Hello Monday with Jessi Hempel

Most of us approach a long break from work with some anxiety. Whether it’s a layoff, parental leave, or a season of caregiving, there’s tension around if and when we’ll return to work and how we’ll explain the gap on our résumé.

DJ DiDonna, senior lecturer at Harvard Business School and author of the new book Big Time Off, wants to change that. This week, he joins Jessi to make the case that stepping away from routine work — for whatever reason, for however long — is one of the most strategic things you can do for your career and your life.

Jessi and DJ discuss:

What a sabbatical actually is, and why two-thirds of them happen because of a negative catalyst, not a choice

Why immediately job-searching after a layoff is like grocery shopping while hungry

The difference between a vacation, a corporate "sabbatical," and the real thing, and why it takes six to eight weeks just to feel like yourself again

What DJ calls "fertile emptiness," and why most of us never let ourselves get there

How to use a sabbatical to run experiments on possible future versions of yourself

The story of a CTO who went to Norway, built a text-to-speech app, and redesigned his entire relationship with work and money

Why functional workaholism is the thing most of us are living with

What AI has to do with the case for stepping back, and why learning from a place of fear versus curiosity makes all the difference

How Jessi's own three-month hiatus from the workplace, during which she wrote a book and raised a newborn, turned out to be a sabbatical she didn't know she was taking

How to start planning for a sabbatical five years from now, even if taking one today feels impossible

Follow DJ DiDonna and Jessi Hempel on LinkedIn.

You can't lead a team through a hard moment if you can't manage yourself first. That's the core of Dr. Becky Kennedy's work. The clinical psychologist and founder of Good Inside built a global movement teaching parents how to navigate the hardest moments with their kids. It turns out those same skills are exactly what the modern workplace needs. This week, Dr. Becky joins Jessi in the studio to translate her parenting playbook for managers, leaders, and anyone who's ever had to deliver hard news, hold a line they didn't fully believe in, or hold it together when someone on their team fell apart.

In this episode, Jessi and Dr. Becky discuss:

Why conviction matters more than confidence, and how to tell if you actually have it before walking into a hard meeting

The AVP method (acknowledge, validate, permit) for regulating your own emotions before they spill into the room

Why self-regulation isn't a two-minute fix, and what Dr. Becky calls "the road to reactivity"

How to separate behavior from identity when giving feedback, and why conflating the two is what makes hard conversations go wrong

Why sturdiness is the key to managing a team through uncertainty and layoffs

The sentence structure to use when you don't have all the answers but still need to show up as a leader

Why empathy requires boundaries, and a tennis court visualization that keeps other people's feelings on their side of the net

What anger is actually telling you, and how to use it productively instead of letting it drive the conversation

Why Dr. Becky is skeptical of the feedback sandwich, and a feedback method to use instead

A simple question managers can ask every week to make upward feedback feel safe and specific

This conversation was originally recorded live and broadcast to LinkedIn Premium members. Premium members can watch the extended version here.

Follow Dr. Becky Kennedy and Jessi Hempel on LinkedIn.

Most of us think of negotiation as something reserved for high-stakes boardrooms—or even hostage situations. But Christopher Voss, former FBI lead hostage negotiator and bestselling author of Never Split the Difference, says negotiation is everywhere: in salary talks, in team meetings, even in conversations with your kids. 

In this episode from the Hello Monday archives, Jessi Hempel sits down with Chris to explore how we can all become better negotiators by focusing on empathy, collaboration, and trust. Drawing on decades of experience, Chris shares practical tools you can use to move conversations forward—whether you’re asking for a raise, dealing with a difficult boss, or navigating conflict at home.

Chris and Jessi discuss:

Why negotiation is really about collaboration and long-term relationships

How to shift from seeking control to building influence

The power of labeling emotions to build trust and lower defenses

Why “no” is often more powerful than “yes”

How to recognize when a negotiation is over—or when it’s time to walk away

Strategies to reframe salary conversations and show your value

This episode was recorded live in-studio. For an extended, behind-the-scenes version, watch on LinkedIn Premium.

We tend to talk about AI and the future of work as a young person's game. Dr. Myechia Minter-Jordan, CEO of AARP, is here to challenge that notion. A physician turned healthcare executive turned nonprofit leader, she joins Jessi in the studio to talk about ageism, AI, and what it means to not just stay relevant, but to move ahead, in the second half of a working life. 

In this episode, Jessi and Dr. Minter-Jordan discuss:

How the fifty-plus workforce is upskilling faster than other generations

How to reframe experience as an asset in a job search, and why soft skills are having a moment

The move Dr. Minter-Jordan made that surprised everyone: going back to business school in her thirties, while practicing medicine

Why mentorship is one of the most powerful tools an older worker has for demonstrating value, and why stepping back from it is a mistake

How Dr. Minter-Jordan got her current job as CEO of AARP

What the trillion-dollar caregiving economy means for employers, and why the policies aren't keeping up

How to approach AI without feeling overwhelmed: start small, stay consistent, and focus on what's relevant to your field

Whether you should de-age your résumé

How to be strategic about timing a career pivot, especially when you have real responsibilities

What Dr. Minter-Jordan would tell a thirty-five-year-old building a career for the long arc

This episode was originally recorded live and broadcast to LinkedIn Premium members. Premium members can watch the extended version here.

Follow Dr. Myechia Minter-Jordan and Jessi Hempel on LinkedIn.

“It’s not your fault.” This is the message Alissa Quart has spent over a decade trying to get people to believe when it comes to economic hardship. Right now, it feels harder than ever to embrace.

Alissa Quart is the executive director of the Economic Hardship Reporting Project, the nonprofit Barbara Ehrenreich built after writing her groundbreaking exposé Nickel and Dimed. A journalist herself, Alissa is the author of seven books, including Squeezed: Why Our Families Can’t Afford America and Bootstrapped: Liberating Ourselves from the American Dream. She's spent over a decade reporting on class, caregiving, and economic precarity.

In this episode, Jessi and Alissa discuss:

Why "insecurity" is a more honest and unifying framework than "affordability," and how it builds solidarity across class lines

The data behind it: 52% of US families are now financially insecure by one measure, and nearly half of workers lack confidence they could find a job they'd want

"Apocalyptic insecurity": the new framework Alissa and economist Lynn Parramore developed to describe how employers use AI dread to manipulate workers

The Frederick Taylor parallel: how AI is repeating the logic of scientific management, a century later

"AI brain fry": the exhaustion of performing enthusiasm for AI at work while feeling something very different about it personally

Why losing the narrative of generational progress is its own kind of psychological injury

The AI dividend, universal basic income, and what a modern New Deal could look like

Why naming the problem matters: how failing to recognize insecurity as systemic — rather than personal failure — can curdle into self-blame and even disordered coping

What Alissa tells her own daughter about finding agency in an uncertain future

Follow Alissa Quart and Jessi Hempel on LinkedIn.