Good Life Project: 7 Keys to Making Work…gulp…fun!

Host: Jonathan Fields
Guest: Bree Groff (author of Today Was Fun)
Release Date: September 4, 2025

Overview

In this engaging episode, Jonathan Fields explores with Bree Groff the transformative concept that work can and should be genuinely fun—most days, at least. Drawing from Bree’s extensive experience as an educator, consultant, and leader, and her new book Today Was Fun, the conversation maps out a practical, deeply human set of seven rules for reclaiming joy, creativity, and authenticity in the workplace. With warmth and humor, they challenge long-held assumptions about professionalism, busyness, conformity, and delayed gratification, offering actionable insights for making every workday—and life beyond work—more meaningful and alive.

Key Discussion Points & Insights

1. Contrasting Upbringings: Fun vs. Formality in Work

• Bree’s early influences: Raised in a family of joyful educators, Bree assumed all work was meant to be fun and fulfilling.
  • Quote: “My mom would come home and she’d say, ‘I have the best days.’ ... I just grew up thinking that my whole career, my life of work ahead of me was going to be joyful.” (03:29)
• Culture shock in corporate America: Moving from teaching to consulting, she was struck by the rigid norms—limited self-expression, performative professionalism, and a sense that her “fullest, most human, vibrant version” of herself wasn’t welcome.
  • Quote: “It felt like, this is not fun... I would wake up some days and think there’s more of me to give, and I’m not giving it because it doesn’t feel safe. And I think that’s a problem.” (05:41)

2. Shaping New Cultures: Authenticity & Small Experiments

• Creating her own workplace rules: As CEO of a consultancy, Bree experimented with “making it up” and introducing more humanity—like starting meetings with honest check-ins or showing up with wet hair.
  • Quote: “My brain works just as well if my hair is wet or dry... There were all these small practices of, like, here I am in wet hair talking about my cat, and our business is still doing well.” (11:18)
• The real cost of conformity: Masking authentic selves and focusing on performance drains energy and creativity—bad for both individuals and business bottom lines.
  • Quote: “There’s a cost to keeping that up all day. But then... when people feel like they need to perform business, what they’re doing is they’re making their work look like everybody else’s work so that they don’t stick out.” (14:09)

3. The Existential Prompt: Writing Today Was Fun

• Mortality as a motivator: Bree’s mother’s terminal illness sharpened her urgency to help people “value their days,” contrasting the preciousness of time with the common wish to fast-forward through workdays.
  • Quote: “It felt like a very deliberate... wishing away their days. It’s such a common thing to say, but that sort of realization of what work was taking from us—it felt like, okay, I have something to say about this.” (19:26)
• Delayed gratification vs. daily joy: She challenges the cultural script of saving enjoyment only for the future, insisting we “bank the joy while you have it.”
  • Quote: “If we delay our gratification for too long, we’re going to look back and think, where did all my joy go? You banked the paychecks. You did not bank the joy.” (22:24)

The Seven Rules for Making Work (…gulp…) Fun

1. Most Work, Most Days, Should Be Fun

• Premise: Creating value for others doesn’t inherently require pain or drudgery; work can and should contain joy.
• Tolerance for imperfection: “Did I get most things. Great, most things most days?” (24:39)
• Counterpoint: Recognizes not all work will be fun all the time, but rejects the notion that work must inherently be dreary.

2. Your Brain Works Whether You’re Wearing a Suit or Stretchy Pants

• Challenge to professionalism: Emphasizes that true professionalism is “good work, on time, with respect”—not about attire or “performative” behavior.
• Quote: “There’s never going to be a great idea that comes out of a meeting room where everybody has perfect posture and is wearing the ties... No one’s bringing their best then.” (32:50)
• Difference vs. defect: Distinguishes genuine differences in style from behaviors that actually impact others adversely.

3. Shoveling Shit Is Fun If You Like Your Co-Shovelers

• The power of relationships: Camaraderie and connection make hard work lighter and workdays enjoyable, much as good company transforms a dull dinner.
• Quote: “If the company at work is good, the content of the work matters less.” (40:46)
• Invitation: To intentionally look for teams with people you genuinely enjoy.

4. Make Brilliant Work; Don’t Let Busyness and Conformity Sabotage You

• Brilliance is possible anywhere: Even seemingly mundane roles have room for creativity and excellence if you’re open to reimagining tasks.
• Quote: “There’s so much joy in creation... I think that leaves a lot on the table and part of the joy of work is getting to feel brilliant.” (46:33)
• Containers for brilliance: Even small gestures (like latte art or warm emails) can be outlets for unique contribution.

5. Keep It Cool—We’re All in It Together

• Emotional reliability: The mood and energy of leaders and colleagues are contagious; “keeping it cool” under stress sets a tone for resilience and collegiality.
• Communicate feelings, don’t hide them: Naming your emotional state prevents unnecessary anxiety and increases team support.
• Quote: “It’s just as simple as naming it. And then everyone’s like, cool, I got your back.” (56:13)

6. You Are the Defender of Date Nights, Crossword Puzzles, and Your Health

• Life outside work is vital: Protect leisure, relationships, and well-being from being consumed by “hungry” work.
• Quote: “Work is hungry. It’s a bottomless pit... and so it’s really up to us to value those parts of our lives, defend them.” (58:54)
• Counterintuitive productivity: Prioritizing life outside work actually enhances professional success and happiness.

7. Get Good at Life, Not Just Work

• Ambition beyond the office: Challenge yourself to “get good” at living—relaxing, sleeping, loving, enjoying—just as much as you seek achievement at work.
• Quote: “What more could you want in life than to have had some good laughs with good people?” (68:47)

Notable Quotes & Memorable Moments

• On fun at work vs. professionalism
  • “I succeed by being the fullest, most human, vibrant version of myself versus... a very palatable, presentable... version.” —Bree Groff [(05:41)]
• On workplace conformity
  • “No CEO is paying for the performance. They’re like, no, where’s the actual goods?” —Bree Groff [(14:09)]
• On existential urgency
  • “If we delay our gratification for too long, we’re going to look back and think, where did all my joy go?” —Bree Groff [(22:24)]
• On camaraderie
  • “If I have friends around who I love, it does not matter if we’re eating crappy food, we’re going to have a beautiful evening.” —Bree Groff [(40:46)]
• On micro-acts of mischief
  • “Maybe you wear socks with a little turtle print... it’s these little acts of humanity and play.” —Bree Groff [(67:05)]
• On living a good life
  • “Good laughs with good people... I want to be laughing most days, not every day, most days. And I think if I can do that most days of my life, to me, I feel like I’ve won.” —Bree Groff [(68:47)]

Timestamps for Important Segments

• 03:29 — Bree’s childhood vision of joyful work
• 05:41 — Culture shock: Expression in education vs. corporate consulting
• 11:18 — Building new workplace norms at her own consultancy
• 19:26 — How mortality catalyzed Bree’s writing and urgency for joy
• 24:39 — “Most things, most days”: Letting go of perfectionism
• 32:50 — The irrelevance of “performative professionalism”
• 40:46 — Why camaraderie trumps role or task in workplace fun
• 46:33 — Unlocking brilliance in any role
• 56:13 — Importance of emotional reliability
• 58:54 — Defending personal time and boundaries
• 67:05 — Getting started: Micro-acts of mischief
• 68:47 — Bree’s definition of a good life

Tone & Style

The episode blends practical wisdom and evidence with candid personal stories, gentle irreverence, and an undercurrent of compassion. Both Jonathan and Bree speak directly to common struggles and hidden desires for authenticity, joy, and connection, inviting listeners to try small acts of “mischief” and bravery to make work (and life) more vibrant and meaningful.

Actionable First Step

Bree’s invitation:
“Try a little mischief... micro acts of mischief. Maybe you wear socks with a flamingo print, maybe you sit more comfortably in a meeting. These little acts... dip your toe into what work looks like when it’s not so buttoned up. And it gives other people permission too.” (67:05)

Final Reflection

Bree’s definition of a good life:
“Good laughs with good people... I want to be laughing most days, not every day, most days. And I think if I can do that most days of my life, to me, I feel like I’ve won. I’ve done it.” (68:47)

Useful for everyone who’s ever wondered: Can we really make work not just bearable, but joyful—even fun? This conversation is both a roadmap and an inspiring call to play, create, connect, and live fully—on and off the clock.