One of the questions I've been asked repeatedly over the years by Shluchim is:
"Should I do a dinner or gala? Will I actually make money?"
My answer is usually another question:
Why are you really doing it?
Because many dinners are not actually about fundraising. They are about validation, image, pressure, or imitation.
"We've arrived."
"Everyone else is doing one."
"We need to look successful."
"Our community expects it."
And sometimes, after months of exhausting preparation, enormous expense, and endless stress, the organization walks away having raised little actual new money while simultaneously draining its staff, volunteers, and donor base.
Now, to be fair, there are communities, particularly in the Northeast, where dinners are deeply embedded in the culture. In some places, people genuinely expect them and support them enthusiastically. Day schools may also operate differently because they have a built-in parent and alumni constituency.
But for many organizations, especially smaller or growing Chabad Houses, the real question is not:
"Can we pull off a dinner?"
The real question is:
"Should we?"
A successful gala is expensive. Not only financially, but emotionally and organizationally.
People often calculate the visible costs:
Venue
Catering
Decor
Entertainment
Printing
Production
But the hidden costs are often far greater:
Staff burnout after months of planning
Volunteer exhaustion
Leadership distraction from actual shlichus
Opportunity cost from neglecting donor relationships and programming
Donor fatigue from constant sponsorship asks and ticket pushing
And then comes the hardest part to admit:
Many gala donations are not actually "extra" giving. Donors often mentally count their table sponsorship, journal ad, or dinner ticket as their annual contribution. So while the dinner may look successful publicly, it can quietly weaken annual fundraising afterward.
I've seen organizations spend enormous energy creating a beautiful event only to realize later that they essentially prepaid their own annual campaign.
So before planning a gala, ask yourself:
What is the actual purpose?
If the purpose is fundraising, then be brutally honest:
How much net revenue do you realistically expect?
Could you raise the same amount, or more, through direct relationship-based asks?
Are your largest donors already prepared to give without needing the production?
Is the dinner expanding your donor base, or simply repackaging existing giving?
If the purpose is community building, ask:
Is a formal dinner truly the best vehicle?
Does it actually bring people together?
Or does it mostly attract the same circle of supporters while excluding many others because of price, culture, or formality?
If the purpose is celebrating a milestone, then celebrate the milestone. Don't disguise a fundraiser as a celebration and then wonder why the messaging feels confused.
A few years ago, we celebrated 25 years of service to the Atlanta Jewish community. Because of COVID concerns, we postponed it and branded it instead as a "26 Years Celebration."
We made a very intentional decision:
The goal was not to raise money. The goal was to create a meaningful, elegant, memorable celebration.
Our financial objective was simply to cover costs.
We built the budget around 260 attendees, charged $180 per person, and secured several sponsors to offset expenses. Because the event was framed properly, people came to celebrate rather than feeling pressured into another fundraising evening.
The event itself reflected that vision:
Excellent food
Great entertainment
A professionally produced video
A photo booth
Branded swag including "26 Years" socks, baseball caps, buttons, and other keepsakes
Interactive upscale touches
Very few speeches
Dancing at the end of the evening
And most importantly:
The event accomplished exactly what it was supposed to accomplish without negatively impacting our annual fundraising.
I'm not arguing that dinners are always wrong. Some organizations execute them exceptionally well.
But I do believe too many organizations jump into gala culture without first asking the harder strategic questions. Sometimes the most impressive thing a leader can do is not produce a glamorous dinner, but instead quietly build sustainable donor relationships, healthy systems, strong programming, and long-term trust.
A packed ballroom is not always a sign of organizational health.
Sometimes it's just a very expensive evening.
Whatever approach you take, may it be thoughtful, intentional, and filled with hatzlacha.