The 60 Day Lead Up...

We’re in the heart of the second half of the year, and I want to hit you with a truth that too many agents miss: September and October are the two most important months of the year to build momentum, drive sales, and separate yourself from the rest of the pack.

Why? Because while most agents think November and December are “dead zones,” the reality is they aren’t. What kills production in Q4 isn’t a lack of prospects—it’s the MANY agents who take their foot off the gas when the calendar flips to holiday season. That means if you get busy now, you not only fill your pipeline for this month, but you also lock in business for November and December while everyone else is asleep at the wheel.

Let’s dig into why these months matter so much—and then I’ll give you 3 September and October-specific strategies you can run with right now to guarantee more at-bats and more wins.

Why September and October Make or Break Your Year

Prospects Aren’t Closed for Business—Agents Are

Look, I get it. People say, “Nobody wants to talk about insurance during the holidays.” That’s a lazy excuse. November and December are filled with families making financial decisions, small businesses trying to close their books strong, and people planning for the new year. That means they’re thinking about risk, budgets, and coverage. Translation: they’re open.

What happens is that agents convince themselves it’s a slow season. They mentally check out, do less prospecting, and put off follow-ups until January. And guess what? The prospect who would have bought ends up with someone else—or worse, goes without.

September and October are your chance to lock up those opportunities before the other guy even shows up.

Momentum is Everything

Ever notice how a football team that goes into halftime hot usually carries that into the second half? Same thing here. If you build strong momentum in September and October, you don’t limp into the holiday season—you roll into it. Every deal you’re working now spills over into November and December. And while other agents are coasting, you’re closing.

The Window is Short, Which Creates Urgency

Let’s be real: September and October fly by. Kids are back in school, holidays are around the corner, and everyone’s calendars fill up fast. That compressed timeline creates urgency—both for you and for your prospects. When people feel like the clock is ticking, decisions get made faster. If you work the right angles, you can turn that urgency into signed applications.

September/October-Specific Strategies to Get More At-Bats

Now that you see the opportunity, let’s talk about how to maximize it. I’m not going to give you the same generic “prospect harder” nonsense. I want you to walk away with strategies tailored to the September/October reality that will put more people in front of you and more deals on your board.

Strategy 1: Back-to-School Networking Blitz

September is a goldmine because everyone is back from summer, kids are in school, and routines are reset. Parents are standing around at practices, PTA meetings are happening, school fundraisers are in full swing. Translation: opportunities are everywhere.

Here’s how you capitalize:

Be Present at School-Related Events: Whether you’ve got kids in school or not, there are games, concerts, fundraisers, and community nights happening constantly this time of year. These are natural networking hubs. Show up, shake hands, and talk about what you do in a conversational way.

Sponsor Something Small and Visible: For a couple hundred bucks, you can sponsor a team, buy water bottles for a fundraiser, or put your logo on a banner at the football field. Parents notice that. And when they’re thinking about insurance—boom, you’re top of mind. More importantly - SHOW UP - go to a handful of games and hand things out to the parents and players. Be a presence. Build relationships. 

Leverage Social Media Around School Season: Post about supporting local schools, share “back-to-school safety tips,” or highlight community involvement. People love seeing local businesses support kids. It builds goodwill and gets you conversations.

September is all about inserting yourself back into the community rhythm. Everyone’s looking to connect again after the summer slowdown—be the agent they connect with.

Strategy 2: Pre-Holiday Financial Checkup Campaign

October is when people start tightening budgets, prepping for holiday spending, and making year-end financial decisions. That’s your sweet spot. Position yourself as the one who helps them get their house in order before the chaos hits.

Here’s what to do:

Run a “Before the Holidays Hit” Campaign: Create a simple message—“The holidays are coming fast. Now’s the perfect time to review your coverage, lock in better rates, and make sure your family is protected heading into the new year.” Send it to your email list, text old leads, and post it on social.

Target Small Businesses: October is when small business owners are looking at their year-to-date numbers and projecting year-end. They’re hyper-aware of expenses and risks. Reach out with a “Let’s make sure you’re set for Q4” approach.

Use the Calendar as Leverage: Say, “If we get this done now, you won’t have to think about it during the holidays.” That’s an easy win for people who want one less thing on their plate.

This strategy works because you’re aligning with what’s already on people’s minds: budgets, family, and planning. You’re not fighting the calendar—you’re using it.

Strategy 3: Thanksgiving Pipeline Prep

October is your month to stack the deck for November. While other agents are coasting, you’re going to build a massive follow-up list that carries you straight through the holidays.

Here’s how:

Audit Your Pipeline: Go through every lead, old quote, and half-finished conversation you’ve had this year. If it’s not dead, it’s alive. Make a master list.

Run a “Gratitude Touch” Campaign: Send a simple, personal note, text, or voicemail to your contacts in October. Something like, “Hey, just wanted to say thanks for connecting with me this year. I’m grateful for the people I’ve gotten to help. If you’re still thinking about coverage, I’d love to revisit before the year wraps up.” It’s soft, warm, and opens doors.

Stack Appointments Before Thanksgiving: Make it your goal to load up your calendar the week before Thanksgiving. People are around, they’re less distracted than in December, and they’re often in “let’s get this done before the holiday” mode.

By mid-November, while everyone else is whining about how “slow it is,” you’re closing deals that you set up weeks earlier. That’s the difference between agents who coast and agents who crush it.

The Bottom Line: Play While Everyone Else Rests

September and October are your chance to separate from the herd. Prospects are still open for business—but the real edge comes from the fact that so many agents aren’t.

While others are telling themselves “November and December are dead,” you’ll be the one building momentum, setting appointments, and closing deals. And the ripple effect carries into January, where you’re already in stride while everyone else is trying to “restart.”

So here’s your challenge: treat September and October like playoff season. Execute these 3 strategies:

Back-to-School Networking Blitz – Get in front of parents, schools, and community events.

Pre-Holiday Financial Checkup Campaign – Align with family and business financial planning before the holidays hit.

Thanksgiving Pipeline Prep – Audit, touch base, and load your calendar with appointments before the holiday slowdown.

You don’t need new leads falling from the sky. You need to work the timing, work the psychology, and work harder than the agents who are already coasting.

Because come December 31st, you’re either going to look back proud that you finished the year strong—or you’re going to be making excuses like everyone else.

And you and I both know excuses don’t pay commissions.