Unpopular Decisions: Real Stories of Bold Career & Life Decisions for People Who Were Taught to Play It Safe

Dion Dawson came back from the Navy with nothing. He served six years, despite knowing on day two that it was not for him. He returned to no journalism career despite being one of the highest-rated military journalists in all the branches. He realized that the world had continued forward without him.  Up until his early thirties, Dion Dawson had never decided anything for himself. Growing up as a...

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. She was secretly enrolled in a coding bootcamp, coding 60 to 90 hours a week, building an entirely new career as a software engineer after being a teacher. This is not a story about secrecy f...

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...

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 h...

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. His mother resigned. He did not. That decision — made at 17 in a church board meeting — cracked open everything Troy thought he knew. If they were wrong about that, they could be...

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...

Connie Rutherford had achieved almost everything that she was taught led to a successful life. The Wall Street career, wonderful friends, and bucket-list travel experiences.   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. At 41, on Wall Street, in the middle of a pandemic, she finally achieved...

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...

"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 up, her Haitian mom would zip up her coat every morning and remind her that as a Black girl, you have to work ten times as hard. She built a multiple six-figure career at DoorDash before the IPO, negotiated h...

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 th...

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 and think the people who fall for romance fraud are not people like us. Tracy Hall was one of those people. A senior marketing executive at eBay in Sy...

“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...

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...

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 earn...

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 inside. She went to Haiti burned out on bureaucracy, disconnected from why she became a doctor in the first place. She wasn't l...

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 true believer. He was a millennial trying to pay rent, manage student debt, and eventually buy a house and start a family — telli...

Quitting startup life is the easy part to name. The harder part is admitting you already knew — and stayed anyway. Megumi Calver has a résumé that made her feel, for years, like she was the problem. Multiple pivots. Short stints. A three-year acting detour that nobody saw coming. A startup where she was the only woman, took the biggest pay cut, organized every happy hour, and was still told she wa...

Career pivot fear doesn't hit hardest when you're at the bottom. It hits hardest when you've built something — a title, a reputation, a salary, a community of people who think they know exactly who you are. Shannon Reinard Demko has spent over two decades in graduate business education and a decade running MindfulMBA, coaching high-achieving professionals through exactly this moment. The one where...

Black K-pop fans have always existed. Kenyah was one of them in 2008 — before most Americans knew what K-pop was and long before anyone called it cool. By college, it wasn't just a hobby. She majored in Korean language and culture, joined the Korean Students Association, became president, and spent years trying to bridge the gap between Black culture and Korean culture on a campus where the two co...

Second opinions in medical care sometimes are the difference between being told you'll walk with a limp forever — and walking normally. In 2024, Chris Eversley, a former NCAA Division I champion and professional basketball player, was playing a game of pick-up basketball. A routine pivot. A knee hyperextension so rare that the artery supplying blood to his lower leg was blocked. Three hours later...

Divorce is one of the hardest things a person can do — not because the decision is unclear, but because everything around it is designed to keep you stuck. The family court system wasn't built for women. The process is slow and disorienting. The cultural narrative still treats divorce as failure. And by the time most women arrive at that decision, they've already been thinking about it for years —...

She told her friends she was going back to school for English. She was actually 60 hours a week into a coding bootcamp — alone, terrified, and not telling anyone in case she didn't make it. Jovonne Cameron didn't transition into tech quietly because she was strategic. She did it quietly because she wasn't sure she could. And she knew that one skeptical question from the wrong person would have bee...

What happens when the family you want doesn’t come with society’s approval? At 41, Connie Rutherford made a decision that came with strong opinions: becoming a single mother by choice through a sperm donor. What followed wasn’t just a fertility journey — it was a collision of family expectations, cultural beliefs, medical decisions, and the quieter question many people carry longer than they admit...

Most people don’t avoid hard decisions because they’re irresponsible. They avoid them because they don’t want to be wrong out loud. In this solo episode, Jameelah shares the decision that sparked Unpopular Decisions: leaving a job that looked fine on the outside — without another one lined up — after a line from Abbott Elementary reframed how she thought about fear. “For me, regrets have always be...

The hardest decisions in life aren’t made in boardrooms. They’re made in kitchens. In doctors’ offices. At 2 a.m. Unpopular Decisions is a podcast about those moments — the ones that don’t come with instructions, only opinions. Hosted by Jameelah Calhoun, the show features candid conversations with leaders, creators, and everyday people who chose differently — and lived with what came next. This i...