Still Figuring It Out

Emily and Marc Pitman
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  • Entrepreneurship

with Emily & Marc. After doing life, family, and business together for thirty years, we are still figuring it out. Both fiercely independent first borns, we are committed to continuing to grow and try new things in our entrepreneurial adventures.

  1. 5d ago

    SFIO 417 - Each Other's Number One Fan with Kristin Steele and Samantha Swaim

    📋 Episode Summary Emily and Marc welcome Kristin Steele and Samantha Swaim of Swaim Strategies for the first couple-to-couple conversation on Still Figuring It Out. Kristin and Sam talk about working together, living together, and building a business rooted in storytelling, strategy, events, justice, and connection. The conversation moves from partner dynamics—back of house and front of house, listening to learn and listening to facilitate—to the deeper question of how people reconnect after years of disconnection. Kristin and Sam describe the "connection recession" they are seeing in nonprofits and beyond: the loss of belonging that happened through canceled gatherings, virtual-only meetings, reduced volunteer programs, and fewer small, meaningful points of contact. They also reflect on freedom in self-employment, the discipline of saying no, and the ongoing work of aligning business decisions with joy, impact, capacity, and values. By the end, the camper van becomes its own metaphor: everything has a place, and if you do not like where you are, you can go.   🔑 Key Takeaways • Couples who work together need shared rules, complementary roles, and the discipline not to both panic at the same time. • Being each other's number one fan matters when work, risk, and life are deeply intertwined. • Different listening styles can strengthen shared work: one person may listen to facilitate while another listens to learn. • The "connection recession" has affected nonprofits by weakening donor belonging, volunteer engagement, and everyday relational touchpoints. • Smaller, more meaningful gatherings can rebuild connection more effectively than assuming one big event will repair everything. • Freedom in business often means remembering you are the decision maker—and that you are allowed to design the matrix that works for your life. • Saying no can be an act of integrity when a project's needs are larger than your available capacity.   🗣 Quote Highlights "You can't both go there." – Kristin "I listen to facilitate, and Kristin listens to learn." – Sam "'Connection recession' is 'a million little paper cuts' that created separation.' – Sam "People are remembering that it can feel good to be together." – Sam "The biggest gateway to freedom is remembering that we're the decision makers." – Kristin "Our joy is typically found in where we make the biggest impact." – Sam "Freedom is walking away from things, too." – Kristin   🧰 Tools & Mentions • Swaim Strategies https://swaimstrategies.com/ • The Fundraising Elevator podcast • Elevate conference • Planning a Successful Major Donor Event by Kristin Steele and Samantha Swaim • Swaim Strategies Substack series on collective effervescence https://swaimstrategies.substack.com/ • Slow Productivity by Cal Newport   👥 Who Should Listen • Couples who work together or are wondering if they could • Nonprofit leaders trying to rebuild donor connection and belonging • Fundraisers rethinking events as meaningful gatherings rather than obligations • Entrepreneurs learning how to say no without abandoning impact • People navigating the balance between self-care, community care, and meaningful work • Anyone interested in how connection, joy, and belonging shape generosity   🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

  2. Jul 15

    SFIO 416 - Momentum Is Not Perpetual Motion

    📋 Episode Summary Emily and Marc continue their Season 4 exploration of transitions with the word "momentum." From physics class and hybrid cars to business, creativity, family, and habit, they consider what it means to work with the energy already in motion. They also question the business-world myth that enough effort will eventually create a flywheel that runs forever. Life keeps changing. Clients change, circumstances shift, families grow, bodies age, and even healthy momentum can carry us farther than our values want us to go. The conversation turns toward a more flexible understanding of momentum: learning when to use it, when to redirect it, and when to step away. Momentum can come from curiosity, disciplined habits, creative work, or forces outside us. The goal may not be to keep moving faster, but to remain centered enough to work with whatever is moving now.   🔑 Key Takeaways • Momentum can help us move forward, slow down, or conserve energy; it is not always about acceleration. • The idea that a business or life will eventually run on its own is often more myth than reality. • When change is constant, the useful question may be, "Where is the momentum now?" rather than "Why did my original momentum disappear?" • Productive momentum is not automatically healthy momentum. • Values help us decide when to keep working and when continuing would pull us away from the life we want. • We get to define success for the season we are in rather than borrowing someone else's metrics. • Habits can create momentum by helping today's choices serve tomorrow's needs.   🗣 Quote Highlights "It was fun to work with the forces that be." – Marc "Momentum wasn't to go faster and faster. It was using momentum in the process of slowing down." – Marc "If change is the constant, then change is the energy." – Emily "I knew that it was not a healthy momentum. I needed to step out of that path." – Emily "You set the standard of success." – Emily "You just need to know what you want and what your values are." – Emily "Tomorrow's me is going to be really happy if today's me does this thing that I don't want to do." – Marc "I'm just going to complete this now so I can close the tab in my mental browser." – Marc   🧰 Tools & Mentions • The Secret Lives of Color by Kassia St. Clair • Nonprofit Academy Summer Camp https://www.nonprofitacademy.com/course/summer-camp-2026/  • English paper piecing • Legendborn series by Tracy Deonn • CliftonStrengths • The Highlands Ability Battery   👥 Who Should Listen • Entrepreneurs trying to define success on their own terms • People who tend to keep working simply because the energy is there • Leaders frustrated when changing circumstances interrupt their plans • Anyone trying to build habits that support their future self • Lifelong learners who recognize curiosity as a source of momentum • People navigating a season in which their family, work, or physical capacity is changing   🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

  3. Jul 8

    SFIO 415 - Stop Studying What You Already Know with Caleb Pitman

    📋 Episode Summary Emily and Marc welcome their son Caleb Pitman—an improvising musician, trumpet player, composer, and graduate student at NYU—for a conversation about music, identity, influence, and developing a voice of your own. Caleb explains why he often prefers the term Black American music to "jazz," honoring the people and traditions that created the musical language he is learning to speak. He describes improvisation not as randomness, but as a deeply structured, evolving language built from history, shared references, individual choices, and careful listening. The conversation expands beyond music into a larger question: What happens when we stop diluting ourselves to make our work acceptable to everyone? Caleb, Emily, and Marc explore the freedom of knowing who you are not for, choosing your influences intentionally, pursuing what you do not yet understand, and allowing excellence, passion, and love to invite others into curiosity.   🔑 Key Takeaways • Calling something by its fuller name can honor the people, history, and intellectual tradition that created it. • Improvisation is not random. It happens within a framework shaped by language, history, rhythm, harmony, and relationship. • Developing a distinct voice requires both active influence and active exclusion. • Making work more "accessible" can sometimes become an excuse for diluting its honesty, complexity, or excellence. • It can be freeing to identify who your work is not for instead of trying to appeal to everyone. • Passion and deep understanding can invite people into curiosity without requiring the work to be simplified. • The areas that confuse or intimidate us may be the most valuable places to study next.   🗣 Quote Highlights "I'm still trying to speak 'composer' into existence, but I say it because I do it." – Caleb "The creators of the musical stew that I'm contributing to—the people who first put the stock down—are Black Americans." – Caleb "There's something really cool about not diluting who you are or what you do." – Caleb "Just make it honest and authentic in what you want." – Caleb "You're composing a frame of reference. Here are the puzzle pieces—improvise within this musical context." – Caleb "Excellence and love invite people to be curious." – Emily "Stop transcribing stuff you understand." – Caleb "I'm still figuring out my voice, which is something everyone has to do." – Caleb   🧰 Tools & Mentions - And Artists • Caleb Pitman — improvising musician, trumpeter, and composer completing graduate studies at NYU • Black American music • Mark Turner • Keith Jarrett's American Quartet and European Quartet • J.S. Bach's Inventions • Artfield Log — Caleb's note-taking practice for capturing reflections after concerts and focused listening   👥 Who Should Listen • Musicians, artists, and creators developing a voice of their own • People thinking about how language can either honor or obscure the origins of an art form • Anyone tempted to dilute meaningful work to make it acceptable to everyone • Coaches, speakers, and entrepreneurs deciding who they are—and are not—best suited to serve • Parents who enjoy hearing their adult children explain the depth of their work • Curious listeners who want to understand improvisation as a disciplined language rather than random expression   🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

  4. Jul 1

    SFIO 414 - Living in Flux

    📋 Episode Summary In their 50th episode, Emily and Marc continue exploring transitions with the word "flux"—the act of flowing, a state of ongoing change, and even a substance that prepares surfaces to form a stronger connection. The conversation begins with a transition hiding in plain sight. For the first autumn in nearly five decades, Emily will have no direct connection to a school calendar. With their children finished with formal education, she and Marc wonder what freedom from that long-standing rhythm might make possible—and how a change can contain both grief and rebirth without requiring a cheerful silver lining. From lava lamps and flowing streams to travel pauses, hometown longing, and the possibility of carrying "settled" within you, Emily and Marc consider whether they have become so accustomed to transition that stability feels unfamiliar. Maybe being settled has less to do with staying in one place and more to do with carrying your center of gravity wherever you go.   🔑 Key Takeaways • Some transitions only become visible when we step back from the immediate event and notice the larger story arc. • A change can contain both grief and rebirth. Recognizing new possibilities does not require covering pain with a bright, reassuring sticker. • Flux is not disintegration. Something can remain connected while continuing to move and change shape. • Curiosity can help us engage with changes in our inner and outer lives rather than insisting that everything remain fixed. • A temporary pause can create calm and spaciousness without becoming a permanent restriction. • Being settled may not require a hometown, one location, or an absence of movement. • Sometimes we pursue a version of belonging that does not fit the life we were actually given.   🗣 Quote Highlights "This is going to be my first autumn with no direct link into the education calendar." – Emily "Is this a death and dying, or is this a rebirth?" – Emily "Being able to grab for that sense of rebirth, even in the grieving, opens us up to embracing the challenges and the experiences that are coming." – Emily "I think it's important that we do experience the grieving, even as a guy that always wants to see the silver lining." – Marc "Flux is the act of flowing—the continuous moving on." – Emily "There's still bonds and connection. It's just moving." – Marc "I know people who have settled that still move. They carry their settled with them." – Marc   🧰 Tools & Mentions • WordHippo https://wordhippo.com/ • Libby https://libbyapp.com/ • Familia by Lauren E. Rico • Flow by Mihaly Csikszentmihalyi • Inner Work by Robert A. Johnson   👥 Who Should Listen • Parents adjusting to life after their children finish school or leave home • People whose lives have long been structured around academic calendars • Anyone holding grief and new possibility at the same time • Frequent travelers or highly mobile people wondering what it means to feel settled • Listeners who find change energizing but are less certain how stability might fit them • People questioning whether the version of belonging they have pursued is actually theirs 🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

  5. Jun 24

    SFIO 413 - Ready, Fire, Recalibrate

    📋 Episode Summary In this episode, Emily and Marc continue their exploration of transitions with the word "recalibrate." What begins with the satisfying shape of the word—and the equally satisfying factors of the number 24—opens into a conversation about pausing, gathering feedback, and noticing whether the direction they chose still fits. They reflect on Scrum, coaching, marriage, work, values, productivity, and the difference between filling every available hour and recognizing when enough has been done. Recalibration does not always require a dramatic life change. Sometimes it is a small adjustment: listening more carefully, taking an unexpected trip to a state park, or asking whether the standard we are using was ever realistic in the first place. The conversation lands on alignment—the inner gyroscope that helps us remain upright while life shifts around us. Recalibrating means staying willing to learn, adjust, and give ourselves permission to move our energy somewhere else. 🔑 Key Takeaways • Recalibration begins with feedback: new information that helps us see whether the original direction still fits. • Pausing to reassess is not the opposite of progress. It can keep us from climbing quickly toward the wrong destination. • Recalibration can happen at both the macro level—moving, changing work, reshaping a marriage—and the micro level of checking in during an ordinary day. • Productivity is not always measured by how many available hours we fill. • Standards we have never clearly named may be unreasonable, impossible, or inherited from someone else. • A "definition of done" can be enough for the next step without pretending the larger work is finished. • Alignment with values can function like an inner gyroscope when circumstances and outside expectations keep shifting. 🗣 Quote Highlights "Recalibrate seems hopeful." – Marc "To me, recalibration starts with data. We have feedback." – Emily "I love the idea of having data that says, 'I can do this better.'" – Emily "I received an invitation to dwell in the reset in a way that may not feel so comfortable." – Marc "The workday is an hour amount of time, not a project amount of time." – Emily "We have this standard that we're holding ourselves to that we haven't taken the time to spell out—because if we did, we'd know it's totally unreasonable." – Marc "I guess a word that goes with recalibrate for me is alignment." – Emily "Yes, I have open tasks left, and I have done enough." – Marc   🧰 Tools & Mentions • Familia by Lauren E. Rico • Libby https://libbyapp.com/ • Scrum • International Coaching Federation Core Competencies https://coachingfederation.org/credentials-and-standards/core-competencies • Stephen Covey's "ladder against the wrong wall" metaphor   👥 Who Should Listen • Self-employed people and high achievers who struggle to decide when the workday is done • Leaders and teams who need space to evaluate what is working before rushing forward • Couples reconsidering how their routines reflect their shared values • Coaches and reflective listeners interested in alignment, active listening, and meaningful pauses • Anyone wondering whether they need a dramatic change or simply a thoughtful adjustment   🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

  6. Jun 17

    SFIO 412 - Still Figuring Out Everything with Jeff Gibbard

    📋 Episode Summary In this episode, Emily and Marc talk with Jeff Gibbard — neurodivergent, multi-passionate entrepreneur, author of The Lovable Leader, and self-described superhero working to make the world kinder, safer, and more equitable. Jeff shares the drive behind his work: knowing that time is limited and wanting to do as much good as he can while he is here. The conversation moves through storytelling, entrepreneurship, marriage, parenting, neurodiversity, and Jeff's user guide framework — a way for people to explain how they work, what helps them thrive, and what makes life more difficult. Rather than putting people into boxes, the user guide creates room for each person to be understood as unique. Jeff is still figuring out "everything." Together, the three explore how growth requires staying open, how isolation can cause us to calcify, and how community keeps challenging us to learn. Figuring it out is not an endpoint. It is the beginning, middle, and end — a willingness to remain a work in progress. 🔑 Key Takeaways • Knowing that time is limited can become fuel for doing good without holding back. • The impact of our effort may not become visible until years later — and may reach people we never expected. • Personal user guides help people describe what they need without requiring them to disclose labels or diagnoses. • Personality and assessment tools can strengthen relationships when they create understanding rather than confining people to boxes. • Conflict shifts when it becomes "me and you versus the problem" rather than "me versus you." • Even the things we think we have mastered change with the context, the people involved, and the moment. • Community exposes us to different ideas and helps keep fear, isolation, and certainty from hardening us. 🗣 Quote Highlights "I'm just a person who's out there trying to do the best I can with the time I've got." – Jeff "Maybe the lesson that we take away isn't that life isn't fair. Maybe it's that you have no idea who you can impact when you leave it all on the court." – Jeff "What if we just asked each person what it is that makes them tick?" – Jeff "You don't need to change, and I don't need to change. We just need to understand one another." – Jeff "It's not me versus you. It's me and you versus the problem." – Jeff "The figuring out is no longer the endpoint, but the beginning point." – Emily "The only way you get here is by being there, at that one point of not knowing." – Jeff "We all have a choice on Mondays to get up and be brave." – Emily 🧰 Tools & Mentions • The Lovable Leader by Jeff Gibbard https://jeffgibbard.com/lovable-leader/ • Rogue podcast https://jeffgibbard.com/rogue/ • The Superhero Institute https://superheroinstitute.org/ • Personal User Guides • Pressure Points productivity program • The Enneagram 👥 Who Should Listen • Leaders and managers who want to create workplaces where more people can thrive • Neurodivergent professionals looking for ways to communicate what helps them work well • Couples and families interested in understanding one another without trying to change one another • Entrepreneurs balancing many interests, projects, and responsibilities • Parents learning to adapt as their children's personalities and needs become clearer • Anyone who wants to stay open, curious, and connected rather than becoming isolated or rigid 🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

  7. Jun 10

    SFIO 411 - Did You Know Some Bridges Sing?

    *]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id= "request-69fca702-0d18-83ea-ac44-13e60a53e910-0" data-turn-id-container= "request-69fca702-0d18-83ea-ac44-13e60a53e910-0" data-testid= "conversation-turn-26" data-scroll-anchor="false" data-turn= "assistant"> 📋 Episode Summary In this episode, Emily and Marc continue their Season 4 exploration of transitions with the word "bridge." The conversation begins with Marc reflecting on his faith journey, modern history, and the book "Jesus and John Wayne" — and how looking back can reveal the structures and systems that shaped parts of his identity. Emily brings the metaphor to physical bridges: covered bridges in Maine, swimming holes, the bridge between New Hampshire and Maine, singing bridges, long Louisiana bridges, and bridges in music. Together, they notice how a bridge can be both structure and process — something built, something crossed, and something that changes depending on whether you are standing on it or looking at it. The episode closes in a tender place, as Emily names the bridge of grief: Marc's mother's birthday, the first year after Emily's brother's death, and the first year after Marc's father's death. Some bridges end. Some keep unfolding. And some remind us that transition is not always one clean crossing. 🔑 Key Takeaways • A bridge can be both a fixed structure and a process — a thing you stand on and a way you move from one place to another. • Looking back can help us see the hidden engineering beneath what shaped us. • Not all bridges feel the same. Some are beautiful, some are scary, some sing, and some make us aware of what is underneath us. • Naming a bridge can change the experience of crossing it. • Emily and Marc notice that they often approach the same metaphor differently: Marc imagines being on the bridge, while Emily imagines looking at it. • Some transitions feel like reaching the end of a bridge and stepping back onto the dirt road. • Grief has its own bridges, especially the first year of birthdays, holidays, and anniversaries after a death. 🗣 Quote Highlights "We can all stand on something and think we're just standing on something." – Emily "Different angles, and different suspensions, and different ways that things come together, can support something." – Emily "Bridge, to me, seems like it's both. It is a fixed structure… but there's a process of walking through it." – Marc "Sometimes a bridge in music is kind of stepping out of the song to reflect, and then to come back into the song." – Emily "It's like walking off the bridge and, oh, this is the dirt road again." – Marc "There's something about coming to the end of the first year of mourning." – Emily   🧰 Tools & Mentions • Jesus and John Wayne by Kristin Kobes Du Mez • A Bug's Life • Music and Lyrics • Three Amigos • My Cousin Vinny   👥 Who Should Listen • People reflecting on faith, identity, and the systems that shaped them • Anyone navigating a transition that feels more like a bridge than a doorway • Listeners who love metaphors, memory, and the way ordinary places carry meaning • People moving through grief, especially the first year after a significant loss • Couples who enjoy hearing how two people can see the same image in very different ways   🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

  8. Jun 3

    SFIO 410 - When Transition Doesn't Have an End Yet

    📋 Episode Summary As the season on transitions continues, Emily and Marc reflect on graduations, hospice, politics, wars, uncertainty, and the possibility that transition may not always end neatly. Sometimes the work is not to find a period at the end of the sentence, but to stay flexible, creative, rooted, and open to being repotted into a larger space. In this episode, Emily and Marc celebrate a quiet milestone: Still Figuring It Out has passed 1,000 downloads. That number becomes a concrete reminder that even a messy, joy-filled project can create connection, community, and meaning beyond what the hosts can see. The word of the day is "convergence," and the conversation moves through definitions, podcasting, friendship, community, personal boards of directors, weather as ancient human small talk, college as a pressure cooker, and the ways relationships sometimes come together — or don't — at the depth Marc hopes for.   🔑 Key Takeaways • The podcast began as a place for joy, and reaching 1,000 downloads gives Emily and Marc a tangible reminder that people are listening. • "Convergence" can mean union, a meeting place, or the coordinated focusing of the eyes — two things coming together so something can be seen more clearly. • Different relationships have different levels of depth, and not every connection is meant to become a soul-nourishing convergence. • Small talk, like talking about the weather, may carry deep ancestral memory from when weather was a matter of survival. • Some seasons of transition may not close cleanly. They may overlap with graduations, grief, politics, family changes, and world events. • Naming transitions can help with balance, but it does not give us control over all the circumstances. • Still figuring it out means staying flexible, creative, and willing to keep growing.   🗣 Quote Highlights "I still feel like our primary goal is to have fun together." – Emily "It gives us joy." – Marc "Convergence can be a meeting place." – Emily "To me, it's the coming together of two things to see something clearly." – Emily "I think I expect everything to 'be' convergence instead of enjoying convergence." – Marc "We're holding a lot that we will go through whether we're ready or not." – Emily "We're getting repotted into more nourishing soil and a bigger space to grow." – Marc   🧰 Tools & Mentions • WordHippo https://wordhippo.com/  • Personal board of directors   👥 Who Should Listen • People who are building something slowly and wondering whether it matters • Listeners who are navigating overlapping family, work, grief, and life transitions • Couples reflecting on shared creative projects and what gives them joy • People who crave deep community but are learning to honor lighter forms of connection too • Anyone wondering whether transition ever really reaches a clean ending   🎺 That Music! Special thanks to Lexi Moreno, Caleb Pitman, and Zoe Czarnecki for the original music. Lexi Moreno – composing / mixing / mastering / guitar Caleb Pitman – composing / mixing / trumpet Zoe Czarnecki – bass

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About

with Emily & Marc. After doing life, family, and business together for thirty years, we are still figuring it out. Both fiercely independent first borns, we are committed to continuing to grow and try new things in our entrepreneurial adventures.

Information

  • Creator
    Emily and Marc Pitman
  • Years Active
    2025 - 2026
  • Episodes
    53
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Still Figuring It Out