Today, we’re making the personal and professional case for some extended time off. Who needs a sabbatical, and most importantly, how do you take one? We cover the logistics, finances, and psychology behind stepping away from work—along with three interviews: Jen Fisher, the Human Sustainability Leader from Deloitte, Progress Coach Jillian Johnsrud, and Rich ... Show More
Dec 2025
Curtain Call: All Stars Return to Talk Financial Independence, Fear, and Growth
Well, here we are—for the last time, for now. A couple weeks ago, I wrote an end-of-year letter that functioned like a little “status update” on how I’m feeling moving into 2026. In this episode, I invite back five of my favorite guests for their own check-ins. We talk about: Wha ... Show More
1h 52m
Dec 2025
Why We Judge Women’s Spending, What We Hide, & What We’re Afraid to Admit
Today’s guest won’t surprise you if you read the introduction to Rich Girl Nation, which recollected the 2018 event that made me think personal finance might not be solely for people with brown bananas and pocket protectors. Lindsey Stanberry, founding editor of Refinery29’s Mone ... Show More
56m 3s
Jan 2025
The Art of the Sabbatical w/ Cady North #935
When most folks hear the word “sabbatical”, their mind probably goes to a professor with a tweed jacket, who has earned tenure at a prestigious university, who is going to use that time to write a book. Or maybe your values are more Judeo-Christian based and so you think of a per ... Show More
53m 9s
Oct 2023
Can I afford to totally change my life?
Longing to quit your job and follow your passion? Or perhaps take a break to travel? Or move to a new place? First, you'll need to look at your finances. In this episode, Jill Schlesinger, a certified financial planner and business analyst for CBS News, walks through her five ste ... Show More
19m 13s
Sep 2025
Can you afford to make a big life change?
Longing to quit your job and follow your passion? Or perhaps take a break to travel? Or move to a new place? First, you'll need to look at your finances. In this episode, Jill Schlesinger, a certified financial planner and business analyst for CBS News, walks through her five ste ... Show More
19m 18s
Mar 2023
Taking a Sabbatical as a Business Owner
<p>In this episode of Rework, Jason Fried and David Heinemeier Hansson, co-founders of 37signals, join host Kimberly Rhodes to discuss the power of taking sabbaticals as business owners.</p><p>Jason recently returned to work after taking his first sabbatical in nearly 23 years. H ... Show More
20m 25s
Aug 2025
Money Diaries, Career Breaks, and Owning Your Financial Story with Lindsey Stanberry
This week, Sim sits down with Lindsey, the creator of the cult-favorite Money Diaries, to uncover the fascinating truths behind how women really spend and talk about money. They explore why financial transparency is still taboo, how values shape spending, and what it takes to con ... Show More
35m 18s
Aug 2025
Wealth Redefined: The Power of Being a Stay at Home Wife with Jasleen Chawla
This week, Sim chats with Jasleen about her journey from corporate life at Deloitte and Goldman Sachs to choosing the stay-at-home wife path and building her own platform on TikTok. They dive into money anxiety, navigating financial conversations in marriage, and why creating pur ... Show More
50m 18s
<p>Jason Fried and David Heinemeier Hansson, co-founders of 37signals, advocate for taking extended breaks from work, as outlined in their book <a href='https://37signals.com/books/#calm'><em>"It Doesn't Have to Be Crazy at Work</em></a><em>."</em> While this pract ... Show More
