When I came back to work at my alma mater in 2011, they had just celebrated the Centennial the year before. The mailing they sent out for the 100-year mark was gorgeous – vintage photos, heavy cardstock, elegant fonts. You could see the pride in every detail.

But there was one big problem.

It cost more to send than it brought in.

When I ran the numbers, the cost to raise a dollar on that piece was $1.40. For every dollar it generated, it cost us $1.40 to get it. We weren’t raising money – we were losing it. It was like we were throwing money overboard and missing a once in a century opportunity!

The issue wasn’t just the over-the-top production. The package was confusing. Too many ask amounts, too many gift designations, and other options. Donors didn’t know where to focus. And when a donor doesn’t know what to do, they don’t give.

The next year, we simplified. One letter. Points of pride on the back. Clear ask string. That mailing had a cost to raise a dollar of 43 cents.
​
Same donor base. Better strategy.

Cost to raise a dollar is exactly what it sounds like. It’s a measure of efficiency. You take your total expenses for a campaign or fundraising channel and divide it by the amount raised.

Formula:
Cost to raise a dollar = Total Expenses ÷ Total Dollars Raised

If you spent $10,000 and brought in $25,000, your cost to raise a dollar is $0.40. That means it cost you forty cents to raise one dollar. Good.

If your cost to raise a dollar is over $1, you’ve got a problem – if you’re not executing a donor acquisition strategy where you expect to lose money upfront to gain long-term donors who’ll give again and again for less.
​
But if you’re not acquiring or upgrading donors – and your cost to raise a dollar is that high? You’re hemorrhaging money.

Recently I was teaching a webinar and got asked whether you should track staff time on any particular fundraising effort in the total expenses when calculating cost to raise a dollar. My answer is no.

I’ve never met a fundraiser who’s sitting around wondering what to do next, and I don’t think tracking every minute of your working hours is a good use of that valuable time.

Staff salaries are in your normal budget. Consider them a constant. Don’t tie yourself in knots trying to figure out if you spent 20 hours on the gala last week or 22 hours.

Examples: For a mailing, count printing, postage and processing costs (if using a mailhouse or other paying part-time folks to stuff mailers). For an event, expenses would include catering, décor, invitations (printing, postage, and processing), printings programs, etc.
​
Keep it simple and you’ll be ahead of the game.

Fundraisers talk a lot about leaky buckets – usually in terms of donor retention. But there’s another leak that’s just as costly: spending more to raise a dollar than you get back. That’s what this metric uncovers.

Most fundraisers are trained to focus on total dollars raised or number of donors who give. And yes, those are crucial. But cost to raise a dollar gives you clarity at the tactical level. It shows you where your fundraising machine is humming – and where it’s grinding your budget into dust.

Cost to raise a dollar is especially helpful when:

• You’re evaluating different channels (direct mail vs. email vs. phonathon)
• You're preparing for a budget meetings and need simple, apples-to-apples comparisons
• Leadership is asking to cut costs, and you need to defend what’s working
• You’re trying to argue against flashy design choices or work-intensive events that don’t move the needle

That Centennial piece taught me something I’ve never forgotten: Beautiful isn’t always effective. Impact matters more than gloss.

It also gave me a compelling number to take into conversations. I could walk into meetings and say, “This mailing costs us $1.40 to raise a dollar. Last year’s only cost 43 cents. Which one do you want to fund next year?”
​
I didn’t need to yell. I just needed to know my numbers.

Some channels will have higher cost to raise a dollar – and that’s okay. Phonathons, acquisition campaigns, certain events – they often cost more. But if you’re tracking those donors and seeing strong retention and future giving, that higher initial cost might be justified. But do that deliberately, for strategic reasons.

In higher ed, campaigns like student philanthropy programs or senior class gifts often have an “upside-down” cost to raise a dollar. That’s not a failure – it’s intentional. We spend more than we bring in because we’re focused on something bigger: starting the donor relationship early, before students graduate, move away, and scatter.

While they’re still on campus, their connection to the institution is at its peak. That’s the right time to invite them into giving – not just for dollars today, but for loyalty tomorrow.

Just don’t confuse “tradition” or “looking nice” with effectiveness. Know what each dollar is doing for you. Make that a habit. Teach it to your team.

And please – for the love of fundraising – don’t let your best-looking piece be your worst-performing one.

If you’ve never calculated your cost to raise a dollar, start now. Pull your last three mailings or campaigns. Be honest about all the expenses, minus staff salaries.

Run the numbers. Then start making decisions that build toward efficiency – and impact.

This metric gives you the insight you need to be smart with the resources you’ve been trusted to steward.
​​
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…

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Fundraisers love numbers – but we don’t always slow down to read them.

When I look at donor giving histories, I’m not just tallying lifetime value or calculating retention. I’m looking for inflection points. Clues. Moments that tell me a donor is thinking differently about their relationship with the organization.

You can spot those moments – if you know what to look for.

In my last blog post, I revealed my strategy for connecting annual giving to major and planned giving for board members. Through this process of telling the long version of donors’ origin stories, I saw patterns that repeated. I kept seeing similar types of gifts that signaled the donor had deepened in their connection to the organization’s mission.

Once you know them, you’ll be able to spot these in the gift histories of your current major donors. After a while, you’ll be able to see these gifts when they happen and optimize your systems to steward these donors to the next level!

Here are three gift types I always flag in donor bios:

1. The “Kick the Tires” Gift

This is the donor’s very first gift. It’s usually modest – $25, $50, maybe $100. But don’t let the size fool you.

This gift is a test. They’re watching how your organization responds. Do you acknowledge quickly? Do you give thanks personally? Do you make it easy to give again? Do they feel seen?

Most board members don’t realize that your largest donors often start right here. Not with a gala. Not with a campaign. But with a small, quiet gift and a lot of curiosity.

Track this gift like it matters – because it does.

By reframing first time gifts as “kick the tires” gifts, organizations leverage their systems to make sure every new donor has an exceptional experience and feels appreciated.

Ask yourself: Do you have any special communication or benefits that help first-time donors feel recognized? How I can I use email, phone, volunteer/board outreach, and mail to have this donor feel the love and their impact?

2. The “Hand-Raising” Gift

You’ve got a donor who’s given $100 a year for a decade. Then suddenly – boom – a $1,000 check shows up.

That’s not random. That’s intentional.

The exact numbers matter less than the jump. A $25 dollar donor jumps to $500. A $1,000 donor jumps to $5,000.

All of these are donors signaling interest. They’re re-evaluating what your work means to them. And they’re inviting you to respond.

When you see this kind of jump, drop everything and make a call. Not to ask for more – but to listen. What changed? What are they excited about? Who or what inspired the new level of giving?

This is your chance to deepen the relationship before they drift away.

Ask yourself: Do I have a notification system that will let me know when “hand-raising” gifts happens? What’s my process when I learn about them?

3. The “Breakthrough” Gift

Here’s where it gets exciting. You see a donor move into five- or six-figure territory, or they’ve set up a multi-year pledge. Maybe they’ve reached out about leaving a bequest.

This donor is no longer an annual donor – they are in the pipeline.

Yes, these bumps happen with personal visits and cultivation, but sometimes the donor decides to make the leap.

When I see this move, I bring them into a different lane. Personal stewardship. Custom impact reports. Invitations to help shape the vision, not just fund it. Because at this level, they’re not just giving – they’re investing.

This is where cultivation becomes partnership.

Ask yourself: How can I make sure I don’t miss any of these breakthrough gifts? What’s my plan to meet this donor and find out what their philanthropic goals are for the long-term?

In conclusion…

Make sure these three moments show up in your reports. More than data points, these three gift types represent real shifts in mindset. Catching them early and responding with intention is how you build a stronger, smarter pipeline.

Because fundraising isn’t just about chasing dollars. It’s about listening to the story those dollars are trying to tell you.

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…

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Each year, I get a little more reflective about what actually moves the needle on Giving Tuesday. It’s one part adrenaline, one part strategy, and one part relationships – the same ingredients that fuel fundraising the rest of the year, just turned up a few notches.

This year? We hit our match. We saw strong donor response. And we learned a few things worth carrying into the next big push.

Here’s what worked:

1. The Match Game, with a Twist

Last year, we had a $20,000 match and hit it – barely. It took extending our deadline to pull it across the finish line. This year, with our donors’ permission, we split that ask into two: two $10,000 matches from two separate donors. One for Giving Tuesday. One saved for Calendar Year-End.

It created a sense of focus. One target, one day. And we met it.

Now we can head into December with some real momentum. “We hit the match on Giving Tuesday” makes a great line in every follow-up email. It tells a success story that donors helped write – and that builds confidence for the next ask.

2. Direct Contact Beat the Megaphone

Most of our gifts came through personal outreach. Not social media. Not big email blasts. Just me and my annual giving staffer reaching out by phone and plain emails from our Outlook inboxes.

That’s where the action happened. That’s where the giving happened.

I’m not knocking digital strategy – it plays its role. But, for us, Giving Tuesday was won in the inbox and on the phone. This reinforces my observations I wrote about earlier this fall about digital burnout and the reprise of analog communications.

3. Board Engagement Started Early

More than half of our board gave on Giving Tuesday. That didn’t happen by accident.

We start talking about Giving Tuesday in September. By November, they’ve heard the plan, seen the goal, and received a cheat sheet with sample language and graphics to share on social. The week before Giving Tuesday, we send that cheat sheet again.

And this year, they showed up. Not just with gifts, but with pride – and we’re closer to hitting 100% board giving for the year because of it.

4. Targeted Appeals to Past Giving Tuesday Donors and LYBUNTs

We made it easy on ourselves this year. Instead of trying to inspire everyone on our list, we reached out to the people who’ve already shown us they like giving on Giving Tuesday.

We pulled two lists:

• Calendar year LYBUNTs (gave in 2024, but not yet in 2025)
• Anyone who has ever given on Giving Tuesday before

When the subject line says, “I know you like to give on this day…” it doesn’t feel like a cold call. It’s a reminder. And it works.

5. Monthly Donors and Pledgers Want to Participate, Too

This one surprised me last year and held true again.

Donors who already give monthly or have pledge commitments still want to be part of Giving Tuesday. They like seeing the school hit a goal. They like contributing to a match. So, they give again.

That meant a few extra gifts came in from already-committed supporters. Nothing huge – but meaningful.
Here’s how we handled those emails:

"I hope you are doing well! I wanted to reach out today to let you know that it is Giving Tuesday and Starr King School for the Ministry has a goal of raising $10,000 to reach a challenge match of $10,000 (for a total of $20,000 for this beloved school).

If you would like to participate, as you have so generously done in the past, your gift would again be matched 100%. Just visit www.sksm.edu/givingtuesday TODAY and you can make your gift online.

Also, we know and appreciate ALL you have done for Starr King as sustainers this year so please don’t feel obligated to give more. I just know you have given to matches in the past and wanted to make sure you knew!"

​No pressure. Just an invitation to be part of something they’ve supported before.

Giving Tuesday doesn’t have to be a guessing game. It’s a day to do what already works in your shop – just more of it, with a little more urgency and clarity.

We focused on:

• Real relationships
• Targeted outreach
• Simple, achievable goals
• And donor behaviors we already knew from our data

It paid off. Not just in dollars, but in board engagement, team morale, and a strong hand to play as we close out the year.

And that’s the kind of success worth repeating.

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…

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So let’s talk about a fundraising skill that never makes the slide deck – but affects every single donor conversation: your ability to receive.

Receiving: the skill of accepting with grace – no strings, no scrambling, no shame. If you can’t accept a compliment without brushing it off, if you downplay a gift or reflexively offer something back the second someone does something kind for you… it might be time to take a closer look at your receivership muscle.

Yes, I said receivership. As in, the ability to simply receive.

Not barter.
Not apologize.
Not prove you’ve earned it.

Just receive.
​​
Now, I know this might sound like a soft skill or a personality quirk. But hear me out. This is mindset work. And for fundraisers, it matters.

Most fundraisers I know didn’t get into this work because they wanted attention or praise. We’re here to serve. We advocate for missions we believe in. We lift others up. But too often, that servant mindset gets twisted into something smaller: self-neglect, chronic under-earning, burnout, or quiet insecurity that whispers you’re not doing enough no matter how much you give.

And if you’re carrying that around – if you’ve internalized the message that your worth is tied to your productivity or output – donors will pick up on it.

Not consciously. But it seeps in.

You’ll hedge your asks.
You’ll downplay your case.
You’ll lead with scarcity instead of confidence.

​You’ll make it harder for them to give.

Here’s the truth I come back to, again and again: Worthiness is inherent. Not earned. Not measured by campaign goals or gift totals. It’s your birthright. Mine too.

But most of us weren’t raised to feel that in our bones. And let’s be honest, nonprofit culture doesn’t always help. We celebrate hustle and sacrifice. We glorify being “lean.” We wear our under-resourced status like a badge. And then we wonder why our donors hesitate.
​
That energy – of not-enoughness – clashes with the generosity we’re asking for. If we want donors to see our missions as worthy of investment, we have to believe that ourselves. And that starts with how we show up in everyday life.

Let someone buy your coffee without rushing to get the next round.

Accept a compliment without shrinking or deflecting. Just say thank you.

Take a breath when someone helps you, instead of jumping into apology or explanation.

These are small things. But they add up. They rewire your nervous system to believe: I can receive. I don’t have to hustle for every drop of goodness in my life.

And that’s the same belief you need when you sit across from a donor and ask for a major gift. It’s the belief that says: This work is worthy. This mission deserves support. And I am a trustworthy guide for your generosity.

That doesn’t come from a script. It comes from the inside out.

If this resonates with you, I’d love to hear how you’ve worked on receiving in your own life. Or where you’ve struggled with it. It’s tender work – but it’s the kind that changes everything.

Let’s stop shrinking. Let’s stop scrambling to prove ourselves. Let’s remember what was true all along: You’re worthy. Your mission is worthy. And it’s okay to receive.
​
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…

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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.
​
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.
​
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
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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… 

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Ever open your email and feel like your brain’s going to short-circuit?

You're not alone. Seventy-four percent of U.S. adults say they feel overwhelmed by email. More than half of U.S. consumers (56%) say they’ll unsubscribe if they receive four or more marketing messages from the same company within 30 days. And it’s not just Boomers. Eighty-one percent of Gen Z and 78% of Millennials say they wish it were easier to disconnect from digital devices.

These are your future major donors asking for fewer pixels and more presence.
​
That’s the opening fundraisers need. The real opportunity isn’t another email subject line tweak or fancy GIF. It’s a return to what’s real: mail and phone. Tangible. Human. Hard to ignore.

​This isn’t nostalgia talking. It’s data. And it might just be the smartest pivot you make this year.

In the race to do more, cheaper, we forgot what actually works.

Physical mail gets opened 80–90% of the time, while emails land between 20–30%. Direct mail spending has even grown recently – reaching about $39.4 billion in the U.S. in 2023.

And here’s the kicker: when mail and digital work together, results jump. In one test, donors who received both mail and email were 60.5% more likely to respond to the mail piece than those who got mail alone.

That tracks with what I saw last year. Inspired by the project Postcards to Swing States, my team handwrote and mailed over 200 postcards promoting our Giving Tuesday match. It was a standout success. Part of the magic was the form itself: a postcard is immediate – no envelope, no delay, just message received.

The phone didn’t stop working. Most programs just stopped dialing.

Organizations that add professional telemarketing to their strategy see an average 27% increase in annual donations compared to those relying solely on mail or digital campaigns.

Why? Because personalized calling does what algorithms can’t – it builds connection.

And that connection drives results. DCM’s 2023 telefundraising trends report found that contact rates have remained stable since the pandemic – holding strong at about 2.5 contacts per hour. Advocacy and political campaigns saw average gift amounts rise by 19% between 2018 and 2023, thanks to high-touch calling models.

I’ve seen the impact firsthand. Last year, I worked with a college to rebuild their phonathon from the ground up: stronger management, better scripting, and smart segmentation. In 2022, they raised $134,317. This year? $396,309. And their youngest alumni – graduates since 2020 – are showing a participation rate over 17%. That kind of traction doesn’t come from wishful thinking. It comes from consistent, human contact. 
​
Telemarketing gets a bad rap, but it’s still the only channel that delivers personalized conversations at scale. It’s strategic because it’s still deeply personal.

So if you think phone is “old school,” think again. It’s working better than ever – for those who use it well.

Here’s where things get interesting: Millennials and Gen Z aren’t avoiding analog as expected but they are getting burnt out on digital.

More than 80% of Gen Z (80%) and Millennials (78%) say they share interesting mail with someone else. That’s a viral loop, but with ink and paper.

They’re open to analog – especially when it connects to the digital world. QR codes. Custom URLs. Interactive print. That’s not outdated. That’s modern engagement with real presence.

Gen X? They’ll still take your call and they appreciate personalized pieces.

Boomers? They’re the MVPs of mail. They read it, they act on it, and yes – they still pick up the phone when the number’s familiar.

We’re in the relationship business, not just the metrics business. Somewhere along the way, digital promised us scale and forgot to tell us we’d lose connection.

If you want your message to stand out, don't just add to the digital pile-up. Get in someone’s mailbox. Pick up the phone. Make it personal. Make it human.

Analog hasn’t vanished – it’s been waiting. And right now? It’s the cleanest path to cutting through.

This isn’t a call to throw out your digital playbook. It’s a nudge to rebalance. To layer your strategy. To stop thinking in either/or.

You don’t need to call everyone or mail every donor. Segment. Experiment. Pair analog with your digital. Measure. Adjust.

I’ve been doing this long enough to tell you: this is where fundraising is heading next.

I’m betting on analog. Because I’ve seen the numbers. I’ve seen the results. And I’ve seen how a phone call or handwritten postcard can do what a hundred emails never could.
​
Let’s go back to what works. Not because it’s old – but because it still moves the needle.

This isn’t a blip or a nostalgia play. The signs are clear: digital fatigue is rising, mail spend is climbing, and younger donors are just as responsive to tangible, personal outreach as their parents and grandparents.

We’re not at the plateau. We’re on the upswing.

That’s why the institutions that recalibrate now – layering mail and phone back into their strategies for all generations – will see the payoff not just in annual giving but in the major gift and planned giving pipelines for decades to come. Early engagement drives loyalty, and loyalty drives legacy.

The inbox is saturated. The mailbox and the phone line are open. The organizations willing to seize that opening today are the ones who will own the donor relationships of tomorrow.

Fundraising’s next edge won’t come from squeezing another 0.2% out of your email subject line. It’ll come from showing up where people are actually ready to listen.

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…

• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
• 31 Ways to Hit the Refresh Button on Direct Mail
• Kickstart the Year: Setting Annual Giving Projections for Success
• Spoilt for Choice: Why Giving Donors Direction Works
• 10 Traits All Former Phonathon Callers Share

Works Cited:

• GlockApps – Email Fatigue and Overload
• GetApp – Why Users Unsubscribe
• Quad + Harris Poll – Gen Z & Millennial Digital Disconnect
• Postalytics – Direct Mail Stats
• Winterberry Group – 2023 Direct Mail Performance
• NextAfter – Mail + Email Synergy Study
• Callin.io – 27% Giving Increase via Telemarketing
• DCM Telefundraising Trends – Contact Rates + Gift Growth
• Lob – 2025 Direct Mail Consumer Insights
• USPS Delivers – Generational Preferences for Mail & Phone

When I worked at the University of South Carolina from 2005 to 2010, I was proud of the cases I built. I wrote compelling scripts and talking points for our phonathon team – clear, detailed, airtight.

I led with numbers, and they were good ones. I talked about the decline in state support, the rising importance of a college degree in the job market, and the long-term economic impact of thriving public universities. I knew the statistics on student loan debt inside and out. I framed the problem clearly and gave donors a chance to be part of the solution.

And it worked. To a point.

​Looking back, those appeals were sharp – but they leaned heavily on logic and numbers. That clicked with some donors. But others? Not so much. Those appeals weren’t wrong. They were just incomplete for the wide range of minds we’re trying to reach.

Fast forward to 2012. I was at The University of Southern Mississippi, learning how to write copy for direct mail. I started ghostwriting letters for different deans, department chairs, and students. At first, I stuck to what I knew: the stats. But it didn’t feel like enough.

I needed a broader emotional range.

So I started interviewing the letter signers, weaving in their voices and their vision – what this place meant to them, not just what they wanted donors to do. That’s when I started seeing the power of storytelling.

When I came to work at Starr King School for the Ministry in 2015, I had to stretch again. The usual notes in higher ed fundraising – nostalgia, school pride, career outcomes – didn’t resonate with a justice-minded, largely layperson donor base. These were Unitarian Universalists who cared deeply about their values and how the school perpetuated those values in the world.

I needed to connect the dots with emotion, shared purpose, and a clear sense of what their giving could do.
​
That meant telling stories that didn’t just inform – they moved people.

Somewhere along the way, I realized this shift wasn’t just about moving from stats to stories. It was about recognizing how different people make decisions.

One person might want the spreadsheet. Another wants the story. A third just wants the ask – clear and bold. And someone else? They want to feel like they’re part of something bigger before they commit to anything at all.

That’s when I remembered a model I’d seen back in 2007, from Mark Murphy at Leadership IQ. It mapped out the four main persuasion styles – and it helped me understand why my old appeals worked for some and left others cold.
​
Here’s the gist:

There are two axes:
• Emotional → Unemotional
• Linear → Freeform

Put those together, and you get four types of decision-makers:

This is where I naturally live. I want the stats. I want the logic. I want the argument that makes sense.

If you're reading this post and wondering, “Where’s the ROI?” – you might be here too.
​
That’s the kind of appeal I built early in my career. And it worked with people like me. But that’s not most donors.

Think of the board member who scans your whole appeal in 14 seconds and writes the check anyway.

They don’t need the backstory. They just want the point. What do you need, what will it do, and how much are you asking?
​
Closers are decisive. If you wander, they’re gone. You need to be bold, clear, and fast.

These folks are organized and thoughtful. They care about the story and the structure. Think of the alum who replies with a thoughtful email after every annual report – who joins the volunteer committee and follows up on the agenda.
​
They want a beginning, a middle, and an end. They respond when you connect emotionally but still give them a path to act.

Picture the alum who tears up thinking about the choir trip to Italy in 1983. They’re not interested in bullet points. They’re here for the moment – the meaning.
​
They want to feel something. And if your message is too structured or too clinical, they’ll check out. But if you pull them in with a meaningful quote or a powerful scene, they’ll stay – and they’ll give.

In major gifts, you can tailor every ask. You’re sitting across from one person, learning what moves them, and crafting your pitch accordingly.

But in annual giving? You’re writing to the whole list. That means your appeal has to layer styles – something for each persuasion type.

• Stats and logic for the Data Scientists
• Clear action steps for the Closers
• Warm structure for the Directors
• Emotional storytelling for the Storytellers

Don’t write the appeal that would convince you. Write the one that can meet your donors where they are – all of them.

When you're working on your next appeal, ask yourself:

• Does it have a story?
• Is there data to back it up?
• Is it structured clearly?
• Is there a moment of emotion?
• Is there a clear ask?

​
Fundraising is communication. And great communication connects.

This is one of my favorite things to teach. Reach out – I’ve got frameworks, real-world examples, and plenty of lessons learned the hard way.

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.

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I had a long conversation a few days ago with a brand-new college grad who’s hoping to land her first job in fundraising. We covered a lot of ground. Some of what I shared was the usual advice. Some of it was the stuff you only hear when someone’s willing to tell you the truth.
​
So here’s my actual advice for those who want to break into fundraising but feel stuck because they don’t have the experience yet.  

To paraphrase the Cheshire Cat from Alice in Wonderland: “If you don’t know where you’re going, any road will take you there.”

If your long-term goal is Executive Director, Chief Development Officer, or Major Gifts Officer, don’t apply for back-office roles like gift processing. Those positions matter (I’m on record as saying that partnership with these important roles is paramount to fundraising success) but they rarely lead to donor-facing roles, no matter how good you are. The leap from behind-the-scenes to front-line is a hard one, even if you’re in the same department.

If your dream job is out front with donors, start out front with donors – even if it’s entry-level. A Leadership Annual Giving or Donor Relations role might not sound flashy, but it will get you in the room with donors and decision-makers.
​
Think long. Think strategically. Your first job should point in the same direction as your dream job.

Front-line fundraising roles have a personal element that doesn’t always come across on a resume. You’re selling your communication skills, your presence, your ability to connect. To put it bluntly, great fundraisers are at least in part personality hires. But, as with many things, if you have to say that you are a personality hire, you probably aren’t one.

The best way around that? Don’t rely only on paper. Talk to people.
​
Tell everyone you know that you want to work in nonprofit fundraising. Your neighbor might be on the board of a food bank. Your friend’s aunt might chair the development committee at a local theater.
​
Ask for informational interviews (which is exactly how this new grad got to talk with me for an hour). Join your local AFP chapter. Volunteer at events. These conversations open doors. Sometimes wide.

Research shows that women tend to apply for jobs only when they meet all the required and preferred qualifications. Men? They'll throw their hat in the ring even if they don’t check all the boxes.

Stop waiting until you’re 100% qualified. There is no one keeping score for jobs you don’t get a callback on (except maybe you). As they say, you can’t win it, if you ain’t in it.

Read the job description. If you’re even halfway there, and it aligns with your long-term goals? Apply. Don’t self-select out.
​
You can learn the rest.

That’s what I told her. And if I were talking to you, I’d tell you the same.

Your career in fundraising won’t be built in a day. But if you start with intention, talk to the right people, and stop waiting for perfect – you’re already ahead of the game.

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.

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Whenever my grandfather was asked what I did for a living, he’d grin and say, “Oh, she’s a professional beggar – and very good at it.”

He meant it playfully. But that joke pointed to something deeper: how fundraising is often viewed in American culture – and sometimes, how we as fundraisers view ourselves.

This work can feel loaded. Talking about money brings up all kinds of things: values, power, pride, fear of rejection. It’s personal. And when that discomfort goes unchecked, it sneaks into our conversations and undermines our confidence.

But here’s what I’ve learned: Your mindset matters more than your pitch.

How you feel about money shapes how you talk about it. And that directly affects whether you avoid the big asks – or step into them with clarity and purpose.

Over the years, I’ve noticed three mindset shifts that help fundraisers move past the awkwardness and into authentic, effective conversations. I call them the 3 Rs: Reciprocity, Receivership, and Reframing.
​
Let’s walk through them.

One of the most harmful myths in fundraising is the idea that we’re taking something from people. That donors are losing when they say yes.

That’s not what’s happening.

Giving is about alignment. When a donor gives, they’re not being depleted – they’re investing in meaning. They’re making their values visible. They’re stepping into a story that’s bigger than themselves.

That’s not taking. That’s inviting them in.

I’ve watched donors light up – not because of tote bags or nameplates – but because they felt connected. When we approach conversations with the understanding that there’s value on both sides, it changes how we show up.

Try this: When a donor shares why they give, listen closely. Then reflect it back. Say, “It means a lot to me that this work aligns with your values.” That simple moment of recognition reinforces that this is a relationship – not a transaction.

Let me ask you something: when someone picks up the lunch tab, do you fidget? When they compliment your work, do you wave it off or make a joke?

That matters more than you think.

If you struggle to receive in small, everyday moments, it’s going to be tough to stand still and grounded when it’s time to receive something much bigger – like a major gift.

Fundraising isn’t just about facilitating generosity. It’s about receiving it. That means knowing your own worth, your organization’s worth, and the worth of the mission you represent.

You’re not just asking for money. You’re offering someone the chance to invest in something meaningful.
​
Try this: The next time someone compliments you – on your work, your outfit, your presentation – just say, “Thank you.” No hedging. No “Oh, this old thing.” Practicing that kind of presence builds your capacity to receive with grace and confidence.

I’ve worked with some truly talented fundraisers – smart, strategic, big-picture thinkers – who freeze at the edge of the ask. I’ve done it myself from time to time.

The relationship is there. The timing is right. The groundwork has been laid. But when it’s time to actually say the number... they stall out.

There’s an old joke in our field about someone like that:
“How is <<that fundraiser>> like a 7/11 store?”
“They never close.”

Funny – but also kind of painful. Because many of us have been that person. I know I have.

We hesitate because we don’t want to feel pushy. We worry we’ll mess up the relationship. But here’s the truth: donors – especially high-net-worth donors – know what we do. They expect us to ask.

And when we don’t? It doesn’t protect the relationship. It creates confusion. When trust has been built, the ask isn’t a surprise. It’s the next logical step.

​Try this: Start using this phrase in conversations: “I’d love to talk with you about a way to deepen your impact.” It’s warm. It’s clear. And it helps you move into the ask without making it weird.

So, what does this mean for you?

If you want to grow as a fundraiser, start by checking your mindset.

• Do you believe there’s value on both sides of the conversation?
• Are you willing to receive, not just facilitate?
• Can you honor the relationship by being direct about the opportunity?

Fundraising isn’t begging. And it’s not manipulation.

It’s invitation. It’s partnership. It’s a shared pursuit of something that matters.

My grandfather may have called me a “professional beggar” – but he wasn’t wrong about the skill it takes to do this work well. He just didn’t know the half of it.

Get your 3 Rs in alignment, and you’ll stop feeling like you’re asking for a favor – and start showing up like the professional you already are.

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.

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