The Things We Have Learned

Rachel Walerstein
  • 5.0 (4)
  • CAREERS
  • UPDATED WEEKLY

The Things We Have Learned is a podcast providing career guidance for LGBTQ+ professionals. Through conversations with Chicago LGBTQ+ leaders from all industries, backgrounds, and disciplines, we'll hear stories that queer what we think leadership is and who gets to be a leader. We'll also gain valuable tips for navigating common workplace challenges.

Episodes

  1. 12/01/2025

    Things I Have Learned Mini: Reflections on Gratitude and Starting Something New

    After a year filled with major life shifts—marriage, a new home, a new job, and my first L&D industry conference—I pause to reflect on what it feels like to build a podcast in the middle of so much change. In this mini episode, I touch on everything from how I'm learning to practice gratitude to understanding the true value of time. I also dig into how setting boundaries, saying no, and carving out space for relationships have reshaped both my life and the show. As a practitioner of transparent facilitation, I also share some of the things I'll be working on for the show during this December break. This episode is for anyone navigating big transitions, building a creative project, or trying to stay grounded while life moves fast. If you're struggling with the creative process, having the courage to press pause, or leaning into gratitude, this mini episode might be for you.

    7 min

  2. 11/14/2025

    The Power of Clear Expectations with Mickey Shalman

    In this episode of The Things We Have Learned, I sit down with my pal, Mickey Shalman (she/her), a queer professional building a long, grounded career in the reinsurance world. We explore the power of clear expectations: how naming what you need, setting boundaries early, and communicating with intention can transform not just your workday, but your whole sense of stability at work. Mickey shares her approach to career longevity, staying engaged in a demanding corporate environment, and navigating the nuances of being out in the workplace. Our conversation touches on the art of balancing ambition with rest, the relief that comes from proactive communication, and the role supportive workplaces play in helping people truly thrive. If you're looking for practical insight on self-advocacy, work–life balance, and values-aligned career growth, this episode offers both clarity and comfort. May this episode serve as an invitation to lead your career with intention, and to ask for what you need without apology.

    1h 1m

  3. 11/03/2025

    People-Centered Leadership with Amy Illarde

    In this episode of The Things We Have Learned, I sit down with my pal Amy Illarde (she/hers), a healthcare marketing professional, certified career coach focused on LGBTQ+ professionals, and community-builder in Chicago. We chat about something that drives both our work: what it truly means to practice people-centered leadership. Amy shares her non-linear career path, the lessons she learned shifting from individual contributor to manager, and how she discovered that fulfillment lives not in titles, but in supporting the humans behind the work. Together, we reflect on centering values, challenging traditional leadership models, and honoring identity as a source of strength. We also explore the power of chosen family, queer community, mentorship, and why leaders who invest in relationships — not just results — build workplaces where people thrive. If you're navigating career growth, embracing your voice as a leader, or learning how to lead with empathy and courage, this episode offers insight, encouragement, and practical wisdom from the world of people-first leadership.

    1h 5m

  4. 10/10/2025

    From Opera to Equity to Restorative Leadership with Jaime Sharp

    In this episode of The Things We Have Learned, I sit down with Jamie Sharp (she/they), an opera singer turned nonprofit and philanthropic leader, to explore what it really takes to sustain yourself while leading change. Jamie, the founder of Cultivart, a resource hub for arts leaders of color and recipient of the 2024 Sphinx  MPower Artist Grant, shares her journey of balancing creative identity with the demands of an equity-focused career. They unpack the often-overlooked leadership essentials: rest, boundaries, and having a hobby that isn’t tied to productivity. Through humor, honesty, and insight, Jamie reflects on the intersection of art, equity, and endurance — and what it means to remain whole while working for change. The conversation also explores mentorship, intergenerational connection, and finding joy beyond work. If you’ve ever felt stretched thin in your leadership role, or wondered how to protect your energy while showing up for others, this episode offers the reminder you’ve been waiting for.

    56 min

  5. 10/03/2025 · BONUS

    Things I Have Learned (On Launching a Podcast)

    In this short mini-episode of The Things We Have Learned, I pause to reflect on the lessons I've learned while launching the podcast. From the technical hurdles to the creative sparks, I share how the process of starting something new is always a learning journey. You’ll hear my candid thoughts on the surprises, challenges, and small wins that shaped the first few episodes, as well as what I hope listeners (like you) will continue to take away from these conversations. It's reminder that leadership and learning don’t just happen in big moments; they also live in the quiet reflections along the way. If you’ve ever thought about launching a podcast, starting a new project, or simply want a behind-the-scenes look at how this show came to life, this episode is for you.

    6 min

  6. 09/26/2025

    Relational Leadership with Kim L. Hunt

    In this episode of The Things We Have Learned, I sit down with Kim L. Hunt (she/her), a dynamic leader whose path has taken her from studying journalism at Iowa State University to impactful roles at AIDS Foundation Chicago. We trace the moments that shaped her journey: changing careers, navigating personal identity in professional spaces, and leaning into relational leadership to build trust and community. Kim opens up about what it meant to come out at work, the challenges of pivoting into nonprofit leadership, and how vulnerability can be a strength in high-stakes environments. Along the way, she shares grounded lessons on leading with empathy, managing transitions, and the power of leaning into one’s values when the road ahead feels uncertain. If you're curious about nonprofit leadership, career transitions, identity and belonging at work, or how to lead with heart in times of change — this conversation is for you.

    1h 7m

  7. 09/19/2025

    How to Embrace Your Oddball as a Leader with Yusef Garcia

    In this episode of The Things We Have Learned, I'm joined by Yusef Garcia (he/him), founder and Principal of Monarq Advisors. Yusef opens up about embracing your oddball identity, forging non-linear career paths, and leading with vulnerability and authenticity in challenging environments. We dive into the moments that shaped his journey — the surprises, the pivots, the resistance — and how he’s built a personal leadership philosophy rooted in being true to self. You’ll hear how he leans into discomfort, tilts toward connection over perfection, and crafts impact in ways that break conventional molds. Whether you're navigating a career shift, questioning what “leadership” really means, or trying to find a voice that feels genuine in your work, this conversation will give you new language, permission, and inspiration.

    1h 13m

  8. 09/12/2025

    Breaking Barriers in STEAM and Mental Health with Emily & Jessica Esquivel

    In the first full episode of The Things We Have Learned, I sit down with Emily Esquivel (she/her), a psychotherapist and Dr. Jessica Esquivel (she/her), a physicist and STEM advocate, a married couple whose professional and personal journeys intertwine in powerful ways. Together, Emily and Jessica reflect on how identity, lived experience, and partnership shape the way they show up as leaders — in the therapy room, in the lab, and in their communities. From navigating mental health in helping professions to breaking barriers as a queer woman of color in STEM, they share how love and authenticity fuel resilience, advocacy, and growth. This conversation offers a window into what it means to lead with vulnerability, build supportive relationships, and honor the fullness of who you are: both at work and at home.

    1h 9m

  9. SEASON 1 TRAILER

    The Things We Have Learned - Show Trailer

    Looking for a new LGBTQ+ leadership podcast? Wish you had a mentor? Consider 'The Things We Have Learned,' a podcast providing career guidance for LGBTQ+ individuals through conversations with Chicago LGBTQ+ leaders.

    4 min

Trailer

Ratings & Reviews

5
out of 5
4 Ratings

About

The Things We Have Learned is a podcast providing career guidance for LGBTQ+ professionals. Through conversations with Chicago LGBTQ+ leaders from all industries, backgrounds, and disciplines, we'll hear stories that queer what we think leadership is and who gets to be a leader. We'll also gain valuable tips for navigating common workplace challenges.

Information

  • Creator
    Rachel Walerstein
  • Years Active
    2K
  • Episodes
    9
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    The Things We Have Learned