Episode 25 - Alone Time, Creative Work and When Money Enters the Room

Episode 25 opens with Steph and Jay checking in on the wonkiness of the world and the mental load of staying aware without getting consumed. They talk about how people cope differently, from staying plugged in to fully tuning out, and why it feels harder than ever to find calm while still caring.

From there, they get into the creative process, especially the role of solitude. Steph shares why working alone is energizing, how deep focus shapes her best work, and why being social doesn’t mean needing people around while creating. Jay reflects on the flip side, how the right city energy can be inspiring, but also distracting when it comes to getting work done.

Then the conversation turns practical: when does money enter creativity. They unpack the difference between making art for the sake of making it and building products where margins, materials, and price points have to be considered early. Steph breaks down the real cost of supplies and why art pricing is often misunderstood, and shares her shift toward art based products that require a more business minded structure. They close with rapid fire on future tech, fixing New York, and weird food combos.

Topics Covered:

• Staying aware in a chaotic world without burning out
• Solitude vs stimulation and how creatives actually work best
• The balance between deep focus and being energized by people
• When money enters creativity and why timing matters
• The real cost of making art and why pricing is misunderstood
• Product thinking vs fine art and working backwards from margin
• Rapid fire: tech we want, NYC fixes, and odd food pairings

This episode is a reminder that creativity needs both space and structure, and learning when to protect your process and when to think like a business is part of the work.

Episode 24 - Focus, Energy and The Journey

This episode captures that strange early January shift after the holiday rush, when the world is technically “back,” but not really moving at full speed yet. Steph and Jay talk about what it feels like to be creatives during a season where other people slow down, while their own momentum keeps building.

They explore how conferences, awards season, and trend cycles flood the culture right after the holidays, and why Steph tends to block a lot of that out to protect her originality. From there, the conversation moves into something deeper: the way creatives pick up on energy in rooms and environments, and how that unspoken tension or empathy often gets channeled into the work.

The episode lands on a central anchor, focusing on the journey, especially when life feels full of landmines, shifting plans, and constant uncertainty. They wrap with a funny rapid fire and a simple reminder about stress: don’t do it twice.

Topics Covered:

• The strange post holiday pace of January
• Creative schedules versus traditional work rhythms
• The flood of conferences, awards, and trend noise
• Protecting originality and filtering cultural overload
• How creatives sense and process energy differently
• Turning empathy and frustration into creative fuel
• Staying focused on the journey amid constant change
• Rapid fire on time, childhood, and risk taking
• Why pre stressing only makes things harder

This episode is your reminder to tune out the noise, stay grounded in your path, and keep your focus on the journey, especially when life tries to pull the rug out from under you.

Episode 23 - Reset, Reflection and Creative Freedom

The first episode of 2026 opens with Steph and Jay turning a casual new year check in into a thoughtful conversation about how creatives actually reset. They talk about why January 1st feels motivating for some people and completely overrated for others, then dig into the real reset of clearing physical and mental clutter so new ideas can take shape.

Steph shares what it looks like to wind down an old way of running a business in order to make room for what’s next, including experimenting with a new product focused direction that blends art and interior design. Jay reflects on how the simple act of organizing can kick the brain back into creative mode and why real adaptation requires space rather than pressure.

They also explore what the holiday season leaves behind, from meaningful moments to small dramas, and how those experiences quietly carry into the new year. The episode wraps with a rapid-fire round that is both funny and unexpectedly sincere.

Topics Covered:

• New Year resets: motivation vs “you can start anytime”
• Clearing clutter and why creatives need space to create
• The connection between cleaning, emotional processing, and mental calm
• Adapting to new plans and building systems for a fresh year
• Steph’s new creative direction: art as product + catalog thinking
• What carries forward from the holidays: gratitude, drama, lessons
• Rapid fire: new year feelings, holiday traditions, and takeaways

This episode stays with you as a reminder that clearing space isn’t just housekeeping, it’s how you make room for what’s next.

Episode 22 - Closure, Hope and End of Year Clarity

Episode 22 is a reflective end of year conversation about perspective, growth, and entering a new chapter with intention. Steph and Jay move from light talk about winter in New York into gratitude, the emotional weight of the holidays, and Jay’s experience navigating a Christmas centered culture as a Jewish person. At the heart of the episode, Steph reflects on a year of closing chapters, clearing energy, and trusting the slow incubation of creativity, while Jay shares how global events and the people in his life continue to shape his thinking and push him to keep learning. They close with a rapid fire that turns thoughtful, touching on kindness, closure, and the small internal shifts that change how we move through the world, offering a grounded and hopeful send off to the year.

Topics Covered:

• Year end reflection and what this year demanded
• Letting go, clearing space, and closing chapters
• Identity shifts, growth, and creative timing
• Gratitude and grounding when the world feels heavy
• The Jewish experience during the Christmas season
• Personal hope for 2026 versus the global outlook
• How humans resist change and adapt under pressure
• Rapid fire on kindness, anonymity, and closure

This episode stays with you as a reminder to clear what no longer fits, protect what matters, and step into the new year more aligned with yourself. See you in 2026.

Episode 21 - Holidays, Creativity, and Knowing When to Slow Down

In this episode of Pickles and Pasta with Steph and Jay, a simple catch-up turns into a thoughtful look at creativity during the holiday season and the push-pull between momentum and rest. They unpack how December’s packed calendars and cultural expectations can derail focus, while still offering surprising inspiration through new experiences and shared adventures. They also talk about resisting the pressure to constantly sell, promote, or discount creative work, with Steph choosing to focus on making art right now and Jay reflecting on how hard it is when “slowing down” feels imposed instead of chosen, all while touching on consumer culture, originality, and creating with intention. They wrap with humor and a rapid-fire round on winter comforts, music habits, and the annual events that quietly shape their creative lives.

Topics Covered:

• Creating during the holidays and how seasonal energy affects focus
• The tension between slowing down and maintaining creative momentum
• Events, stimulation, and how new experiences fuel inspiration
• Selling versus making and owning the value of creative work
• Consumer culture, trends, and the search for originality
• Choosing rest and reflection without losing purpos
• Rapid fire on winter favorites, music, and influential annual events

A reflective, honest conversation about honoring your creative rhythm during a season that pulls you in every direction. Whether you’re slowing down, speeding up, or somewhere in between, this episode is a reminder that intention matters more than timing.

Episode 20 - Family, Perception, and Looking Past the Label

In Episode 20 of Pickles and Pasta with Steph and Jay, the conversation kicks off with full moon energy and how heightened sensitivity can shape your mood, reactions, and awareness. From there, they dive into how family dynamics quietly (and sometimes loudly) shape who we become, including confidence, self-image, patterns we inherit, and the narratives relatives create about us that can be hard to shake. They also explore how perception works in everyday life: what we assume when we first look at someone, how stereotypes and appearances distort reality, and how our own fears or insecurities can get projected onto other people. The episode wraps with rapid fire fun covering a brand they fell out of love with, the “no downside” food they’d eat forever, and something they dislike doing but love the payoff of.

Topics Covered

• Full moon energy, sensitivity, and emotional awareness
• Family influence on identity, confidence, and behavior
• Unlearning family narratives and projected expectations
• Big families, perception, and confidence versus intimidation
• First impressions, stereotypes, and the art of perception
• Projection, social media overload, and the need for quieter mental space
• Rapid fire on brand regret, indulgent foods, and the payoff of hard work

If this episode hit home, take it as a reminder to stay curious about your patterns, your people, and what you might be assuming at first glance.

Episode 19 - Dogs, Seasons, and the Art of Paying Attention

In this episode of Pickles and Pasta with Steph and Jay, a simple bagel run spirals into a conversation about city dogs, shared sidewalks, and what it really means to be a considerate pet owner, before widening into a discussion on seasons, creativity, and where inspiration actually comes from. Steph talks about winter as creative hibernation, why New York remains her greatest muse, and how even a 239-million-dollar painting at Sotheby’s didn’t move her, while Jay reflects on how walking the city versus the suburbs shifts what you notice and ultimately create. They close with rapid-fire questions on fear versus respect, favorite seasonal transitions, and whether spending 24 hours with someone you can’t stand is worth it if it genuinely makes the world better.

Topics Covered:

• City dog culture and what “curb your dog” should mean
• Pet ownership as shared-space responsibility
• Thanksgiving’s complicated meaning and why gratitude still matters
• How seasonal shifts shape mood, energy, and creativity
• Winter hibernation vs. NYC as an inspiration engine
• Real artistic inspiration vs. what the market decides is valuable
• How walking the city vs. suburbs changes what you notice
• Rapid fire: respect vs. fear, favorite season shift, 24 hours with someone you can’t stand

If you’ve ever side-stepped a leash, wondered where your inspiration really comes from, or felt yourself changing with the seasons, this one will feel familiar. Tune in, walk with them through the city and the suburbs, and see what it sparks in your own life.

Episode 18 - Friendship, Change, and Coming Home to You

In this episode of Pickles and Pasta with Steph and Jay, the duo opens up about what it means to shrink yourself to fit in across friendships, small towns, social media, and work. Steph shares how moving from New York’s fashion world to a quiet Pennsylvania suburb caused her to dial back parts of who she was without even noticing, and how divorce, grief, and building Have Some Fun Today shifted her relationships over time.

Together, they look at how different seasons of life change your circle, why some friendships naturally fade, and why others are worth holding on to. They dig into self-awareness, reconnecting with your creative self, and choosing relationships that support who you are now.

Topics Covered:

• Shrinking to fit in and the subtle ways we make ourselves smaller
• Social media self-editing and the pressure to be “just right”
• Friendship seasons and why some relationships fade or deepen
• Life transitions like divorce, loss, and reinvention that reshape our circles
• Returning to yourself through awareness, inner work, and creativity
• Choosing better rooms and people who match your full energy
• Rapid-fire fun on favorite times of day, dream business skills, and movie characters they’d befriend

A reflective, candid, and ultimately hopeful conversation about outgrowing old versions of yourself — and finding the people who love you as you really are.