah Calhoun talks about what actually happens emotionally when you’re trying to become someone new and why reinvention often feels less like empowerment and more like intentionally triggering yourself.
Because every leap she has taken, her divorce, her career br...
"I don't have to do this anymore."
After another frustrating conversation with a micromanaging boss, Bie Aweh realized that she was ready to break free from the golden handcuffs.
But, growing ...
Mo' money, mo' problems? Financial Behavior Specialist, Jamie Piper, rejects that.
It's not about the amount of money you have or don't have. It's how you feel about it!
Two months ago, we asked you what holds you back from making the bold career pivots and life decisions you wanted to. The number one answer: MONEY!
The wrong salary. The wrong budget. The wrong investments. If we could just get the numbers right, we would finally f...
She lost $317,000 to a man she loved—and didn’t realize the truth until he was arrested.
Most of us have a quiet certainty that it could never happen to us.
We are educated. We have good instincts. We are the one who watch Tinder Swindler on Netflix a...
“As a Black woman in these spaces, you’re only as good as you are agreeable.”
That’s what Alexandra Pinckney says she learned the hard way.
A strategic marketing leader with experience at household name media companies and a high-growth tech company, Alexandra was hired to lead a team, build revenue, and drive change. By her account, and of her colleagues, she did all of that and more. She closed a multi-mil...
We're relaunching one of our favorite episodes from season one!
Most people, when an authority figure tells them it is over, believe it.
Not because the authority is always right. Because it is easier to accept that you might be wrong.
Chris Eversley had four doctors tell him his body was compromised forever. Knee stuck at 55 degrees. No jogging. No basketball. No bike. A limp for the rest of his life. They said it with confidence,...
There is a version of staying that looks like growth.
You set better boundaries. You go to therapy. You book the yoga retreat. You ask for the raise. You hire the coach. You optimize the systems. You tell yourself you are doing the work.
And you are. Just not the work that actually needs doing.
For 18 months, Jameelah Calhoun did everything right in a job that was everything wrong. Promotions earned. Recognition given.
But al...
Most people think choosing yourself means leaving something broken.
Dr. Norrisa Haynes left something real. And she'll be the first to tell you it wasn't really a choice between love and career. It was a choice between two identities, and which one she could actually live ...
Most people who stay somewhere too long aren't believers. They're just running the math.
Miles Bruner spent years as a mid-level Republican fundraising operative while privately voting Democrat and watching the party become something he no longer recognized. He wasn't a tr...
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