12 Skills Fundraisers Need For What Comes Next: #6 Thinking Upstream

Yes, yes — I know.

Yesterday we talked about Systems Thinking, and today we’re talking about Thinking Upstream.

That is a lot of thinking in a row.

Before anyone panics, this is not the kind of thinking where we sit around, stare thoughtfully into the middle distance, and say things like, “Hmmm,” while absolutely nothing changes.

When I say thinking, I mean how we frame the situation before we act.

Where we look first. What we assume is causing the problem. What story we’re telling ourselves about why something is happening.

Because once the story is set, the response usually follows — whether it’s helpful or not.

Which brings me to a story you’ve probably heard before, but that’s worth retelling because it is uncomfortably accurate.

The River Story (Fundraising Edition)

A group of people are standing by a river when someone notices a person floating downstream, clearly in distress.

One of the group jumps in, pulls the person out, gets them on the river bank, and helps them recover. Everyone exhales. Crisis averted.

Then another person floats by. And another. And another.

Pretty soon, everyone is scrambling. People are diving in, hauling folks out, coordinating help, shouting instructions. It’s exhausting. It’s chaotic. It’s urgent and relentless - the river rapids are now full of people floating by . . .

Finally one person stands up and walks away, heading upstream.

“Where are you going?” someone yells. "These people need help and there are more coming!"

“To see why people keep ending up in the river,” they reply.

Upstream, they discover the problem: a bridge with a giant hole in it. People keep falling through.

No sign. No barrier. No orange cone. No handwritten Post-it that says, “Hey, maybe don’t walk here.”

You’d think someone would’ve addressed that by now.

But, well . . . people are people.

Why Fundraisers Live Downstream

Fundraisers are very good at pulling people out of rivers.

Campaign underperforming? Jump in. Revenue soft? Jump in harder. A donor is upset? Drop everything. A deadline appears out of nowhere? All hands on deck.

Downstream work is urgent. It’s visible. It’s rewarded. It’s where fundraisers earn their reputations as fixers and responders.

Upstream work, by contrast, looks suspiciously like not doing anything. (Dare we say there's no apparent ROI? (oh, but there is - but I digress).).

It’s quiet. It’s preventative. It doesn’t come with applause, adrenaline, or last-minute heroics.

And that’s why it’s so often postponed until “later,” which, as we all know, is a magical time when everything is calmer and everyone suddenly has capacity. (Tell me when "Later" arrives; so far I've not seen it. Not by that definition anyway.)

Thinking Upstream Does Not Mean Abandoning The River

Let’s be clear.

Thinking upstream does not mean ignoring the people currently floating downstream.

You don’t leave folks in distress while you wander off to contemplate infrastructure like some kind of detached philosopher.

Thinking upstream means asking a second question in addition to responding:

And then — this is the harder part — being willing to address that answer, even when it’s less dramatic than another rescue.

How Systems Thinking and Thinking Upstream Actually Work Together

This is where it’s worth pausing, because Systems Thinking and Thinking Upstream are not two separate skills you deploy independently.

They’re a matched set.

Systems Thinking is what helps you see the whole — the interdependencies, the feedback loops, the way pressure moves through an organization instead of disappearing.

Thinking Upstream is what helps you notice where in that system things begin.

You need both.

Without Systems Thinking, “upstream” is just a vague idea. You don’t know what feeds what, so everything feels downstream. Every problem looks like it appeared fully formed, demanding immediate attention.

Without thinking upstream, Systems Thinking risks turning into, well, navel gazing.

Lots of insight. Lots of elegant diagrams. Very little actual change.

Together, though, they do something powerful.

Systems Thinking lets you recognize that there is an upstream — that today’s crisis is often yesterday’s design choice.

Thinking Upstream gives you a way to act on that awareness — to trace causes, adjust earlier decisions, and redesign parts of the system before they create new emergencies.

One without the other is incomplete.

Together, they move you from constant reaction to intentional design.

And that’s not thinking for thinking’s sake.

That’s thinking so the work gets easier later. And "thinking", in our terms, leads to planning which leads to actions which lead to habits which lead to RESULTS.

This Isn't a New Idea (Which Should Be Comforting)

If this concept feels familiar, it’s because it is.

Chip and Dan Heath wrote an entire book — Upstream — about exactly this phenomenon.

Their central argument is simple and quietly devastating: we spend enormous energy reacting to problems we could have prevented if we were willing to look earlier, slower, and deeper.

Sound familiar?

Fundraising is full of downstream heroics and upstream avoidance.

What Thinking Upstream Looks Like in Fundraising

Thinking upstream isn’t a retreat exercise or a strategy deck. It shows up in small, often unglamorous decisions.

It looks like:

• fixing data entry standards before buying new software

• clarifying expectations before launching another initiative

• repairing stewardship processes before chasing new donors

• documenting decisions so you don’t have to re-litigate them every year

• saying “not yet” instead of “sure, we can squeeze that in”

Upstream work is rarely exciting in the moment.

But it’s deeply satisfying six months later when you realize you didn’t have to stage a dramatic rescue because the bridge didn’t collapse in the first place.

Why We Resist Upstream Thinking (Even When We Know Better)

There are a few reasons this skill is harder than it sounds.

First, upstream work doesn’t produce immediate wins. You don’t get congratulated for preventing a crisis that never happened.

Second, upstream problems tend to be shared problems; no single person “owns” them, which makes them easy to ignore and hard to fix.

Third — and this one matters — downstream work feeds our identity.

Fundraisers are helpers. Fixers. Responders. We are very good at stepping in when things go wrong.

Upstream thinking asks us to trade some of that adrenaline for foresight.

That’s not a moral failing. It’s a cultural habit. And habits can be changed.

Where To Spot Upstream Opportunities

If you want to practice thinking upstream, look for patterns.

• Appeals that need “saving” every year

• Events that drain energy disproportionate to their impact

• Staff burnout that keeps resurfacing

• Donors who consistently feel confused or unseen

• Data issues that never quite get resolved

Those aren’t random failures, they’re signals.

They’re people floating downstream, quietly pointing you toward a hole in an upstream bridge.

Thinking Upstream Is a Form of Care

This part often gets overlooked.

Thinking upstream isn’t just strategic, it’s humane.

Poor upstream design creates constant urgency downstream. Constant urgency erodes trust, energy, and joy.

Good upstream thinking respects:

• staff time

• donor relationships

• organizational capacity

• your own nervous system

It says, “We don’t have to keep living like this.”

And sometimes, that’s the most radical thing you can say in fundraising.

This Is Not About Perfection

You’re never going to eliminate every hole in the bridge.

People will still fall in the river. Stuff will still break.

Fundraising will always involve uncertainty because humans are complicated and emotions are real.

Thinking upstream doesn’t promise a problem-free future.

It promises fewer avoidable emergencies.

And that’s a very different — and very worthwhile — goal.

Tomorrow We Plan Downstream (On Purpose)

If thinking upstream is about noticing patterns and causes, then tomorrow’s skill — Downstream Planning — is about realism.

Because even with the best upstream thinking, things will still go sideways.

Downstream planning isn’t pessimism.It’s professionalism.

For today, though, the invitation is the next time you feel the urge to jump into the river yet again, pause just long enough to ask:

That question alone is a skill.

And it’s one worth practicing.