- Sandy Gallagher
- Read Time: 6 Minutes
What You Need To Know
May doesn’t create new problems, it exposes them. When everything feels urgent, don’t try to do more. Stay focused on the relationships that matter most.
Choose a few key people, take the next step with intention, and protect time for what actually moves your work forward. You don’t need a new strategy, just discipline in the one that works.
Key Takeaways
- Narrow your focus to 5 to 10 key relationships
- Go deeper, not broader, in your outreach
- Lead with purpose, not urgency
- Protect time for what matters most
- Take one simple step to keep momentum going
May Is Coming. Now What?
If you work in a school, or have kids in one, you can feel it coming. The calendar is already full. Events are stacking one on top of another. Evenings will soon disappear, and weekends will follow. Layered into all of it is a quiet but persistent thought…
How am I going to handle this month?
And, as a nonprofit or development leader, there’s likely an added pressure…
We need to connect with donors before summer.
It’s why people call it “Maycember.” All the pace of December, but worse, none of the structure. And, when teams are in the thick of it…or near the end of it…they’re feeling the same thing. Busy…with no confidence any meaningful progress is being made.
We see this pattern every year. May doesn’t create new challenges, it exposes existing ones. When the pace increases:
- Priorities blur
- Relationships default to convenience
- Messaging becomes rushed
And without realizing it, teams slip back onto a familiar cycle of overthinking and overactivity. They’re moving constantly, but not always with intention or direction.
So, rather than asking…How do we survive May?
Let’s ask…When May hits, how do we stay anchored to what actually works?
In this article, we outline just how we’d approach Maycember in real time to ensure we anchor ourselves and our work in what we know matters…relationships.
When Everything Feels Urgent, Narrow Your Focus
In the month before summer hits, everything starts to feel equally important.
- The event this week.
- The meeting or follow-up you need to schedule.
- The donor you’ve been meaning to call.
- The ‘we should probably reach out to them before summer’ list.
So you try to hold it all and progress stalls.
Instead, choose a smaller set of relationships and protect them. Focus on 5 – 10 relationships that actually matter right now. Define the next right step for each. Take it and let the rest wait.
If May is full (hint: it is), focus is your only leverage.
When You Feel Pressure to Reach Everyone, Go Deeper, Not Broader
There’s a natural instinct in a hurried season to widen the net. More emails. More touches. More ‘just checking in before summer.’
It feels productive and responsible, but often that activity leads to communication that is rushed and easy to ignore.
Instead, resist the pull toward volume and stay with depth. If a relationship is already in motion, stay with it, move it one step further. Think…
- A thoughtful follow-up rather than a quick check-in
- A real conversation rather than a general update
- A clear next step rather than an open loop
You don’t need to reach everyone before summer. You need to meaningfully advance the right people with intention.
When Conversations Start to Feel Rushed, Anchor in the “Why”
In a busy month, communication tends to get compressed. You find yourself saying…
- Before summer…
- As we wrap up…
- One last opportunity…
All true, and all timing based. Inherently, this results in very little meaning and certainly nothing rooted in answering the donor’s real question…’Why does this matter?’
Instead, slow down just enough to reconnect your outreach (that intentional outreach to the prospect already in motion) to purpose. Even a short message can carry clarity and meaning:
- What is being sustained or strengthened right now?
- Why does it matter?
- Why does this donor belong in this story?
Urgency without meaning gets ignored. Clarity cuts through and creates meaningful engagement.
When Your Schedule Takes Over, Decide What Won’t Budge
May will fill itself. That part isn’t solvable. What is solvable is whether the most important work gets squeezed out. Here’s a hint…without intention, it most certainly will.
Instead, decide in advance what doesn’t get pushed…what gets prioritized. Protect something small but meaningful:
- 30 minutes, twice a week for donor planning
- A short, weekly check-in on your top relationships
- A commitment to follow through on conversations already started
You don’t need more time or to control your entire calendar. You just need to protect a certain few things within it.
When You Start Overthinking, Do One Simple Thing
This is where the hamster wheel of how shows up again. Not in theory, but in practice. You start thinking:
- Is this the right time?
- What should I say?
- Should I wait until after this event?
And in a month like May, that thinking quickly turns into delay.
Instead, simplify the action. Make one call. Send one note. Follow up on one conversation. Not ten, just one. Because momentum doesn’t come from perfect timing, it comes from starting.
The Real Answer to “How Do I Survive May?”
May doesn’t have to be something you survive. It can be something you move through, intentionally.
You may not be able to control or slow the pace, but you can control your focus. The risk isn’t the busyness. The risk is that the busyness causes you to drift from what you know works. The drift from clear priorities, from meaningful relationships, and from the work that actually moves things forward.
At Mission Advancement, we know the basics aren’t boring, they are bankable. Clear focus, relational depth, consistent cultivation and stewardship. It’s simple, not complex, and not accidental either.
Before the month begins (that gives you 16 days), take 20 minutes and ask:
- Which relationships matter most right now?
- What is the next step for each?
- What will we protect, no matter how full the calendar gets?
Then start with one. May doesn’t require a new strategy, it just requires doubling down and staying disciplined in the one strategy that works.
