Good Enough

Brittany Greenfield
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  • Entrepreneurship

This is a podcast for high-achieving founders, operators, executives, and leaders who know that excellence matters, but endless refinement kills momentum. As a serial tech entrepreneur, Brittany Greenfield has built and exited companies in high-pressure environments where speed, clarity, and execution are everything. In each episode, she sits down with world-class leaders to explore one of the most important skills in business and life: knowing where the line is. Good enough is not settling. It is strategy. Through candid conversations, practical frameworks, and real stories from leaders who have had to make hard calls, Brittany unpacks how to prioritize what truly matters, define done, move faster, and let go of the rest. From perfectionism and decision drag to burnout, leadership bottlenecks, and the discipline of completion, Good Enough helps listeners trade overthinking for momentum. Because the path to great does not start with perfect. It starts with good enough.

  1. 1d ago

    Stop Chasing Volume. Start Choosing Precision. with Greg Woodward | #16

    What if better results had less to do with doing more—and everything to do with making better moves? In this episode of Good Enough, Brittany Greenfield sits down with Greg Woodward, founder of Woodward Strategies, to unpack the psychology behind why some sales reps and teams consistently outperform others—even when they’re putting in the same hours and making the same number of calls. Greg explains why consistency beats perfection, how subconscious resistance shapes prospect behavior, and why filling the “tank” with enough data can keep leaders from making costly decisions too soon. In this episode, you’ll learn: ● Why doing the reps matters more than winning every individual attempt ● How perfectionism can disguise itself as procrastination—and how to move past it ● Why sales teams should focus on precision, personalization, and the right personas instead of simply increasing activity ● How “chunking” and focused time blocks can dramatically improve both productivity and quality The goal isn’t to make more moves. It’s to make the right moves, consistently—and let small improvements compound over time. Tune in and discover how to trade volume for precision, embrace the inevitable volatility, and make your next move a little better than the last. Connect with Greg Woodward LinkedIn: https://www.linkedin.com/in/gregorycwoodward/ Connect with Brittany Greenfield Website: https://www.wabbi.com LinkedIn: https://www.linkedin.com/in/brittanygreenfield

  2. Sep 22

    The Hidden Shame Behind Perfectionism with Dr. Melissa Robinson | #15

    What if the people you think are the problem actually just need more clarity? What if the thing keeping you from moving forward isn’t perfectionism—but shame? In this powerful conversation, Brittany Greenfield sits down with Dr. Melissa Robinson Weinmiller to unpack the hidden connection between shame, self-criticism, procrastination, and decision avoidance. Drawing from more than 30 years as a classically trained musician, her experience with toxic leadership, and her work in empathetic leadership, Dr. Melissa reveals why self-empathy—not more pressure—is what can help us break the cycle and regain momentum. In this episode, you’ll discover: ● Why perfectionism can turn into procrastination and decision avoidance ● The difference between being critical of yourself and judging yourself ● Four steps to practicing self-empathy and breaking the shame cycle ● Why empathy isn’t a “soft skill”—and how it can strengthen leadership, creativity, and innovation ● How to stay human and authentic as AI takes on more of our cognitive work At the heart of this conversation is a simple but powerful reminder: being human means being imperfect. Learning to meet yourself with empathy can create the space to learn, lead, innovate, and keep moving forward. If you’ve ever told yourself, “I should be better,” this episode is for you. Hit play—and discover what becomes possible when you stop letting shame put you in a box. Connect with Dr. Melissa Website: https://eqviaempathy.com/ Connect with Brittany Greenfield Website: https://www.wabbi.com LinkedIn: https://www.linkedin.com/in/brittanygreenfield

  3. Sep 8

    It’s Not Your People. It’s Your Systems. with Lia Garvin | #14

    What if the people you think are the problem actually just need more clarity? In this episode of Good Enough, Brittany Greenfield sits down with Lia Garvin, author, leadership expert, and host of Managing Made Simple, to challenge one of the most common assumptions leaders make: that performance problems are always about the people. Lia explains why clear systems, expectations, context, and communication can transform how teams work—and why even the smallest businesses need systems to succeed. Together, Brittany and Lia explore: ● Why clarity beats micromanagement: Giving people clear expectations and context helps them make better decisions independently. ● The power of simple systems: Systems don't have to be complicated—they can be as simple as defining the three steps that absolutely need to happen. ● How to make feedback conversations easier: Lia shares a practical “sit-down” approach that combines ownership, recognition or constructive feedback, and a clear action plan. ● Where AI, automation, and hiring fit: Start by identifying the most frustrating, repetitive task in your day and ask whether it should be automated, delegated, or eliminated. Lia's philosophy is refreshingly simple: good enough systems reduce the number of steps it takes to get something done. You don't need a perfect process—you need a clear one that helps people know what matters, what success looks like, and what to do next. If leadership feels overwhelming, this conversation is a reminder that the answer may not be to work harder or find better people. Sometimes, you just need to make the work easier to do. Connect with Lia Garvin Website: https://www.liagarvin.com/ Connect with Brittany Greenfield Website: https://www.wabbi.com LinkedIn: https://www.linkedin.com/in/brittanygreenfield

  4. Sep 1

    The Leadership Power of Better Questions with Chuck Wisner | #13

    In this episode of Good Enough, Brittany Greenfield sits down with leadership consultant, executive coach, and author Chuck Wisner to rethink what effective communication really looks like. Chuck explains why great leaders don’t need to have all the answers—they need to create the conditions for better questions, deeper dialogue, and shared understanding. His “open hand” approach to communication helps leaders move away from command-and-control and toward collaboration, curiosity, and trust. Together, Brittany and Chuck explore: ● The “open hand” approach: How revealing your thinking, concerns, and standards can turn confrontation into collaboration. ● The four questions leaders should ask: What do you want? What are your concerns? ● What are the power dynamics? And what standards are shaping your judgment? ● Why leaders need to say “I don’t know”: The higher you climb, the more you have to rely on the expertise of others and learn together. ● How to recognize your own patterns: Learning to notice when defensiveness, assumptions, or old habits are driving the conversation. Chuck offers a simple practice you can use tomorrow: pick one of the four questions and use it to open the conversation rather than close it. Because leadership isn't about being the smartest person in the room—it's about creating the space where everyone can think, contribute, and move forward. Connect with Chuck Wisner: Website: https://www.chuckwisner.com/ Connect with Brittany Greenfield Website: https://www.wabbi.com LinkedIn: https://www.linkedin.com/in/brittanygreenfield

  5. Aug 25

    You’re Not Stuck—You’re Playing the Wrong Game with Ashley Rudolph | #12

    What if the thing holding you back isn’t a lack of ability—but an outdated definition of success? In this episode, host Brittany Greenfield sits down with Ashley Rudolph, who went from individual contributor to VP in just five years, often as the only woman, Black woman, or youngest person in the room. Now, after a decade of studying what helps high achievers advance, Ashley coaches senior leaders at companies including Airbnb, Meta, and Citi to stop being the “best kept secret” and start getting recognized for the leadership they already possess. As Ashley explains, the skills that make you successful early in your career—being the best at your individual work—aren’t necessarily the skills that make you successful as a leader. The conversation explores the pivotal shift from proving what you can do to creating impact through others, and why invisible contributions can be some of the most valuable work a leader does. In this episode, you’ll discover: ● Why high achievers often struggle when they reach senior leadership ● How to redefine success beyond individual accomplishment ● Why the “invisible work” leaders do can create enormous impact ● How to become more intentional about the way you show up as a leader If you’ve ever wondered why working harder isn’t translating into the recognition or influence you want, this conversation will help you rethink the game—and give you a new way to play it. Connect with Ashley Rudolph: Website: https://www.workwithashleyr.com/ Connect with Brittany Greenfield Website: https://linktr.ee/brittanygreenfield

  6. Aug 18

    Perfectionism, Progress, and the Pressure We Put on Ourselves | #11

    What if letting go of perfection is the key to doing your best work? In this episode, host Brittany Greenfield sits down with Ann Dux for an honest conversation about perfectionism, progress, and the pressure we put on ourselves to get everything right. Ann shares her perspective on embracing imperfection, moving forward before you feel completely ready, and redefining what success looks like when you stop chasing an impossible standard. In this episode, you’ll discover: ● Why perfectionism can keep you from making meaningful progress ● How to embrace “good enough” without lowering your standards ● The power of taking action before you have everything figured out If you’ve been waiting for the perfect time, perfect plan, or perfect version of yourself, this conversation is your reminder that progress starts when you’re willing to begin. Connect with Ann Dux: Website: https://duxcommunications.com/about/ Connect with Brittany Greenfield Website: https://www.wabbi.com LinkedIn: https://www.linkedin.com/in/brittanygreenfield

  7. Aug 11

    The Decision You’re Avoiding with Amy Lessinger | #10

    What if the one decision you’re avoiding is the one that changes everything? In this episode, Brittany Greenfield sits down with Amy Lessinger, a leader who built a billion-dollar real estate brokerage during one of the worst market crashes in history. Instead of playing it safe, Amy made a bold, irreversible decision that not only saved her business—but reshaped how she thinks about leadership, risk, and growth. Together, they unpack why most leaders get stuck at critical inflection points—not because they lack strategy, but because they’re avoiding the uncomfortable decision they already know they need to make. Amy shares how embracing failure, owning risk, and letting go of perfectionism can unlock momentum and drive real progress. Key Takeaways: ● Why inaction—not failure—is the biggest regret for leaders ● How “zero-failure cultures” quietly kill growth and innovation ● The power of making irreversible decisions that move you forward If you’ve ever felt stuck, overanalyzed your next move, or waited for the “perfect” moment—this conversation is your wake-up call. The path forward isn’t clearer—it’s just waiting for you to choose it. Connect with Amy Lessinger: Website: https://www.amylessinger.com/ Connect with Brittany Greenfield Website: https://www.wabbi.com LinkedIn: https://www.linkedin.com/in/brittanygreenfield

  8. Aug 4

    Win the Moment, Change Everything with Lissy Alden | #9

    What if success isn’t about winning the game—but mastering the smallest moment in front of you? In this episode, Brittany Greenfield sits down with Lissy Alden to break down the concept of “organizational fitness” and why most teams fail not from lack of vision—but lack of consistent execution. Drawing on sports psychology and real-world leadership, Lissy shares how shifting your focus from outcomes to daily inputs can unlock confidence, momentum, and long-term performance. From redefining what “good enough” really means to building habits that actually stick, this conversation challenges the way we think about productivity, leadership, and growth. Key Takeaways: ● Why “winning the moment” is the key to sustainable success ● How small, repeatable actions build real confidence and momentum ● The difference between activity vs. true accomplishment If you’ve ever felt stuck chasing perfection or overwhelmed by big goals, this episode will show you how to start small, stay consistent, and build a system that actually works. Connect with Lissy Alden LinkedIn: https://www.linkedin.com/in/lissy-alden/ Connect with Brittany Greenfield Website: https://www.wabbi.com LinkedIn: https://www.linkedin.com/in/brittanygreenfield

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About

This is a podcast for high-achieving founders, operators, executives, and leaders who know that excellence matters, but endless refinement kills momentum. As a serial tech entrepreneur, Brittany Greenfield has built and exited companies in high-pressure environments where speed, clarity, and execution are everything. In each episode, she sits down with world-class leaders to explore one of the most important skills in business and life: knowing where the line is. Good enough is not settling. It is strategy. Through candid conversations, practical frameworks, and real stories from leaders who have had to make hard calls, Brittany unpacks how to prioritize what truly matters, define done, move faster, and let go of the rest. From perfectionism and decision drag to burnout, leadership bottlenecks, and the discipline of completion, Good Enough helps listeners trade overthinking for momentum. Because the path to great does not start with perfect. It starts with good enough.

Information

  • Creator
    Brittany Greenfield
  • Years Active
    2026
  • Episodes
    16
  • Rating
    Explicit
  • Copyright
    © 2026 Brittany Greenfield
  • Show Website
    Good Enough