Today Was Fun with Bree Groff — How to Design for Better Work

Welcome back to Snafu with Robin Zander.

In this episode, I’m joined by Bree Groff, consultant, writer, and author of Today Was Fun.

We talk about why mischief belongs at work, how humor and flirtation create real psychological safety, and the bold design choices behind her unforgettable book cover. Bree shares how she moved from CEO roles to full creative freedom, and how that shift helped her find her voice. We discuss marketing in 2025, how AI might reshape work and writing, and why personal agency, not hours, is the most important lever in a workweek. 

Bree offers practical insights for leading with joy, helping kids future-proof their lives, and deciding what’s “enough” in a world that always demands more. She also reflects on writing the book while parenting, consulting, and building her own business, and what it means to embrace the joy of not knowing what comes next.

Bree will also be joining us live at Responsive Conference 2025, and I’m thrilled for you to hear her on stage.

If you haven’t gotten your tickets yet, get them here.

Books

• Trickster Makes This World: Mischief, Myth, and Art — Lewis Hyde

• Anansi Boys — Neil Gaiman

• Work Less, Do More: Designing the 4-Day Week — Alex Pang

• Shorter: Work Better, Smarter, and Less―Here's How — Alex Pang

• Rest: Why You Get More Done When You Work Less — Alex Pang

• Perennial Seller: The Art of Making and Marketing Work that Lasts — Ryan Holiday

• Today Was Fun — Bree Groff

• The 4-Hour Workweek —Tim Ferriss

• Responsive: What It Takes to Create a Thriving Organization — Robin Zander

Podcasts/Videos

• TED Talk: How to Start a Movement — Derek Sivers

Start (0:00) The Story Behind the Book Cover (00:07.822)

• Robin opens with a personal observation: Bree’s nails are the exact shade of green as her book cover – a smiley face on a highlighter yellow-green background. 

• Bree laughs and explains the choice behind the bold, offbeat cover:

• It was designed by Rodrigo Corral, known for iconic covers like The Subtle Art of Not Giving a Fck*.

• When she first saw it (at 3 a.m.), she gasped and loved it — it stood out and made a statement.

• The smiley is cheeky but not cheesy; it suggests optimism with a bite.

• The color isn’t quite yellow — it’s that “gross green” that almost hurts to look at. That tension is the point.

• “It’s got some edge... not your straight-up yellow.”

• This tension – bright and fun, but just a bit weird or off –  is exactly the tone she wanted for the book and for herself.

The Wink That Makes Work Fun Again (01:51)

• Robin brings up his old graduation photo: he posed slightly off-center, adding a knowing smirk. At the time, he didn’t know why he chose that shot, but later realized it made people curious, like a small rebellion baked into something formal.

• Bree relates completely. She talks about:

• Why humor and a bit of mischief matter in professional settings.

• The concept of flirtation – not romantic, but playful:

• A wink in a branding campaign.

• A reference that only a few insiders get.

• A running joke between team members.

• Mischief creates risk and intimacy, both essential for real connection.

• These small acts of rebellion are actually signs of psychological safety and creativity.

• “You need a little bit of flirtation at work... a wink that says, ‘we’re in this together.’”

• She argues that fun isn’t a distraction – it’s a sign that something is working.

Tricksters, SNAFUs, and the Role of Risk in Work (05:49.219)

• Robin brings in the idea of the trickster, from folklore characters like Anansi and Coyote to his podcast title SNAFU. These figures don’t follow the rules, and that’s what makes them interesting.

• Bree expands on the connection between play and professionalism:

• There’s a cultural script that says “seriousness = competence.”

• But in her experience, some of the best work moments involve play, risk, and even slight embarrassment.

• Being human together – laughing too loud, saying something weird, trying something bold – is what builds bonds.

• Real joy at work comes from these edge moments, not the sanitized ones.

• “You have to go beyond professionalism to access the most fun parts of work.”

• They agree that creating spaces where people can color outside the lines is not just fun – it’s productive.

Beyond Palatable: From People-Pleasing to Belonging (08:29.068)

• Robin shares a lesson from his mother: that once you leave high school, life is no longer a popularity contest. But he’s realized that in business, especially branding, people often still chase approval and “likability.”

• Bree offers a deeper lens:

• Being “palatable” – meaning universally acceptable – is actually the opposite of being memorable.

• People who try to please everyone end up blending in.

• What she wants is to be delicious, or at least striking, not for everyone, but unforgettable to some.

• She draws a line between

• Fitting in: performing a version of yourself to meet social norms.

• Belonging: being your full, vibrant self and finding others who welcome it.

• “Please don’t chew me up. I’m not palatable — I’m not trying to be.”

• This philosophy shows up in her book’s voice, design, and in how she shows up in the world.

Selling a Book in 2025: Bottles in the Ocean (12:21.838)

• What's it been like trying to promote a book in 2025?

• Bree describes her strategy as both scrappy and intuitive:

• She thinks of book marketing as sending “a million notes in bottles” – not knowing which will land.

• Her approach includes:

• Partnering with a publicist.

• Creating swag kits with branded gear.

• Pitching the book to “chatty” communities (e.g., alumni groups, newsletters, podcast audiences).

• Posting regularly, even when it feels silly.

• She cites the idea of “luck surface area”: the more interesting things you do, and the more people you tell, the more chances something will stick.

• “You do interesting things and talk about them a lot... and maybe something takes off.”

• Still, she acknowledges that luck plays a role. There’s no guaranteed playbook, just momentum and hope.

Is It Worth Talking About? (14:47.63)

• Robin references a quote from Tucker Max: that all marketing, in the end, is just word-of-mouth.

• Bree shares what guided her during the writing process:

• Her goal was to create something remarkable — in the literal sense:

• Something people would want to talk about.

• Not just good – but distinct, resonant, and weird enough to share.

• She wanted to avoid the “business book voice” – flat, generic, overly polished.

• She lights up when she talks about:

• Strangers sharing the book on social.

• Friends are texting her about it.

• An old college boyfriend resurfaced after reading it.

• “When that starts happening... You realize the machine is working.”

• She’s less interested in best-seller lists and more focused on impact – ideas spreading from person to person, because they hit.

Finding Her Voice: From Blogger to Book Author (16:36.665)

• Bree traces the evolution of her writing life:

• Started a travel blog in her early 20s and loved it immediately.

• Played with writing publicly over the years: occasional posts on LinkedIn, Fast Company, and later Substack (which began two years ago, alongside early book ideation).

• Writing always felt natural, but being a public voice within organizations came with constraints:

• “Even when I was CEO, I still felt the need to toe the party line.”

• Going solo changed everything:

• No longer represents a company’s brand – just her own.

• Writing feels more honest, bolder, and more fun when it’s “Bree Groff’s opinions” alone.

• Stepping out independently accelerated her writing voice and gave her creative freedom.

Writing in the Age of AI (18:19.63)

• Robin asks: Does writing still matter in the world of AI?

• Bree’s take:

• She’s a verbal processor — writing is how she discovers what she believes.

• “I never know how an article is going to end… I write my way into the idea.”

• She rarely uses AI in writing (aside from Grammarly). She prefers human composition even for emails.

• Writing helps her organize and refine her thinking:

• “I’ll write a sentence and go – wait, do I believe that? And rewrite.”

• What writing offers that AI can’t (yet):

• Emotional authenticity.

• A confessional power — like stand-up comedy: humans telling uncomfortable truths, out loud.

• She hopes we’ll someday have digital labels like:

• “This was made by a human.”

• Robin presses for Bree’s take on what AI changes – for better or worse.

• Bree’s pessimistic view:

• Mass unemployment is a likely risk.

• Not convinced by the “tech creates more jobs” argument – even referencing Jevons Paradox: as things become more efficient, we just use more of them.

• “I can’t quite think my way out of the unemployment problem.”

• Bree’s optimistic vision:

• We’re burned out. AI could fix that.

• If used right, AI can reduce workloads, not eliminate humans:

• “Wouldn’t it be great if we used these efficiencies to help people live happy, regulated lives?”

• This would require a policy change, like tax incentives for companies that adopt a 4-day workweek.

• But she admits: that’s a long shot.

• “It would take a lot for companies to prioritize reducing burnout over cutting costs.”

Entrepreneurship Isn’t a 4-Day Workweek (And That’s Okay) (25:04.686)

• Robin challenges Bree’s hope with reality:

• Entrepreneurship is chaotic and demanding, as when he launched both a restaurant and a conference in one year.

• When building something from scratch, the work is relentless.

• “There’s no 4-day workweek when you’re going zero to one.”

• He notes Bree’s book could become a “perennial seller,” but only if she builds that momentum now — and that means hustle.

• Bree agrees — and offers nuance:

• She’s in a launch phase. The last 6 weeks have been intense:

• Nights, weekends, articles, appearances.

• Her daughter is in a full-day camp to support this push.

• But it’s intentional and temporary.

• She frames her philosophy like this:

• Overwork can be fun, energizing, even addictive –  if it’s seasonal.

• She’s already planned recovery:

• A two-week log-off in late August.

• A blocked-out first week of September for reset.

• Bree continues on the myth of “reasonable” work limits:

• There’s nothing special about 40 or 60 hours. The only reason we cap out is that we literally run out of time.

• Businesses will take as much as you give, and now AI won’t hit those limits.

• So we have to decide what’s enough, not the market.

• “If we’re going to cap work somewhere, why not cap it lower and enjoy our lives?”

• She reminds us:

• Deadlines and pace are levers, not laws.

• You can pull other levers, like starting earlier, extending timelines, or balancing your team differently.

• Robin shares that his intense physical regimen (handstands, running, cold plunges, hikes) isn’t about health prescriptions — it’s about joy.

• That same mindset applies to work. If building his company lights him up, great – but it’s a personal choice, not a universal blueprint.

• Bree underscores that agency is key: the danger arises when a founder’s choice to overwork becomes the cultural expectation for everyone else.

• A CEO has different stakes than employees; assuming equal sacrifice is unfair and toxic.

• Overwork becomes problematic when choice is removed or social pressure distorts it.

• They introduce the idea of opportunity cost:

• Every hour spent grinding is an hour not spent with loved ones, moving your body, or simply resting.

• Many delay self-care with the illusion they’ll "catch up later" – but your body and relationships exist in the now.

• Robin recalls a brutal 2016: two startups, no time, lost relationships – a visceral reminder that everything has a cost.

Work, But Make It Weird (36:39)

• Robin draws a parallel between their playful ethos and The 4-Hour Workweek: redefining productivity with mischief and authenticity.

• He asks Bree how leaders can lead differently – more playfully – without violating norms or HR policies.

• Bree delivers a gem:

• Her team once suggested that a CEO explain their product to a bunch of 7-year-olds on a picnic blanket.

• They scripted techy questions ("What’s your tech stack?") for the kids, hired a comedy consultant, and filmed the whole thing.

• It was wild, unexpected… and the most beloved part of an otherwise traditional company week.

• The magic was in the vulnerability and humanity of the CEO — letting people into his home, sharing space with kids, and showing joy.

• Bree’s advice to leaders:

• Rearrange the office furniture for no reason.

• Use Comic Sans in a slide just to annoy a designer.

• Hide jokes in presentations that only two people will catch.

• Amuse yourself. That’s reason enough, and it models psychological safety and play for everyone else.

• Robin calls this “the courage to play” – the bravery to step out of line just enough to invite others into the fun.

• Bree builds on this:

• We’re often afraid that having fun will make us look stupid – but that fear is misplaced.

• She quotes Amy Poehler: “Nobody looks stupid when they’re having fun.”

• Play is an act of self-assurance, not frivolity.

• Bree shares a personal win: she turned a project Gantt chart into a hand-drawn arcade-style horse race.

• No one else joined in, but she loved it.

• And that joy, in and of itself, is a worthy output.

Work According to a 10-Year-Old (42:21.176)

• Robin asks: How does Bree’s daughter describe what she does?

• Her answer? “You help people work together.”

• Bree beams — that’s not far off.

• Her daughter has even become her little publicist, linking nail polish to Bree’s book and promoting it to strangers.

• Robin dreams of having kids and wonders about their future in a rapidly evolving world.

• Bree is grateful her daughter is 10, not 22 – the future feels so uncertain that not knowing is oddly freeing.

• College may or may not matter; she might be a marketing manager or start an artist retreat in Tuscany.

• The one stable prediction? Human connection.

• Jobs built on empathy, presence, and the hug – literal or metaphorical – will always have value.

• Robin jokes (but not really) about resisting the idea of robot romantic partners.

• Bree wonders: Will we be seen as biased for resisting AI companionship? Is that the next generational tension?

The Only Skill That Might Still Matter in 2040 (43:55.959)

• Robin asks: What durable skills should Gen Alpha learn in a world of AI and noise?

• Bree’s first thought: “understanding human behavior” — but AI might already be better at that.

• So she lands on something deeper:

• The skill of knowing what kind of life you want to lead.

• It’s rarely taught, and sorely needed.

• That’s why so many people wake up at 40, mid-career, with a law degree but no love for the law, and end up switching to something that finally feels like them.

• Teaching kids to listen to their appetites and curiosities might be the most powerful, future-proof education we can offer.

• Bree argues that most people were never taught to ask foundational questions about the life they truly want:

• From childhood to college, we follow preset tracks – curriculum, majors, careers.

• If you’re lucky, you get an elective or two. But real self-inquiry? Rare.

• We’re missing education on key lifestyle preferences:

• What kind of schedule do I like?

• What kind of people energize me?

• Do I want to live in a city or near nature?

• How much solitude, structure, or chaos is ideal for me?

• Bree believes this underdeveloped self-awareness is the root cause of burnout:

• People follow “the path,” get promoted, tick boxes, and still feel unsatisfied.

• Companies gladly fill the vacuum with corporate ladders and titles – senior director, VP, etc.

• But we rarely stop to ask: Do I want my boss’s job?

• Her hope for her daughter: not just career success, but aliveness.

• To develop the instincts and courage to ask: What do I want to get out of my short time here?

• And to find joy in helping others experience a bit more light while they’re here, too.

“Who Are You and What Is Your Purpose?” (51:33.666)

• Robin shares a surprising memory: a third-grade class titled Who Are You and What Is Your Purpose?

• He doesn’t remember the content – school was tough for him then – but the title stuck.

• It captured something real and deep that still resonates.

• Bree lights up: “Okay, I take it all back – someone was teaching this, and it was you!”

• They land on a core truth: that mischief, self-knowledge, and authenticity are deeply intertwined.

• Knowing who you are is the first step.

• And honoring the weird, playful part of yourself makes life better — and work richer.

Order, Chaos & a Trello Board (53:51)

• Robin pivots: What did Bree learn about writing through this book, especially while juggling parenting and client work?

• Bree shares her full process:

• She started with a Trello board: each list represented a chapter.

• Over many months, she collected bits of inspiration: ideas from the shower, great quotes, Substack entries, research snippets – all filed as cards.

• This meant when it came time to write, she wasn’t starting from scratch.

• Her trick: separate idea collection from prose creation.

• Once she had a "pile of disorganized meat," she could stitch it together with intention.

• She scheduled 4-hour blocks to write ~1,000 words per session – 50 sessions = a 50,000-word book.

• She was thoughtful about pacing and reader experience:

• "That was a heavy part – maybe time for a joke.

• "I’ve been light for a while – maybe we need some grounding research."

• The outcome: a process that respected her creativity, time, and humanity.

The Joy of Not Knowing What’s Next (54:45.848)

• Robin asks: Now that the book is out, what’s next?

• Bree doesn’t know, and that feels exciting.

• She’s booked through the fall with workshops, consulting, media, and speaking.

• But beyond that? It’s open.

• She’s leaning into serendipity:

• Publishing the book drew new, inspiring people into her life – people like Robin.

• She’s open to building the classic “author-speaker-consultant” portfolio.

• Or possibly returning to SYPartners, depending on what fits.

• Or a totally new path.

• What makes it possible?

• A jumpy career history – she’s used to leaps.

• A baseline of financial stability – and a partner with a more predictable job.

• Uncertainty isn’t terrifying when you trust yourself to figure it out.

• “I can see through October. That’s enough.”

• Robin wraps with heartfelt praise:

• Few first books feel as personal and reflective of their author as Today Was Fun.

• Even fewer come with so many shared connections vouching not just for the content, but the author herself.

Where to Find Bree Groff (58:13.58)

• He urges people to read the book and see Bree on stage at the Responsive Conference (Sept 17–18).

• Bree shares where to find her:

• Website: breegroff.com

• Substack, LinkedIn, Instagram – all linked from her site.

People Mentioned:

• Rodrigo Corral

• Lewis Hyde

• Neil Gaiman

• Tony Hsieh

• James Clear

• Tucker Max

• Alex Pang

• Ryan Holiday

• Tim Ferriss

• Amy Poehler

• Derek Sivers

• Justin Gordon

• BJ Fogg

• Seth Godin

Organizations / Companies

• Zander Media

• SYPartners

• Nobel

• Zappos

• Microsoft

• Trello

• Substack

• AOL

• LinkedIn

• Instagram