If you’re treating Giving Tuesday like a one-and-done campaign, you’re missing the point – and the potential.
​
I want you to think of it differently. Think of Giving Tuesday as your momentum builder. The snowball at the top of the year-end giving hill. Not just a date on the calendar, but the kickoff to your most generous season of the year.

When you plan it right, Giving Tuesday becomes the moment your donors start paying attention again. The moment they re-engage, make that first gift, and feel the energy behind your mission. It gives you stories to tell in December, a list of donors to follow up with, and progress to build on.

This isn’t about chasing trends. This is about strategy.

And if you want it to work, you’ve got to start now.

My friend, Jake Strang said it best:

“As fundraisers, we need to ask ourselves what our donors are asking themselves: ‘Why today?’”

That question is everything. Your donors want to make a difference – not just by giving, but by giving on a day that matters.

Giving Tuesday answers that question. It creates urgency. It offers momentum. It taps into a global spirit of generosity and focuses it on your mission.

But only if you’ve done the work to meet them there. If the messaging isn’t clear, if the plan is rushed, if it’s just another email in the inbox… you’ll miss the moment.
​
The magic is in the lead-up. And the lead-up starts now.

1. Line up your challenge match now.

A matching gift is one of the strongest incentives you can offer on Giving Tuesday. But the kind of donors who fund matches – your board, your loyal givers, your major donors – need time.

Time to understand the impact.
Time to coordinate logistics.
Time to feel ownership of the campaign.

Don’t treat your match as a checkbox on a planning list. Build it as a strategic asset. Ask now, while there’s room to shape it well.

2. Invite your major donors into the campaign early.

Don’t just ask them for money. Give them a role.

They can:

• Make their own gift early to seed momentum
• Participate in challenge matches
• Help recruit other donors or ambassadors
• Share their own giving story on video or social

Major donors want to be part of something bigger. Giving Tuesday gives you a clear “why now” to help them say yes.

3. Pre-load your pledge list.

Here’s one I swear by: Take pledges before the day. Use events, meetings, or board gatherings to ask for early commitments.

Then, on Giving Tuesday, your team has a clear list to follow up with. These aren’t cold calls – they’re reminders. “Today’s the day.” That kind of focused effort drives real results.

4. Plan for analog tactics (they still work).

Want to send handwritten postcards? Want to use the phone effectively? Want to get a thank-you letter in the mail before year-end?

You need to start now.

Donors are inundated with email. But the mailbox? That’s a quieter space. A handwritten note cuts through. A real phone call builds connection. These tactics take time, and that’s exactly why they work.

5. Build your multi-channel plan early.

When you start now, you don’t have to rely on one message in one channel. You can actually coordinate email, social, print, phone, and even live events with intention.

That’s how you stand out.

You can code your appeals. Track what’s working. Share updates in real time. You have space to think like a strategist, not a last-minute firefighter.

6. Leave a little space for improv.

You’re not planning to control every detail. You’re planning to give yourself room to respond.

Maybe a donor offers a surprise match. Maybe a social post gains traction. Maybe the campaign falls just short at midnight, and you need to extend.
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When your plan isn’t packed too tight, you can adjust with ease – and sometimes those pivots are what make the day feel alive.

Treat it like what it really is: your launchpad.

The starting line for your most generous season.
The moment your donors start leaning back in.
The energy surge you’ll need to carry you through December.
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And the best part? You don’t need to overhaul your shop to make this happen. You just need to start early, plan with purpose, and stay connected to why it all matters in the first place.

If you’re looking for a sign to start working on Giving Tuesday 2025… this is it.

Get your match lined up.
Draft that pledge form.
Sketch out your outreach plan.

Then get ready to make this the year your Giving Tuesday becomes more than a day – it becomes a difference-maker.
​
Cheers,

P.S. Like this kind of insight?
Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

If you liked this… 

• What Worked for Giving Tuesday 2024
• How to Build a Philanthropy Calendar That Drives Digital Donations
• All About Giving Days (Interview with Jake Strang)
• Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work
• Spoilt for Choice: Why Giving Donors Direction Works

In fundraising, we’ve spent decades perfecting donor-centered language – polished, warm, affirming. And there’s value in that. But as we lean further into equity, honesty, and shared power, we’re realizing something: partnership requires candor. Community centric fundraising built on that sort of trusting partnership is the future.

You can’t build trust on flattery. You build it on clarity.

That’s what my new resource is really about. It’s not a script. It’s not a list of ways to smooth over discomfort. It’s a toolkit for having honest conversations with donors – without losing connection, mission, or respect.

I’ve lost count of how many times I’ve been asked this question: "What do I even say when a donor asks [fill in the awkward, unexpected, or slightly skeptical question here]?"

If you’ve worked in fundraising for more than five minutes, you’ve felt that moment. Someone hits you with a curveball – maybe it’s well-intentioned, maybe it’s a little tense – and suddenly your mind goes blank. You want to respond with confidence and kindness, but your brain’s still trying to find the first word.

That’s why I created The Real Deal Fundraiser’s Quick Guide to Donor Questions.

It’s a free resource packed with clear, kind, mission-centered answers to the questions we all get asked – and sometimes dread. Whether it’s “Why do you need my gift if you already got a big one from [another donor]?” or “Can I trust you’ll use my money wisely?”, this guide helps you find your footing and keep the conversation moving in the right direction.

Underneath it all is a simple framework I first learned in phonathon and have used ever since:

Listen. Acknowledge. Support. Continue.
It’s not a script – it’s a mindset. And it works.

• Listen – Really listen. Not just to the words, but to the tone and subtext.
  If someone says “I’m retired,” don’t assume what that means. Are they joyfully gardening between river cruises, or feeling anxious on a fixed income? Same phrase, very different needs.
• Acknowledge – Show them they’ve been heard.
  “Sounds like you’ve had a big transition recently,” or “You’ve earned some rest after working hard for so long.”
• Support – Make your case with warmth and clarity.
  “We have donors in all life stages who support the mission in different ways.”
• Continue – Bring it back to the goal of the conversation.
  “I know you really care about [cause/mission]. We’d love to have you involved in a way that works for you – let’s discuss some options.” Then offer monthly giving, IRA Rollover gifts, etc.

This isn’t about avoiding tough topics. It’s about having the tools to meet them head-on – with empathy, strategy, and the kind of language that invites real partnership. Here’s an another example:

Donor: “What percentage of my gift actually goes to the mission?”

You: "Totally fair question. 100% of your gift supports our mission. That includes the people, infrastructure, and tools that keep programs going strong. We believe in full transparency, and you can always review our IRS Form 990 to see how resources are stewarded."

Pro Tip: Don’t shy away from the unglamorous parts of nonprofit work. They’re essential.

​Want to see the rest of the answers in the freebie? It’s loaded with examples. You’ll see how to apply this framework in real situations, with real donor language, and keep things moving forward without losing the heart of the conversation. Every answer in this guide is rooted in respect for donor autonomy and full transparency – two values that keep relationships healthy and real.

Think of it as a conversational compass – something you can adapt to your voice and situation – rather than a one-size-fits-all speech. You’ve got the passion and the instincts. This will help you put it into words – quickly, confidently, and with the clarity today’s donors (and communities) deserve.
​
Cheers!

P.S. Like this kind of insight?
Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

If you liked this…

• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• Discovery Visits Demystified: Tips for Effective Donor Meetings
• The 3 Questions Donors Ask About IRA Rollover Gifts (and How to Answer Them)
• What to Say to Donors in Uncertain Times: The Near, Dear, Clear Fundraising Framework
• Leveraging National Estate Planning Awareness Week for Planned Giving Success

Let's pretend the TikTok comment section is a search history.

This was a meme engagement prompt circulating around Tiktok, so I adapted it for nonprofit fundraisers. And the results were funny but also a bit depressing.

• "Free spa day near me."
• "Easy six-figure grant."
• "Jobs where I don’t go to bed anxious."
• "Work from home jobs where no one yells at me."
• "How to plan a gala on $250."

​
I’ve written about burnout. But this felt different. These aren't just punchlines. They're quiet cries for help disguised as jokes. And they struck a nerve. The comments rolled in: funny, raw, painful, *real*. This wasn’t just a social media prompt. It was a mirror for the nonprofit fundraising sector.

Fundraisers turn burnout into memes because humor is safer than honesty.

Because saying "I'm not okay" feels like a risk.

Because the system rewards silence and penalizes boundaries.
​
Gallows humor isn't just venting – it's a way our nervous systems regulate under pressure. When enough people laugh at the same joke, it signals: you're not the only one. You're not imagining it. This job is breaking people. Quiet cracking, indeed.

That the expectations of nonprofit fundraising are structurally absurd:

• Raise millions but don't spend on staff.
• Be warm and authentic but hit your metrics.
• Work for the purpose, but not for the pay.

​We joke because naming it plainly would require everything to change.

• Name it. Share the meme *and* the meaning.
• Don’t confuse burnout with weakness.
• Support each other. Community is armor.

​You're not alone. And you're not crazy. We need more honest conversations on LinkedIn and in the workplace. We need to acknowledge that burnout isn’t a personal failure. It’s an occupational hazard.
So, if you're a fundraiser trying to find your way back to sanity, find me over on Tiktok or subscribe here to my weekly newsletter. Let’s keep this conversation going!

Cheers!

Jessica

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

If you liked this… 

• How to Spot and Stop Fundraising Burnout Before It Leads to Turnover
• Take Your PTO: Why I’m Logging Off – and Why You Might Need To, Too
• How to Climb Out of Burnout in Quarantine (with special tips for fundraisers)
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• Wear the Suit: Presence starts in your mind, not your closet