THINKDROP 45: It's Rollercoaster Month. Stop Looking for the Seatbelt.
Monday: a prospect I chased for three months finally says yes.
Tuesday: he goes dark.
Wednesday: a client I thought was gone reopens the conversation like nothing happened.
Thursday: a deal I'd already mentally closed gets pushed to "let's revisit in Q4."
Friday: someone I hadn't spoken to since June sends a brief out of nowhere.
That's not a bad week. That's rollercoaster month.
Every year I forget this, and every year it costs me a few days of frustration before I remember: September doesn't restart business — it re-negotiates it.
Everyone comes back from the summer at a different speed, with a different budget, a different priority list, and nobody tells you which one you're dealing with until you're already mid-conversation. The rules of the game get rewritten every morning, and they'll keep getting rewritten until early October, when things finally settle into a rhythm everyone can plan around.
The mistake is treating each swing — the yes that goes quiet, the maybe that turns into money, the reschedule that reschedules itself — as a verdict on the work, on the pipeline, or on you. It isn't. It's just rollercoaster month running its course.
Here's what actually works this month.
Pierre Stanghellini
Founder @ HARi.wtf
1. Expect the Ground to Move
The prospect who ghosts on Tuesday isn't necessarily gone. The client who reopens on Wednesday isn't necessarily back for good. Both are true at once, and neither is final.
Judging your month by any single data point in September is how you talk yourself out of the work that's actually paying off.
TRY THIS: Before you react to any one signal — good or bad — wait 48 hours and see if it repeats. One data point is noise. Two is a pattern.
2. Silence Is Not Disappointment
Someone not replying in September usually means they're still digging out from their own backlog — not that they've decided against you.
Taking it personally is optional, and it's the most expensive thing you can do with your energy this month.
TRY THIS: For every prospect gone quiet, send one short, no-pressure nudge — then move on to the next conversation instead of refreshing your inbox.
3. Control Activity, Not Outcomes
You cannot force a delayed conversation back on schedule. You can control how many new conversations you start today.
In a month this unpredictable, activity is the only lever that's fully yours — so overinvest in it deliberately, especially on the days when nothing seems to be landing.
TRY THIS: Set a daily minimum of new outreach — calls, emails, intros — that doesn't depend on how yesterday went. Hit it regardless of mood.
4. Build a Floor Outside the Pipeline
Patience and discipline are easier to hold onto when they're not the only thing keeping you upright.
This year, mine is simple: a little more prayer, a little more deliberate time off the clock, away from screens and deal updates.
Not as a reward for a good week — as ballast for the unpredictable ones.
TRY THIS: Pick one non-negotiable outside of work — a walk, a workout, a quiet ten minutes, whatever grounds you — and protect it especially on the days the business news is bad.
5. Luck Rewards Motion
The deal that came out of nowhere on Friday didn't come from a perfect plan. It came from having stayed visible and active through three days where nothing seemed to work.
Positivity in September isn't naivety — it's a bet that the volatility eventually shakes something loose, and it usually does.
TRY THIS: End each day by writing down one thing that moved forward, even small. On the chaotic days, this is the only proof you have that momentum is still building.
5-Point Recap
The ground will move daily until early October — plan for volatility, not stability.
One quiet prospect or one reopened deal is a data point, not a verdict.
You can't control timing or moods on the other side of the table — only how much you show up today.
Protect something steady outside of work — it's what makes the unpredictability inside work bearable.
Stay in motion — opportunities in a reshuffled market go to whoever's still active when it lands in their favor.
Food for Thought
October will feel normal again. The calendars will sync back up, the replies will come on schedule, and the whiplash of this month will already be hard to remember. That's exactly why it's worth naming while you're in it: rollercoaster month rewards the people who kept their hands up, not the ones scrambling for the seatbelt.
Every "yes" that goes quiet, every deal that reopens out of nowhere, every conversation that gets pushed and then suddenly isn't — none of it is a verdict. It's just the market re-shuffling itself in real time, and you happen to be standing in the middle of it. The version of you that treats each swing as personal will spend September exhausted and second-guessing. The version of you that treats it as weather — something to dress for, not something to take personally — will come out the other side with a pipeline that's actually stronger, because you kept showing up while everyone else was waiting for it to calm down.
It won't calm down until it's ready to. Your job isn't to control the timing. It's to still be standing, still be reaching out, still be steady, when it does.
So take another look at the photo up top. That's rollercoaster month in one frame. Which one have you decided to be this month? It's really up to you.
Pierre Stanghellini
Let's connect; drop me a line directly at pierre@hari.wtf .
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About the Creator
Pierre Stanghellini is a creative strategist, systems thinker, and curator of mental rabbit holes. He created Thinkdrop Weekly to feed the brains that don't want the same old Business advice. If you're building something bold, beautiful, or strange, this is your corner of the internet.
About HARi.wtf
HARi.wtf is a creative strategy studio for businesses that hate business-as-usual. Born in Hong Kong, in 2017, we work with restless founders, operators, and teams who'd rather break things thoughtfully than grow them blandly. We don't do generic decks or bloated strategies; we build clarity, guts, and traction.
From street-level restaurants to global brands, from Asia to Europe, we help shape ideas that move fast when it matters, and slow when it counts.
Explore more at HARi.wtf
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