An October Newsletter

An October Newsletter

Oct 12, 2026

This is my newsletter to my email subscribers for my website. And it was too good NOT to post it here... so here are my thoughts...

Ah Fall…

October is here in full effect.

The leaves are changing. The marathoner’s have came, saw, conquered… The citizenry of Chicago have navigated the changes, reroutes, and complex maze that is festival and city block closure season… (we’re almost at the end y’all).  And with all that we are a few short day’s away from Cookies & Conversations being a State certified LLC for 7 years!  

7 Years!!! Can you believe it?  7 whole years of taking this little idea, this figment of my imagination and transforming it into something truly tangible.  Edible.  Conversational.  Impactful.  From the Cookie Kits launched November 6th 2019, to the pop ups that watched the fresh baked cookie appear, to the physical Brick and Mortar bakery that opened in the Lacuna Lofts in 2022, to the closure and restructuring/redirect into the event curation space.  

It’s been a lot.  It’s been humbling.  It’s been financially taxing (if y’all don’t know by now I’m a bougie girl that likes nice expensive things and experiences).  But it’s been thrilling.  It’s been enriching.  It’s been enlivening.  It’s been an incredible opportunity to explore how I’ve come to understand business, product, and artistry.  Lessons I could not get without going through the motions of doing.  

One of the greatest gifts to me stewarding Cookies & Conversations, while also shortly after launching, coming out and exploring Queerness, is that everything about what I have been looking to create has come to head with exploring systems, institutions, and my deep humanity as it intersects with those systems.  I’ve had the ability to ask questions about the rules, the standards, the expectations presented, examining the importance of those rules, who authored them, what purpose do/did they serve, to what end, and if those rules still appropriately applied to me. 

Another gift of Cookies & Conversations has been learning how much of an artist I actually am.  For so long I’ve been tryin to run Cookies & Conversations by models that just never fully fit. When getting my license in the first place I stumped the folx at SBA because I wanted to sell a product that had food contained in it but it wasn’t fully something you could consider food.  It didn’t fit neatly into the box of dry good. If I think back to what product that was recognizable to the public that would be most cleanly associated with my cookie kit, I’d say it would be an Easy Bake Oven or an Advent calendar. A product that had edible contents.  When I tell you we went back and forth when it came to the "How do I denote myself," "what I can do," "what listened and insurances I needed," it was still not fully black and white.  That’s been true from day one.  If you can’t wrap Cookies & Conversations up in one category, then how can you use 1 method to execute the vision? What combination of systems or methods will apply to brand and business?

When I look at the evolution of this brand, I think of my favorite musical artists, fashion houses, visual artists, filmmakers, and choreographers… I think of how their work has evolved and yet stayed true to their initial inception.  All I needed was time.  Time to build a catalogue.  Time to create some things and see what made sense.  Time to explore various avenues and forms of direction.  From day 1 I knew I wanted Cookies & Conversations to be an inflection point, sparking people into presence and to gathering.  I didn’t know in what way a food company could do that.  Branding likes simplicity. Easy to Communicate.  And that’s not been something I’ve been able to do until now. 

So on the eve of Cookies & Conversations 7th year, I want to present to you the clearest definition of what Cookies & Conversations is. 


Cookies & Conversations is a company dedicated to facilitating human connection.  We execute that through our team building facilitation, our networking mixers, our catering services, and our community activations utilizing our gourmet cookies and customizable conversation prompts. Led by Chef Leah, our founder and Pastry Chef Instructor, she uses the power of food, culture, history, and play to unlock curiosity and interactions in an age where opportunities to build living community have been challenged by the ubiquitousness of tech.

For all of you have been along on this journey with me, thank you.  For your patronage, for your celebration, for keeping up with me, for sharing and telling your friends, for your honest constructive feedback. I couldn’t do this without you.  I couldn’t make this happen, to plan, to figure out, to try and fail and try, try again. I need people.  And this business of mine, is literally people forward.  Figuring out how to not exploit, how to be fair, to be environmentally minded, to not be extractive… which a majority of the models are built on, has been a challenge, especially because... I like nice things that have big price tags!!!  It’s like that line people in Man on Fire kept repeating to Denzel when he found them… it’s just business.  No it’s never been just business.  I would have made a much better dent, established a much different kind of footprint if it was that for me.  This idea of mine, this vision, has to give back and make the world a brighter place.  If it can’t do that, it will never be worth it for me, the artist is in charge.  And that’s the line I’m constantly battling.  To make something worthy of experiencing, and doing the least harm as possible.

So to you all, be on the look out for my latests offerings.  I’m working hard with some new amazing folx who behind the scenes are helping me make sense of it all.  If you’re looking for cookies, the Preemptive Holiday Cookie orders have gone live.  Cookie Orders begin fulfillment November 16th through December 26th.  Also November 1st begin to book our curated offerings facilitating your next team building, Networking event, Holiday Party, or Onboarding.  Cookies & Conversations takes the guesswork out of the soft skills reacquired for connection. 

Cookies & Conversations is my art. It is my life’s work.  It does fuel my passion. The ups and downs have been hard, but they’ve been mine, and damnit, for me, the experiences has given me something I could never gain just from reading about it in a book. I've had to live it.  I’ve had to FAFO.  I’ve had to do it scared.  Is this the way to a secure stable life? No. It’s the creative's path, full of evolution and change.  Nothing stays the same.  Now that doesn’t mean it should come with poverty wrapped in a bow, see my upcoming events, but it does mean there has had to be a period of working to understand and learn my craft in a way that the decisions I make about it come from MY authority.  Now, I can seek out the kind of mentorship, the kind of guidance, the kind of investors that are much more aligned with my visions, instead of following a script and finding myself down a road that may be very comfortable, but potentially stale and unfulfilling… like a crumble cookie. (shots fired)

See y’all in the next post. 

-Chef Leah

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