REWIND: When Your Biological Clock and Career Collide: A Wall Street Woman's Decision to Become a Single Mother by Choice

REWIND: When Your Biological Clock and Career Collide: A Wall Street Woman's Decision to Become a Single Mother by Choice

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 her dream of motherhood, but not in the way that she, her family, or society expected. She decided to become a single mother by choice using donor sperm. Because, she had finally asked herself the right question. What would I regret for the rest of my life if I did not do this? Connie is Black and Taiwanese. Her father is Black, military, and a devout Catholic. Her mother is from Taiwan and deeply traditional. Neither of them was happy when she told them she was pregnant. Her mother told her she felt sorry for her children for being denied a father. Connie did it anyway. This is the episode that started Unpopular Decisions. And in AAPI Heritage Month, it felt like exactly the right moment to bring it back.  This episode is for you if you have been suffering from 'not now' syndrome. You have been waiting for the right partner, the right timing, or the right conditions before giving yourself permission to pursue your dreams, and you are starting to wonder how long you are willing to wait. What You Will Hear in This Episode * Growing up with parents who said getting pregnant would mean getting kicked out * What dating in New York looked like after a devastating breakup that taught her never to let someone have that much power over her again * The trip to Grenada with her best friend where the conversation finally shifted from dating strategy to a different kind of plan * Freezing her eggs at 38, what she did not know going in and what she wishes someone had told her * The Wall Street stigma she was navigating being a woman of color in a predominantly white environment and the fear of being seen differently as a single mother * The five failed cycles, the embryos that came back abnormal, and the midnight article that changed everything * Her father's cancer diagnosis and what it clarified about time and legacy * Why she declined the genetic screening on her final cycle and what happened when she trusted the old school approach * What she would tell women who feel like it might already be too late * What dating looks like now and why having her daughters completely changed what she is looking for Listener Takeaways * The question is not what are the pros and cons. The question is what would you regret for the rest of your life. Those are very different calculations. * The conditions will never be perfect. The right time is the time you finally decide it is. * Get your fertility checked. The information is not the enemy. Not having it is. * There is no one path to motherhood. Donor sperm, donor eggs, surrogacy, foster care, adoption, etc. all leads to the same profound destination. * Asking for help earlier is not weakness. It is the one thing Connie says she would do differently. * Choosing this does not mean you have given up on partnership. It means you stopped letting the absence of one determine everything else. The conversations on Unpopular Decisions are for informational and entertainment purposes only. Nothing in this episode constitutes legal, financial, medical, or professional advice. Every situation is different. If you're navigating something significant, please consult a qualified professional who can speak to your specific circumstances. CONNECT WITH US ✨ Subscribe to Unpopular Decisions to hear more stories of diverse professionals choosing authenticity over approval ✨ Share this episode with the friend who’s feeling stuck YouTube [https://www.youtube.com/@unpopulardecisions] | Instagram [https://www.instagram.com/unpopulardecisionspod/] | Threads [https://www.threads.com/@unpopulardecisionspod?xmt=AQG0y-oNrulUphvMCh69YewZXONqZf_EMbCtRzRbUdFgYDg] | LinkedIn [https://www.linkedin.com/company/unexpected-collective] | Website [https://unpopulardecisions.com/]  CONNECT WITH OUR GUEST ✨ Follow Connie Rutherford on Instagram and TikTok @searchingfortadpoles OR visit her website: https://www.connierutherford.com/ [https://www.connierutherford.com/] ✨ Buy her memoir Searching for Tadpoles [https://www.barnesandnoble.com/w/searching-for-tadpoles-connie-rutherford/1147818448?ean=9798317801779]: The Journey To Motherhood of A Single Mother By Choice  CONNECT WITH JAMEELAH ✨ Follow Jameelah Calhoun on social media LinkedIn [https://www.linkedin.com/in/jameelah-calhoun/] | Instagram [https://www.instagram.com/lifeaholicny/] Are you in the middle of a career pivot? Book a consultation [https://calendly.com/jameelah-calhoun/career-reinvention-strategy-session-clone-1] with Jameelah for a Pivots & Positioning Strategy Session. My approach blends strategic clarity, emotional intelligence, and real-world experience reinventing my own career across 6 industries and 6 functions. The goal is to help people move from overthinking to aligned action with greater clarity, conviction, and momentum.

Growth Is Exposure Therapy: What Nobody Tells You About Reinventing Your Life | S2 Ep. 5

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 breaks, launching this show, has followed the same pattern. The thing the leap required her to do was always the exact thing she had been most afraid to do.  We talk about the psychological hangover of major life decisions. Leaving jobs. Starting over. Becoming a beginner again after years of being competent. The grief of losing the identity and safety systems that once made your life make sense. And the uncomfortable reality that the things you avoid most aggressively are often the exact skills your next chapter requires. This episode pulls together lessons and clips from previous Unpopular Decisions conversations, including a first gen professional who hid her career pivot to tech because of imposter syndrome, a Black woman who sued her employer, an executive who lost her life savings to romance fraud, and a high-earning daughter of immigrants who walked away from her career three weeks postpartum.  Because sometimes the panic isn’t proof you’re making the wrong choice. Sometimes it’s just proof you’re no longer hiding from yourself. This episode is for you if you are in the middle of a change that is not yet feeling like the liberation you expected. This is your sign that you are not doing it wrong. What You’ll Hear in This Episode * Why reinvention can feel psychologically destabilizing * The emotional side of career breaks, divorce, and entrepreneurship * Growing up associating competence with worth * Why being a beginner again feels humiliating at first * The difference between danger and discomfort * How immigrant-family expectations shape fear and achievement * Why your next chapter often requires the exact thing you avoid Listener Takeaways * Anxiety isn’t always evidence you’re making the wrong decision * Familiar pain often feels safer than unfamiliar possibility * Starting over threatens identity before it builds confidence * Growth can feel like grief before it feels like freedom * Staying stuck is still a decision The conversations on Unpopular Decisions are for informational and entertainment purposes only. Nothing in this episode constitutes legal, financial, medical, or professional advice. Every situation is different — if you're navigating something significant, please consult a qualified professional who can speak to your specific circumstances. CONNECT WITH US ✨ Subscribe to Unpopular Decisions to hear more stories of diverse professionals choosing authenticity over approval ✨ Share this episode with the friend who’s feeling stuck Youtube [https://www.youtube.com/@unpopulardecisions] | Instagram [https://www.instagram.com/unpopulardecisionspod/] | Threads [https://www.threads.com/@unpopulardecisionspod?xmt=AQG0y-oNrulUphvMCh69YewZXONqZf_EMbCtRzRbUdFgYDg] | LinkedIn [https://www.linkedin.com/company/unexpected-collective] | Website [https://unpopulardecisions.com/]  CONNECT WITH JAMEELAH ✨ Follow Jameelah Calhoun on social media LinkedIn [https://www.linkedin.com/in/jameelah-calhoun/] | Instagram [https://www.instagram.com/lifeaholicny/] Are you in the middle of a career pivot? Book a consultation [https://calendly.com/jameelah-calhoun/career-reinvention-strategy-session-clone-1] with Jameelah for a Career Reinvention Strategy Session. My approach blends strategic clarity, emotional intelligence, and real-world experience reinventing my own career across 6 industries and 6 functions. The goal is to help people move from overthinking to aligned action with greater clarity, conviction, and momentum.

Breaking Free of Golden Handcuffs: A First-Gen Mom Walks Away from Her Six-Figure Career | S2 Ep. 4

"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 her first real salary when a mentor refused to let her undersell herself, and became a VP of HR at a fintech company. She did everything the responsible way. Then she had a baby and came back from maternity leave straight into 12-hour days. She found herself walking her newborn at midnight with no streetlights around and realized she had to make a change.  Three weeks ago, she quit. But, she has not told her immigrant parents yet. This episode is happening in real time. Bie does not have a clean story. She does not have a plan for what comes next. What she has is a seven-month-old who reminds her every day that she has only scratched the surface. This is what the messy middle actually looks like. This episode is for you if you have been sitting with the feeling that the career you worked incredibly hard to build has started to cost you more than it is giving back. And if you are trying to figure out what healthy courage looks like versus recklessness. What You Will Hear in This Episode * What golden handcuffs actually are — the equity, the RSUs, the lifestyle inflation — and how they keep high earners in place long past the point of fulfillment * Growing up first-generation, watching her Haitian and Cameroonian immigrant parents work as CNAs, and what those lessons about resilience and endurance cost her later * How a mentor at DoorDash refused to let her accept her first offer and changed her financial life * The IPO that transformed everything and what actually happened to all that equity * The night she was walking her newborn at midnight in a Houston suburb with no streetlights and finally understood she needed to stop * Why she has not told her parents yet, what she is afraid of, and how she is planning that conversation * The FU fund: what it is, how she built it, and why she watched it every single morning as a reminder she could leave * What identity grief looks like when your entire sense of self has been built around performing excellence in professional spaces * Why 300,000 Black women lost their jobs at the beginning of 2025 and why she chose to leave voluntarily in the middle of that * The FMLA resource every employee needs to know about and how to use it strategically before making a bigger decision * What success looks like for this season and why her blood pressure numbers are the metric she is watching first Listener Takeaways * Resilience is a gift and a curse. The same thing that gets you through impossible situations will also keep you in situations you should have left. * Your child does not need you to provide everything. They need you to show up as your best self. Those are not the same thing. * FU money is not a luxury. It is a plan. Six months of expenses minimum. Twelve is better. Start building it before you need it. * The in-between feels unproductive. It is actually doing essential work. Give yourself the time to decompress before expecting transformation. * You can leave with integrity. Four weeks notice, performing until the last day, leaving the bridge intact. You can bet on yourself and still be strategic about how. * Always be interviewing. Even during your career break. Stay sharp, stay relevant, stay ready. ✨ Subscribe to Unpopular Decisions to hear more stories from first generation professionals betting on themselves (Youtube [https://www.youtube.com/@unpopulardecisions] | LinkedIn [https://www.linkedin.com/company/unexpected-collective] | Instagram [https://www.instagram.com/unpopulardecisionspod/] | | Website [https://unpopulardecisions.com/]) ✨ Follow Bie Aweh's journey on Instagram @allhailqueenbie [https://www.instagram.com/allhailqueenbie/] ✨ Share this episode with the friend who’s feeling stuck with golden handcuffs The conversations on Unpopular Decisions are for informational and entertainment purposes only. Nothing in this episode constitutes financial, legal, or professional advice. Every situation is different. If you are navigating a significant career or financial decision, please consult a qualified professional who can speak to your specific circumstances. FMLA, Family and Medical Leave Act, provides eligible employees up to 12 weeks of job-protected leave. Eligibility requirements and paid leave provisions vary by state and employer. Consult your HR business partner for specifics.

Your Net Worth Is Not Your Self-Worth: The Psychology Behind Money Decisions | S2 Ep. 3

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 feel okay. So with the economy the way it is, we decided to go deeper to understand why financial psychology holds high-achieving professionals back. Because 80% of financial decisions are made emotionally, not rationally. And nobody in the finance industry is talking about that. Jamie is a financial behavior specialist, not a financial planner, not a wealth manager, not one of the get-rich gurus. She works with high achievers on the specific and underserved space between having money and feeling okay about it. On the beliefs formed in childhood that still run the show. On the shame that most people carry silently about their financial lives. On the money mindset animal archetype that explains why you do what you do with money before you even realize you are doing it. Her unpopular decision: to tell high achievers that chasing more money is not the answer. That contentment does not live on the other side of the next salary milestone. That your net worth does not determine your self-worth. In a world full of people telling you to make more, spend less, and invest better — this is a different conversation entirely. This episode is for you if you have hit a financial milestone that was supposed to feel like arrival and found yourself already looking at the next one. What You’ll Hear in This Episode * Why 80% of financial decisions are made emotionally and what that means for every budget and financial plan you have ever tried to follow * The stat that broke Jamie's clients open: millionaires and billionaires asked how much is enough all gave the exact same answer * The four money archetypes — Bear, Deer, Owl, and Dolphin — and what yours reveals about the beliefs driving your financial behavior * Why shame is the most under addressed emotion in people's relationship with money and what self-acceptance actually changes * The specific ways financial anxiety shows up in high achievers who look completely fine on the outside * Why more money does not guarantee more contentment and what actually does * The difference between real financial risk and perceived financial risk and how to tell them apart * Why everything you want is on the other side of a decision and staying in the in-between is one of the most expensive places to live * A free quiz to discover your money archetype at illumoney.com and a listener discount code for Jamie's work Listener Takeaways * Your net worth does not determine your self-worth. Period. Full stop. * There is a reason for every financial behavior you have. You are not broken. There is nothing wrong with you. * More money does not guarantee more contentment. Aligning how you invest your time with your actual values does. * 80% of change is self-awareness and self-acceptance. The tactics come after, not before. * Staying in the in-between feels safe. It is actually one of the most expensive and disruptive places to live. * Money comes and goes. Time once spent is gone forever. That is the hierarchy worth building around. ✨ Subscribe to Unpopular Decisions to hear more inspirational stories of choosing courage over consensus ✨ Discover your money archetype at https://illumoney.com/guides/inner-zoo-guide/inner-zoo-quiz/ [https://illumoney.com/guides/inner-zoo-guide/inner-zoo-quiz/] and use code ‘UD25OFF’ for a listener discount on Jamie reveal programs (https://illumoney.com/start-your-journey/ [https://illumoney.com/start-your-journey/]) ✨ Follow us on Youtube [https://www.youtube.com/@unpopulardecisions] | LinkedIn [https://www.linkedin.com/company/unexpected-collective] | Instagram [https://www.instagram.com/unpopulardecisionspod/] | | Website [https://unpopulardecisions.com/] The conversations on Unpopular Decisions are for informational and entertainment purposes only. Nothing in this episode constitutes legal, financial, medical, or professional advice. Every situation is different. If you're navigating something significant, please consult a qualified professional who can speak to your specific circumstances.

She Didn't Think It Would Happen to Her: A Romance Fraud Survivor on Trusting Again | S2 Ep. 2

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 Sydney, Australia, a single mother rebuilding her life after divorce at 40, and by every measure a woman who had it together. Over 18 months, he built a world for her. He became the reflection of everything she had said she wanted. And then he took $317,000 of her life savings. Her retirement savings. Her tech shares. Everything she had built. In this episode of Unpopular Decisions, Tracy Hall shares the story of being defrauded by Hamish McLaren, one of Australia’s most notorious con men—and the decision to speak publicly about it. This isn’t just a story about money. It’s about trust, identity, and what happens when the person you believed in never existed. This episode is for you if you have ever judged someone for being deceived, or quietly believed that your intelligence and instincts would protect you, and are ready to understand why that belief is exactly what fraudsters count on. This episode discusses romance fraud, financial loss, and the emotional weight of rebuilding after manipulation. If you or someone you know has been affected by financial fraud, please know you are not alone and the shame belongs to the criminal, not you. * Find Tracy at https://tracyhall.com.au/ [https://tracyhall.com.au/] and pick up her book The Last Victim [https://www.amazon.com/Audible-The-Last-Victim/dp/B0CWBKYZB6/ref=sr_1_1?crid=2PW5ZBXEM08PQ&dib=eyJ2IjoiMSJ9.GyJQ4UMe4kxKw1Ivs_6YpM_NJfE2eh8ZV1JB4YcyRBI5Z-MfIRQEnlqi4KLTguGQ8aJcY6pYPSijniM_W4uckyHug6pd6_ZxLcVHoW0nzBWoq4gFlS103BAO2au8bSE1qlQJpt_s395QNiABT86fUA.DfgWqOFWJy3d0x0-q1pwexTc4is2bZcNjv8ClqNbDn0&dib_tag=se&keywords=the+last+victim+tracy+hall&qid=1777342214&sbo=6l4LV4wiIM4ZjN%2Ffpg3jyQ%3D%3D&sprefix=tracy+hall+the+last%2Caps%2C117&sr=8-1] for the full story. * Subscribe to Unpopular Decisions on your favorite podcast app and follow us on Instagram [https://www.instagram.com/unpopulardecisionspod/]and LinkedIn.  What You Will Hear in This Episode * Who Tracy was before all of this: the career, the fresh start after divorce, the quiet optimism she was building into her forties * How Hamish McLaren built a world for her over 18 months and why her intuition never kicked in * The moment she saw a Crime Stoppers video and realized the man she loved was being arrested * The calls from jail, the letters, the flowers sent to her office, and how he tried to keep his hold on her * The 18-month information vortex: why not knowing the truth was as damaging as the fraud itself * The podcast Who the Hell is Hamish that changed everything for her healing * Why the hardest lie was not the money but the manufactured love * Shame as the loneliest emotion and how it creates distance from yourself and everyone around you * Why she chose to speak publicly when everyone around her said not to * The global scale of fraud: $21 billion lost in the US alone in 2025, organized crime compounds in Southeast Asia, and AI technology two years ahead of anything we have seen * Why the shame belongs to the criminal, not the victim * What you actually need before deciding to speak up or pursue legal action * Her book The Last Victim and the work she does now educating people around the world Listener Takeaways * When we wear rose-colored glasses, all the red flags are just flags. Emotional elevation is a tactic, not a coincidence. * The most sophisticated manipulators do not love bomb you. They are patient. They wait. They let you set the pace. * Your brain cannot rest without the full story. Unanswered questions are not just painful — they are a barrier to healing. * Shame creates distance from others and from yourself. It is the loneliest emotion and it belongs to the criminal, not you. * You will not bounce back from this. You will move forward with it inside you. And that is not a failure. That is the truth. * The desire to make something purposeful out of pain can be greater than the fear of what speaking up might cost. It takes time to get there. It got there for Tracy. The conversations on Unpopular Decisions are for informational and entertainment purposes only. Nothing in this episode constitutes legal or financial advice. If you have experienced financial fraud, please report it to your local law enforcement or relevant consumer protection authority. In the US, reports can be filed with the FBI's Internet Crime Complaint Center at ic3.gov. Time is important: if you can report within 72 hours you have a greater chance of recovery.