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.

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Follow Jules here:

⁠https://www.instagram.com/julesthelawyer/⁠

⁠https://www.tiktok.com/@julesthelawyer⁠

⁠https://www.youtube.com/@julesthelawyer

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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? anna@thefiveyearplanpodcast.com

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The Five Year Plan

IG: https://www.instagram.com/thefiveyearplanpodcast/
TikTok: https://www.tiktok.com/@thefiveyearplanpodcast
Newsletter: https://substack.com/@thefiveyearplan
Email: anna@thefiveyearplanpodcast.com

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Timestamps:

00:49 "Fame" as a Brand Strategy

05:45 Joking About Big Ambitions

07:26 Growing Up and Choosing Law

10:12 Law School Why and Structure

15:01 Robbed by Legal Reality

17:30 Starting TikTok

23:28 Leaving Big Law for Nonprofit

26:41 Two Full Time Jobs

30:25 Persona Protection and Haters

31:54 Strawberry.Me

33:15 Quitting Law for Content

34:47 Living Without a Plan

37:11 Handling Online Criticism

40:37 Rapid Fire Fan Questions

41:00 Pets and Marriage Banter

42:29 MasterChef Audition Saga

45:40 Thrifting Like a Pro

48:09 Wedding Dresses and Disaster

51:16 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.

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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? anna@thefiveyearplanpodcast.com

—

The Five Year Plan

Instagram: https://www.instagram.com/thefiveyearplanpodcast/TikTok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: anna@thefiveyearplanpodcast.com

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Timestamps:

00:00 Meet Rachel Barbaro

00:49 The Sunday Scaries

02:26 Ego Versus Intuition

03:37 Redefining Success

04:15 From Corner Office

07:11 Kids And True Self

09:56 When Goals Disappoint

11:54 Dip Or Sign

14:48 Six Month Check

17:46 Control In Toxic Jobs

22:24 Find Your Purpose

24:16 Purpose When Lost

27:13 Interview Them Too

28:36 Asking About Culture

29:15 Interview Recon Tips

30:38 Unhappiness vs Existential

32:43 Setting Conditions for Joy

34:59 Phone Boundaries Focus

38:22 Fear of Change Loop

42:32 Burnout Body Signals

47:11 Highest Leverage Priorities

49:09 Coach Me Rapid Fire

52:59 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.”

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Follow Graze Anatomy Here:
Instagram: https://www.instagram.com/thegrazeanatomy/
Website: https://thegrazeanatomy.com/

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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?
anna@thefiveyearplanpodcast.com

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The Five Year Plan
Instagram: https://www.instagram.com/thefiveyearplanpodcast/
TikTok: https://www.tiktok.com/@thefiveyearplanpodcast
Newsletter: https://substack.com/@thefiveyearplan
Email: anna@thefiveyearplanpodcast.com

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Timestamps

00:00 From Nurse to Founder

01:46 Do You Feel Successful

04:42 Childhood Dreams and Roots

06:20 Immigrant Expectations

09:39 Why Nursing Wasn't Enough

13:30 Creative Outlet Food Blog16:42 Breaking Into Food Styling

19:50 Learning for Free Mindset

21:16 First Charcuterie Breakthrough

24:00 Turning Orders Into Business

27:08 Passion Versus Burnout

28:17 Sponsor Career Coaching

29:39 Quitting Nursing Benchmarks

31:01 Validating With Feedback

32:24 Balancing Two Jobs

33:26 Origin Of The Name

34:31 Graze Or Nay Game

36:53 Fear And Skill Building

39:20 New Stress Tradeoffs

42:16 Slow Seasons Mindset

47:00 Big Clients And Reviews

50:28 Working With Your Spouse

52:31 Protecting The Relationship

54:45 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 career
• The 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 it
• The physical and mental signs we sometimes normalize when we're unhappy
• Why apathy can be a bigger warning sign than hating your job
• What it means when you haven't lost your ambition — your ambition has just moved
• Why knowing it's time to leave doesn't mean you have to leave tomorrow
• How to start making a plan when you know something needs to change

Because 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.

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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?

anna@thefiveyearplanpodcast.com

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Help Plan The Five Year Plan

Have 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

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Follow TFYP:

Instagram: ⁠⁠https://www.instagram.com/thefiveyearplanpodcast/⁠⁠

Tik Tok: ⁠⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠⁠

Newsletter: ⁠⁠https://substack.com/@thefiveyearplan⁠⁠

Email: anna@thefiveyearplanpodcast.com

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Timestamps

00:00 Should You Quit

01:55 Season Or Forever

09:41 Track The Patterns

14:00 Try To Fix It

19:19 Do You Want That Future

25:11 Health Warning Signs

28:37 When You Stop Caring

33:47 Make A Quit Plan

36:32 Final Thoughts

00:00 Should You Quit

01:55 Season Or Forever

09:41 Track The Patterns

14:00 Try To Fix It

19:19 Do You Want That Future

25:11 Health Warning Signs

28:37 When You Stop Caring

33:47 Make A Quit Plan

36:32 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=en

https://www.tiktok.com/@hi.itsgillian

https://www.youtube.com/@hi.itsgillian

---

Follow Kiyoko Beauty Here:

https://www.instagram.com/kiyoko.beauty

https://www.tiktok.com/@kiyokobeauty

---

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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?

anna@thefiveyearplanpodcast.com

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The Five Year Plan

Instagram: ⁠https://www.instagram.com/thefiveyearplanpodcast/⁠

Tik Tok: ⁠https://www.tiktok.com/@thefiveyearplanpodcast⁠

Newsletter: ⁠https://substack.com/@thefiveyearplan⁠

Email: anna@thefiveyearplanpodcast.com

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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/hilaryhendersonn

⁠https://www.tiktok.com/@hilaryhenderson

https://www.youtube.com/@hilaryhenderson

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Sponsors:

Thank you to Strawberry.Me for sponsoring this episode.

Want to partner with us?

anna@thefiveyearplanpodcast.com

----

The Five Year Plan

Instagram: https://www.instagram.com/thefiveyearplanpodcast/

Tik Tok: https://www.tiktok.com/@thefiveyearplanpodcast

Newsletter: https://substack.com/@thefiveyearplan

Email: anna@thefiveyearplanpodcast.com

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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.

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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!!!

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Follow Janine here:

IG: @janineilya

TikTok: ⁠@janine.ilya

Youtube: ⁠@janineilya

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Share Your Story: ⁠⁠⁠⁠⁠The Confessions Vault ⁠⁠⁠⁠⁠

⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠ |⁠⁠⁠⁠ Instagram⁠⁠⁠⁠ | ⁠⁠⁠⁠Substack ⁠⁠⁠⁠

Email: annashuyizhang@gmail.com

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/@thefiveyearplanpodcast⁠

IG: ⁠https://www.instagram.com/thefiveyearplanpodcast⁠

Substack: ⁠https://substack.com/@thefiveyearplanpodcast⁠

Email: annashuyizhang@gmail.com