Harvard, the "How-To" trap, and a Winter playlist.

Hi Friends!

It’s officially the holiday season. For me, this time of year means a birthday (shout out to the fellow winter babies), repeatedly reminding my daughters that, "No, we aren’t listening to Mariah until the day AFTER Thanksgiving," and the inevitable reflection that comes as we near the end of Q4.

I’m feeling a mix of immense gratitude and heightened focus. This year has been a massive learning curve. When friends ask me how the business is going, I tell them I don’t even know where to start, but one thing is certain:

I realize how many years went by inside a corporate role where I wasn’t truly growing.

I was navigating, sure. I was making people happy. But I wasn’t evolving. The work wasn’t rooted in building the new or pushing myself to be uncomfortable.

That idea that a body in motion stays in motion absolutely applies to our brains. The cognitive load I once carried has been replaced with radical growth. I feel in my bones that this work is not only satisfying, but it keeps me agile. I’m not afraid to say I’m 49 out loud, because guess what? I’m not even halfway there.

If 2024 was about building the foundation, 2025 is about establishing systems that scale.

This month, I’m sharing a major mindset shift I had while walking the halls of Harvard, a playlist to get you through the shorter winter days, and a look at why "helping" sometimes hurts your business.

Let’s dig in.

What I’m Practicing

The Shift from "How-To" to "Who Can?"

I recently returned from speaking at the BOLD Conference at Harvard. It’s an incredible two days focused on showing young women what business leadership paths actually look like.

Walking onto that campus, the weight is palpable. It’s Harvard. Five-story brick buildings, mature trees surrounding the quads, and women behind me debating how they solved a math equation on a test (you can’t plan this stuff). Some of these buildings have dates by the front door that are older than the entire West Coast.

At first, it feels elite. Untouchable. You catch yourself thinking, “I don’t belong here. At any moment, they’ll escort me off campus and back to the Peet’s Coffee on the corner.”

But then, the goldfish grows to the size of its bowl. You adapt. You realize the people in the room are smart, driven, and ambitious—but they are just people.

And you realize you aren't there by accident.

The experience crystallized something I’ve been thinking about for months regarding my own business. A while back, I noticed my inbound requests were mostly people in transition wanting to learn how to do what I do. Today? It’s Founders and SVPs asking to work with me.

What changed? I stopped answering tactical questions.

Most service providers (and leaders) get stuck because they create content that answers: "How do I do this myself?"

• "Here is my 7-step framework."

• "Copy this template."

This attracts students. It attracts DIY-ers. It attracts people who have more time than money.

Upmarket buyers—the C-Suite, the senior leaders—aren't asking "how." They are asking: "Who?"

• "Who can solve this for me?"

• "Who can see the blind spots I’m missing?"

They have hit the pain threshold where the problem costs more than the solution. They are optimizing for speed and certainty, not a free tutorial.

The Lesson: If you want to move upmarket in 2026, stop asking yourself, "What can I teach people today?" Start asking: "What problem can I diagnose and solve?"

When you spend more time diagnosing the problem than teaching the tutorial, the right people—the ones ready to invest—will find you.

What I’m Loving

Flowers in Winter

The Pacific Northwest gets dark this time of year. While we’ve had a good run of sunny days lately, when the sun sets at 4:30 PM, you notice.

With the holidays, family gatherings, and perhaps a long car ride to visit relatives, you need good tunes. So, for you, I built a custom playlist called "Flowers in Winter."

It’s designed to be the background track for your December and beyond—upbeat enough to keep you moving (even into the evening) or a great backdrop for a dinner party. For those that know me, you know I can’t imagine a home without music.

Consider this my holiday gift to your ears. 🎁

🎧 Listen here: Spotify Playlist

Shining a Light

If the word "sales" makes you want to run for the hills, you need to know Renee Hribar.

We often talk about "executive presence" in terms of speaking or writing, but it also applies to how you handle the commercial side of your business. Renee creates sales strategies for service-based business owners who want to lead with authority, not desperation. She takes the "ick" out of the ask.

Having little to no background in sales myself, I knew I needed a coach. Renee’s 1:1 mentorship and group work have propelled me forward in ways I know could help some of you, too. Plus, she’s truly one of the funniest people I’ve met.

If you are looking to elevate your sales approach for 2026, check her out. And tell her Jess sent you. 👉 Her website is here.

ICYMI

🎙️ The Cost of Being Invisible

I recently sat down on the FroBro Podcast to go deep on digital reputation.

(First of all, we have to acknowledge the name. If nothing else, you have to give him credit for catchy branding and differentiating himself from the sea of marketing pods!)

We discussed why your digital footprint is something to build, curate, and nurture, and why "quiet competence" is a very 2000s strategy that’s leaving money on the table today.

Catch the full conversation here: Apple Podcasts

Where’s Jess?

I’ve been on the move. As we do each month, I want your guess as to where I am. You all know I was in Boston, so that’s easy—but where specifically might I be in the city?

Reply to this email with your guess. The first person to get it right gets a shoutout in the January newsletter and something special in the mail from me personally!

Happy Holidays, all! 🎄

Enjoy, breathe, listen to good music, and perhaps most importantly—know that being yourself is the ultimate power move in 2026.

— Jess

Thanks for being here. 💛

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➡️ Got feedback? Hit reply and tell me what you think. I’m always looking to level up.

See you next month!
Jess