Caroline and Allison return from a summer hiatus and welcome Juliana Pereira, co-author of Pivot Quest, after attending her talk with co-author Luis at Hummingbird Books in Chestnut Hill, moderated by Caroline. Juliana explains she met Luis while working at a business school during a rebranding project, then later partnered with him after he proposed a “Duolingo of career pivoting” concept. She describes three years of research interviewing 100+ career pivoters across 25 countries, finding that pivots are typically triggered by life events (divorce, loss, layoffs, moves) and often accompanied by bodily stress signals, anxiety, and identity fears. Key themes include that people never start from scratch, pivots build on existing skills and community, and success comes from curiosity and not defining oneself by a job title, illustrated by an 83-year-old with 16 pivots.

Find Juliana’s book at https://pivot-quest.com/

Topics

00:56 Back From Hiatus

01:34 Book Talk Recap

02:59 How They Met

04:17 Research Across Cultures

06:11 Body And Identity

07:19 Never Start From Scratch

11:13 Curiosity And Growth

13:21 Unusual Pivot Story

15:53 Wrap Up And Part Two

Tara, Caroline and Allison talk about cleaning out Allison’s closet and a lockbox, then shift to the episode topic: creating a “blank canvas” at home. They describe an “art consult” with a client who owned meaningful travel art, where they removed all artwork from the walls, clustered pieces together to see what “talks,” and gave standout pieces their own moment, emphasizing that “not everything can sing.” They suggest taking art down, patching and spackling, and reimagining gallery walls as a simple, low-cost way to refresh a space, including rotating art to avoid being “overhung.” The conversation connects overdoing wall art to over-accessorizing and touches on the psychology behind excess, then parallels the approach to purging and reorganizing closets, ending with light talk about capris returning as a trend.

Topics

00:30 Summer Catch Up

00:36 Lockbox Closet Banter

01:38 Blank Canvas Idea

01:55 Art Consult Method

03:11 DIY Gallery Wall Reset

04:13 Overhung Homes Debate

05:54 Jewelry And Armor

07:38 Closet Cleanout Psychology

09:27 Capris Comeback Talk

11:36 Wrap Up And Callback

Tara, Caroline, and Allison discuss Tara’s outdoor wedding in Maryland, where ticks prompted worries about Lyme disease; Alison shares experiences spotting ring rashes on her children and getting prompt antibiotic treatment. They pivot to “attention restoration theory” (ART), describing it as looking at things differently than intended and applying it to interior design by reorienting rooms, combining functions, and repurposing objects like placing a ginger jar on a patio to elevate an outdoor “second living room.” They note how client trust affects how far designers can push ideas. Tara applies the concept to personal styling, helping a client dress more age-appropriate while still feeling sexy, and they discuss using scarves and even men’s ties in multiple ways to elevate outfits. Tara explains how to subscribe to her newsletter at tarawestfashion.com and mentions creating mood-board tips for dressing for sporting events like the World Cup, Wimbledon, and F1.

Topics

00:33 Wedding Weekend Recap

00:58 Tick Panic Storytime

02:26 Lyme Disease Fears

03:26 Today’s Topic ART

03:52 Designing By Reframing

05:10 Client Trust And Scope

06:41 Styling Too Young

07:50 Age Appropriate Wardrobes

09:17 Scarves And Ties Hacks

10:46 Newsletter And Event Outfits

11:50 Sporty Style Chat

12:27 Wrap Up And Goodbye

Tara, Caroline and Allison discuss how guest connections often become meaningful collaborations, highlighting Lacy Garcia of Willow, a women’s financial planning firm focused on empowering women to understand finances. Allison shares that attending Lacy’s talk was especially impactful as she navigates a divorce after never handling bills, accounts, or financial decisions during her marriage, and she describes feeling controlled by not having her name on accounts or utilities. The conversation emphasizes normalizing financial literacy, having money conversations in marriage, and the value of prenups as protection rather than a sign of expecting divorce. Allison reflects on moving from intense anxiety and grief to a steadier emotional place by fully feeling her emotions and leaning on friends, including a supportive community of divorced women. The group also discusses supporting children through divorce by creating calmer, healthier home environments.

Find Lacy Garcia at https://www.trustwillow.com/

Topics

00:30 High Noon Catch Up

01:14 Guest Spotlight Lacy

02:11 Divorce Money Wake Up

04:03 Learning The Basics

07:53 Prenup Talk

09:17 Emotional Recovery

11:22 Friends And Community

13:47 Kids And Resilience

15:45 New Home Energy

17:44 Closing Thanks

Tara, Caroline and Allison discuss how guest connections often become meaningful collaborations, highlighting Lacy Garcia of Willow, a women’s financial planning firm focused on empowering women to understand finances. Allison shares that attending Lacy’s talk was especially impactful as she navigates a divorce after never handling bills, accounts, or financial decisions during her marriage, and she describes feeling controlled by not having her name on accounts or utilities. The conversation emphasizes normalizing financial literacy, having money conversations in marriage, and the value of prenups as protection rather than a sign of expecting divorce. Allison reflects on moving from intense anxiety and grief to a steadier emotional place by fully feeling her emotions and leaning on friends, including a supportive community of divorced women. The group also discusses supporting children through divorce by creating calmer, healthier home environments.

Find Lacy Garcia at https://www.trustwillow.com/

Topics

00:30 High Noon Catch Up

01:14 Guest Spotlight Lacy

02:11 Divorce Money Wake Up

04:03 Learning The Basics

07:53 Prenup Talk

09:17 Emotional Recovery

11:22 Friends And Community

13:47 Kids And Resilience

15:45 New Home Energy

17:44 Closing Thanks

Caroline and Allison welcome back Jen (Bean) DeLalio of JKate Designs from Southampton to discuss her pivot from software programming and consulting into interior design and how she built a Hamptons-focused portfolio. Jen shares that her projects span Westhampton through Amagansett, with a coastal, easy-breezy style that also leans slightly traditional and patterned. She explains the importance of professional photography as a non-negotiable marketing investment, describing how photographing her sister’s Bergen County renovation and a major East Hampton project helped elevate her website and content, including a project video produced through a charity-auction win. They also talk about maintaining a tight design process, screening out difficult clients during inquiries, and using a “secret” inspo image to confirm client preferences. Jen shares where to find JKate Designs online.

Find Jen on the socials at @jkatedesigns or at https://jkate-designs.com/

Topics

00:29 Part Two Welcome

00:43 Meet Jen Bean

01:52 Podcast Fan Moment

03:08 Hamptons Roots

03:39 Design Style Sweet Spot

04:28 Pro Photos Matter

05:21 Sister Reno Breakthrough

07:54 East Hampton Dream Project

09:24 Marketing Budget Reality

10:29 When to Walk Away

11:14 Client Process Tricks

12:04 Where to Find Jen

12:36 Final Sign Off

The guest is Jen (Bean) DeLalio, a high school friend of Caroline’s. They reminisce about shared Boston summers and Caroline’s multi-day Cape wedding. Jen describes her early career as an econ major who entered tech consulting in 1998, later working as a systems analyst at The New York Times before moving full-time to Southampton. After taking an NYU night class in interior design and working in an antique shop and design showroom, she returned to remote web-based software work as a contractor for about 10 years while renovating her own home and helping friends. In 2015 she launched JKate Designs via a Houzz profile, balancing demanding early projects with consulting and parenting. She explains how the Haven Workshop in 2022 helped her adopt stronger business systems, marketing, and financial goals, prompting her to leave consulting and scale with subcontracted procurement, bookkeeping, and CAD support.

Find Jen on the socials at @jkatedesigns or at https://jkate-designs.com/

Topics

00:33 Guest Arrival

01:19 Jen Bean Backstory

02:20 Wedding Weekend Tales

03:42 Career Pivot Begins

05:34 Hamptons Design Roots

06:44 Launching JKate Designs

07:42 First Clients Juggling

09:43 Haven Workshop Breakthrough

11:02 Systems Strategy Lessons

12:37 Building The Team

13:53 Where To Find Jen

Allison and Caroline discuss heavy pollen before recapping Sparkle in the Park, a longtime Emerald Necklace Conservancy fundraiser. They describe multiple last-minute pivots: switching from a perceived-privileged luncheon to an evening tented dinner, then losing the City of Boston tent permit and relocating the event to board member Georgia Lee’s private home. They highlight the home reveal and the dramatic design transformation by David DeCicco Designs and Julie Freed/Freed Events, and note the event raised significant funds and may return as a May 5 lunch next year. The episode topic shifts to hostile architecture—design choices that manipulate behavior (e.g., anti-sleep benches, airport armrests, uncomfortably cold restaurants)—and briefly connects the idea to “hostile fashion,” including restrictive skirts and high heels.

Topics

00:28 Pollen And Missing Host

01:02 Sparkle In The Park Recap

02:13 Event Backstory And Pivots

03:56 Swing Mishap And Next Year

05:02 Hostile Architecture Explained

06:22 Everyday Examples And Comfort

07:45 Designing Atmosphere On Purpose

08:46 Hostile Fashion And Met Gala

10:46 Clothes As Social Signals

12:17 Wrap Up And Sign Off

The gang welcomes back Rachel Wexler, a leadership development partner who helps leaders and teams get unstuck and build new ways of operating aligned to their goals. Wexler discusses executive presence as showing up with confidence and conviction by knowing strengths and development areas, clarifying the gap between identity and reputation, defining a bigger “why,” and understanding needs and boundaries. She describes working with both women and men, including executives with egos, and using data-driven tools like the Hogan Assessment to ground “soft” topics in statistically reliable insights about how people are perceived. Wexler shares her career pivot from education product development and workforce development work at Penn Foster (2015–2023), deciding to leave as she approached 50 to avoid regret, and learning resilience and iteration through social media. She outlines her business focus on coaching/consulting and sharing ideas about humanity, authenticity, trust, and high-performance teams.

Rachel on LinkedIn: https://www.linkedin.com/in/rlwexler/

Instagram: @ RWexlerLeadership

https://www.rachel-wexler.com/

Topics

00:32 Rachel Is Back

01:52 Executive Presence Basics

03:02 Identity Versus Reputation

05:05 Handling Ego With Data

07:52 Friendship And Business Plans

08:58 Pivoting Into Entrepreneurship

12:15 Turning 50 Leap

12:46 Social Media Growing Pains

14:34 Where The Business Goes Next

16:15 Presence Tip Before Meetings

17:11 Socials And Farewell

The guest is Tara’s longtime friend Rachel Wexler, who recently launched her own business after 20 years leading product and strategy teams. Rachel describes her evolving role as a “leadership development partner,” working with leaders and teams through coaching, leadership programs, small-group work, and team offsites to help organizations use internal talent well, build trust, and create environments where people can be authentic. She explains using tools like 360 feedback—speaking with peers, direct reports, senior leaders, and sometimes people in a client’s personal life—to identify key themes and “name what’s really going on” beneath the surface. Rachel shares an offsite example that began with a personal question to humanize teammates and shift focus from deadlines to connection. She says her favorite part is helping people, especially women, see their strength and value.

Rachel on LinkedIn: https://www.linkedin.com/in/rlwexler/

Instagram: @ RWexlerLeadership

https://www.rachel-wexler.com/

Topics

00:29 Meet Rachel Wexler

00:48 Friendship Backstory

02:10 Launching Her Business

03:01 What She Actually Does

05:24 Why Leadership Work Matters

06:54 Reading the Room Skills

09:34 Inside a Team Offsite

12:51 Favorite Part of the Job

14:53 Where to Find Rachel

15:35 Wrap Up and Thanks