I was new to fundraising and had been invited to accompany our head of major gifts on a visit with someone I considered a very important donor. To me, this was graduate school. I had spent the drive rehearsing everything I thought I was about to learn. I watched how confidently my colleague walked into the room, how naturally he greeted everyone, and how easily he settled into conversation. Surely there was a formula to this work—some polished combination of preparation, timing, and perfectly chosen words that separated experienced fundraisers from nervous newcomers like me.

Then, within moments of sitting down, he smiled warmly, reached out to shake the donor’s hand, and called him by the wrong name.

I remember thinking, Well, that was a short career.

The donor laughed. My colleague laughed. The mistake was corrected, another handshake was exchanged, and the conversation moved on as though nothing of consequence had happened. Ninety minutes later, we walked out after one of the warmest, most engaging conversations I had ever witnessed.

I honestly cannot remember whether a gift was discussed that afternoon. What I remember is the drive home, when I realized I had been paying attention to entirely the wrong things.

For years, I thought that meeting taught me that experienced fundraisers know how to recover gracefully from mistakes. Looking back, I think it taught me something much more valuable. It challenged one of the assumptions I had carried into the profession, that people are sitting across the table evaluating our performance.

We spend an astonishing amount of energy trying to sound polished, informed, and impressive when, more often than not, people are simply hoping we will be genuine. They want to feel heard. They want to feel understood. They want to believe the person sitting across from them is interested in who they are, rather than what they might eventually contribute.

That lesson stayed with me because fundraising slowly became something very different from what I expected. Like most people entering a new profession, I focused on acquiring skills. I wanted to become better at making an ask, better at telling stories, better at communicating impact, and better at understanding why one person chose to support a cause while another politely declined.

Those things certainly matter. But somewhere between board meetings, coffee conversations, school tours, gala dinners, and more auction paddles than any reasonable person should witness in one lifetime, I found myself becoming interested in something else entirely.

I became interested in how people move through the world.

When someone asks what I do for a living, I usually tell them I raise money for public schools. It is the shortest answer, and technically it is true. The longer answer is that I spend my days listening to people talk about the experiences that shaped them.

The longer answer is that I spend my days talking with people about what becomes possible when a community chooses to invest in its schools. I tell them about the student whose trajectory changed after discovering robotics, the middle schoolers who found their voices through creative writing, and the high school students who gained confidence by producing their own radio shows and podcasts. I tell them about elementary students who worked with a real author, wrote their own stories, and held published books in their hands.

These are stories about curriculum, certainly, but they are also about something larger: the moment a student discovers an ability, an interest, or a version of themselves they had not known was there. Money makes those opportunities possible, but it is almost never the most interesting part of the story.

I have heard stories about first jobs, second chances, businesses that succeeded, businesses that failed, aging parents, growing families, and the handful of people each of us can name who quietly changed the direction of our lives. Money is certainly part of those conversations, but it is almost never the most interesting part.

Perhaps that is why I eventually stopped thinking of fundraising as a profession centered solely on philanthropy and began thinking of it as an extraordinary excuse to study people. There are not many careers that allow you to sit across the table from thousands of individuals while they tell you what has mattered in their lives. If you do that long enough, patterns begin to emerge—although not the patterns I expected.

When I first entered fundraising, I assumed generosity and wealth naturally traveled together. It seemed like a reasonable conclusion. Surely the people with the greatest capacity to give would become the most generous people I knew.

Experience has a wonderful way of exposing tidy little theories.

Over the years, I have met philanthropists whose generosity has transformed schools and changed countless lives. I have also met people with every imaginable resource who guarded not only their money, but their time, attention, encouragement, and willingness to notice anyone outside their immediate orbit.

Then there were the people who quietly dismantled my assumptions altogether.

I have lost count of the parents who apologized because they could “only” make a modest gift while volunteering an extraordinary number of hours each year. I have met retired teachers who seemed almost embarrassed by the size of their donation, despite having already devoted an entire career to children.

Young families have apologized because daycare cost more than their mortgage, retirees because they were living on fixed incomes, and single parents because they wished they could do what someone else had done.

One of the strangest recurring conversations in fundraising is listening to remarkably generous people apologize for not being generous enough.

For a long time, I nodded sympathetically and moved the conversation along. I do not do that anymore because I eventually realized they were measuring generosity with a calculator, and somewhere over the years I had stopped doing that myself.

That does not mean money is unimportant. I have seen firsthand what transformational philanthropy makes possible. Large gifts create incredible opportunities, strengthen schools, support teachers, expand programs, and open doors for children who might never have had those opportunities otherwise. They deserve to be celebrated.

What changed was not my appreciation for philanthropy. What changed was my understanding of the quieter habits that so often surround it.

I began noticing that the people who left the greatest impression on me were not necessarily the people who wrote the largest checks. They were often the people who remembered names, asked one more question before telling their own story, thanked the volunteer stacking chairs after an event, noticed the student standing awkwardly by herself, or somehow managed to make everyone around them feel important without making a production of it.

They were the people who listened without glancing over someone’s shoulder to see whether a more useful person had entered the room. That particular skill may be rarer than any of us would like to admit.

At first, I thought these were simply unrelated acts of kindness. Over time, I began to wonder whether they were all expressions of the same instinct: a willingness to recognize that another person’s experience matters, even when it offers us nothing in return.

Working in a small nonprofit gives you an unusually close view of this. The job is intimate by design. You may be discussing strategy with a major donor in the morning, moving folding tables in the afternoon, writing an appeal before dinner, and answering a question about the silent auction at an hour when no one should be thinking about a silent auction. There is very little distance between the people, the mission, and the work.

That closeness teaches you things no campaign report can capture. It teaches you who stays to help when the event is over. Who notices when a volunteer is overwhelmed. Who thanks the staff member whose name will never appear on the stage. Who treats the person processing the gift with the same respect as the person receiving the recognition.

It also teaches you that generosity begins long before anyone reaches for a checkbook.

It begins in ordinary moments that rarely attract attention because they seem too small to count. A parent notices the new family standing alone at a school event and walks over to introduce herself. A board member quietly pulls another chair into the circle because someone has just arrived. A donor remembers the intern’s name six months later. Someone writes the thank-you note, makes the phone call, or asks the second question instead of waiting impatiently to tell the next story.

Someone forgives a mistake that could easily have been used to make another person feel small.

None of those moments will ever make an annual report. There is, regrettably, no spreadsheet column for “noticed the person standing alone.” They will not appear in a campaign total or be projected on a screen at a gala. No one will stand at a podium and announce that a person made room at the table, paid attention when it would have been easier not to, or extended grace when embarrassment was available.

Yet I have come to believe those moments reveal more about our generosity than almost anything else.

Money can measure capacity. It cannot always measure sacrifice. It cannot measure attention, kindness, patience, or the choice to make another person feel welcome. It cannot tell us whether a gift was given joyfully, reluctantly, anonymously, strategically, or because someone understood exactly what it feels like to need help.

A number can tell us what someone contributed. It cannot tell us the whole story of what they gave.

And perhaps this is where generosity becomes more demanding than philanthropy. Writing a check can be deeply meaningful, but it is also finite. We write the number, sign our name, and the transaction is complete. A generous way of living asks something of us over and over again. It asks us to notice people when we are distracted, to listen when we would rather speak, to make room when the circle already feels comfortably full, and to resist measuring everyone by what they can do for us.

It asks us to become less impressed by status and more attentive to character.

I am not certain we can ever accurately judge another person’s generosity. We rarely know the full measure of anyone’s resources, obligations, fears, or sacrifices. The gift that appears small to one person may require far more of another. The person whose name appears nowhere may have spent a lifetime giving in ways no institution knows how to record.

But I do think we can examine our own generosity—not only by looking at what we donate, but by paying attention to what happens around us.

Do people feel welcome when we enter a room? Do we listen closely enough to remember what they told us? Do we notice the person standing alone, the colleague whose idea has been overlooked, the volunteer doing the unglamorous work, or the friend whose voice sounds slightly different than it did last week?

Do we make other people feel as though there is room for them?

Sixteen years after that first donor meeting, I remember very little about the strategy, the organization’s needs, or whether anyone discussed a gift. I remember a man being called by the wrong name and choosing laughter instead of offense. I remember a seasoned fundraiser who did not become flustered or defensive. And I remember two people moving beyond an imperfect moment and finding their way into a genuine conversation.

What I witnessed that day was not simply a graceful recovery. It was generosity in one of its most ordinary and revealing forms: one person allowing another to be human.

Perhaps that is the measure worth paying attention to—not only how much we give, but how much grace we offer. Not only how generously we support the causes we value, but how generously we treat the people directly in front of us.

When people leave our presence, do they feel measured? Or do they leave with a little more room to be human?

Not because I want to. Not because I’m one of those girls with labeled bins, matching hangers, and the emotional stability to “edit my wardrobe” on a Sunday afternoon. No. I do it because I hit a breaking point where I can no longer pretend I wear all the things in there.

And yet, every time, I act stunned.

I stand there staring into my closet like it’s betrayed me. As if these clothes got here on their own. As if I was set up by a coordinated ring of cardigans.

The problem is, cleaning out a closet sounds like a practical task, but in reality it is a deeply personal exercise in delusion, nostalgia, and low-grade psychological warfare.

Because it’s not just a closet.

It’s a museum of every version of yourself you’ve ever been.
The girl who had a job that required real pants.
The girl who thought she was going to wear more blazers.
The girl who bought one slightly edgy thing and then immediately got scared.
The girl who keeps things because apparently “maybe someday” is a wardrobe category.

At some point, I also became a collector of plaid button-down shirts. I don’t remember making that decision. I was a Southern California girl. I still wear flip-flops in Seattle well into October, so clearly part of me is refusing to adapt. But somewhere in the last 25 years, plaid quietly became a personality trait. A friend recently informed me I’m no longer allowed to buy another plaid button-down shirt. I laughed... until I looked in my closet and realized she wasn’t being dramatic. She was staging an intervention.

Then there are the emotional support garments. The things you never wear but cannot get rid of because they represent the person you keep thinking you might become. A girl who attends chic lunches, wears white pants without incident, and has somewhere meaningful to go in a silk sleeveless top.

I do not know her. But I have invested in her heavily.

Every item requires a decision, which is where the unraveling begins.

Do I love it?
Does it fit?
Have I worn it in the last year?
Why did I buy this?
Who was I when I purchased this?
Was I going through something?
Am I still?

At some point, I inevitably start trying things on, which is always a terrible idea. Now I’m sweaty, annoyed, standing in bad lighting, and in a blood feud with a blouse.

There is always one item that sends me over the edge. Something I forgot I owned, still with tags, which means at one point I bought it, brought it home, put it in my closet, and then went on living as though it had never existed. That is not shopping. That is a cry for help with a return policy.

And because I apparently believe every annoying task deserves an extra layer of administrative nonsense, I also did the thing where I ordered the giant bags from one of those online resellers.

They send you these huge bags, you fill each one with up to 30 pounds of clothing, and ship them back so they can sell your items online and create your “closet.”

That word alone is generous.

Because first, it took weeks for them to upload my clothes. Weeks. By the time the email arrived, I had nearly forgotten what I’d sent and assumed my wardrobe had been absorbed into some giant national pile of abandoned J. Crew.

Then I clicked on my so-called closet.

I’ll tell you something: it was as ugly as my actual closet.

There was no styling. No finesse. No attempt to suggest that any of these garments had once been purchased by a girl with standards. They called blazers jackets. Jackets. A beautiful silk tank looked like it had been pulled from the bottom of a hamper. Everything looked limp, defeated, and vaguely ashamed. It was less “curated resale” and more “evidence of giving up.”

And I understand they probably receive thousands upon thousands of items. But still. Steam something. Button a blouse. Show a neckline a little respect. If they had even the faintest styling process, they would make more money. I’m not asking for Vogue. I’m asking for one sign of life.

By then I was no longer trying to make money. I was offended on behalf of my clothes.

And of course, after all that, you earn what can only be described as cents. Not money. Not income. Cents. The kind of amount that makes you wonder whether this was a resale platform or a character-building exercise.

So now, in addition to cleaning out your closet, you are being humbled by your own former purchases and the secondary market’s opinion of them.

Still, I keep going.
Pile to donate.
Pile for maybe.
Pile for absolutely not but somehow not ready to part with.

By the end, the room looks worse than when I started, and I’ve become emotionally reattached to at least three things I was fully prepared to get rid of an hour earlier.

But when it’s done? Euphoric.

A little more space. A little more clarity. A tiny illusion that I am now the kind of girl who has her life together. Until I shove one more “maybe” sweater back on the shelf and quietly close the door.

Because growth is important. But apparently so is that one black top I haven’t worn since 2019.

Almost three years ago, we said goodbye to the house where I raised my twins. Not just a house, obviously. The house. The one in the neighborhood I loved, the one full of history, the one where life happened for years in all the ways that matter most once they are gone. Holidays, family dinners, kids coming and going, friends around the table, backpacks on the floor, noise, comfort, chaos. It held a whole era of my life, and leaving it was hard in a way that had very little to do with real estate.

I moved to a smaller place in another part of the same community, which was the right decision and also an emotionally annoying one. Practical, yes. Healthy, probably. But just because something is right does not make it easy. In my case, moving turned out to be less fresh start and more slow-motion emotional excavation.

What I did next will not shock anyone who has ever confused an object with a memory. I put almost everything in storage.

At the time, this felt completely reasonable. I was not just storing furniture or dishes. I was protecting a life. Or at least that is what I told myself while boxing up serving platters, lamps, framed photos, chairs, and who knows what else. Every single thing seemed charged with meaning. It was impossible, in that moment, to tell the difference between what I truly loved and what I was simply not ready to lose. So I kept almost all of it.

Now, nearly three years later, I can say something both freeing and slightly ridiculous: I do not even remember some of what is in that storage unit.

At one point I was convinced I needed all of it. Now I am fairly certain there are boxes in there I could open and respond to the way one responds to a stranger at a party: polite interest, but no real connection. That has been one of the more humbling parts of this. I was so emotionally attached to things that, once removed from my daily life, turned out to have far less hold on me than I thought.

That has made me realize that a lot of what we think is attachment is really familiarity. We are not always clinging to the object itself. We are clinging to the life around it.

That dining room table was never just a table. It was where we gathered. The neighborhood was never just a location. It was a rhythm of life. The house represented family, history, belonging, and a version of myself I loved being. So of course I did not want to let it go. Of course I tried to save pieces of it. That is what makes simplifying your life so hard. It is rarely about the stuff. It is about what the stuff has come to mean.

And still, for all of that, I can honestly say that simpler has turned out to be better.

Not in a smug, minimalist, I own three beige bowls and now I know inner peace kind of way. That is not who I am. I still like beauty. I still like a home that feels warm and inviting. I still think a good dining room can improve your mental health. But I have come to appreciate, in a very real way, the relief of having less to manage.

Less to clean. Less to organize. Less to keep track of. Less to repair. Less to feel responsible for. A big house comes with a big invisible to-do list, and for years I think I had just accepted that as normal. Until it was gone.

That has been the surprise for me. Not that I miss the old life in certain ways - I do. I miss the neighborhood. I miss the memories attached to that house. I miss having a big dining room where family and friends could gather around a table and stay there for hours. I miss what that space made possible.

But I do not miss the weight of everything that came with it.

Talking with my friend reminded me that even when the circumstances are different, there is something universal about this part of life. The sorting through. The letting go. The figuring out what is worth carrying forward and what you are finally ready to put down. It is emotional, yes. But I also think the reflecting is good. The moving on is good.

Not because the past did not matter, but because it did.

That has been the lesson. You can love a chapter without trying to live in it forever. You can be grateful for a life you had without preserving every prop from the set. You can miss something and still know it was right to leave it.

It took me a while to get there. Much longer than I expected. But here I am. Life is lighter now. Simpler. Less burdened by upkeep and clutter and the pressure of managing too much. I would not trade the peace that has come with less.

That is the part no one really tells you. Simplifying your life does not always feel freeing at first. Sometimes it feels like loss. Sometimes it feels like letting go before you are ready. But eventually, if you are lucky, it starts to feel like relief.

And relief, at this stage of life, is wildly underrated.

Not in a dramatic, “I need to move to Portugal and become a surfer” kind of way, although I remain open to Portugal if anyone has an open guest house and low expectations. (Lisa? Cliff? - consider this an early application.)

More in the quiet way life eventually makes you take inventory. What still matters? What never did? What have I spent too much time worrying about? What do I want more of? What am I finally willing to stop pretending is worth my energy?

I started writing the rough draft of this on a plane home after spending time with family, which is always a slightly dangerous place to reflect because you are trapped in a seat, mildly dehydrated, and suddenly convinced you understand the meaning of life somewhere over Oregon.

But I had just spent time with my nephew and two nieces, and I kept thinking how much I love them, how quickly time moves, and how ridiculous it is that I do not see them more often. So that is now on the list too. More time with them. More visits. More showing up. Fewer vague promises about “we need to get together soon,” which, as we all know, is where good intentions go to die.

I’ve discovered that the older I get, the shorter the list becomes. Not because life gets simpler - it absolutely does not. The dishwasher still breaks. Family group texts still occasionally require diplomatic intervention and, in extreme cases, the strategic use of the block feature. Someone will always need something right after you’ve finally sat down.

But the priorities get clearer.

After enough years, enough mistakes, enough joys, enough surprises, and enough moments that didn’t go according to plan, you start to recognize a few things worth carrying forward.

Here are ten of mine.

1. Trust God has your back.

I have always believed God has my back. But the older I get, the more I can see it.

Not always in the moment, of course. In the moment, I am usually busy worrying, overthinking, making a backup plan, revising the backup plan, and wondering if I need a backup plan for the backup plan.

But looking back, I can see the pattern more clearly. The times I leaned on God and somehow found strength I did not think I had. The things I worried about that never happened. The disappointments that redirected me. The doors that closed and, annoying as it was at the time, turned out not to be mine to walk through.

Faith, for me, has become less about needing certainty and more about trusting God in the unknown. Trusting that I do not have to carry everything myself. Trusting that I do not have to have every answer. Trusting that even when life does not unfold the way I planned, God is still with me in it.

I still believe in doing the work, making the call, taking the step, and showing up. But I am learning to pray more, lean on God more, and loosen my grip a little after that.

The future has never once improved because I worried more.

2. Be kind. Be useful.

I’ve spent much of my career around generosity, and one thing I’ve learned is that people underestimate the impact of small acts of kindness.

The world tends to celebrate big achievements, but most of life is built on smaller moments. The encouraging conversation. The introduction that opens a door. The person who notices someone sitting alone. The volunteer who quietly helps without needing recognition. The friend who checks in when everyone else has moved on.

Kindness is not weakness. It’s not naivety. And it doesn’t require perfection.

It simply requires paying attention.

Being useful is different from being impressive, and kindness is often more powerful than either one. The people I admire most are rarely the loudest people in the room. They’re usually the ones quietly making things better for everyone around them.

3. Let people be who they are.

This is one of the hardest lessons because it requires accepting reality instead of potential.

People are going to make choices you wouldn’t make. They’re going to ignore excellent advice. They’re going to repeat mistakes, frustrate you, disappoint you, and occasionally leave you wondering if they were listening to a single word you said.

You can love people without managing them.

You can support people without fixing them.

You can care deeply about someone while accepting that their journey belongs to them.

There is a tremendous amount of freedom in realizing that other people’s growth is not your responsibility.

4. Call the friend.

For years I convinced myself that staying in touch counted as staying connected. A quick text. A social media comment. A birthday message. Better than nothing, certainly.

But the older I get, the more I realize that friendships are built in conversations, not notifications.

Call the friend. Meet for coffee. Go for the walk. Sit across from someone and talk long enough to move past the headlines of life and into the real stuff. Relationships don’t survive because we care about people. They survive because we make time for them.

And if there’s one thing age teaches you, it’s that the people who have walked through life with you are among your greatest treasures. You will find me in Napa with some of my besties from my 20’s this year…

5. Stop waiting for permission.

One of the great surprises of adulthood is discovering that nobody really knows what they’re doing all the time.

At some point, I assumed there would be a moment when someone officially handed me a certificate confirming that I was qualified. Qualified to lead. Qualified to speak up. Qualified to try something new. Qualified to change directions.

The certificate never arrived.

If there is something you want to do, start. Write the article. Learn the skill. Apply for the job. Launch the idea. Reinvent yourself if necessary. Most people are too busy wondering whether they’re qualified to spend much time judging whether you are.

6. Protect your peace.

This lesson has probably saved me more energy than any other.

Not every opinion requires a response. Not every misunderstanding needs correction. Not every criticism deserves your attention. Some situations improve dramatically when you stop participating in them.

This is particularly difficult for those of us who enjoy being right.

Or, more specifically, those of us who enjoy explaining exactly why we’re right.

But I’ve learned that peace is often worth more than winning. Sometimes the healthiest thing you can do is step back, take a breath, and let life move on without your closing argument.

7. Be present.

This one sounds simple, but it may be one of the harder lessons of modern life.

Put down the phone. Look people in the eye. Listen when someone is talking instead of mentally preparing your next response, checking a text, or wondering if that email really needs an answer right now.

The older I get, the more I realize how much of life happens in the small, ordinary moments we are tempted to rush through. Dinner at the table. A walk with a friend. A quiet morning. Someone telling a story you’ve heard before but maybe need to hear again.

Presence is a gift. It tells people, you matter enough for me to be fully here.

And honestly, most of us do not need more content, more noise, or more things demanding our attention. We need more real conversations. More laughter that happens in the same room. More listening. More noticing. More enjoying each other while we are lucky enough to be together.

8. Use the good stuff.

This lesson has taken me an embarrassingly long time.

The good candle. The nice lotion. The pretty dishes. The outfit you’re saving for an occasion that may or may not ever appear. Why do we do this?

At some point I realized I was treating life like a rehearsal for a future event where everything would finally be perfect. The house would be spotless. Everyone would be available. The weather would cooperate. My jeans would fit exactly as intended.

That day rarely arrives.

So now I try to use the good stuff. Not every day, but more often. Because Tuesday counts. Dinner at home counts. A random evening with people you love counts. Life isn’t the dress rehearsal.

This is the show.

9. Take the trip.

There will always be reasons to wait. Work gets busy. Money feels tight. The timing isn’t perfect. The dog needs something. The house needs something. The suitcase somehow never got put away from the last trip.

I’ve learned that life is remarkably skilled at providing reasons to stay home.

What it doesn’t provide is a guarantee that you’ll always have the chance to go later.

The trips I remember most aren’t always the fanciest ones. They’re the ones where something unexpected happened, where someone laughed until they cried, where I saw something new, or where I simply got to spend uninterrupted time with people I love. I’ve never returned from a meaningful trip wishing I had stayed home and cleaned out a closet.

10. Remember that someday is not a day on the calendar.

This may be the biggest lesson of all.

For years, many of us live with a running list in our heads. Someday I’ll travel more. Someday I’ll write the thing. Someday I’ll make the change. Someday I’ll spend more time with the people I love.

Then one day you realize that someday isn’t coming.

It’s here.

That doesn’t mean blowing up your life or making reckless decisions. It simply means paying attention to the life that is happening right now instead of postponing everything meaningful until some future version of yourself has more time, more money, more courage, or fewer responsibilities.

The truth is, life has always been happening now.

So that’s what I’m taking into the next decade: a little more faith, a little less worry, more laughter, more phone calls, more adventures, more gratitude, and a greater appreciation for ordinary days.

I’ve learned that life is rarely as predictable as we hope, but it is often far richer than we expect.

Here's to the next decade - may I worry less, love more, and never forget that today is the day I used to call someday.

We board the plane, put in our AirPods, pull out our books, queue up our downloaded shows, and silently agree not to acknowledge the existence of the strangers around us for the next several hours. It’s not unfriendly exactly. It’s just modern. Efficient. Protective. Everyone preserving their own little bubble at 35,000 feet.

Usually, I participate enthusiastically in this arrangement.

But on my flight from Seattle to Boston, there was an open seat between me and the man in the aisle, and before the plane even took off, he started talking.

Total Bostonian. Irish. Former firefighter. Thick accent. Opinionated in the charming way only older Boston men can be - or at least I imagine. The kind of man who referred to his wife exclusively as “my bride,” without a trace of irony.

Usually on flights, I’m aggressively unavailable. Headphones. Book. Minimal eye contact. The universal signs for: I wish you well, but please don’t involve me in your life story.

But for whatever reason, that day I didn’t put my headphones on. And somehow, for the next five and a half hours, we talked almost nonstop.

The funny thing is, this is also very much who I am. I can talk to almost anyone. I genuinely love hearing people’s stories. I love finding out where someone grew up, what they did for work, what shaped them, what they’ve seen. Some people collect souvenirs when they travel. I seem to collect conversations.

Still, there’s a difference between being open to people and unexpectedly connecting with someone. Most interactions stay pleasant and surface-level. This one didn’t.

We talked about kids and careers and marriage and travel. Somewhere over the middle of the country, he taught me how to play Sudoku, patiently explaining strategies while I stared at the little boxes like they were advanced calculus. He told stories about Boston and the fire department and growing older. He talked about his two sons. Constantly, he referred to his wife as “my bride.”

Not “my wife.” “My bride.” Which somehow told me everything I needed to know about him.

At some point during the flight, he insisted I write to him when I got home so he could send me something he wanted me to have. Very old-school. Very proper. Very adorable. He handed me his address carefully, like this was serious business.

And apparently it was.

When I got home, I actually did write to him. I sent a card and some Seattle Chocolates, which is how I found myself unexpectedly entering a handwritten-correspondence era with an 80-year-old Irish Boston firefighter I met on an airplane.

A month ago, my book club had read The Correspondent, a novel built around letters and human connection, and I had told the girls this whole story - about the man on the plane, the address scribbled down before landing, and the fact that I had actually mailed him a card like it was suddenly 1986 again.

Then this week, a letter arrived from Boston. Typed, of course.

And I already know I’m bringing it to book club next month because honestly, it’s too wonderful not to share.

The letter was funny and warm and full of personality. He explained that his bride could not enjoy the Seattle Chocolates because she’s gluten free.

“I did the only thing that made any sense,” he wrote. “I ATE THEM ALL.”

It made me laugh out loud.

Somewhere near the end of our flight, as we were taxiing to the gate, he turned to me and quietly apologized in advance because he needed assistance getting off the plane. He explained that meant I’d probably be the last one off too.

Until that moment, I hadn’t realized how old he really was. I told him I didn’t mind at all. And I truly didn’t.

So we sat there while everyone else stood up immediately despite the fact that the plane doors were still closed and nobody was going anywhere for at least another ten minutes - one of the stranger rituals of modern air travel. Eventually, I helped him get his bag down and walked off the plane beside him as the flight attendant pushed him in a wheelchair. He could walk, he just needed assistance off the plane.

I’ve thought about that flight a lot since then. Partly because it was such a lovely reminder that there are still people in the world who are curious and open and willing to connect without agenda. But also because it made me realize how much we all miss when we move through life trying to optimize every moment of it.

Headphones on. Eyes down. Get work done. Protect your peace. Avoid unnecessary interaction.

And look, sometimes that’s fair. Not every stranger becomes a meaningful part of your week, or your month, or your memory.

But every once in a while, someone does.

An 80-year-old Boston firefighter who calls his wife “my bride.” A five-and-a-half-hour conversation at 35,000 feet. A typed letter waiting in your mailbox a few months later.

Nothing about it was important in the way we usually define importance. It didn’t solve a problem or advance my life in any measurable way. And yet months later, I’m still thinking about it.

Because for five and a half hours somewhere between Seattle and Boston, the world felt a little less disconnected than it usually does.

All because I didn’t put my headphones on.

It’s a Tuesday in late May. The sun is out. Kids are counting down the days until summer. Teachers are quietly composing their out-of-office replies. Parents are planning vacations, booking camps, buying end-of-year teacher gifts. The whole world has that collective exhale energy - that “we made it through another school year” vibe that is genuinely one of the best feelings in community life.

And then there’s me.

I am at my desk, staring at a spreadsheet, doing the kind of mental math that should require a prescription. I am calculating gift pipeline probabilities in my head the way some people calculate a restaurant tip - automatically, compulsively, and with way too much riding on the outcome. I have a goal. I have a deadline. And the deadline is not August 31st, which is when our fiscal year actually ends, like a normal organization. No. My deadline is whenever that last school bell rings. Because when school lets out, we stop fundraising. We give the community a break from us. We pack up our case for support and we wish everyone a lovely summer and we do not, under any circumstances, send a fundraising email in July. They are truly sick of us.

This is called being respectful. It is also called strategic relationship management. It is also, if I’m being completely honest, called we tried it once and the response rate was so demoralizing we never spoke of it again.

So here we are. May bleeding into June. The most wonderful, terrible, beautiful, anxiety-inducing stretch of our nonprofit fundraising calendar. The final act. The last call. The moment where everything you’ve been building since September either comes together or you spend August quietly figuring out how you can reach the goal next year and how to tell the district you didn’t quite make it.

No pressure.

Here is something I want my non-fundraiser friends to understand about this time of year, we are operating on a frequency you cannot hear. We are at every end-of-year event - the concerts, the celebrations, the eighth grade promotion ceremonies - present, engaged, genuinely moved by all of it, and also running a parallel mental track that sounds something like: outstanding pledge, follow up Thursday, that board member said she’d make an intro, did that major grant come through yet, where is that grant, why haven’t we received that grant yet. We are the people in the room who are most aware of what it cost to make the room possible and most aware of what it will cost to make next year possible. We are delightful company. We contain multitudes.

The particularly funny, and by funny I mean cosmically absurd, thing about our fundraising deadline is that it is entirely self-imposed. Nobody requires us to stop in June. The community is not legally protected from our emails come July 4th weekend. But we care about these relationships. We care about not being the organization that follows up on a pledge while you’re trying to enjoy a barbecue. We have boundaries. We have values. We have also, after years of this work, developed a finely tuned sense of when we are pushing our luck.

The result is that June becomes the most load-bearing month of the entire year.

Every conversation has weight. Every “let’s grab coffee before summer” gets immediately calendared. Every donor who has been in the “deciding” column since February suddenly becomes very important to me in a way I hope comes across as warm and relational and not at all like someone watching a parking meter run out. I am reaching out. I am following up. I am being genuinely enthusiastic about mission impact while also being acutely aware that we have seventeen business days left and I need six more yeses.

And the community? Bless them. They are blissfully, beautifully unaware.

They are at school picnics. They are on field trips. They are deep in the logistics of summer travel. One of my most generous donors once called me back from what was clearly a very loud trampoline park, told me he was “totally in for whatever he gave last year”, and then had to go because his kid wiped out. I took the pledge. I sent the confirmation email before he got back in his car. I am a professional.

The ghost donors deserve their own paragraph. Actually, they deserve their own memoir, but I’ll summarize. These are the people - wonderful people, genuinely generous people, people I have real affection for (and I’m being sincere) - who had a great conversation with me in October. An enthusiastic conversation. A “we are absolutely going to support this year” conversation. And then life happened, as life does, and somehow it is now late May and I am crafting what I internally call the “friendly nudge” email, which is the fourth or tenth email, and it is neither friendly nor a nudge, it is a small prayer disguised as a paragraph.

They almost always come back. Usually in the last two weeks. Always unbothered.

Some years we hit the goal before the bell rings. Those years feel like grace. You spend the last week tying up loose ends with the particular serenity of someone who has already checked the most important thing off the list. I highly recommend it. I have experienced it a handful of times… and I’ve been in my current role for almost 12 years.

Other years we are in it until the very last day. The kind of close where you are refreshing email more often than you want to admit, not proudly, just honestly. Where you know exactly how much is still outstanding and exactly which conversations could still move. Where you go home at the end of the second-to-last day before school gets out and you sit with the reality that tomorrow is it, and it’s either going to happen or it isn’t, and you’ve done everything you can, and also you’re going to send one more email tonight just in case.

Those years are when this job asks the most of you. And also, weirdly, when it gives the most back.

Because here is the thing about chasing a goal that actually means something, the urgency is real because the mission is real. We are not selling a product. We are not hitting a quota. We are funding the education of kids in public schools because the state does not do it adequately, has not done it adequately, and is not trending toward doing it adequately anytime soon. Every dollar we raise is a class that happens, a teacher who stays, a kid who gets something they wouldn’t have gotten otherwise. When I am refreshing my email on Tuesday evening over dinner out with friends, that is what I am refreshing it for.

This year, at our annual fundraiser, I watched elementary kids recount how the Spelling Bee changed them - kids who had worked and competed and discovered something about themselves they didn't know was there. I watched middle schoolers talk about Gator Time like it was the best part of their week, because for a lot of them, it was. I watched high schoolers describe producing their own Radio and Podcast program with the kind of confidence that only comes from being trusted with something real. They were on a stage, in front of their community, because someone funded that. Because we funded that. I stood in that room thinking about the spreadsheet waiting on my desk and the goal we hadn't yet hit - and also thinking that this, right here, is the most effective fundraising tool I have ever witnessed.

Not because I planned it that way. Because it's just true. Not the spreadsheet. Not the ghost donors or the pipeline or the seventeen-business-day countdown. This. The thing we funded existing in the world, doing what we said it would do, for exactly the kids we said it would serve.

June is hard. June is funny if you let it be. June is load-bearing and absurd and exhausting and, on the good days, the best reminder of why any of us do work that asks this much of us.

The bell rings, the community scatters, and I will stand there knowing we gave it everything we had. I will exhale too - deeply, loudly, and very dramatically - and then immediately open my laptop to start drafting the September appeal. And the auction isn't going to plan itself.

But first, does anyone know if that grant came through?

I’ve spent years watching this moment unfold in school gyms, hotel ballrooms, waterfront homes, and auction tents. And despite how much nonprofits obsess over centerpieces, auction packages, seating charts, and signature cocktails, the success of a fundraising event almost always comes down to one thing: does the ask feel real?

Not polished. Not overly produced. Not emotionally engineered within an inch of its life. Real.

That is much harder to achieve than people think.

A surprising number of fundraising asks fail because organizations misunderstand what donors are actually responding to in the room. They assume people give because the video was emotional enough, or because the auctioneer was charismatic, or because someone important stood onstage and delivered a compelling speech. But most experienced donors have attended enough nonprofit events to recognize performance when they see it. They know when they are being carefully managed toward a number. They know when a speaker is reciting talking points they did not write and do not deeply believe. And perhaps most importantly, they know when an organization is asking from confidence versus asking from anxiety.

That distinction matters enormously.

Ironically, some of the worst fundraising asks come from organizations trying far too hard to create “the moment.” The music swells. The script stretches on too long. Every story is layered with so much emotional weight that the audience begins to feel manipulated instead of inspired. The room starts to tighten. People stop leaning in and start quietly retreating into themselves.

But I also think nonprofits sometimes overcorrect when talking about emotional fundraising. Somewhere along the way, some people decided that sophisticated fundraising should be entirely restrained and data-driven, as though emotion itself is somehow unsophisticated. That is not true either.

The best asks are often emotional because the work itself is emotional. A teacher describing the moment a struggling student finally connects with learning. A parent explaining what support meant during a difficult year. A superintendent talking honestly about the quiet things students lose when funding disappears. Those moments should feel human. If nobody feels anything during a fundraising event, something important is probably missing.

The difference is that genuine emotion and manufactured emotion are not the same thing. Audiences can feel that difference immediately. The strongest fundraising asks allow emotion to emerge naturally from truth, specificity, and credibility. They trust the audience enough not to oversell every feeling. They understand that people are perfectly capable of connecting the dots on their own if you give them something honest to connect to.

That honesty extends directly into one of the most overlooked strategic decisions nonprofits make: who should actually do the ask.

Boards often default to the most visible person in the room. The wealthiest board member. The local celebrity. The polished executive. The person least afraid of a microphone. Occasionally they choose someone simply because they “sound” like a fundraiser, which usually means they speak with the cadence of a luxury car commercial. But the best asks come from people with emotional credibility — someone the audience trusts, someone who understands not only the mission itself, but the emotional ecosystem surrounding it. Someone who can communicate belief without sounding rehearsed.

That person is not always the Executive Director. Sometimes it absolutely is. Sometimes it is a teacher, a parent, a student, or a superintendent. Sometimes the most effective speaker is the person who least resembles a professional fundraiser because the audience senses they are speaking from lived experience rather than performance.

I once watched a speaker lose their place midway through an ask. They paused, laughed nervously, admitted they were emotional, and continued without pretending to recover perfectly. The room gave more generously than anyone expected that night. Not because the delivery was flawless, but because it was human.

Nonprofits underestimate how deeply audiences crave authenticity now. We are living in a time saturated with corporate language, optimized messaging, polished branding, and carefully engineered emotional experiences. Donors can feel when something has been focus-grouped into lifelessness. Ironically, the more “perfect” an ask becomes, the less trustworthy it sometimes feels.

Timing matters too, and this is where many events quietly lose money.

Too many organizations place the ask at the very end of the evening because they think it should serve as the grand finale. But by then, people are mentally drifting. Babysitters are texting. Guests are checking watches. Some attendees have already left. Others are thinking about traffic, parking, or whether they can quietly slip out before the dessert auction.

An ask placed too late often loses both emotional momentum and practical attention.

The most effective asks usually happen somewhere between halfway and three-quarters of the way through the program, when the room is fully engaged but not yet fatigued. There is still energy in the audience. People are emotionally present. They have absorbed enough of the mission to care, but they have not yet started transitioning mentally toward the end of the night. This seems obvious, but it is remarkable how many organizations build an entire evening around fundraising and then place the fundraising portion at the exact moment people are least attentive.

The best fundraising events understand something important: the ask is not an isolated five-minute speech near the end of the evening. It is the emotional culmination of everything that came before it. The tone of the welcome. The pacing of the program. The credibility of leadership. The warmth in the room. The clarity of the mission. The trust donors feel in the stewardship of the organization.

Donors notice all of it.

And sophisticated donors especially notice whether an organization respects their intelligence.

One of the most effective fundraising lines I have ever heard was also one of the simplest: “If you believe this matters, we invite you to help sustain it.”

No guilt. No theatrics. No exaggerated urgency. Just clarity, confidence, and respect for the audience.

Because the truth is, most people attending fundraising events are not hoping to be emotionally cornered into writing a check. They are looking for reassurance that their generosity will mean something. That the organization understands both its mission and its responsibility. That there is competence behind the scenes. Stewardship. Vision. Humanity.

A truly effective ask does not make donors feel pressured.

It makes them feel certain.

The funny thing is, I’m not an obvious procrastinator. I get things done. I meet deadlines. I can pull off an event, answer emails, solve twelve problems before lunch, and remember meaningless obscure details. But apparently tires are my limit. Something about researching them, comparing prices, making the appointment, and pretending I understand tread life pushed me right over the edge. So I did what any capable adult would do: I thought about it repeatedly and took no meaningful action.

But today was the day. I called a few places, got a few quotes, nodded seriously at numbers I barely understood, and finally landed on Costco Tires. Because Costco is where responsible decisions go to feel slightly fun. You go in for tires and come out with a kayak, a 40-pack of sparkling water, and a rotisserie chicken.

The plan was simple: drop off the car, wait an hour and a half, maybe wander around, maybe buy one practical item and seventeen emotional-support snacks. There was only one small complication. I had my dog with me.

A 25-pound, very sweet, very well-behaved, deeply curious dog who had no idea he was about to become part of a Costco social experiment.

I walked up to the entrance with the kind of confidence that says, “This might work,” and the kind of doubt that says, “This absolutely will not.” I said something brilliant like, “Hi… I have my dog because my car is getting tires…” I got I got a yes at the door and didn’t ask any follow-up questions. The nice woman looked at my dog and said he is sooo cute... and just like that, we were in.

I have never seen a dog casually walking through Costco. Not once. Costco is not exactly known for its relaxed pet-friendly ambiance. It is a place of oversized carts, aggressive sample strategy, bulk paper products, and people who will absolutely take you out with a flatbed for the last sample of something they weren’t even planning to buy. And yet there I was, strolling through Costco with my dog on a leash like we were taking a peaceful Sunday walk through a lovely park, if the lovely park sold six pounds of cheese and patio furniture.

He was thrilled. I was trying to act like this was completely normal.

He sniffed everything. Every box. Literally, everything that was at his nose level. He inspected Costco with the seriousness of a federal agent looking for contraband. The meat section, however, was his North Star. He kept pulling toward it as if he had suddenly discovered his life’s purpose. I was trying to look calm and in control while gently whisper-yelling, “Absolutely not,” and steering him away from what he clearly believed was a walk-in shrine built entirely in his honor.

Somewhere between the cereal and the paper towels, I had one horrible flash of panic that he might lift his leg on a pallet of Cheerios and end both my Costco membership and my dignity in one tragic moment. Thankfully, he remained a gentleman. Mostly.

Then a woman stopped me in front of a pyramid of 48-packs of LaCroix, which felt like an oddly appropriate place to discuss Costco dog policy. “Wait,” she said. “They let you bring your dog in here?” I explained, casually, as if I understood the policy and was not simply riding the wave of one kind woman’s judgment call. I told her about the tires, the wait, and the nice woman at the door.

She told me she had asked if she could bring her dog in, and the woman had been rude and said absolutely not. Then she pointed to her cart. Inside was a carrier. Fully zipped. Completely sealed. Not a paw, nose, or single guilty whisker visible. Her tiny dog was basically in witness protection.

She was worried she was going to get kicked out of Costco, but also furious on principle, which is honestly a very relatable emotional combination. She had gone full covert operation. Meanwhile, I was standing there with my 25-pound dog fully out in the open, strolling past the vitamins like he had an Executive Membership.

The injustice was real.

I suddenly felt like I had been granted some kind of secret Costco dog privilege I had not earned and did not fully understand. She had smuggled in a tiny dog you couldn’t even see, while mine was walking around in public, sniffing bulk granola and trying to redirect us toward the tri-tip.

This is what procrastination does. It doesn’t just delay a task. It creates a weird little universe around it.

If I had changed my tires weeks ago, like a normal responsible adult, none of this would have happened. No calling around for quotes, pretending I understood the differences. No wandering Costco with a dog who behaved better than most people in the sample section. No chance encounter with a woman smuggling a tiny, fully zipped-up fugitive in her cart.

And because Costco was not done with me yet, after the tires were installed and the dog had completed his unauthorized retail tour, I pulled into the Costco gas station. I had just bought tires and groceries with my membership card. My dog had essentially completed his own Costco experience under that same membership.

But when I scanned it at the gas pump, the machine informed me my membership had expired. Expired. After tires. After groceries. After the dog’s meat-section pilgrimage.

Apparently my membership was valid for automotive services, bulk snacks, and one medium-sized dog field trip, but gasoline was where Costco decided to draw the line. Which, at that point, felt like Costco politely letting me know I had officially overstayed my welcome.

And honestly, maybe that is the lesson. Procrastination is not a strategy. It is usually annoying, occasionally expensive, and rarely recommended.

But every once in a while, it does hand you a story. Today’s story came with new tires, no gas, one very happy dog, and a tiny dog in witness protection.

Not exactly the afternoon I expected. But memorable? Absolutely.

But after years of doing this work, I’ve learned that by the time you get to the ask, much of the outcome has already been shaped. Not guaranteed—fundraising has a way of keeping you humble—but shaped. The ask does not work because someone says the perfect words. It works because the room has been prepared to hear them.

The hard part is making the ask matter.

This year’s Breakfast of Champions felt like a turning point, not because everything was perfect, but because it reflected how much intention it now takes to bring people together in a meaningful way. We set out to get back to our pre-COVID numbers—600 people in the room. We landed at about 550, which felt significant, not because attendance is the point, but because a full room changes what is possible. It creates energy, credibility, and a kind of shared momentum that you simply cannot replicate any other way.

Rebuilding an event after COVID has been its own kind of work. People did not simply return to rooms because we opened the doors again. Habits changed. Calendars changed. Attention changed. The easy “of course I’ll be there” became “let me check,” which now often requires a follow-up or two and a bit more intention than it used to. Getting people back in the room required persistence, relationships, and a belief that gathering still matters - not for the sake of the event, but for what can happen when a community shows up together.

We had Joel McHale as our host, which helped in all the ways you would expect. He brought humor, familiarity, and the rare ability to make a school fundraiser feel both meaningful and genuinely engaging at that hour. Having someone like Joel in the room gets attention, and attention matters. But attention is not the same as commitment. A recognizable name might help people show up. It does not, on its own, move them to give in a way that reflects the depth of the need.

That is where the real work begins.

The space between the start of the program and the ask is where fundraising actually happens. It’s where people move from “this is nice” to “this matters.” It’s where they stop being observers and start considering their role in the outcome. And it’s far more nuanced than most people realize. You are not trying to convince people that education matters. They already believe that. You are trying to help them understand why their participation matters, right now, in a very specific and tangible way.

Agreement is easy. Action is a decision.

In a district like ours, community funding fills the gap between what people assume schools have and what they actually need to deliver the kind of education this community expects. It helps retain strong staff. It supports curriculum. It sustains enrichment, arts, and student experiences that make school feel alive and relevant. These are not extras in the casual sense of the word. They are the things that shape how students experience their education day to day.

The challenge is that when this funding is working, much of it becomes invisible. Programs exist, so people assume they were always going to exist. Opportunities are there, so they feel automatic. The gap disappears because it has been filled, and when that happens, it becomes harder to explain why continued support is necessary.

That is the paradox of successful community investment.

So the work becomes making that impact visible without overstating it or turning it into something it’s not. People don’t need a perfectly polished pitch. They need clarity. They need to understand what is at stake and how their participation changes the outcome. That requires discipline. It means choosing the right stories, the right voices, and the right moments. It also means resisting the temptation to say everything, because more information rarely leads to more giving.

That is why impact on stage matters so much. Students and educators can do what no talking point can. They make the work tangible. They remind the room that this is not about an organization trying to hit a number. It is about students having access to meaningful opportunities, teachers having the support they need, and a district being able to offer the kind of education this community values.

There is a moment in every strong fundraising event when the room changes. People settle. They listen differently. They lean in just a bit more. It’s subtle, but it’s real. And when that shift happens, the ask no longer feels like an interruption. It feels like the point.

The ask is simply where that becomes visible.

The “Why We Give” moment works when it connects values to action. It reminds people that giving is not just a transaction; it is a choice about what we are willing to support, protect, and prioritize. The best asks don’t pressure people into giving. They invite them to step into something they already care about.

That’s what I’ve come to understand about this work. Fundraising is not about persuading people to care about something they don’t care about. It is about helping them see the role they can play in something they already value. It is about creating enough trust, clarity, and emotional truth that generosity feels not only possible, but necessary.

And when it works, when people give in a meaningful way, it is not because the event was flawless or the host was funny or the coffee arrived on time, although the coffee absolutely matters. It is because the room understood the need and felt connected to the solution. It is because people saw themselves as part of the answer.

Fundraising isn’t about asking well. It’s about preparing a room to say yes.

Not the vague, sparkly kind of magic.

I mean the real kind. The kind with texts flying, ideas stacking, someone saying, “I know just the person,” and suddenly what started as a nice auction item becomes the one everyone in the room wants.

That happened at our fall fundraiser last year.

A friend of mine and her husband have become, at this point, far more than a little TikTok famous for their cooking videos - feeding their family of seven, their kids’ friends, and apparently half the athletic community. They have 454.8K followers and 16.6 million likes, as of this writing. And honestly, once you know them, that tracks. They are adorable, wildly likable, and the kind of people who make feeding a crowd look joyful, effortless, and suspiciously easy.

She offered up a private dinner for 12 as an auction item.

That alone would have been a fabulous auction item.

But then something even better happened.

A business owner in our community who runs a small chain of specialty food stores donated all of the groceries for the dinner and dessert. A winery provided the wine. Our florist created beautiful arrangements for the table, and a home and gift store owner added gorgeous décor. Best of all, every one of those businesses was locally owned by people right here in our community. Most of these owners are women.

So this was no longer just a dinner.

It became an experience.

A mood.
A story.
A whole evening with personality, warmth, style, and the kind of thoughtful detail that makes people raise their paddle a little faster.

It sold high at auction, as it should have.

Because here is what people outside fundraising sometimes miss: donors do not just bid on things. They bid on meaning. They bid on delight. They bid on something that feels personal, special, generous, and beautifully put together. They bid on a story they can step into.

And that is exactly what these women created together.

This is also where the real lesson is.

Women are often incredibly good at seeing how separate things can become something bigger. A meal becomes a gathering. Groceries become abundance. Flowers become atmosphere. Table décor becomes a whole vibe. A donated item becomes something people talk about long after the event is over.

That is not fluff. That is skill.

And in fundraising, it matters more than people realize.

Some of the best fundraising does not start with, “What can we ask one person to donate?”

It starts with, “Who do we know? What do they do beautifully? Who else could add to it? And what could happen if we layered all of that together?”

That is where the magic lives.

Not in pressure.
Not in begging.
Not in sad little auction items that look like they were assembled in a panic with a glue gun and cellophane.

In creativity.
In collaboration.
In knowing your community.
In understanding that one donor or one business can be wonderful, but several generous women and locally owned businesses bringing their talents together? That is when things start to get really interesting.

And maybe that is what I loved most about this item.

Yes, it raised important money for our schools. Yes, it was a huge seller. Yes, from a fundraiser’s perspective, I was thrilled.

But it also felt like such a perfect reflection of how good things actually happen in a community.

People say yes.
Women build on each other’s ideas.
Local business owners show up.
Someone adds beauty.
Someone adds abundance.
Someone adds the finishing touch.
And together, they create something no one could have made alone.

That is fundraising at its best.

Not just raising money, though of course we love that part.

But creating something meaningful, generous, and memorable enough that people cannot help but lean in.

I have seen this over and over in my work: when smart, creative, generous women come together, good ideas get better. They make things warmer, more thoughtful, more beautiful, and usually more successful.

This auction item was a perfect example. What made this so memorable was not just the bidding, but the collaboration behind it. That is the kind of fundraising I love most - thoughtful, generous, community-driven, and far better than anything one person could create alone.

I wear white jeans all the time in the spring and summer. Not daily, because I’m reckless, not insane. But often enough that I should have accepted by now that every time I put them on, I am entering into a binding agreement with fate.

And here’s the thing… I know the moment I zip them that the day is already over for those pants. There will be a smudge. There will be coffee. There will be a rogue pen mark, a streak of yellow highlighter, or something so unidentifiable it feels less like a stain and more like a targeted attack. It’s not if. It’s what kind.

White jeans, for me, have become less of an outfit and more of a weekly mystery. What am I working with this time? A little desk grime? A dramatic knee situation? A little coffee spill, I didn’t realize it missed my mouth and landed on the back of my pants. Hmmm…

There was also the time I wore them to work, got in the car, got out of the car, walked into the office, sat down at my desk, looked down, and there was already a smudge on them. How? From where? I had barely even participated in the day. Typical.

The other day, I was on my way to dinner with friends and did what I can only describe as a routine damage check. I looked down and there, on my white jeans, was a paw mark from my dog. An actual paw mark. Before dinner. On the way there. Which felt especially rude, because these were not just any friends. These were put-together friends. Friends who always arrive looking fresh and charming and somehow do not have stains, things in their teeth, or smeared mascara.

I, on the other hand, was apparently arriving as the girl whose dog had already weighed in on the outfit.

In fact, a rough version of this very post was composed by voice note right there in the car while I was staring at the paw print on my leg, because honestly, at that point, what else is there to do but document the decline.

And the thing is, I seriously try. I check the mirror. I lint roll. I make a real effort to present as a competent, polished adult woman who has a grip on her life. And then, without fail, there is always some small piece of visual evidence suggesting I was assembled in the back of a moving vehicle.

At this point, I don’t even react anymore. I look down, see the damage, and just nod like, yes… of course. This is the agreement we made. Because eventually I stop trying to win against white jeans and start accepting that I am in a long-term relationship with chaos. I show up, I do my best, and by the end of the night, my pants have a full short story on them.

And honestly, I respect it. There is something deeply optimistic about continuing to wear white jeans when I know exactly how it’s going to end. It’s not denial. It’s commitment. It’s choosing the aesthetic over the outcome. It’s saying, “I understand the risks, and I’m going anyway,” which, if we’re being honest, is the same energy behind most of my life decisions.

So no, I will not stop wearing white jeans. I will continue to put them on with quiet confidence, fully aware that by the end of the day I will look like I brushed up against a minor emergency.

This post is dedicated to Clorox, and the Tide Pen. Thank you for standing by me, cleaning up what you can, and minding your business on the rest.

There was something different about letters. You had to sit down and actually think. You had to say something real. You weren’t tossing off a quick reaction while standing in line at Starbucks or half-watching TV. You were writing to someone. And maybe that’s part of why I keep thinking about Substack, because in a weird modern way, it feels a little like that.

I have no official data on this, but in my little corner of Substack, people are remarkably supportive of one another. Not fake nice. Not networking nice. Actually nice. Thoughtful, encouraging, generous. It has made me wonder whether Substack attracts a certain kind of person, or whether reading and writing regularly just brings out something better in people. I’m an optimistic person by nature, so maybe that’s part of it. But I’ve always believed most people are good at heart, and my little corner is only about 150 people right now. If this many thoughtful, kind, interesting people are out there, then there have to be thousands more.

I’m sure there are corners of Substack that are messy and competitive and annoying, because it’s still the internet. But in my little corner of it, people really do show up for each other. They read what you wrote. They say something thoughtful back. They recommend your work. They notice when you’ve said something honest, or funny, or hard to admit. It starts to feel less like posting into the void and more like showing up somewhere people are actually paying attention.

And that feels rare and I keep wondering why.

Why does this particular space, full of opinions and ambition and talent and ego and strangers, somehow feel more generous than a lot of the internet, and honestly sometimes more generous than real life?

I don’t think it’s because Substack is filled with unusually evolved people. I think it may be simpler than that. I think writing slows people down.

There’s a big difference between reacting and reflecting, and most of life right now rewards reacting. Fast opinions and quick judgments. Instant certainty. Everybody rushing to say something before they’ve even fully figured out what they think. Writing asks more of you, and so does reading. When you read someone’s work regularly, you’re spending time inside the way they think, their cadence, their humor, their perspective. Even if you don’t agree with everything, you get more than the headline version of them.

That matters. It’s a lot easier to dismiss people when all you see is a sentence, a label, or a caption. It’s harder to flatten someone into a type when you’ve been reading them for months. You start to hear the person underneath the opinion.

Maybe that’s part of what makes this place feel different. Not that everyone agrees, thank goodness, because that would be boring. But there seems to be more room for each other here. More curiosity and willingness to stay in the conversation. More people saying, I may not see it exactly the way you do, but I’m still here.

That feels old-fashioned in the best way, and I mean that as a compliment. It reminds me of a time when people wrote letters, or at least complete thoughts. I do remember writing letters to friends growing up, which now makes me sound like I was born in the 1800s and waiting on a telegram. It was a time when people didn’t just react. They responded.

Maybe that’s why Substack feels so refreshing. It feels a little more human.

Because many people are carrying a lot, private grief, stress, hope, money stuff, family stuff, big questions they’re still trying to sort out. Then they sit down and write something real, and someone on the other side of a screen actually takes the time to read it and say, keep going. That’s not nothing.

We talk a lot about how negativity spreads online, and it does. Cynicism spreads. Snark and meanness spread. But I’m starting to think support spreads too. One thoughtful comment changes the tone. One generous recommendation makes someone else want to be generous too. One person showing up sincerely makes it easier for the next person to drop the performance and be sincere too.

So maybe what feels special about Substack isn’t that it’s full of perfect people. Maybe it just creates the kind of space where people are more likely to be thoughtful with each other, more likely to act like other people actually matter.

A place where people can have different opinions, different values, different lives, and still make room for each other. A place where thoughtful disagreement doesn’t instantly become a cage match. A place where people can be smart, messy, funny, sincere, wrong sometimes, and still worth listening to.

It does make you wonder what would happen if we brought even a little more of that into real life. Not in some big dramatic world peace way. Just in normal life. In conversations, friendships, and families. In the way we respond when someone says something we weren’t expecting. In the way we listen before deciding who they are.

Maybe we’d understand each other a little better. Maybe we’d be a little less quick to sort everyone into categories and a little more willing to let people be whole, complicated humans.

I know. That’s a lot to ask these days. But again, I’m an optimist most of the time.

But still, if a bunch of strangers on the internet can create pockets of that, maybe we’re doing better than we think.

Or maybe Substack is just one of the last places left where people still act like they were raised to write thank-you notes. Honestly, I’m open to both theories.

… out of curiosity, I just looked up how many people are on Substack, and apparently it’s around 20 million. So maybe I’m onto something, or maybe I just won the lottery with my little corner of it. ❤️

Everyone is undefeated.
Everyone believes this is the year.
Even the guy who hasn’t watched a game since 2007 suddenly has strong opinions about bullpen depth and lineup strategy, as if he’s been in the dugout all winter.

It is the same energy as a nonprofit.

New fiscal year. Fresh goals. Clean spreadsheets. A board member says, “What if we just doubled revenue?” and everyone nods like that is a perfectly reasonable thing to say out loud.

Hope is doing a lot of heavy lifting.

But here is the thing, baseball and fundraising are basically the same sport, just with fewer hot dogs and more follow-up emails.

You do not win in one swing.
You win with consistency. With patience. With showing up again and again, even when you would rather fake your own Wi-Fi outage than send one more follow-up email.

A single? That is your $100 donor.
A double? Your $1,000 gift.
A home run? That donor who says, “I’ve actually been thinking about doing something bigger,” and you try to act normal while internally setting off fireworks.

And the walk?

The walk is the underrated hero of both baseball and fundraising.

Because sometimes the win is just... not striking out.

Every fundraiser has struck out.
You sent the email. Silence.
You made the ask. They said, “We’ll think about it,” which we all know lives somewhere between “maybe” and “this was a mistake.”

But then - next inning - you get a yes.
Or a “not now” that turns into a yes six months later after a few more convo’s, a coffee and a prayer.
Or someone forwards your email to a friend who somehow becomes your biggest donor and also owns a winery.

And if anyone understands that emotional rollercoaster, it is Mariners fans.

The Mariners made it all the way to the ALCS last season for the first time since 2001. They took the series to seven games, led it more than once, and still fell just short of the World Series. Which is both heartbreaking and, somehow, still impressive. It is also, now that I think about it, an excellent metaphor for fundraising.

Sometimes you do almost everything right.
You build momentum.
You get people excited.
You think, this is it. This is our year.

And then the gift does not come through.
The sponsor goes quiet.
The donor says, “Circle back in the fall,” which is fundraiser language for “I need this to leave my calendar immediately.”

But that is what a real run looks like.

Not perfect. Not clean. Not one big cinematic moment where everything comes together and the music swells.

Just people showing up. Taking the next swing. Staying in it long enough for something to break your way.

Baseball teaches something fundraisers need to hear far more often: failing seven out of ten times is still Hall of Fame behavior.

Imagine if we treated fundraising like that.

Instead of asking, “Why didn’t this donor give?”
we said, “Great, we’re batting .300. Let’s go.”

Also, can we talk about the dugout?

No one wins alone. Not in baseball, not in fundraising.

There is always a team behind it all. The board member texting, “I think I can fill one more table.” The person chasing sponsorships. The staff member fixing the registration list. The database manager quietly preventing total collapse while everyone else runs around talking about vision and impact.

Database people are the bullpen. I said what I said.

And then there is the crowd.

In baseball, they cheer.
In fundraising, they show up.

They buy the ticket. Fill the room. Make the gift. Bring the friend. Raise the paddle. Say yes. Say maybe. Say not yet. And sometimes come back around when the timing is right.

That is the magic.

Because most people do want to be part of something good. They just need an invitation that sounds like a human wrote it.

So here we are.

New season. New campaign. Same goal.

Show up. Take the swing.
Celebrate the singles.
Laugh at the strikeouts.
Stay in the game long enough for something good to happen.
And every once in a while, knock it out of the park.

And if not?

There is always the next inning.

Let’s Go Mariners!

For years, I thought showing up properly meant having it all buttoned up first. The thoughts organized. The outfit right. The work polished. The house presentable. The email answered. The tone cheerful. The hair doing something other than quietly protesting.

And then, at some point, life became very... layered.

Not tragic. Not dramatic. Just full.

Full of responsibilities, people, loose ends, grocery lists, unread texts, existential fatigue, and the humbling discovery that if you bend down too fast to pick something up, your whole body now wants a written explanation.

At a certain stage, you stop arriving anywhere as a finished product. You arrive as a woman who absolutely meant to drink more water, answer that email, return that call, and switch the laundry, but instead spent twenty minutes looking for her sunglasses while wearing them.

And honestly? That version still counts.

And let’s be clear - some of the women showing up a little undone are absolute boss babes. Highly successful. Highly capable. Fully in charge. They are leading meetings, making decisions, carrying entire operations on their backs... and also maybe realizing halfway through the day there’s still a tag hanging off the side of their shirt.

I say this as someone who walked into work recently, sat down, got through emails, had a full conversation with a colleague, and only discovered - upon removing my jacket - that there was a tag cheerfully hanging off the side of my shirt the entire time. Not a small tag. A tag. Did it affect the quality of my work? It did not. Did anyone mention it? They did not. Were we all fine? We were. These things are not mutually exclusive.

I think there is something oddly freeing about no longer needing to appear flawlessly assembled before participating in your own life. You can just come in as is. Smart, capable, funny, a little tired, maybe carrying too much, maybe forgetting one important thing and three unimportant ones, but still there. Still contributing. Still loving people well. Still getting good things done.

Some of the best people I know are not the ones gliding into every room as if they were steamed and pressed by a private team backstage. They are the ones showing up a little windswept, slightly behind, emotionally multitasking, with lipstick in their purse and seventy-three tabs open in their brain. And yet they show up.

They make the call.
They send the note.
They go to the lunch.
They do the hard conversation.
They bring the cookies in a store-bought container and dare anyone to complain.
They stop waiting to become some shinier, calmer, more optimized version of themselves before fully entering the moment.

That, to me, is a kind of confidence.

Not the confidence of “I have mastered life.”
The confidence of “I do not, in fact, have this fully under control, but I’m here.”

There’s a lot of power in that.

Because once you stop apologizing for being human, you get your energy back. So much of adulthood is wasted on little disclaimers. Sorry I’m late. Sorry this is messy. Sorry I forgot. Sorry I look tired. Sorry this isn’t better. Sorry I’m not more organized, more together, more effortless, more whatever the current standard is supposed to be.

Case in point: I had just pulled into my destination and was parking when someone called and said, “I texted you.” I immediately started apologizing for not seeing it, even though I had been driving and had not even had a chance to look at my phone yet. Apparently, I was prepared to take personal responsibility for not checking my phone while operating heavy machinery. That is how conditioned we are to lead with sorry.

What a colossal waste of a perfectly good life.

Some days are polished. Some days are survival with lip gloss.
Both are valid.

And maybe that is one of the better things about getting older: you begin to understand that perfection is not required for presence. You do not need to be flawless to be effective, lovable, invited, respected, interesting, or enough. You just need to show up without turning your own imperfections into a public relations crisis.

Wear the thing.
Say the idea.
Host the dinner.
Start the project.
Go to the event.
Push send.
Raise your hand.
Let it be a little uneven.

Most of life is happening in the imperfect version anyway.

And the people worth knowing were never asking for perfection. They were just hoping you’d come.

I recently had one of those mornings…

I had a meeting with someone I’ve worked with forever - one of those steady humans you can always count on. We’ve filmed more school moments together than I can track: kids building robots, kids breaking robots, kids explaining robots with the confidence of NASA engineers, and teachers in the background praying nothing sparks.

So I walked into our meeting in full “nonprofit brain” mode - thinking about everything and solving nothing. You know that feeling where you’re mentally answering emails, making lists, worrying about things that haven’t happened yet, and also wondering if you left the house with your glasses on your head? That.

But instead of talking logistics, we started talking about life.

Just casually.
And suddenly he unknowingly became the the spiritual equivalent of one of those giant red RESET buttons you’re not supposed to press—but suddenly everything changes when you do.

We talked about choices.
About God’s timing.
About how you don’t realize he’s covering you until you look back and go, “Ohhhh, that makes sense now.”
We talked about anxiety.
And gratitude.
And stress.
And how gratitude is basically the emergency brake for spiraling.

I explained how, when I start to get anxious, I stop and count what I’m grateful for, and thank God for every single thing on that list.

Some people meditate.
Some do yoga.
I apparently do gratitude triage.

And as I said it out loud, it hit me:
This conversation itself was something to be grateful for.

Here’s the funny thing I’ve learned:
Some people are like human chamomile tea.
You don’t know how much you needed them until you’re suddenly calm and thinking clearly again.

These are the people who:

• unintentionally talk you off a cliff you didn’t realize you were speeding toward

• ask one harmless question and somehow unlock your entire emotional inbox

• make you laugh at yourself right when you were about to submit your resignation to stress

• say one sentence that rearranges your insides more effectively than therapy

• ground you— - quietly, casually, without even realizing they did anything

They’re not trying to counsel you.
They’re not trying to deepen your spiritual life.
They’re not trying to prevent your head from exploding.
They’re just… being themselves.

And God absolutely sends them on purpose.

Not in a “voice from the clouds” way.
Not in a “burning bush” way.
Honestly, we’d ignore that anyway because we’d be too busy making a to-do list about it.

Instead, He sends a person.

A familiar one.
A steady one.
Someone who knows you well enough to notice you’re five seconds from overwhelm -even if all you said was “busy week.”

So today, this person showed up right on schedule.
We were supposed to talk video concepts.
We ended up talking about gratitude and perspective and life.
And afterward, I felt… reset.

Centered.
Clear.
A little lighter.

Nothing in my schedule changed.
But I changed.
Because one conversation reminded me that gratitude is bigger than stress, and God is very much in the details.

So here’s to the people who ground us without knowing it.
The mid-morning reset buttons.
The accidental spiritual chiropractors who realign our attitude with one well-timed comment.
The humans who make us breathe again, laugh again, and remember we’re not carrying everything alone.

May we notice them.
May we cherish them.
And may we occasionally try to be the calm in someone else’s chaos -

even if we don’t realize we’re doing it.

My calendar fills up with coffees, lunches, quick phone calls, and the occasional meeting with our superintendent. It’s the time of year when relationships built slowly over months - or sometimes years - turn into the gifts that sustain our schools.

People sometimes imagine major gift fundraising as a glamorous affair. Black tie galas. Perfectly rehearsed asks. Carefully crafted proposals.

In reality, it looks a lot more like coffee.

Coffee at 7:30 a.m. before work.
Coffee squeezed in between school drop-off and soccer practice.
Coffee that turns into a follow-up lunch three months later.
Coffee that slowly turns into trust.

Over the years, I’ve developed what I jokingly call the Coffee Test.

If someone will meet you for coffee, they care.

Maybe not enough to give a major gift yet. But enough to listen, enough to connect, enough to stay in the orbit of the mission.

And sometimes those quiet moments turn into something extraordinary.

The truth is, much of major gift fundraising is invisible work. The donor sees a 45-minute meeting. The fundraiser knows it took months - or years - to get there.

And occasionally, you don’t even realize you’re stewarding a donor at all.

One of the most extraordinary gifts I’ve ever received started with a small boy and a jar of coins.

One day, I got a call from a principal at one of our elementary schools. She told me about a student who had brought a jar filled with small trinkets back from a trip to China - where he had originally been born - and decided to sell them to raise money for the schools.

His teacher invited me to stop by their classroom, so I drove over to meet him.

When I arrived, he proudly showed me the jar where he had been collecting the money from selling his treasures. It looked like the kind of decorative jar you might buy in a market - likely the same jar that once held the trinkets he had brought back from China.

Now it was filled with coins and small bills.

He handed it to me with complete sincerity, the way only a child can when they believe deeply in what they’re doing.

We took a picture together with his teacher, chatted for a while, and I thanked him for caring so much about his school.

We still have that jar.

At the time, I had no idea it would become part of one of the most extraordinary gifts I would ever receive.

A few months later, I met his mom at a school event. She was warm and thoughtful, and we connected easily. Over the next year I invited her to events and we would catch up when we saw each other.

Nothing unusual. Just normal relationship building.

Then one day, right after the last bell rang on the final day of school, I was getting ready to head home for the summer when our administrative assistant came into my office.

“Someone is here to see you,” she said. “She wants to make a donation.”

In walked the student’s mom.

We chatted for a few minutes and caught up. Then she said something that stopped me cold.

“I want to help you reach your annual goal.”

That year our goal that year was $1.2 million. Around the schools we had large campaign thermometers so families could see how we were tracking.

She had already made a gift of a few thousand dollars earlier that year, so I asked her what kind of gift she was thinking about.

She smiled and repeated,

“I want to help you reach your goal.”

At that point we were still a long way from it.

Fundraising for the year was essentially finished. We had some money that we knew would trickle in over the summer, but the big push was over.

She asked again, calmly,

“How far from your goal are you?”

I told her I would pull a quick report.

When I did, the number was just about $300,000.

I told her.

She reached into her bag, pulled out her checkbook, and began writing.

Then she slid the check across my desk.

I about fell out of my chair.

I remember saying something like, “Are you serious?”

She was.

She was leaving for vacation the next day, and after she left my office, I just sat there for a moment trying to take in what had happened. In fundraising, you have moments you remember forever, and sometime leave you speechless. This was one of them.

Later, we invited her and her husband to meet with our superintendent, district leaders, our board president, and me. We wanted to thank them properly and talk about how their gift would support students.

During that meeting they shared the story behind the gift.

Her husband was still working abroad at the time, and despite the time difference - late nights for him and early mornings for her - they talked about it nearly every day. She had originally planned to give $1,000 and had been carrying that check around in her purse, even though they had already made a generous gift earlier that year. But every time she looked at the fundraising thermometer at the school, she felt like it wasn’t the gift she was meant to give.

For weeks, they prayed about what they felt called to do. I will never forget them telling me they truly believed God had placed this on their hearts. It was not casual or impulsive. It came from a place of deep faith, conviction, and generosity - and that has stayed with me ever since.

A few years, later their family moved away from our district and purchased a large piece of land. What began as a move toward a quieter life turned into something much bigger. Instead of simply living on the land, they chose to dedicate it to serving young adults with special needs, creating a place where people could gain job experience, community, and purpose.

In other words, they continued doing exactly what they had done in our schools - looking for ways to give back wherever life placed them.

And it all started, at least in my world, with a boy selling trinkets and a jar full of coins.

Fundraising books often talk about “the perfect ask.”

But moments like this remind me that major gifts rarely begin with perfect scripts or carefully crafted proposals.

More often they begin with small human moments.

A conversation in a hallway.
A coffee before work.
A school visit.

Most of the work of major gifts is invisible.

You show up.
You listen.
You connect people to something meaningful.

Major gifts don’t begin with perfect proposals.

They begin with trust.

And sometimes they begin with something as simple as a small jar of coins handed to you by a child who just wanted to help his school. That young man is now in college, and there is no doubt in my mind that he will continue to make a difference wherever life takes him.

The world needs more people who lead with that kind of heart. I have a feeling he will carry that with him wherever he goes.

I have a few purses I really like, and like any creature of habit, I pick one for the season and commit to it like it’s a marriage. That bag and I go everywhere together all winter. We’ve been through rain, errands, coffee runs, Target stops, emotional support lip gloss purchases. She knows my lifestyle. She has seen things.

And then, sometime around spring, I become violently sick of her.

Not because she did anything wrong. She’s been loyal. Dependable. A real workhorse. But one day I look at her and think, I cannot spend one more day with you. It’s over.

That’s when I know it’s time to switch purses, which sounds simple until you remember that changing purses is not a task. It is an event. A project. Something you need to block time for, like jury duty or a root canal.

Because the second I start emptying it out, it becomes clear I have not been carrying a purse. I have been hauling a mobile junk drawer.

Out comes 23 receipts, most of them faded beyond recognition, as if they were recovered from a shipwreck. Three chapsticks, even though I can never find one when I actually need it. Two lip glosses. Loose change. A cough drop with no wrapper. A pen that doesn’t work. Sunglasses I’ve been “looking for” for two months. A random gift card with somewhere between $0 and $11.63 on it. A granola bar so old it now feels historically significant. Not to mention the band-aids, a single earring and a key you are afraid to throw out that lives in the bottom of every purse for years.

And my purses are not even that big.

That’s the most offensive part. It’s not like I’m carrying a beach tote or a suitcase. This is a normal-sized handbag, yet somehow it contains the personal effects of a woman fleeing a small country.

There is always at least one item that makes me stop cold and wonder who I even am. Why is there a single bobby pin - I don’t even use them, one Advil, a crumpled Post-it with no note, and what appears to be a rock? Was I preparing for a migraine or starting a tiny campfire?

And of course the whole exercise becomes weirdly emotional. I find things I forgot I had. Things I’ve been missing. Things I was forced to replace because I thought they were gone forever. Apparently they weren’t gone. They were just living rent-free in a side pocket I haven’t opened since two Novembers ago.

By the end, I’m sweating, annoyed, and somehow less organized than when I started. I move the essentials into the new bag, then stare at the remaining pile like it has betrayed me personally.

But when it’s done? Euphoric.

A fresh purse. A new era. A cleaner, more organized version of myself.

For at least four business days.

Then it’s back to receipts, rogue lip products, and enough loose change to buy a cashmere sweater.

That’s not a hot take. It’s not frustration talking. It’s simply what you see when you’ve been inside the system long enough.

I’ve been working for the schools foundation since 2015. Before that, I served on the foundation board when my kids were in elementary school, which gave me an inside look early on. My kids went through this district for their entire K–12 education and graduated in 2020. That puts me in a very particular place - sitting squarely in the middle of the gap between what schools need and what funding actually covers.

As a board member, I saw the bigger picture. As a parent, I saw what made school meaningful for my own kids. And as someone working inside the foundation, I know what isn’t funded, what has to be raised locally, and how much effort it takes each year just to keep certain programs in place.

Once you see all sides of that equation, it’s hard to unsee it.

When the Numbers Don’t Match the Need

Washington is constitutionally required to fund basic education, but the reality on the ground is more complicated. The state covers part of the cost using a staffing-based model and other formula assumptions that do not always reflect what it actually takes to run a modern school system.

Even OSPI’s own funding materials make clear that Washington schools rely on a mix of state, local, and federal dollars - and that local levies continue to play a significant role in supporting what the state does not fully provide.

That gap shows up everywhere, and I’ve watched it in real time. But what stands out most to me isn’t frustration - it’s what happens when the gap is bridged.

I’ve been in classrooms where a principal and teacher are genuinely lit up because an enrichment grant made something possible - hands-on learning, creative exploration, a project that finally lets kids build, experiment, perform, or design instead of just talk about it.

You can feel the shift immediately.

Students lean in.

Teachers get excited.

Learning gets louder, messier, and more alive.

I’m thinking of one classroom in particular - desks pushed aside, kids on the floor with materials spread everywhere, half the room debating, the other half building. It wasn’t quiet. It wasn’t tidy. It was focused, energized, and completely student-driven.

The teacher was fully in it - moving around the room, asking questions, guiding conversations, letting students take the lead.

That experience existed because someone in the community helped fund it. Without that support, it would have stayed an idea instead of a moment.

I’ve seen that funding gap show up in very practical ways:

Special education funding that still does not always keep pace with actual need

Staffing allocations that can look reasonable on paper and much harder in practice

Mental health needs that continue to grow faster than available resources

Curriculum costs that rise faster than the dollars meant to cover them

Technology and digital tools that increasingly rely on local support to stay current

The Levy Cap: Simple on Paper, Complicated in Real Life

Layered on top of underfunding are Washington’s levy limits - policies intended to promote equity, but ones that also create real constraints for districts trying to meet community expectations. The rules are formula-driven and statewide, which means districts do not simply have unlimited ability to raise more locally when needs rise.

I’ve lost count of how many times someone has asked, “Can’t we just raise more locally?”

And I’ve gotten very used to answering, “No. We’re capped.”

There’s usually a pause after that - the kind where people are recalibrating what they thought they understood.

The cap is the cap, even when the needs are obvious.

High Expectations, Shrinking Flexibility

Schools in districts like ours have always relied on community support. That part isn’t new, and it’s important to say out loud.

What has changed is how little flexibility exists now to absorb costs or protect programs when funding falls short.

I remember when many programs felt more stable. Not fully funded - but stable. They didn’t require constant defense just to stay in place. There was more room to adapt, more room to absorb increases, and more room to plan ahead without wondering what would have to be cut next.

Now, keeping those same opportunities in place often requires ongoing advocacy, fundraising, and explanation - year after year.

Sometimes it feels less like growing programs and more like guarding them.

Expectations haven’t changed. The margin for flexibility has.

Costs Have Changed - The Model Hasn’t

At the same time, the cost of running schools has accelerated in ways the funding model does not fully capture:

• Special education and mental health supports

• Curriculum updates and instructional materials

• Technology, software, and cybersecurity

• Safety requirements

• Transportation

• Professional development

• Facilities that need constant care

None of this is optional. None of it is extravagant.

And not all of it is fully funded through the state model alone.

Districts aren’t being dramatic when they talk about budget pressure. They’re describing a system that expects modern outcomes while funding a much simpler version of school.

So Where Does That Leave Us?

I’m not writing this as a policy expert or a legislator.

I’m writing it from more than a decade of sitting in the room with district leaders, principals, teachers, and community members through the work of a separate 501(c)(3) schools foundation - helping turn real needs into real support and seeing firsthand how Foundation dollars can create flexibility when public funding falls short.

What’s needed isn’t complicated:

• A funding model that reflects actual costs

• More flexibility for communities within a fair statewide system

• Recognition that enrichment isn’t a luxury to the students who experience it as part of a meaningful education

• Adjustments that keep pace with reality

• A more honest partnership between the state and local districts

Because the current approach - the state funding part of the system and communities figuring out the rest - isn’t sustainable, no matter how committed the people are.

The Hopeful Part (From Where I Sit)

Even with all of this, there are things I see every day that keep me grounded.

I see teachers who keep innovating, even when resources are tight.

I see students take on new tools and ideas with ease, reminding me how capable they are when given the chance.

I see principals and teachers juggling more than anyone realizes because kids don’t pause their growth while adults debate funding formulas.

And I see parents - not all, but many - who want schools to feel alive for their kids.

I also see how much difference local support makes.

When the state stops short, community generosity creates room for creativity, deeper learning, and opportunities that stretch students beyond the minimum.

When I think back to that classroom - desks pushed aside, students building and debating, a teacher guiding rather than directing - it’s a reminder of what’s possible when resources meet imagination.

Those moments don’t happen by accident. They happen because someone decided they mattered enough to support.

That’s why I keep doing this work.

Not because schools need extravagance.
But because kids deserve opportunity.

The people inside our schools are doing everything they can.

It’s the system around them that needs to catch up.

Sources consulted: OSPI public school funding materials, recent Washington legislative analyses on levy limits and enrichment funding, and 2025–26 OSPI updates on special education and operating-cost pressures.

They do not announce themselves.
They are not usually the ones using words like curate as a verb.
They just quietly make life better.

And honestly, in a world full of chest-thumping, overposting, oversharing, overexplaining, and people calling themselves “thought leaders” before they’ve had one thoughtful thought, this feels worth mentioning.

The older I get, the more I am drawn to the people who do not need to perform their goodness for everyone in the room.

They’re just… lovely.

Not boring. Not bland.
Lovely.

And that word deserves a comeback.

Because lovely people are underrated.

They are the ones who text after something hard and don’t say, “Let me know if you need anything,” which everyone knows is the emotionally elegant cousin of doing absolutely nothing.

No, the lovely ones say, “I’m dropping dinner by at 6,” or “I’m outside,” or “I took care of it.”

They are the people who remember your kid’s name, your dog’s weird health issue, your big meeting, your mother’s surgery, and the fact that you once mentioned you like vanilla latte’s and one shows up when you need it most.

That sort of remembering tells you everything you need to know about a person.

I’ve known a lot of people over the years through work, life, raising kids, school events, sports, committees, fundraising, board meetings, and all the places women end up doing unpaid emotional labor in cute jackets.

And if there is one thing I have learned, it is this:

Character reveals itself in the small stuff.

Not in the glossy bio.
Not in the glossy Christmas card where everyone appears to have cooperated willingly and in perfectly coordinated outfits.
Not in the LinkedIn post about leadership.

In the small stuff.

How someone treats the assistant.
Whether they follow through.
How they act when there is nothing to gain.
Whether they make people feel bigger or smaller after an interaction.

Because you notice that kind of thing now.

You notice the people who stay a little longer to help stack chairs.
The ones who carry the extra bag.
The ones who introduce the person standing awkwardly alone.
The ones who make a gathering feel warmer without becoming the center of it.

That is a gift.

And it’s funny, because when you’re younger, you think charisma is everything. To be fair, some loud people are delightful. This is just my love letter to the ones who don’t need the spotlight to make a room better.

You think the funniest person wins.
The loudest person wins.
The person with the best stories, best house, best vacation photos, best whatever.

And then you get older and realize the real winners are the people you can count on when life gets chaotic.

Because life always gets chaotic.

At some point, all of us end up needing the friend who will sit in the hospital waiting room. Or remember to ask how your dad is doing. Or show up to the thing. Or send the note. Or tell the truth gently. Or make you laugh one inch away from crying.

Those are elite human beings.

And they are almost never the most self-congratulatory people in the room.

I think about this a lot because my work has given me a front-row seat to human nature.

You see generosity in all kinds of forms.

Yes, sometimes it looks like a big donation or a sweeping gesture.

But more often, it looks like someone quietly paying attention.

Someone asking a thoughtful question.
Someone taking time.
Someone following up.
Someone saying, “I’ve been thinking about that family,” and meaning it.

That kind of person is gold.

And the thing is, they often don’t even know they’re exceptional.

They just think they’re doing what anyone would do.

Which is almost funny, because no - not everyone would do it.
Not everyone remembers.
Not everyone notices.
Not everyone bothers.

The people who do are carrying more of the world than we give them credit for.

I also think there is something deeply comforting about realizing that the best qualities in a person are not flashy.

You do not need to be the most beautiful, the most brilliant, the most fascinating person at the table.

You can simply be the person who makes other people feel seen.

That is a kind of greatness no one talks about enough.

And maybe that’s why I find myself paying more attention now.

Not to the loudest person.
Not to the most polished person.
Not even to the most impressive person.

To the kind one.
The steady one.
The one with good energy, as my daughters would say.
The one who is easy on the nervous system.

Honestly, that may be my favorite category of person now: easy on the nervous system.

Mature.
Warm.
Funny without trying too hard.
Capable of having a real conversation.
Does not turn every discussion back to themselves like a human boomerang.

A dream, really.

Maybe this is just what age does to you.

It makes you less interested in sparkle and more interested in substance.

Less dazzled by image, more moved by decency.

More aware that the people who change your life are often the ones who never intended to.

They just kept showing up, and before you knew it, they had become part of the architecture of your life.

The ones you trust.
The ones you call.
The ones you never forget.

So here’s to the people who make life better without making a big production of it.

The chair-stackers.
The follow-through people.
The warm texters.
The rememberers.
The quiet noticers.
The ones who carry the extra load without needing applause.

They may not be the loudest people in the room.

But in the end, they are usually the best.

I have a lot of besties.

The kind you collect in different chapters of life.

Childhood friends. College friends. Post-college friends. Work friends. Mom friends. The ones who meet you exactly where you are in a particular season of life. I love every one of them.

But every once in a while, one group deserves its own story.

The beach years besties.

Mine came from college and those years right after - our twenties - when everything felt wide open and a little chaotic and we were all still becoming ourselves.

A group of us ended up living near the beach for a while. Venice. Manhattan. Hermosa. The South Bay. That stretch of life where you worked hard, played harder, and somehow still made it to work on Monday.

Mostly.

Two of them were sisters - both with a talent for bringing the fun wherever they went. If they were involved, odds were good the night was going to turn into something memorable. One of them I met at my first job out of college. Two days in, she popped her head over my cubicle wall and said,

“Hi… what are you doing this weekend?”

Not “Nice to meet you.”
Not “Where are you from?”

Just straight to the important question.

And that was basically the beginning of the beach years - the very fun, slightly chaotic ones.

Suddenly there was a whole crew of us - friends from college, work, and shared apartments - all orbiting around the same few miles of coastline and determined to squeeze every possible ounce of fun out of our twenties.

We didn’t have much money.

A lot of meals were rice and soy sauce. Sometimes, on the good days, Goldfish crackers.

Our waiter at Killer Shrimp in the Marina never quite understood why it was always, “Hold the shrimp.”

We’d just eat the rice.

But life felt simple and incredibly fun.

There were Thursday nights with two-dollar pitchers.
We’d go out early… then run home to watch 90210 and Melrose Place… and then head back out again.

.

No cell phones back then.

If you didn’t make it home in time to regroup, you just had to go out and find your crew somewhere along the Strand.

And somehow you always did.

There were day parties on the Strand. Beach volleyball. Road trips. Night swimming in the ocean. Pitchers of beer. Boxed wine. Dating. Sharing clothes. All you can drink mimosa brunches. Spending our whole paycheck at Cal Beach Sushi. Laughing so hard you could barely breathe.

The bouncers at the local bars all knew us.

At one point I lived in Venice Beach with one of my girls. One night we came home to find our entire block caution-taped off and surrounded by police.

Turns out no one had mentioned we were living right on the border of a slightly sketchy neighborhood.

In hindsight, maybe we should have noticed the apartment across the street had bars on the windows.

But we were in our twenties and mostly just thought, How cool is this? We live in Venice.

We stood there staring at the flashing lights like… well, that seems like something someone should have told us.

Needless to say, we didn’t stay in that apartment much longer after the police incident.

And as I’m writing this now, I suddenly remember that we had a goldfish in that apartment.

Why did we have a goldfish?

To this day I honestly have no idea.

We were girls in our twenties - untethered, free, living by the beach, working just enough to pay rent and buy two-dollar pitchers. Apparently at some point we also decided we needed a pet fish.

I still can’t explain that decision.

Those were the years when life felt like an adventure almost every day.

The kind of years when friendships form naturally because you’re simply living life together.

And those women were there for so many of my big moments too.

They celebrated with me in some of life’s happiest times and showed up when life was harder too.

They’ve laughed with me, supported me, and seen me through different chapters of life.

One of my besties eventually moved to London for work and lived there for years. We even managed to continue the fun there on a visit or two - because apparently the beach years besties can cause a little harmless chaos internationally. She’s back now on the same coast, and of course we picked up right where we left off.

Others landed in different states and cities. Life slowly scattered us in different directions, the way it tends to do.

Two of my girls moved back to Chicago, but the fun simply relocated with them. One of them got married and had a baby — which felt slightly shocking to those of us who still thought of ourselves as the beach years besties. Naturally, we introduced that baby to his first bar.

Boyfriends. Jobs. Moves. Marriages. Families.

We stayed in touch as much as we could.

But it was never quite the same as those years when everyone lived together, down the street or a few blocks away.

Still, something about friendships like that never goes away.

Because the women who knew you in those years knew you before the polished version of life showed up.

Before careers were fully formed.
Before responsibilities multiplied.
Before the years started stacking up.

They knew the original version of you.

And they carry pieces of your story.

Each of them brought something extra to those years. Together, even the simplest plan somehow turned into an adventure. We laughed a lot, convinced each other that going out was always the right decision, and somehow managed to turn ordinary nights into stories we still tell today. One of us could even get us into any bar in the South Bay - no matter how long the line (you know who you are). We sometimes fought but always forgave. And somehow, every time we were together, the night was guaranteed to be more fun.

Over the years we’ve found ways to reconnect - sometimes after long stretches of life happening in between - and the funny thing is the laughter comes back almost immediately.

Maybe a little wiser now.

Definitely with better wine.

But still the same girls who helped shape who you become.

And I love every single one of them.

They are in so many of my best memories.

And they will always have a place in my heart.

They know who they are.

And if you’re lucky enough to have a group like the beach years besties - the girls who knew you before life got more complicated, when you were still becoming yourself - then you know exactly what I mean. 💛