Your September Sprint (plus: Taylor, trolls & AI prompts)

Hi Friends!

Happy Thursday-before-Labor Day.

For many of us, this weekend marks the unofficial end of summer—a last hurrah. But I call BS on that. Just because kids go back to school doesn’t mean the warm nights, outdoor glasses of wine, or short-season wardrobe need to end.

Still, as the calendar flips, there’s a quiet energy to September. For me, it’s a time to refocus. The athlete in me always feels the urge to finish strong.

You too?

In that spirit, I’m doing something new:

30 LinkedIn audits in 30 days.

If you—or someone you know—has been meaning to level up their digital presence, now’s the time.

➡️ Maybe they just started a new role.
➡️ Maybe they’re launching a business.
➡️ Maybe it’s been sitting on the to-do list since January.

Let’s cross the finish line together.
📅 Book your spot here

What I’m watching:

The Taylor + Travis effect

I can’t write this on August 27 without mentioning yesterday’s headline: the engagement of the decade.

The collective pause—people canceling meetings to celebrate the news—was very real.

And here’s what struck me: it wasn’t just the couple PR’ing themselves.

It was brands: Starbucks, Walmart, Heinz jumping into the moment.
And while some social media managers might eye-roll at brands “hijacking” a personal milestone, I see it differently.

This is the ripple effect of a well-built brand.

Taylor didn’t get here overnight.

She:

• Shared the messy parts—writing about love, even when it cast her in a less-than-perfect light.

• Shined a spotlight on others—her fans, her team, her community.

• Made bold moves—rerecording her albums, reclaiming her catalog.

She brought us along for the ride—through heartbreak, reinvention, and record-breaking tours. So now, when she’s having a moment, we’re all in it with her.

You might not be the next Taylor. But you can absolutely build a brand that resonates.

This newsletter is for:

• You, who’ve been thinking about building a professional brand but don’t know where to start.

• You, who want to share your story, but aren’t sure how.

• You, who know your brand travels with you—whether you’re at a company, between roles, or building your own thing.

Not your thing? No worries. You can unsubscribe here.

Still with me? Let’s dig in.

What I’m Practicing

AI imagery, reverse prompting & learning in public

AI is everywhere—and it’s easy to feel stuck between avoidance and overload.

I’ve played with many tools to generate images—ChatGPT, Claude, Perplexity, Gemini, Napkin, Ideogram (which weirdly only gave me images of young Asian women 🤷🏻‍♀️). But what helped most wasn’t picking the perfect tool—it was improving my prompts.

Here’s my framework now:

• Subject: The main focus (person, object, etc.)

• Environment: The setting

• Lighting: Soft? Dramatic? Morning light?

• Color: Brand palette or mood-based tones

• Mood: The emotional vibe you’re going for

Think of it like giving feedback to a junior designer—you have to unpack what’s in your head.

Next, I click into an image and use the paintbrush tool to highlight a specific area I want changed.

⭐️ Pro Tip: Try reverse prompting.

Upload an image you like → ask AI to describe it in prompt format → tweak the prompts to match your use case → generate new versions.

Here’s what I created with that approach, using a Messi image as my starting point. 👇🏼

Got a favorite AI tip? Hit reply. I’m keeping a live doc and would love to add yours to my list.

What I’m Loving

Outlive by Dr. Peter Attia

Medicine 3.0 = playing offense, not defense.

Attia’s writes about being proactive and ensuring we are doing the things now that we want to still be able to do long into the future. The concept of the Centenarian Decathlon really stuck with me:

• Can you carry two full bags of groceries up stairs?

• Get off the floor with a grandkid in your arms?

• Hoist your suitcase into an overhead bin on an airplane?

Until you are 95.

It’s not about optimization. It’s about mastering the fundamentals. Repeating the basics so you don’t lose them.

Work is the same. Branding is the same.

This fall, I’m focusing less on hacks, more on habits.

Shining a Light

Naina Raju, my summer intern

Naina is a high school junior from New Jersey. I said yes to mentoring her with modest expectations.

She blew me away.

She:

• Sent detailed agendas before every call

• Built dashboards tracking 10+ client metrics

• Ran peer audits—for me and for clients

• Wrapped with a full end-of-summer report

Takeaways?

1. Gen Z is more than okay—they’re thriving.

2. I was wrong. She brought value every step of the way.

3. If you're considering an intern next year, check out StandOut Connect.

ICYMI

🎙️ Let’s talk podcasts

You know I love social, but podcasting has become a second superpower.

I’ve been a guest on 11 podcasts this year, with 10 more queued up.
Not because I have free time—but because I have a system.

Now I show up with:

1. A short, strong bio

2. Thoughtful talking points

3. Clear CTAs

4. Having researched the host

Podcasting builds trust and opens doors. It’s content. It’s networking. It clarifies your talk track. It’s fun!

Thinking of guesting? Curious about the prep? Want a co-pilot to help you shape your story?

You know where to find me.

Where’s Jess?

Last month, Jen Weddell correctly guessed I was at the Met Museum in NYC. 👏🏼👏🏼👏🏼
(Yes, they did have Prince’s actual Purple Rain shirt on exhibit.)

This month’s clue?

PNW folks might have an edge on this one 😉

Reply with your guess—the winner gets a shoutout next month!

Thanks for being here.

➡️ Did a friend forward this to you? Subscribe here. You’ll get pro tips and inspo about once a month.

➡️ Want some 1:1 time with me to discuss your next steps. Book a 25 minute discovery call here.

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

See you next month!
Jess