The Joy-Rises in September

A sales strategy for life planning

Back when I worked in the corporate world, my year was ruled by quarters. While I was never in sales myself, the team I managed directly supported the sales team, and that meant we learned a lot about when to hustle and when to ride the wave. To a one, the most successful sales people I worked with, those that repeatedly made President’s Club, said the same thing…

“You can’t make up for a bad first quarter.”

These folks understood something about the way money rolls down hill during a calendar year. They realized that if they missed their quota in Q1, they were playing catch up the rest of the year, and if they bonked again in Q2 there was no math that got them to quota for the year. So, they never missed in Q1. It didn’t matter what they had to do.

It also meant that by the time they got to Q4, their success was on lock.

They never took their eye off the prize, and made sure every single deal was closed by December 31st, but they backed off the fire power a little in Q4 and shifted focus.

They started thinking about next year.

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September 1st is the official start of Fall in my brain. I could give a shit that the calendar disagrees with this notion and often the weather, although it is playing along nicely this year. September is my happy month. The madness (and humidity) of summer is behind me, the sounds of football fill my ears, there are firepits and changing leaves and cozy sweaters and pumpkin bread (I said nothing about a PSL).

But taking a note from my sales mentors, its also my strategy month. Typically, the rest of my current year is planned out already. The vacations are paid for, the Halloween costumes are ordered, and I know I’ll be frantically stalking fifty-two pages of Shutterfly holiday cards before I know it. I have committed my energy for the remainder of 2025.

But what about 2026?

Who do I want to be next year? What do I want to open myself up to? Where will my Q1 hustle be dedicated?

It’s a hard shift that happens come September 1st, so I just started thinking about these questions on Monday, and the answers are currently encased in thought bubbles bouncing around my brain. Some have landed and are already taking shape. Others feel buoyant still, floating around such that I have only glimpsed what’s inside. But I can perceive their gestalt, even if I’m not yet sure of their make up.

Strategy is my sweet spot, the space where I experience flow, where I am automatically energized by mindcrafting the work ahead. It’s the possibility that intrigues me, future joys that exist as mere outlines for now, their insides poised to be filled with what I and those I choose to work with pour in to them.

This is when I am my most creative. It’s when I dare to dream without reality using a perfectly coiffed fingernail to pop a hole in each beautiful bubble. In September, I can tell her to fuck off until January. So I dream big in September, and lean hard in to a future vision of myself that feels aspirational so I have something to live in to.

In no particular order, here are the joy-rises on my horizon for 2026.

1. Travel - Any time I am about to go do or see something, my husband asks me “Are you excited?” I usually balk at the question because its the wrong adjective for how I actually feel. Something more precise is called for. But when I’m airport-bound to hop on a plane to travel somewhere I’ve never been before, I am excited. I want to explore in 2026, go big and go bold. My daughter is older now and can handle more intense travel. She’s learning to speak a second language and can survive on granola bars and cheese sticks if she has to. It’s time to up our game. I’m also all about taking my work abroad. One of those upcoming adventures is a 5-day creating writing retreat in Northern Italy in September 2026 that I’m co-leading with Soul Speak Press. Message me for details if you, too, would be excited to join me.

   

2. Substance - I feel like 2025 was my year to dabble. I did a little of this, tried a touch of that, experimented with a bunch of shit, and got a taste of everything. I needed to do that. There was much to learn and so I said “Yes” to a lot of little things to harness the broadest and most diverse set of experiences possible. But now I’m the announcer for the US Open trying to cover six tennis matches at once. My head is not just on a “left…right…left…right” pivot, it’s doing the bobble on a 360 degree axis. I can’t sustain that, nor do I want to. I’m reflecting on what I enjoyed most in 2025 so I can intentionally invest in diving deeper there. That’s true in my professional world and also my personal one. Striving for greater substance in one area or with one human will inevitably mean a letting go in other areas and with other humans. I’m not great at letting go, so that intentionality will have to be dedicated to both directions.

3. Comfortable - Recently, my husband and I had a conversation about money. The conversation was borne from three weeks of straight bullshit as the future of his job was batted around by two parties in a pissing match over who has the bigger dick. It was an important lesson for us in humility and the desire to control our financial future no matter who wins the dick competition. My husband asked what my financial goal was, and I said “To be comfortable.” As you can imagine, for someone who leans heavily on literality, “comfortable” was a bit vague for him. We’re working on the definition of that term, honing in on what it would feel like to be “comfortable” and what amount of money would be required for us to achieve that end. There are some clear cut things that need to happen for us to get there, and tackling those are my goal for 2026.

“Comfortable” will require me monetizing some of my writing. Still working out how I, me, myself, and I feel comfortable doing that, but you can help me get started by buying me a coffee, a Joy💣, or offering a tip for something that feels valuable to you. I appreciate it!

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Writing this, it’s become clear to me why I’m not a New Year’s resolution kinda gal. I frankly find it odd to wait for the new year to do my vision board or set my intention for the next 365 days. I always thought that was just a bah-humbug-hangover, but now I’m realizing its because I do my planning in September, set my sites while the sun still sits high in the sky, blow my wishes out in to the Universe months ahead of the official flip of the calendar.

And so, this is how I’ll be spending my next four weeks. Cataloguing all of the joy-rises I want to see burst forth in to my sky in 2026 and noodling on what I can do to create the conditions that allow and encourage that vision. I’ll also be evaluating the letting go, carefully holding each commitment in my hands and weighing if it feels heavy, hard, or hurtful. I know I struggle with the opening of my hands, bereft to let anything fall through, but that is part of the work of this time of year too.

I’m curious to know what bubbles are bopping around in your brain. What joy is poised on your horizon? As one of my favorite writers here on Substack, Jennifer Esposito, asked recently, what are you not doing now that you want to be doing?

Now’s the time to noodle on it.

Settle in to September with me. Let’s get strategic and see where the joy rises.