The Room Where It Happens (Strategic Edition)

Because who’s in the room shapes what happens next.

Before you start mapping goals or crafting lofty vision statements, start with this deceptively simple question:
Who’s in the room?

The number of people in the room matters.
But the mix of people matters more.

Invite those who can think strategically and act decisively.
And make sure the plan that comes out of the room actually belongs to the people who can bring it to life.

For Core Strategic Planning

If you’re doing the roll-up-your-sleeves kind of work—the decisions that set direction and priorities—you want 8 to 15 people.

Small enough for real dialogue.
Big enough for diversity of thought.

Your core team should include:

  • The CEO or department lead—the keeper of the vision.

  • The people who can actually make things happen in their areas.

I once sat in a “strategic” session that included every director and their deputies. With that many voices, it stopped being strategy and turned into status updates. The conversation got stuck in the weeds before it ever reached the mountain.

The insights and concerns of those doing the work are essential—but they can be gathered as research ahead of time and reviewed before the session begins.

For Larger Input Sessions

When you’re gathering ideas from across departments—think brainstorming, listening sessions, or early-stage planning—20 to 40 people works well.

This is where de-siloing starts.
At one strategy session, they brought together all the department heads for the first time in years. One by one, big initiatives hit the table—and one by one, many were stopped.

No one had paused in years to ask the simplest questions:
Why do we do it this way?
Why did that process start?
Why are we still doing this?

When people finally see the bigger picture, they gain permission to rethink what’s working—and what’s not.
These sessions spark the kind of honest conversations that lead to real decisions about what to stop, start, and keep doing.

With visual tools, breakout groups, and strong facilitation, those insights don’t just stay as talk—they turn into traction.

For Company-Wide Alignment

If you’re hosting a big all-hands or alignment session—50 to 200+—the focus shifts from decision-making to energy and engagement.

This is where visual facilitation becomes essential.
When conversations are visualized in real time, everyone can see how their work connects to the larger story—and feel part of the movement.

And Don’t Forget the Support Roles

A facilitator to keep the discussion balanced.
A timekeeper to hold the line.
And (my favorite) a graphic facilitator to draw the ideas out—literally—so everyone can see where the conversation is going.
(We’ll dive deeper into these roles in another post.)

Because when you get the right people around the table, that’s when strategy stops being a meeting… and starts being a movement.

💡 This post is Part 1 of The Strategic Spark Sessions — your field guide to hosting strategic planning sessions that light a fire under your team to ignite action.
Follow along to catch the next post in the series.

My favorite Black Friday ads ever. (It's not about selling stuff.)

Don’t come to our store.

As a freelance copywriter, I dig Black Friday for all of the great ads. Just imagine, it’s Black Friday madness circa early 2000s. People camping outside Best Buy like it’s Coachella, freezing their butts off for the chance to score a TV at 70% off. The doors open, the stampede begins, and humanity collectively loses its mind over a flat screen.

Every retailer out there was playing the same game: bigger deals, flashier ads, more chaos. But then, in 2015, REI—an outdoor retailer with actual guts—did something no one saw coming. They closed their doors on Black Friday. Shut down. Lights off. And they gave all 15,000 employees the day off and told the rest of us to, wait for it… #OptOutside.

Instead of encouraging you to buy more stuff you probably don’t need, REI suggested you take a hikeOr go skiing. Or just hang out in a park. It was bold, it was brilliant, and it flipped Black Friday on its head. Now, every year, they double down on this move, closing their doors and giving their employees a paid day to enjoy the outdoors. Turns out, people love a company with a backbone.

**** From a creative perspective: #OptOutside is a pun on opt in or opt out. Our brain appreciates a twist on the familiar.

Don’t buy our stuff.

But wait, REI wasn’t the only brand shaking things up. In 2011, Patagoniaran an ad in The New York Times that basically said, “Don’t buy this jacket.” The ad showed one of their jackets front and center, but instead of a shiny list of features, it outlined the environmental cost of making it: water wasted, carbon emitted, all the not-so-fun stuff we tend to ignore.

The kicker? That ad made their sales go up 30%. Why? Because it wasn’t just an ad; it was a manifesto. Patagonia wasn’t just selling jackets—they were selling values.

And they didn’t stop there. Patagonia has built an entire ecosystem around sustainability:

  • They partnered with eBay to create a marketplace for people to buy and sell used Patagonia gear, giving it a second life. Now, they’ve got a “Worn Wear” section on their site for buying pre-loved items.

  • Since 1985, they’ve pledged 1% of sales to environmental causes. They even co-founded a nonprofit to encourage other businesses to do the same.

  • In 1996, they switched to 100% organic cotton, ditching the pesticides and showing the world how it’s done.

**** From a creative perspective: An ad that says don’t buy this is completely unexpected and is a scroll stopper.

These moves aren’t just marketing stunts—they’re proof that a brand can make money and make a difference. And that’s the magic here: brands like REI and Patagonia don’t just slap their values on a poster. They weave them into every decision they make. It’s values at the core, not the crust.

How to Put Your Values at the Core of Your Small Biz


You might not be REI or Patagonia (yet), but that doesn’t mean you can’t bake your values into everything you do. Here are five ways to start:

  • Maybe you’re an interior designer, and you donate furniture to Humble Design, an organization that helps people recovering from homelessness furnish their first homes.

  • Maybe you’re an analytics company, and you give your employees time off to volunteer.

  • Maybe you’re a graphic designer, and you support the marketing efforts of a nonprofit.

  • Maybe you’re an accountant, and you donate to the Audubon Society—just because you love birds.

With much gratitude for you,

 

Diving into a brainstorm: ClubMed

It’s summertime. And though I took some trips earlier in the summer, this freelance San Diego copywriter never wants to leave in August because the ocean water is finally warm.

But in honor of our favorite time of year to go on vacation, I wanted to share one of my all-time favorite campaigns with you: Club Med’s "The Antidote for Civilization." It’s an oldie, but it’s a classic! Before this campaign, Club Med was all about showing off the fun you could have at their resorts. But then, they took it to the next level by positioning Club Med as a getaway from the everyday grind.

This approach is a great example of brainstorming by focusing on what your product isn’t—essentially, looking at the opposite. So, here’s how I’d brainstorm for Club Med:

 Imagine Club Med at the center of a mind map with these branches extending from it:

  •  No worries

  • Excitement

  • Custom activities/menu

  • Escaping your daily routine

For this brainstorm, we’re going to dive into that last idea: escaping your regular life.

  1. Club Med is all about stepping away from your everyday routine.

  2. We’ll play around with the concept of escape and change.

  3. We’re leaning towards contrasting “civilization” with “modern life” for our final statements.

 Of course, to get here would include dozens of versions of headlines. (Can AI help generate these? You might get a few choice phrases but you are not going to get the “big idea.”

Hope this helps spark some creative ideas!

I need to venti about coffee and branding.

Imagine a café that decided to give laptops the boot because they want people to actually sit at tables, order coffee, and enjoy food, rather than babysit a coffee cup for hours.

So, they slapped up this sign.

So as a freelance copywriter, I naturally thought, there’s a way to put a more positive spin on this so people don't walk away feeling icky.

What’s the opposite of staring at a screen all morning? Yep, talking to someone. Let’s brainstorm ideas that focus on real, human connection.

Connect IRL, Not URL.

Order coffee, eat food, make friends. But please keep your table clear of laptops.

or

Conversations Over Clicks.

We’re big proponents of human interaction. Drink coffee, eat food, share a laugh. But please keep your laptop in your bag.

This is a coffee shop, is there a way to bring a coffee reference into this?

Real Conversations Brewed Here.

During our morning rush hour, 7-9 am, please leave your laptop in your bag.

Screens can be an addiction. Let’s play off of that.

Digital Detox Zone.

Let’s drink coffee, eat cake, and keep our laptops closed 7-10 am.

Do you have any ideas for better messaging for this?

What happened to the third space?

Starbucks grew on the promise of being that third space. Not work, not home, but a special place. Customers could enjoy all the comforts of home: sit in a comfy chair, stare out the window, talk with a friend, and drink coffee. It was about connections and community, not just the coffee.

Then CEO Howard Schultz nailed it, saying, “I’ve never thought of the third place just as a physical environment. For me, the third place has always been a feeling. An emotion. An aspiration that all people can come together and be uplifted as a result of a sense of belonging.”

The concept of being a third space was Starbuck’s differentiator. It was their thought-provoking POV.

But then they grew, cut costs, and it just became about the coffee.

Starbucks leasing agents are the best in the business. They know how to maximize every dollar per square foot. So, at the height of COVID, Starbucks closed their local shop that had sofas inside and tables outside and no drive-through and built a new Starbucks from scratch. To their credit, they laid out the drive-through lane first and then built the store. Now there’s only outside seating (which you can use almost year-round in San Diego). And probably 95% of their business is now drive-through rather than walk-in.

Starbucks now sells coffee, not community. And so does McDonald’s, which is cheaper.

Starbucks lost their differentiator. So if you want to have a cup of coffee with this San Diego freelance copywriter, this is the neighborhood cafe that I’ll take you too. (It appeals to my love of sketch art.)

What makes your business different? What’s your thought-provoking POV?

DIYFamilyFilms Nails It

Alright, buckle up, because DIYFamilyFilms just dropped an ad campaign that's the equivalent of a marketing mic drop. I'm scrolling through my feed, and bam! An iPhone video course that hits differently. (I haven’t bought it yet but I’m going to! And no, this is not an affiliate venture.)

Let's dissect the brilliance:

The Head-turning Hook

Lead Message:

"Why I stopped taking pics/videos of my son every day."

Hold up, did a photography/video course just lead with not taking photos? Genius. It's unexpected, it's attention-grabbing and head-turning.

Opening Text

"When you take out your phone for every cute moment because you don't want to miss it but you end up with a ton of digital clutter."

And just like that, we're all nodding in agreement. Founder Tenille is in our heads, she gets it. Digital clutter? Guilty as charged.

Understanding Parents

"Time with your child is so precious and you don't want to forget the special moments. I get it."

Yes, you get it, and now we're hooked. Speak our language, sister!

The Sell - Benefit First

"Reduce digital clutter and screen time by learning how to use your phone properly to create home videos that you actually want to watch."

Not diving into course features but hitting us with the benefits. Unexpected benefits, mind you. Reduce digital clutter? Sign me up. Reduce screen time? Double yes.

The Pitch

"Learn the DIY family films method once and have a skill for life. Get 70% off our easy way to follow course built for busy parents! Works with iPhones and Androids."

A skill for life? Check. Discount for busy parents? Check. Works with both iPhones and Androids? Check and mate. This is a pitch with a punch.

Website Check

Clarity Line

Boom, instant clarity on what the course is about. No beating around the bush.

Overcoming Objections

She's a parent like us, low-tech on the phone, reduce screen time, stuff you won’t find on YouTube. Objections crushed, moving on.

Before and After

Instead of the cliché before and after, she labels it "Digital clutter to home movies." It's not just clever; it's a visual punch in the face.

DIYFamilyFilms isn't just selling a course; they're selling a solution to a problem we didn't even realize we had.

Bravo, bravo!








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Bears Be Aware: Edit a sign, save a life.

I was on a trip to Montana with childhood friends on their annual trek to their grandparents’ ancestral home.

At a trailhead, I spotted this mini-guide for bear survival that is a great lesson in information hierarchy. I love it: It has a cute attention-grabbing headline that rhymes: BE BEAR AWARE followed by a clarifying subhead. The information is broken down into three sections:

  • Avoid Confrontation

  • Secure Food Items

  • Carry Bear Spray

I would suggest they change the third subhead, though. While carrying bear spray may be helpful, for any visiting city slickers, it’s probably more important to know not to run.

Here's how I would revise the third subhead and copy:

DO NOT RUN.

  • Carry bear spray. Move cautiously out of the area.


I would also switch the 2nd and 3rd blocks of copy as I think it’s more important to tell people not to run than to secure their food. (Though if they don’t secure their food, the bears will come, so it is all important.) The edited sign looks like this:

Now for the final edit. I would cut copy length because the shorter the copy, the greater the chance more people will read it.

BE BEAR AWARE

  • Grizzly & Black Bears May Be Encountered.

AVOID CONFRONTATION

  • Make noise while walking. Hike in groups if possible. Control your pets.

DO NOT RUN

  • Carry bear spray. Move cautiously out of the area.

SECURE FOOD ITEMS

  • Store food & garbage in vehicle or hang in a tree. Keep a clean camp. Pack out garbage.





Rick Rubin and the Creative Act

I was impatient and ordered the kindle edition of Rick Rubin’s book, The Creative Act: A Way of Being. It’s a book of short self-contained  chapters so you can pick it up and read a blurb for a dose of inspiration.  (And really, I could create a graphic this long for each chapter, it really is a quotable volume.)

Considering all the recording artists that Rubin has worked with, he doesn’t name drop. A couple of times he gives a specific example of how he has coached an artist but you are left to guess who. 

In making art, the audience comes last. - Rick Rubin

This quote hit me because it reflects the difference between art as self-expression and using creative art to sell a product. As a creative professional, sometimes my copywriting or graphic recording can approach art, but it still has a purpose to sell, clarify or inform. 

Yesterday I was in a session with a team and we were selecting what campaign ideas to refine. There was one campaign that was clever and everyone loved. But it was a longer read and wasn’t as clear, it wouldn’t serve the client as well. We had other campaign directions that could delight a customer and sell the product that we chose instead. 

5-minute Homepage Makeover for a Restaurant

Does your website pass the 5-second rule?

Can a viewer find out what you do within that period of time? (And, preferably, fall in love with your services or products?)

I came across a site that needed help with the falling in love part.

Some members of my extended family were in town, and we were to go to a restaurant to dine with some even more extended family. I checked the restaurant’s website for the address before setting out, and noticed that the site looked like it was from 2008.

The website didn’t make me excited to go visit any of these waterfront restaurants.

Yawnsville.

There are two things I would immediately do to improve it.

  • Write a big, beautiful, benefit-driven headline to sell the stunning waterfront locations.

  • Use big photos to showcase those locations.

(Because dinner is always more fun when you can watch sea lions sunbathe on a dock and witness standup paddleboarders fall in the water.)

 Watch this video  to see a quick makeover.

Your homepage is such valuable real estate. Make sure you make the most of it.

I hope this helps you!

Write on! :)