The Executive Coach to CEOs: Why Getting What You Want Can Leave You Unhappy | Rachel Barbaro

First, a little gift for you: Here is the exact Weekly Planner Template I use. You can download it for free and use it too :) This topic was HIGHLY requested by you. Reminder that if you ever want to submit a topic, question, or story, you can do so via the Confessions Vault . In this solo episode of The Five Year Plan, I’m sharing 5 practical tools you can use in your day-to-day life to remain ambitious without burning out. Each tool is drawn from academic research, my conversations with my past guests, and my own personal experience as a lawyer turned creator entrepreneur. We get into:Rethinking the to-do list that leaves you feeling behind Scheduling rest before you’re exhausted Choosing what to prioritize when everything feels important Using the 100/80/done rule to decide what deserves your best effort Finding an “unproductive” hobby purely for the joy of it ----Sponsors: Thank you to Strawberry.me for sponsoring this episode. Visit https://strawberry.me/thefiveyearplan to get 50% off your first coaching session.Want to partner with us? [email protected] IG: @thefiveyearplanpodcastTikTok: @thefiveyearplanpodcastNewsletter: https://thefiveyearplan.substack.com/Email: [email protected]

Dr. Noam Raiter is a family doctor and content creator challenging the idea that taking your career seriously means giving up the other parts of yourself. What started as a creative outlet during medical school became a second career—despite warnings that posting about fashion, makeup, or even vacations could undermine her future in medicine.In this episode, Noam shares how being diagnosed with a brain tumour at five shaped her relationship with medicine, why she questioned becoming a doctor after years of working toward it, and how she found a way to pursue both medicine and content creation without choosing between them.We talk about the pressure to make your job your entire identity, burnout in high-achieving environments, navigating social media as a professional, the double standards women face around appearance, overcoming the fear of being judged, and why having interests outside your career can make you better at your job. Plus, why Noam still doesn’t know what she wants to be when she grows up—and why she sees that as a good thing.---Follow Noam Here:Instagram: @noamraiterTikTok: @noamraiter---Sponsors:Thank you to Strawberry.me for sponsoring this episode. Visit strawberry.me/thefiveyearplan to get 50% off your first coaching session.Want to partner with us? [email protected] Five Year PlanInstagram: @thefiveyearplanpodcastTikTok: @thefiveyearplanpodcastNewsletter: substack.com/@thefiveyearplanEmail: [email protected] Timestamps: 00:00 Meet Noam Raiter01:08 Childhood Personality02:37 Brain Tumor Diagnosis04:34 Why Medicine Matters06:49 Doubts In Med School09:59 26 Hour Shifts Explained11:24 Med Culture Shock12:46 Burnout And Creativity15:32 Starting On Social Media18:09 Professionalism Fears19:53 Doctors Lawyers And Identity25:26 Podcast Origin Story26:06 Career Coaching Sponsor26:47 Why She Kept Posting30:32 Fear of Employer Backlash31:51 Handling Peer Criticism36:13 Hidden Curriculum Explained38:58 Gendered Double Standards42:21 Owning Feminine Identity48:06 The Problem with Five Year Plans51:04 Doctors Orders Rapid Fire54:17 TFYP Question

Thank you to ⁠⁠Strawberry.me⁠⁠ for sponsoring this episode. Visit ⁠⁠strawberry.me/thefiveyearplan⁠⁠ to get 50% off your first coaching session.It’s officially been six months since I sat down with Jules the Lawyer —the first real interview I ever did for The Five Year Plan. This week, I’m bringing back our conversation from Season 1 about career, identity, and figuring out who you are beyond your job title: Jules Romano, better known as Jules the Lawyer, is a lawyer turned full-time content creator who built an online following by sharing the realities of working in law, her signature humour, and her journey to becoming a “famous person.”In this episode, Jules shares how she balanced practising law with creating content, why burnout eventually forced her to choose, and the identity crisis that followed. She opens up about finding herself outside work and being told she wasn’t living up to her potential.Plus, Jules shares her MasterChef audition story, thrifting tips, and disaster stories from her wedding. --- Follow Jules here:⁠https://www.instagram.com/julesthelawyer/⁠⁠https://www.tiktok.com/@julesthelawyer⁠⁠https://www.youtube.com/@julesthelawyer--- Sponsors:Thank you to Strawberry.me for sponsoring this episode. Visit strawberry.me/thefiveyearplan to get 50% off your first coaching session.Want to partner with us? [email protected] Five Year PlanIG: https://www.instagram.com/thefiveyearplanpodcast/TikTok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: [email protected]: 00:49 "Fame" as a Brand Strategy05:45 Joking About Big Ambitions07:26 Growing Up and Choosing Law10:12 Law School Why and Structure15:01 Robbed by Legal Reality17:30 Starting TikTok 23:28 Leaving Big Law for Nonprofit26:41 Two Full Time Jobs30:25 Persona Protection and Haters31:54 Strawberry.Me 33:15 Quitting Law for Content34:47 Living Without a Plan37:11 Handling Online Criticism40:37 Rapid Fire Fan Questions41:00 Pets and Marriage Banter42:29 MasterChef Audition Saga45:40 Thrifting Like a Pro48:09 Wedding Dresses and Disaster51:16 Thoughts on Edmonton 54:06 TFYP Question

You’ve worked hard, checked the boxes, and built a life that looks good on paper. But you still find yourself thinking, “Is this really it?” How do you figure out what’s missing—and what to do next?In this episode, executive coach Rachel Barbaro joins us to unpack why achievement doesn’t always translate into fulfillment and how to get clearer on what you actually want. Rachel works with founders, CEOs, and senior leaders across banking, law, healthcare, and tech, helping them navigate burnout, career pivots, and the pressures of high achievement.We explore how to distinguish a difficult season at work from a sign you want something different, why familiar unhappiness can feel safer than change, and how to recognize when you’re pursuing someone else’s definition of success.We also talk about building a personal board of directors, creating more room for joy, and taking a next step when you have too many interests—or no idea where to begin.--- Follow Rachel here: Linkedin: https://www.linkedin.com/in/rachelbarbaro/Instagram: https://www.instagram.com/rachelbarbaro/— Sponsors:Thank you to Strawberry.me for sponsoring this episode. Visit strawberry.me/thefiveyearplan to get 50% off your first coaching session.Want to partner with us? [email protected] — The Five Year PlanInstagram: https://www.instagram.com/thefiveyearplanpodcast/TikTok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: [email protected]: 00:00 Meet Rachel Barbaro00:49 The Sunday Scaries02:26 Ego Versus Intuition03:37 Redefining Success04:15 From Corner Office07:11 Kids And True Self09:56 When Goals Disappoint11:54 Dip Or Sign14:48 Six Month Check17:46 Control In Toxic Jobs22:24 Find Your Purpose24:16 Purpose When Lost27:13 Interview Them Too28:36 Asking About Culture29:15 Interview Recon Tips30:38 Unhappiness vs Existential32:43 Setting Conditions for Joy34:59 Phone Boundaries Focus38:22 Fear of Change Loop42:32 Burnout Body Signals47:11 Highest Leverage Priorities49:09 Coach Me Rapid Fire52:59 TFYP Question

Most people don’t walk away from a stable career they actually like. Sophia Cong did.Sophia is a former nurse and the founder of Graze Anatomy, one of Toronto’s leading charcuterie and grazing companies. What started with Sophia making charcuterie boards out of her home while working 12-hour nursing shifts has grown into a business serving clients like Chanel, Sephora, Google, Microsoft, and Tiffany & Co.In this episode, Sophia shares why she left a nursing career she was good at to pursue something more creative, how she tested and validated Graze Anatomy before quitting, and why she waited until the business matched her nursing income for three consecutive months before going all in.We talk about immigrant parents and traditional definitions of success, the guilt of walking away from a career you spent years building, starting over without feeling like you’re starting from zero, working for free to learn a new skill, turning a side hustle into a real business, navigating the uncertainty of entrepreneurship, and why Sophia believes “the more you do, the luckier you get.”---- Follow Graze Anatomy Here:Instagram: https://www.instagram.com/thegrazeanatomy/Website: https://thegrazeanatomy.com/----Sponsors:Thank you to ⁠Strawberry.me⁠ for sponsoring this episode. Visit ⁠strawberry.me/thefiveyearplan⁠ to get 50% off your first coaching session. Want to partner with [email protected] The Five Year PlanInstagram: https://www.instagram.com/thefiveyearplanpodcast/TikTok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: [email protected] Timestamps00:00 From Nurse to Founder01:46 Do You Feel Successful04:42 Childhood Dreams and Roots06:20 Immigrant Expectations09:39 Why Nursing Wasn't Enough13:30 Creative Outlet Food Blog16:42 Breaking Into Food Styling19:50 Learning for Free Mindset21:16 First Charcuterie Breakthrough24:00 Turning Orders Into Business27:08 Passion Versus Burnout28:17 Sponsor Career Coaching29:39 Quitting Nursing Benchmarks31:01 Validating With Feedback32:24 Balancing Two Jobs33:26 Origin Of The Name34:31 Graze Or Nay Game36:53 Fear And Skill Building39:20 New Stress Tradeoffs42:16 Slow Seasons Mindset47:00 Big Clients And Reviews50:28 Working With Your Spouse52:31 Protecting The Relationship54:45 TFYP Question

Thank you to Strawberry.me for sponsoring this episode. Get 50% off your first coaching session at strawberry.me/thefiveyearplan.How do you know when it’s time to quit your job, change careers, end a relationship, or walk away from something you’ve spent years building?In this solo episode of The Five Year Plan, Anna breaks down 5 questions to ask yourself when you’re trying to figure out whether you’re going through a difficult season — or whether something is fundamentally no longer right for you.Drawing from her own decision, along with lessons from more than 50 hours of conversations with people who have made major life and career pivots, Anna explores the difference between temporary discomfort and knowing it’s actually time to move on.In this episode, you will learn: How to tell the difference between “this is hard” and “this is wrong for me”Why you should try changing your circumstances before changing your entire careerThe question: Do I actually want the future this path is leading me toward?Why your gut feeling can matter even when you can't logically explain itThe physical and mental signs we sometimes normalize when we're unhappyWhy apathy can be a bigger warning sign than hating your jobWhat it means when you haven't lost your ambition — your ambition has just movedWhy knowing it's time to leave doesn't mean you have to leave tomorrowHow to start making a plan when you know something needs to changeBecause sometimes the question isn't whether you can keep going. It's whether you actually want the life waiting for you at the end of the path you're on.-------- Sponsors: Thank you to ⁠⁠Strawberry.Me⁠⁠ for sponsoring this episode. Visit ⁠Strawberry.me/fiveyearplan⁠ for 50% off your first coaching session. Want to partner with us? [email protected] Help Plan The Five Year PlanHave a topic you want Anna to cover, a guest you want to hear from, or a question you want answered on the show?Submit here: https://forms.gle/W4xNQhL3Sqxd1WiK7--- Follow TFYP: Instagram: ⁠⁠https://www.instagram.com/thefiveyearplanpodcast/⁠⁠Tik Tok: ⁠⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠⁠Newsletter: ⁠⁠https://substack.com/@thefiveyearplan⁠⁠Email: [email protected] ---- Timestamps00:00 Should You Quit01:55 Season Or Forever09:41 Track The Patterns14:00 Try To Fix It19:19 Do You Want That Future25:11 Health Warning Signs28:37 When You Stop Caring33:47 Make A Quit Plan36:32 Final Thoughts00:00 Should You Quit01:55 Season Or Forever09:41 Track The Patterns14:00 Try To Fix It19:19 Do You Want That Future25:11 Health Warning Signs28:37 When You Stop Caring33:47 Make A Quit Plan36:32 Final Thoughts

Most entrepreneurship stories start with someone quitting their job and going all in. Gillian Liu did the opposite.Gillian is the co-founder of Kiyoko Beauty, one of the largest Asian beauty retailers in North America. She and her co-founder started Kiyoko as a side project in 2021 and grew it into a $10 million business — all while keeping their corporate jobs.In this episode, Gillian shares why she waited nearly five years to leave her 9–5, how keeping her job actually helped Kiyoko grow, and why she thinks we’ve romanticized the idea that becoming an entrepreneur means risking everything.We talk about immigrant parents and traditional definitions of success, fear and financial security, building a business on nights and weekends, knowing when to delegate, and why you don’t necessarily have to blow up your life to build something big.Follow Gillian Here: https://www.instagram.com/hi.itsgillian/?hl=enhttps://www.tiktok.com/@hi.itsgillianhttps://www.youtube.com/@hi.itsgillian--- Follow Kiyoko Beauty Here: https://www.instagram.com/kiyoko.beautyhttps://www.tiktok.com/@kiyokobeauty--- -------- Sponsors: Thank you to ⁠Strawberry.Me⁠ for sponsoring this episode. Visit Strawberry.me/fiveyearplan for 50% off your first coaching session. Want to partner with us? [email protected] The Five Year PlanInstagram: ⁠https://www.instagram.com/thefiveyearplanpodcast/⁠Tik Tok: ⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠Newsletter: ⁠https://substack.com/@thefiveyearplan⁠Email: [email protected] ---- Timestamps:00:00 Meet Gillian Liu00:47 Childhood Goals01:57 Immigrant Success Mindset03:38 No Entrepreneurs Around05:43 Excellence And Pressure09:07 Resentment To Respect11:10 Biochem To Business Pivot16:16 Kiyoko Origin Story19:56 Bored In Consulting25:33 Choosing A Co Founder27:03 When It Got Real27:54 Mom Becomes COO28:33 Making It Feel Real30:03 Balancing Two Jobs31:54 Toxic Startup Wakeup35:20 Delegation Over Perfection40:57 Why Not Quit Yet46:51 Fear And Monkey Bars49:13 Owning Entrepreneur Identity53:33 Kiyoko North Star Vision54:22 Off Plan Segment 56:51 TFYP Concluding Question

Most of us spend years working toward a career before we ever find out what that career actually looks like day-to-day. In 2021, Hilary Henderson, a stand up comedian, was working a desk-job as a policy analyst when she had that realization. Hilary studied international development and economics, earned her master’s in public administration, and built a career in policy — only to realize the life she had worked so hard for wasn’t one she actually wanted.In this episode, Hilary shares how she went from policy analyst to stand-up comedian, what it was like becoming a beginner again, and how she eventually knew it was time to leave her 9–5. We talk about bombing, perfectionism, sexism in comedy, and why sometimes the only way to figure out what you want is to be willing to try something you might fail at.------Follow Hilary here: ⁠https://www.instagram.com/hilaryhendersonn⁠https://www.tiktok.com/@hilaryhendersonhttps://www.youtube.com/@hilaryhenderson-------- Sponsors: Thank you to Strawberry.Me for sponsoring this episode. Want to partner with us? [email protected] The Five Year PlanInstagram: https://www.instagram.com/thefiveyearplanpodcast/Tik Tok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: [email protected] ---- Timestamps: 00:00 Meet Hillary Henderson01:36 Ten Years Ago Dreams03:51 Policy Passion Reality Check07:25 Comedy Roots Early Life09:48 Post Grad Cliff Content11:49 Learning Stand Up Basics14:05 Turning Down Ottawa Job17:19 First Open Mic Story21:09 Grinding Mics Content Sales22:57 Burnout Tipping Point26:24 Sexism In Comedy Industry30:55 Handling Being Undervalued31:58 Control What You Can33:03 Bombing Defined33:45 First Bomb Lessons35:27 Lawyer Court Bomb37:03 Shame Versus Mistakes39:13 Perfectionism And Drafts40:23 Starting The Podcast43:26 Becoming A Beginner Again48:38 Reps Stress And Burnout50:16 Comparisons And New Careers52:34 Smash Or Pass Game55:46 Five Year Vision

In January 2025, Janine Ilya fell into a week-long coma.Against all odds, she woke up. But she couldn't walk, couldn't speak properly, and had lost much of her memory. She had to relearn everything—from taking her first steps to rediscovering who she was.This isn't just a story about surviving. It's a story about what happens when you're given a second chance at life—and how coming face-to-face with death changes the way you think about time, ambition, relationships, and what really matters. If you've been waiting for the "right time" to start living, this conversation is your reminder that tomorrow is a promise none of us are guaranteed.---- Special note from Anna:Guys.... this is the final episode of Season 1. Thank you for being part of an incredible first season. Whether you've listened to one episode or all of them, I can't thank you enough. Stay tuned for Season 2 this fall!!! --- Follow Janine here: IG: @janineilya TikTok: ⁠@janine.ilyaYoutube: ⁠@janineilya---- Share Your Story: ⁠⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠ |⁠⁠⁠⁠ Instagram⁠⁠⁠⁠ | ⁠⁠⁠⁠Substack ⁠⁠⁠⁠Email: [email protected]

This week, Anna dives into one of the most universal - and quietly terrifying - questions we ask ourselves: Am I falling behind??In this solo episode (and the second last episode of Season 1!!!), Anna unpacks where "feeling behind" comes from, why high achievers are especially vulnerable to it, and how to redefine success when your life doesn't follow the timeline you imagined.Special shoutout to the listener who submitted their story to the Confessions Vault and inspired this entire episode. Your fellow planners are rooting for you!! Share Your Story: ⁠The Confessions Vault ⁠TikTok: ⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠IG: ⁠https://www.instagram.com/thefiveyearplanpodcast⁠Substack: ⁠https://substack.com/@thefiveyearplanpodcast⁠Email: [email protected]