Shows / Dots and Dreams
Dots and Dreams
Real, vulnerable stories of navigating major life transitions like career pivots, relocation, motherhood, reinvention. Sharing all the honest and real-time moments of building something new, raising two small kids, and navigating it all. Hosted by Jenny Sidorova.
dotsanddreamspodcast.substack.com
Episodes
Dots and DreamsEpisode 12: Nobody Was Going to Give Her Permission. So She Gave It to Herself.
Simone Thomas spent years quietly carrying a specific, almost impossible-sounding dream: a string of boutique hotels scattered across the world, something…
Dots and DreamsEpisode 11: She's Not Ready for Her Kid to Leave. And She's Not Sure Who She'll Be When He Does
Jenny's oldest friend Julia is about to become an empty nester. Her son Ethan leaves for college in three months. And Julia, who never considered herself "a…
Dots and DreamsEpisode 10: I Don't Believe in Work-Life Balance But I Do Believe in Non-Negotiables.
Jenny Sidorova was lying on a bed in a lakeside room in Kamouraska, Quebec, on vacation with her then-boyfriend's family, when her BlackBerry buzzed with a…
Dots and DreamsEpisode 9: Why Love Will Be Your Most Important Relationship to Lean on During Career Highs and Lows
When Jenny Sidorova got laid off in December 2024, she expected the hardest part to be the job search. What she didn't expect was how much the search itself…
Dots and DreamsEpisode 8: How to Navigate a Career Pivot in The AI Era And Why Self-Gratitude is The Only Answer
Jenny Sidorova got laid off in December 2024, at the tail end of her second maternity leave, and walked straight into a job market being rewritten in real time…
Dots and DreamsEpisode 7: How to Start Over in a New City and Why Routine, Curiosity, Reinvention, and Time Alone Will Be Your First Friends
Jenny has moved over 20 times in her adult life. And every single time, she has arrived somewhere with a closed heart and had to find her way back to herself…
Dots and DreamsEpisode 6: I Love My Kids But Miss My Old Life. And How to Stop Feeling Guilty About It
Jenny had her first child in October 2020 and felt like everything that made her her had been wiped away. In this episode of Dots and Dreams, Jenny gets honest…
Dots and DreamsEpisode 5: The Midlife Crisis Women Aren't Allowed to Have
Have you ever stuffed your face into clean laundry to hide your crying, and had no idea why? That's where this episode begins. A summer evening in 2021, a…
Dots and DreamsEpisode 4: I'm Worried About AI, How to Keep Up, How My Kids Will Grow Up, and Will the World Fall Apart?
Two letters. Not new to the world, but ones Jenny never expected to think about as often as she has in the last 18 months. Two letters that have brought her…
Dots and DreamsEpisode 3: Going Through Big Change is Lonely. The Pull is What I Focus On.
Jenny's first layoff happened in 2025, her seventh job search since grad school, and the scariest one she'd ever faced. But the hardest part wasn't…
Dots and DreamsEpisode 2: I Don't Fit In Anywhere, And Why That's a Superpower
She'd lived in Paris, San Francisco, New York, and the Basque Country. She spoke multiple languages and could walk into almost any room in the world. And yet…
Dots and DreamsEpisode 1: I Got Everything I Ever Wanted. So Why Can't I Enjoy It?
Twenty years. That's how long Jenny chased French citizenship, and when she finally got it, she felt nothing. No tears. No celebration. Just quiet, unsettling…
Dots and DreamsThe Dots and Dreams Trailer is Here
Have you ever achieved something you dreamed about for 20 years and felt nothing when you finally got it? Or felt like a puzzle piece that just didn't fit…