Gianna's Gem: Why "Perfect" Is Killing Your Events (And What to Do About It)
/Hi there,
Last week, I was coaching a rising event manager who was stuck. She'd been planning her company's first major user conference for six months, and guess what? The company still hadn't sent out invitations.
"We’re still refining the agenda," she told me. "My CMO wants to make sure everything's locked in and perfect before we send out invites."
I recognized that look in her eyes immediately as I could recall being in a similar situation as a Head of Events with a C-Suite who were often paralyzed by “shipping” anything if it wasn’t perfect (and what perfect looked like changed on the weekly!). It's the paralysis that comes from believing that if you just plan a little more, research a little deeper, polish a little longer, check a few more times, you'll finally achieve the "perfect" event (or insert anything else here).
Here's what I told her…and what I wish someone had told me fifteen years ago: Perfect is the enemy of good.
Gianna’s Gem: In event planning, “motion” is the enemy of “action”.
The Difference Between Motion and Action
James Clear nails this in Atomic Habits (a favorite book of mine I shared with you in last week’s Gem): Motion makes you feel like you're making progress, but it doesn't actually produce results. Action, on the other hand, delivers outcomes.
In event planning:
Motion looks like:
Endlessly researching venues without booking site visits
Creating the perfect planning spreadsheet (and then recreating it)
Attending webinars about event marketing without implementing anything
Researching but not reaching out to speakers
Perfecting every budget line item instead of putting a stake in the ground and understanding there will be fluidity as you negotiate with vendors
Action looks like:
Booking three venue tours for next week
Sending that imperfect-but-good-enough speaker invitation today with a caveat that the event date might be X, Y or Z to gain intel.
Testing one new registration strategy with your next small event
Creating the post-event survey now
Sending save the dates even though the agenda isn't 100% finalized
Launching a website with a caveat that speaker announcements will be coming each week
Gianna's Gem: Planning is motion. Doing is action. And only action teaches you what actually works.
The Learning Paradox
Here's what I’ve learned over my 23 year career in event planning: you can read every book and blog post, look at ever pinterest board, and listen to every podcast about how to plan events, but you won't actually know how to plan events until you've planned some events because that’s where the phrase “live and learn” rings true. Even to this day, I learn something new while planning every event.
I learned more from the Airtable event where the video in the overflow viewing room failed during our CEO's keynote than I did from a decade of "perfect" keynotes. I learned more from the AWS sponsorship nightmare where we almost didn’t get our booth than from all the other shows where everything was easy. I learned more from planning a challenging milestone birthday in Sardinia than from seamless milestone birthdays planned with my favorite properties in Napa.
Why? Because repetition creates pattern recognition. Experience builds instinct. And failure teaches you what books simply can't.
The problem is: most event professionals don't get the luxury of planning hundreds of events. You might plan one major conference per year. Maybe a handful of smaller events. How do you gain the wisdom that comes from repetition when you don't have the volume?
This is where working with a coach or consultant, taking a guided course, or even volunteering to plan events becomes your competitive advantage.
The Consultant Edge: Borrowing Someone Else's Reps
When you work with an experienced event consultant, you're not just hiring someone to help with logistics. You're borrowing their 10,000 hours. You're accessing their pattern recognition. You're leveraging their war stories so you don't have to create your own.
For example: I've planned events for Google, AWS, SoftBank, Airtable, Windsurf, and dozens of other companies as a consultant. I've executed conferences for 100 people and 30,000 people. I've managed budgets from $50K to $50M+. I've dealt with every team/vendor nightmare, every venue/AV disaster, every stakeholder conflict you can imagine (and plenty you can't…stay tuned for my next book!).
When you work with me (or any seasoned consultant/coach), you get to:
Mentally Rehearsal and Visualise based on Their Shared Experience
"Here's what happened when we tried that agenda format..."
"I learned the hard way that you need to..."
"Based on similar events, here's the pitfall we need to avoid..."
You're essentially running simulations in your mind based on their real-world outcomes. Neuroscience shows that mental rehearsal activates similar neural pathways as actual experience. You're training your brain without having to make (and pay for) the mistakes yourself.
Anecdotal Wisdom That Shortcuts Your Learning Books and courses teach principles. Consultants teach specifics.
"For tech audiences in San Francisco, this type of event sponsorship is risky and here's why..."
"When negotiating with this particular hotel chain, always ask for..."
"Your sponsor fulfillment should happen like this, not like that, because I've seen what happens when..."
Real-Time Decision Support Instead of making your best guess and hoping it works out, you get instant feedback:
"That registration flow will create bottlenecks because of X, let's consider adjusting it."
"Your budget allocation is too heavy on F&B and too light on AV, here's why and how I recommend rebalancing."
"This vendor quote is 30% above market rate, let me show you the comps."
The Course Advantage: Structured Learning Without the Trial-and-Error Tax
A well-designed course (like my Event Strategy Masterclass) does something different but equally valuable: it gives you the frameworks, systems, and best practices that took me years to develop, delivered in a fraction of the time and cost. If you can’t afford a coach or consultant, a self-paced course with exercises to give you “action” practice can be another great strategy to start getting in your “reps”.
AND…If you can convince your company to let your colleagues take it with you, studies have proven that learning in peer groups with discussion along the way improves engagement, retention and bonding by 140%!
Here's what a strategic course offers:
Accelerated Pattern Recognition Instead of planning 50 events to recognize patterns, you study 50 case studies. You learn:
What makes successful conferences stand out
Why certain event formats consistently outperform others
How to negotiate contracts to save money and get key concessions and some downloadable templates to save you time
Systematic Thinking Courses give you repeatable frameworks:
My SUCCESS framework for event design (see last week’s Gem if you missed it)
The attendee journey audit process
Budgeting models and frameworks you can use immediately to implement with your own events
Stakeholder management strategies and communication pro tips to unblock you and help you be more strategic and influential
These aren't theories, they're systems I refined through hundreds of events. And they let you operate from a playbook instead of reinventing the wheel. I feel blessed for having had the opportunity to work with some of the most admired brands in the world and it truly is my mission to be able to scale my reach and share what I’ve been blessed to have learned by the best in class.
Community Learning The best courses create peer communities where you learn from each other's experiences. Someone's venue negotiation strategy becomes your blueprint. Another person's speaker management disaster becomes your cautionary tale.
But Here's the Key Thing Both Consultants and Courses Provide...
They give you permission to take imperfect action.
When you're working with someone who's already made the mistakes, you stop needing everything to be perfect. You learn which details actually matter (the why and intention behind every component, attendee journey and brand experience) and which ones don't (the exact shade of blue in your linens and the type of silverware and china you select for the tables).
You gain the confidence to:
Send the invitation even though the agenda has TBDs
Draft a successful event brief and gain approvals swiftly because you know your why
Launch registration before your website is perfect
Make decisions quickly because you trust your consultant's guidance and therefore present to stakeholders with confidence
This is action. This is progress. This is how events actually get planned.
My Early Career: The Volunteer Advantage
Before I landed at Google, I was exactly where many of you are now or have been: passionate about events but lacking real world experience. I needed reps but didn't have a portfolio. So I did something that changed everything:
I volunteered. A lot.
I volunteered to plan my company's holiday party, my team’s offsites. I volunteered to help people in the industry I admired for free. I volunteered at a number of charity organizations I believed in. Were these glamorous? No. Did they pay extra? Absolutely not. But here's what they did:
They gave me reps.
Every volunteer event taught me something AND also introduced me to new people, partners and even mentors.
By the time I interviewed at Google, I had a portfolio of events that demonstrated I could execute. I had stories of problems I'd solved. I had proof of action, not just motion.
Your Action Plan: Start Now, Imperfectly
If you're reading this and feeling stuck in motion, here's how to shift into action today:
1. If You Can't Plan High-Volume Events:
Work with a consultant or mentor who has. You'll compress years of learning into months. You'll avoid expensive mistakes. You'll build confidence faster.
Take a strategic course that gives you frameworks and community. You'll gain systematic thinking and peer learning that shortens your path to expertise.
Attend events critically. Don't just enjoy them, dissect them. What worked? What didn't? What would you do differently? Every event you attend becomes a case study for your mental database. I still audit events for my clients and always learn something in the process myself.
2. If You Want More Hands-On Experience:
Volunteer for event roles:
Offer to help plan your company's next team offsite
Coordinate a community meetup or local chapter event
Help a nonprofit with their fundraising gala
Manage your friend's milestone birthday party (or baby shower)
Start small but start now:
Plan a 20-person dinner party with a theme and run-of-show
Host a workshop or panel discussion
Coordinate a small networking event
Document everything:
Take photos
Track what you learned
Build your portfolio
Create case studies
Each of these is action. Each one teaches you something books and planning documents can't.
3. Embrace "Good Enough" and Iterate:
Ship the imperfect invitation. You can always send updates.
Book the venue that's 90% right. Perfection doesn't exist, and you're losing time and negotiating leverage by waiting.
Launch with what you have. Version 2.0 will be better because you'll have real feedback, not theoretical concerns.
Test and learn. Try one new thing each event. Measure what happens. Adjust for next time.
The Compound Effect of Imperfect Action
Here's what most event planners miss: every small action compounds.
That imperfect first event teaches you lessons for the second one. The second event builds skills for the third. By your fifth event, you're operating at a level that would have taken you years to reach through "perfect" planning alone.
Meanwhile, the person who's still researching, still planning, still waiting for perfect? They're on event zero.
And here's the beautiful part: you don't have to make all the mistakes yourself.
Working with a consultant means you borrow their compounding experience. Taking a course means you leverage their accumulated wisdom. Volunteering means you gain real reps without the having to commit to a second full time role. Attending events critically means you learn from others' successes and failures.
All of these are forms of action. All of them move you forward. None of them require perfection.
The Bottom Line
Perfect is a mirage. Motion is a trap. And the only way to actually get better at event planning is to plan events, even imperfect ones.
Whether that means:
Working with a consultant or coach who's already made the mistakes
Taking a course that gives you proven frameworks
Volunteering for opportunities to gain experience
Attending events to study and learn
Simply starting with what you have right now
The path forward is the same: Take action. Learn. Iterate. Repeat.
Because here's what I know after 23+ years in this industry:
The best event planner isn't the one who planned the perfect event. It's the one who took imperfect action, learned from it, and got better every single time.
You don't need more time to plan.
You don't need more resources to research.
You don't need permission to be perfect.
You need to take action. Today. Imperfectly. And trust that the learning will come through the doing.
That rising event manager I mentioned at the beginning? After our coffee, she gained the confidence to send her event invitations that week. Were they perfect? No. Did they work? Absolutely. And more importantly, she learned what resonated with her audience: data she never would have gotten from another week of "perfecting" the message.
That's the power of choosing action over motion.
That's the gift of learning from others' experience.
That's how you build a career (and events!) that matter.
So here's my challenge to you: What's one imperfect action you can take today?
Not tomorrow. Not next week. Today.
Whatever it is, do it imperfectly. Do it now. And trust that the learning, the confidence, and the excellence will emerge through the doing.
Because perfect is the enemy of good.
But action? Action is the path to great.
You've got this.
XX,
Gianna
What I'm Loving This Week: And for all my favorite vendors, partners and products, visit: https://www.giannagaudini.com/gianna-recommends
Treehouse Hotel Silicon Valley
I had a chance to site visit this charming, fresh new property (one of only three in the world) located next to Google’s Sunnyvale campus in the heart of Silicon Valley last week. In a sea of sterile tech campuses and cookie-cutter business hotels, Treehouse Hotel Silicon Valley, a sister brand of 1 Hotels, is a breath of fresh air, literally and figuratively. Ranked #1 on Tripadvisor and named Best Cool New Hotel in the 2025 Metro Silicon Valley Best Of Awards, this property proves that playful doesn't mean unprofessional, and that nostalgia can coexist beautifully with innovation. From the moment you enter the greenhouse-style lobby, complete with a VW bug completely covered in plantlife and other nostalgic charms, you're transported to a world where stump-shaped side tables, owl-embroidered pillows, record players in rooms, and toy soldiers in Mason jars remind you that creativity thrives when we don't take ourselves too seriously. The property features Celeb Chef Stephanie Izard's Valley Goat restaurant, a beer garden with 30+ beers on tap, an gorgeous event barn with large windows and tall ceilings making it perfect for gatherings of all kind, and outdoor spaces designed with Silicon Valley's agrarian heritage in mind…think Google campus meets country chic meets Santa Cruz in character.
What I love most is how Treehouse delivers high-quality experiences without traditional luxury stuffiness. The rooms are thoughtfully designed, impeccably clean, and packed with whimsical touches that spark joy while still feeling high quality and premium. It's wellness-focused, sustainability-committed, and genuinely welcoming for everyone from families (kids' robes! in-room camping experiences!) to business travelers hosting offsites. This is a place that gives you permission to play, think big, and reconnect with the natural world. If you're planning an event in the Bay Area and want your team to actually relax, recharge, and think creatively rather than just grind through another conference agenda, Treehouse Silicon Valley is your answer. If you need an intro, reach out.
Gianna Gaudini is an event strategist, advisor, and author of the Amazon bestselling book "The Art of Event Planning." She's held leadership roles at Google, AWS, SoftBank Vision Fund, and Airtable, creating unforgettable experiences that drive business results. For more insights on creating exceptional events, visit GiannaGaudini.com or connect with her on LinkedIn.
Want to work with Gianna or take her Event Planning Masterclass? Visit giannagaudini.com/learn-from-me
