Top 3 Mistakes to Avoid When Booking Party Entertainment in New England
Last week, I showed up to a corporate holiday party in Boston where the client had booked me for 7 PM. Great, except the venue had scheduled dinner service until 7:45 PM. So there I was, trying to perform close-up magic while servers were literally reaching over my shoulder with plates of salmon. The COO looked at me apologetically and said, "Is this... normal?"
No. No, it's not.
After 15+ years performing at events across Boston, New Hampshire, Maine, and Connecticut, I've seen the same three mistakes kill otherwise perfect parties. The good news? They're all completely preventable if you know what to look for.
Mistake #1: Booking Entertainment Without Considering Your Event Timeline
Here's what happens more often than you'd think: Someone books a magician (or any entertainer) without actually mapping out when that person will perform. They just know they want entertainment "at some point during the night."
Why this backfires:
Your entertainer arrives during cocktail hour when half your guests are still in traffic on I-93
You schedule a performance during dinner when people are focused on their plates, not the show
The entertainment ends up competing with toasts, awards, or other program elements
I once performed at a New Hampshire wedding where the couple scheduled my act during cake cutting. Guess what everyone was watching? (Spoiler: It wasn't me making cards vanish.)
The fix: Before you book anyone, create a detailed timeline with your venue or planner. Identify the natural "dead zones" where guests are waiting, mingling, or between activities. That's where interactive entertainment like close-up magic thrives. For stage acts or performances that need attention, schedule them when you have a captive audience—typically right after dinner or during a dedicated program segment.
Pro tip for New England events: Factor in traffic. If you're hosting an evening event in Boston during winter, assume people will arrive 15-30 minutes late. Build that buffer into your entertainment start time.
Mistake #2: Choosing Entertainment Based Solely on Budget
I get it. Budgets are real, and you can't spend unlimited money on entertainment. But here's where I see clients shoot themselves in the foot: They book the cheapest option without considering whether it actually fits their event.
A Connecticut corporate client once told me they'd hired a "budget-friendly entertainer" for their annual gala. Turned out to be a balloon artist. For an executive dinner. With no kids present.
The actual cost of cheap entertainment:
Your guests remember your event for the wrong reasons
You lose the opportunity to create a memorable experience
You might actually waste money on something that doesn't deliver value
Think about it this way: What's the real budget impact of entertainment at a corporate event? If you're spending $15,000 on venue, food, and drinks for 100 people, does it make sense to go with a $300 entertainer who makes your entire investment feel less impressive?
The fix: Instead of starting with "What's the cheapest option?", ask "What's the right investment for the experience we want to create?" For a Maine wedding with 150 guests, spending $1,500-$2,500 on quality entertainment is roughly 5-10% of what you're already investing in the day. For a Boston corporate event, great entertainment might be the only thing your attendees actually remember about the night.
What "right-priced" entertainment gets you:
A professional who shows up on time and prepared
Someone who can read a room and adjust their performance
Quality equipment and presentation
Insurance and reliability
Want to know if you're getting a fair deal? Check out how professional magicians approach corporate entertainment pricing to understand what goes into the investment.
Mistake #3: Booking Entertainment That Doesn't Match Your Audience
This is the mistake that keeps me up at night because it's the most common and the most avoidable.
Picture this: A family reunion in New Hampshire books a magician who specializes in nightclub-style comedy magic. Half the audience is under 10 years old. The performer's material lands like a lead balloon because nobody told him there would be kids present.
Or: A Connecticut tech company hires a traditional stage magician for their 30-person leadership retreat. The show is designed for audiences of 200+. In an intimate setting, it feels weirdly formal and disconnected.
Common audience-entertainment mismatches I see:
Booking a kids' entertainer for an adult corporate event
Hiring a loud, high-energy performer for an elegant wedding reception
Getting a stage act when your venue only supports close-up entertainment
Choosing formal entertainment for a casual, laid-back party
The fix: Before you book anyone, ask yourself three questions:
Who's actually attending? (Age range, professional level, cultural considerations)
What's the vibe we want? (Elegant, casual, energetic, intimate)
What's the physical setup? (Stage, mingling space, seated dinner)
Then—and this is critical—actually communicate this to the entertainer during your initial conversation. A good performer will tell you honestly if they're the right fit. If someone says "yes" to every event without asking questions about your specific situation, that's a red flag.
I've turned down gigs because I knew I wasn't the right fit. A client in Boston once wanted someone who could do a 45-minute stage show with big illusions. That's not my specialty—I'm a close-up and corporate entertainer. I connected them with a colleague who was perfect for what they needed, and everyone won.
For New England event planners: Regional considerations matter too. A corporate event in downtown Boston might have different expectations than a wedding in rural Maine. The intimacy and warmth that works perfectly at a Connecticut country club might feel too casual for a formal Boston gala. Make sure your entertainer understands the local context.
The Common Thread: Communication Prevents Everything
Notice what all three mistakes have in common? They happen when there's a gap between expectations and reality.
The solution isn't complicated: Have real conversations before you commit. Ask your potential entertainer about their experience with events like yours. Share details about your timeline, audience, and goals. A professional will ask follow-up questions and might even suggest approaches you hadn't considered.
Red flags during initial conversations:
They don't ask about your specific event details
They're pushy about closing the deal immediately
They can't provide references or examples of similar events
Their availability seems suspiciously unlimited
Green flags that indicate you're working with a pro:
They ask about your audience and goals
They offer suggestions for timing and logistics
They're upfront about what they can and can't do
They have clear processes for booking and planning
Making Your New England Event Actually Memorable
Here's what I tell every client during our first conversation: The best entertainment isn't about showing off or being the center of attention. It's about creating an experience that makes your guests feel something—surprise, delight, connection, joy.
That happens when you avoid these three mistakes and instead approach entertainment as a strategic part of your event, not an afterthought.
Planning a corporate event, wedding, or private party in Boston, New Hampshire, Maine, or Connecticut? Let's have a conversation about what would actually work for your specific situation. I promise to tell you honestly if I'm the right fit—and if I'm not, I'll point you toward someone who is.
Because the worst mistake of all? Booking entertainment without doing your homework first.
