DJ DiDonna defines a sabbatical as "intentional extended leave from your job." DJ is a Harvard Business School senior lecturer and the author of Big Time Off: The Transformative Power of Sabbaticals and How to Take One, out now.

Planning one, on leave, heading back, leaving to build something new, or facing a re-org you didn't ask for? Monique and DJ talk about sabbatical vs. vacation, regret insurance, and what to do if time off finds you first.

Ideas to try

• Journal before, during, and after your time away.
• Spend 30 to 60 minutes alone, no phone, no music, writing what your life wouldn't feel complete without. Then ask: am I making time for this?
• Picture yourself five to ten years from now. What would you regret not doing? What story do you want to tell your grandkids?
• Find someone who has taken extended leave.

Timestamps

• (00:00) - Welcome and DJ's background
• (02:24) - What is a sabbatical, and how is it different from a vacation?
• (03:53) - What does DJ want to debunk about sabbaticals?
• (06:04) - Why is a sabbatical "regret insurance"?
• (09:54) - What are the common catalysts that lead people to step away?
• (11:27) - When time off is forced on you, how do you reframe it?
• (14:40) - Monique's 12 weeks off: was that a sabbatical?
• (18:02) - DJ's answer: functional workaholism and the power of exemplars
• (21:25) - Why do people resist time off for themselves, even when sabbaticals are normalized?
• (24:09) - Can you work on a sabbatical, and what counts as work?
• (27:28) - What if you're driven and need to go now? Do you still need time off?
• (32:13) - Type A and the gift of time: getting out of your head and into your body
• (37:41) - Quiet reflection or community: what did the research find?
• (39:23) - What has evolved in DJ's thinking since writing the book?
• (44:50) - What first steps can people try?

Links

• Get the book, Big Time Off: https://www.amazon.com/dp/1668060892
• DJ DiDonna: https://www.djdidonna.com
• The Sabbatical Project: https://www.thesabbaticalproject.org
• Ask Monique: https://forms.gle/iGZv2bVnhBSXbnbc8
• Connect with Monique on LinkedIn: https://www.linkedin.com/in/moniqueschafer
• The Great Life Experiment: https://greatlifeexperiment.com/

There's no one right way. Let's experiment together.

"You are too old to hire and too young to retire."

That's the line a friend used with Monique that sparked this week's episode, recorded (as always) from the car. It's a worry a lot of people in their 40s and 50s are starting to have. If you're feeling caught in that in-between - too experienced for more junior roles or ones that consume your whole life, yet you are not ready (or not able) to stop working - then this one's for you.

Monique unpacks where that feeling comes from, why it's more common than you'd think among people with 15-20+ years of experience, and shares one practical exercise you can start today to reconnect with the value you already bring with no resume rewrite required today.

In this episode:

• The real story behind "too old to hire, too young to retire" conversation
• Why feeling stuck hits hardest right when you're most experienced
• How to face the market reality (skills, industries changing) without spiraling
• Why you're not actually "behind" on AI, even though it feels that way
• One tactical daily exercise to reconnect with your value
• Why your soft skills — and being multi-passionate — aren't a liability

If this resonates, share it with a friend who's in the thick of it, and subscribe so you never miss an episode.

PART 3 OF "NAVIGATING CAREER CHANGES": This episode is a must-listen for anyone navigating the messy middle of career transitions, whether you're contemplating leaving a job or grappling with identity loss after a layoff.

Dr. Fishman, a psychologist and former tech researcher, shares his personal journey of grappling with his identity after being laid off from Facebook and his decision to walk away for another 'successful' career that was no longer fulfilling.

He emphasizes the importance of embracing your emotions without judgment and recognizing that feeling unfulfilled is a common human experience. You’ll discover how to confront your fears about leaving a stable job, and why prioritizing your happiness is crucial not just for you, but for those you care about.

In this enlightening conversation, you’ll gain insights on:

- The psychological implications of career transitions and how they affect your identity.

- Strategies for navigating feelings of grief and loss associated with leaving a job.

- The importance of experiencing joy in the ordinary and redefining what fulfillment looks like.

- How to shift your mindset and recognize that your current life may already hold the happiness you seek.

Dr. Evan Fishman is a psychologist, former Meta researcher, and founder of The Beloved Institute. After years studying motivation—from academia to Silicon Valley—he realized that many of the world's highest achievers weren't searching for another strategy, they were searching for themselves.

Connect with Dr. Evan Fishman

LinkedIn | TikTok | Website

Connect with Monique Schafer:

LinkedIn | Instagram | YouTube | Website

In this week's episode of the Great Life Experiment, Monique interviews

Keri-Lynne (KL) Shaw who shares her journey from corporate CHRO to entrepreneur, emphasizing the importance of proactive negotiation, understanding total compensation, and strategic exit planning. This episode offers practical insights for high performers and anyone looking to maximize their career and financial potential.

Key discussions in this episode:

• The importance of negotiation at every career stage
• How to assess and maximize total compensation
• Strategies for proactive exit planning and negotiations
• Lessons from corporate leadership on salary and equity
• Overcoming fears and limiting beliefs around money and career
• The role of coaching and community in career success
• The impact of market disruptions on career trajectories
• Building a business after leaving corporate roles

Chapters

00:00 Introduction to Keri-Lynne Shaw and her mission

01:56 Keri-Lynne's career journey from HR to founder of The Salary Bump

03:30 A pivotal moment during the pandemic: realizing her salary was undervalued

05:56 How to have a conversation about salary and equity with confidence

08:06 The importance of understanding total compensation and benefits

11:50 Debunking myths about negotiating later in your career

17:09 Practical steps to prepare for salary negotiations

22:10 Questions to ask during the interview to gauge compensation

26:58 Strategies for proactively exiting a role with a package

32:56 The differences between proactive exits, reorganizations, and layoffs

36:55 Overcoming fears and mindset blocks around negotiation

40:05 Building a community and support system for career growth

44:08 The power of sharing behind-the-scenes and authentic stories

48:04 Final advice for high performers feeling stuck or undervalued

• LinkedIn | TikTok | Instagram | Website | Youtube | Podcast | TV Show

• LinkedIn | Instagram | YouTube | Website

Got a question that's keeping you up at night? Need a new way to look at a problem?

'Ask Monique' is your chance to get personalized insights. Submit your questions about business, professional life, or personal development, and let's dive into the messy, beautiful, and ever-changing world together.

https://forms.gle/iGZv2bVnhBSXbnbc8

Many of us move through life believing our future has already been decided—by our upbringing, our circumstances, our career path, or the rules we’ve been taught not to question.

But what if those limitations aren’t fixed at all?

In this episode, Monique sits down with Jacob Warwick, known as the “Billion Dollar Man,” to explore how negotiation is really about changing the way we think. Together, they unpack why curiosity is more powerful than confrontation, how challenging predetermined beliefs opens doors to new possibilities, and why the stories we tell ourselves often become the biggest obstacle to creating the life we truly want.

Whether you’re navigating compensation negotiation, a career transition, advocating for yourself, or simply wondering what’s possible beyond the limits you’ve accepted, this conversation will inspire you to rethink what’s negotiable—not just in business, but in life.

(00:00) – Introduction

(01:05) – Meet Jacob Warwick: The Billion Dollar Man

(04:32) – Why Jacob wants to teach negotiation without using the word "negotiation"

(13:39) – The biggest mistakes people make before negotiating

(18:45) – Internal promotions, confidence, and advocating for your value

(24:54) – The "Predetermined" mindset and challenging invisible rules

(26:15) – Curiosity as your greatest negotiation advantage

(32:30) – Why "No" is often where the real negotiation begins

(35:57) – The hidden cost of success and redefining wealth

(39:48) – Jacob's extraordinary personal story and rewriting his own future

(48:04) – Responsibility, resilience, and choosing your own path

• Substack Publication | https://www.predetermined.com/
• Website | https://www.thinkwarwick.com/

• Website | https://greatlifeexperiment.com/
• Instagram - thegreatlifeexperiment_podcast | https://www.instagram.com/thegreatlifeexperiment_podcast
• Instagram - @itsmoniqueschafer | https://www.instagram.com/itsmoniqueschafer
• YouTube | https://www.youtube.com/@GreatLifeExperiment

Got a question that's keeping you up at night? Need a new way to look at a problem?

'Ask Monique' is your chance to get personalized insights. Submit your questions about business, professional life, or personal development, and let's dive into the messy, beautiful, and ever-changing world together.

https://forms.gle/iGZv2bVnhBSXbnbc8

Life doesn’t slow down when you’re overwhelmed.

In this episode, Monique explores what it’s like when all aspects of life demand attention at once - work, parenting, health, leadership, and personal projects. She examines how to stay present and effective without letting overwhelm take control.

Monique reframes difficulty as an opportunity rather than a failure. She shares practical strategies for navigating busy seasons with clarity, intention, and self-compassion. Through stories and reflections from her own life, she demonstrates how to use friction as a signal, make strategic decisions about what truly matters, and how to protect energy while still showing up fully.

(00:51) - How Are You, Really? (03:12) - The Reality of Full Seasons (05:22) - Using Difficult Moments to Your Advantage (06:50) - Acknowledging Frustration Without Paralysis (08:51) - Brain Dumps & Clearing Mental Overload (11:37) - Glass Balls vs Rubber Balls Framework (13:42) - Protecting Your Team & Shielding Priorities (15:24) - Delegation, AI, Virtual Assistants, and Family Advisors

• Website | https://www.thegreatlifeexperimentpodcast.com
• Instagram - thegreatlifeexperiment_podcast | https://www.instagram.com/thegreatlifeexperiment_podcast
• Instagram - @itsmoniqueschafer | https://www.instagram.com/itsmoniqueschafer
• YouTube | https://www.youtube.com/@GreatLifeExperiment

Got a question that's keeping you up at night? Need a new way to look at a problem?

'Ask Monique' is your chance to get personalized insights. Submit your questions about business, professional life, or personal development, and let's dive into the messy, beautiful, and ever-changing world together.

https://forms.gle/iGZv2bVnhBSXbnbc8

In this episode, Monique gets honest about breaking her own consistency streak and why giving ourselves grace matters in a messy, overwhelming world. She talks about holding space for real feelings at work and at home, and shares practical, down‑to‑earth ways she’s using AI in real life—from planning a family trip to synthesizing feedback and even learning to build with AI through a product boot camp. Take what resonates, leave the rest, and keep experimenting.

(01:36) - Consistency, Priorities, and Starting Again (04:24) - When the World Feels Heavy (05:39) - Permission to Pause and Give Yourself Grace (07:30) - Holding Safe Spaces at Work (10:47) - Planning a Family Spring Break with AI (Practical Trip-Planning Use Case) (15:27) - Using AI to Synthesize Performance Review Data Responsibly (18:19) - Building a Front-End Using Natural Language (20:00) - APIs and Backend Learning (22:01) - Why Experimenting Builds Better Product Leaders

• Website | https://www.thegreatlifeexperimentpodcast.com/
• Instagram - thegreatlifeexperiment_podcast | https://www.instagram.com/thegreatlifeexperiment_podcast
• Instagram - @itsmoniqueschafer | https://www.instagram.com/itsmoniqueschafer
• YouTube | https://www.youtube.com/@GreatLifeExperiment

Got a question that's keeping you up at night? Need a new way to look at a problem?

'Ask Monique' is your chance to get personalized insights. Submit your questions about business, professional life, or personal development, and let's dive into the messy, beautiful, and ever-changing world together.

https://forms.gle/iGZv2bVnhBSXbnbc8