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

----

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