Jason Caldeira Jason Caldeira

The Summer That Wasn’t.

Summer is almost over, and I’m left wondering where it went. Not in the dreamy “time flies when you’re having fun” way, but in the “I barely lived it at all” way. As a parent, I can’t shake the math: I only have a few summers left where my kids actually want to spend them with me. And I wasted one. I feel like I barely showed up for it.

We had plans. Pretty good ones actually. The kind you imagine in January when the snow is piled high and you swear you’ll make every warm day count. But we didn’t do enough of the things. We didn’t go to the places. We barely left the house most days.

Maybe it’s because it’s hard to enjoy a twist cone when the world feels like it’s falling apart. I’ve spent so much of this season worried — about my business, the businesses I love and frequent, the people in our community. Everywhere I look, someone is either losing everything, cheering for someone else’s loss, or pretending nothing is wrong. It’s exhausting. And it made this summer feel… heavy.

So yeah. This summer wasn’t the best. And that stings — not because I think every summer needs to be Insta-worthy, but because I can’t get this one back. It’s in our rearview now. But I can learn from it.

I can decide that the next chapter will be different. That the transition into this new school year — new high school for my oldest, middle school for my youngest — will mark the start of a more intentional season for all of us. I can keep building my business. Keep hunting for the right projects and the right clients. Keep showing up for my family, my work, and my community, even when the world feels like it’s burning.

Summer may have slipped through my fingers. But I’m holding on tight to what’s next.

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Jason Caldeira Jason Caldeira

Why Small Businesses Have to Charge More (and Why That’s a Good Thing).

Yesterday I posted a quick thread about the cost of mayo at my local grocery store. It wasn’t that deep — just one of those “wow, $8 for a jar of mayonnaise?!” kind of posts. The kind you think will get a couple head-nods or maybe a “same here!” in the comments.

Instead, people got weirdly mad. And belligerent. And insulting.

Some said I was lying. Some called me moron, loser, libtard. Others told me I should’ve just gone to Walmart, as if that was the only reasonable response. Like the problem wasn’t the inflated price of groceries, but my refusal to shop at a giant corporate retailer.

And listen… I get it. Life is expensive. Everyone’s looking for ways to stretch their dollar. But what struck me most was how quick people were to defend the idea that cheap = good. That big box prices are the gold standard. That anything else is a scam or a ripoff.

That same thinking is what gets small business owners in trouble.

Because if you’re a small business trying to match those big-box prices — if you're absorbing costs just to stay “affordable” — you will inevitably burn out. Or break even. Or close. And none of those are really options.

Here’s what’s true: you will never be able to compete on price with a giant retailer. And you shouldn’t try to.

Big stores move mass quantities. They underpay workers. They negotiate bulk contracts. They don’t care if your shopping experience is beautiful, or if the product is thoughtful, or if the packaging made you smile. They are optimized for one thing: volume. Move more, make more.

But you? You’re a small business. You care about what you’re making and selling. You probably are the team. You pick your ingredients. You know your customers. You design your experience down to the music playing and the way your packaging feels in someone’s hands. That’s not extra. That’s the whole point.

So yes, your prices will be higher. They have to be.

That higher price covers your time. Your craft. Your rent. Your values. Your survival.

When small businesses try to race to the bottom price-wise they lose everything that makes them special. And eventually they just lose… period.

If you’re afraid to charge what something is worth because you don’t want to scare people off, I get it. It’s vulnerable to ask for more. It feels risky. But here’s the hard truth: pricing for survival is not greedy. It’s responsible. And it’s necessary.

Because here’s the reality most people don't want to say out loud:
If your business doesn’t make money, it disappears.
If you don’t get paid, you burn out.
If you can’t afford to grow, you stagnate.

And then the thing you built — the thing your community loved — goes away. Not because it wasn’t good. But because it wasn’t priced to last.

So the next time someone asks why your product or service costs more than what they can get at Target or Amazon, tell them this:

“I care too much to cut corners. And that’s reflected in my pricing.”

And if they still don’t get it, they’re probably not your customer anyway.

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Jason Caldeira Jason Caldeira

What happens when you disappear for a bit.

This past week, we packed up the car, loaded the kids and the cooler, and headed into the woods. (Well, sorta. More like camping-meets-The Villages — IYKYK). Nothing but pine trees, fire pits and classic campground-style activities. No email. No social media. No breaking news alerts or trending topics. Just firewood, bug spray, and the sound of kids actually being kids again. It was exactly what I needed.

Running a small business — especially one that’s creative, personal, and built from scratch — can feel like a never-ending loop. You’re always on. Always reachable. Always supposed to be doing something that moves things forward. But the truth is, creativity doesn’t thrive in that kind of environment. It starts to feel transactional.

Getting away helped me reset. It reminded me that stepping away from the work is part of the work. When your brain gets to wander — without the pressure to produce — you start to think differently. You remember why you started all this in the first place.

I know that’s easier said than done. You might be juggling client emails, inventory, deadlines, social media, late invoices, and whatever else your particular version of entrepreneurship comes with. But I promise, even a few hours unplugged can shift things in a good way.

So this is your very gentle nudge: find a pocket of time this week to get off the grid — even if it’s just metaphorical. Shut the laptop. Turn off the notifications. Take a walk without your phone. Sit outside with a coffee and don’t do anything.

Your business will still be there when you get back. But your mind might be a little clearer. Your ideas a little brighter. Your energy a little more yours again. And that’s when the good stuff starts to show up.

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Jason Caldeira Jason Caldeira

The Little Place That Made Us Turn the Car Around.

This past weekend, my wife and I were driving around running errands when we passed a little storefront with a sign that said Junebug Cafe. Without even thinking about it, we both said out loud, “That place looks awesome!” It was one of those instinctive reactions — a quick visual read that immediately left an impression. We ran our errands, and about an hour later we made it a point to stop in just to see what it was all about. (And I desperately needed a coffee.)

The moment we stepped inside, everything made sense. Great food, great coffee, delightful people… we talked to the staff, learned a bit about the business, and walked out as genuine fans.

But here’s the part that stuck with me: had the exterior not caught our eye, we never would have known the place existed. We wouldn’t have stopped. We wouldn’t have become customers. We wouldn’t have told other people about it. In a city like Chicago you’re constantly surrounded by businesses just like these, so standing out is no small feat.

That’s the power of design and branding. It’s not just about making things look nice — it’s about creating a feeling, a signal, a reason to care. It’s about making people notice.

A strong visual identity does heavy lifting. It communicates who you are before you say a word. It helps your business stand out in a crowded world. And in many cases, it’s the reason someone gives you a second look — or pulls over just to see what you’re all about. And it doesn’t have to be complicated or over-designed. This storefront was simple and charming, and just felt right.

If you’re a small business owner, that kind of presence matters. Especially when every customer counts. A thoughtful, well-designed brand can be the difference between being overlooked and becoming someone’s new favorite spot.

That’s why I do the work I do. Because good design doesn’t just look good — it actually works.

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Jason Caldeira Jason Caldeira

Is “Good Enough” Really Good Enough?

Let’s talk about “good enough” shall we? Those AI design tools that promise a logo in seconds, a brand in a box, a website by lunch. It’s fast, it’s cheap, it looks… fine. And if you squint hard enough, “fine” starts to feel like a win.

But here’s the thing: if you’re building a business — something real, something with heart — fine isn’t going to cut it.

AI can spit out an okay-looking brand. So can Canva and your cousin with a free trial of Photoshop. But none of those things can tell your story. None of them can figure out what makes your business different. None of them are going to help you stand out in a sea of other businesses who also chose “fast and cheap” and ended up looking like a slightly altered version of the same template.

“Good enough” might save you a few bucks now, but it’ll cost you more in the long run. In missed opportunities. In forgettable first impressions. In customers who don’t feel anything when they find you — because there’s nothing to feel.

A real brand — the kind that works, the kind that builds trust, the kind that gets people to stop scrolling and actually pay attention — isn’t generated. It’s designed. Intentionally. With curiosity and care and strategy and skill.

That’s what I do. I help small businesses build brands that are unmistakably theirs. That sound like them. Look like them. Feel like them. Brands with actual depth — because it turns out, people are pretty good at spotting the difference between authentic and generated.

So, if “good enough” is working for you, great. But if you’re ready for something better — if you want a brand that feels like it’s truly yours — let’s do this.

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Jason Caldeira Jason Caldeira

Summering While Floundering.

There’s something disorienting about trying to run a business and be a human in the summer – especially this brand of summer. You’re trying to enjoy the season — get outside, make memories, spend time with your kids or your partner or your friends — but at the same time, the world around you feels increasingly unstable.

The economy is weird. Politics are weirder. Your expenses are up, your inbox is overwhelming, and that potential client who said they’d be ready “after the holiday weekend” is now ghosting you entirely. It’s a lot.

And yet, you're still trying to soak it up. Still packing the cooler, still watching fireworks, still making small talk at the farmers market like you’re not low-key panicking about where your next check is going to come from.

If you’re floundering right now, you’re not alone. I don’t know a single small business owner who isn’t feeling some version of this: stretched thin, trying to stay optimistic, trying not to let the weight of the moment pull them under.

This is the part no one talks about when they romanticize entrepreneurship. The part where you’re not just the CEO — you’re also the janitor, the customer service department, the social media manager, and the person holding it all together while pretending it’s totally fine.

It’s not totally fine. But that doesn’t mean you’re doing it wrong.

You’re just living in the tension of what it means to be a small business right now: creative, hopeful, under-resourced, and still showing up.

One thing I’ll say — because I’ve seen it again and again — is that a clear brand can take some of the pressure off. When your brand is doing its job, it gives you breathing room. It reminds people what you’re about, even when you’re too overwhelmed to say it out loud. It helps you attract the right customers and build trust without having to push or sell so hard. And when you do need to step away for a few days? It keeps working in the background.

That doesn’t mean branding solves everything. But it can give you a little more space. And in a season like this, a little space can be everything.

So if you’re floundering a little while also trying to soak up these fleeting summer days, I just want to say: samesies. Keep going. You’re doing more than enough. And when you’re ready to get some support — whether it’s with your brand, your message, or just a fresh outside perspective — I’m here.

Enjoy the popsicle. Answer that email later.

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Jason Caldeira Jason Caldeira

The Struggle is Reallllll.

But you don’t have to go it alone.

If you’re a small business and you’re struggling right now, you’re not the only one. It’s tough out there (understatement of the year). People are hesitant to spend. The cost of goods has shot up. Leasing prices are rising in most cities. Online marketplaces run by soulless billionaires don’t have your best interests at heart. And even your favorite neighborhood spots are quietly adjusting their hours or scaling back just to stay afloat.

There’s a lot of pressure to pretend everything’s fine — to keep up appearances, keep showing up, keep pushing forward like it’s business as usual. But the truth is, small businesses were never meant to do this alone. We’ve always been about community. About mutual support. About finding ways to keep going together.

So if you’re feeling stuck or uncertain or just plain tired, consider this your reminder: you don’t have to power through in isolation. You can reach out. To your people. Your peers. Your vendors. Your creative collaborators. To me. To the customers who’ve been in your corner since day one. You’d be surprised how many folks are willing to help if you just let them in.

And yes, I’m going to bring this back to branding. Because branding isn’t just how your business looks. It’s how your business connects. It’s the tone in your voice when things get quiet. It’s the way you remind your audience that you’re still here. Still open. Still part of the fabric of this community. It’s how you remind them that you’re still worth their attention. And if they want you around, they need to show up.

Now is not the time to go silent. It’s the time to show up with honesty and heart — to let people know what you’re going through and why you still believe in the work you’re doing.

Your branding materials can help you do that. They can give shape to your story, even when the story’s still unfolding.

And if you need a hand figuring out how to say what you need to say or look the way you need to look — whether that’s a reintroduction, a reset, or just a little encouragement — we’re here. This is exactly why we built our little design studio.

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Jason Caldeira Jason Caldeira

A Shift in Perspective.

What yoga’s teaching me about design.

This month my yoga instructor has been offering an intention of “perspective”. About how the way you hold your body — or your breath, or your focus — can completely change how something feels.

One small shift, and suddenly the thing that felt hard feels… different. Not easier, necessarily. But more doable. More aligned.

And lately, I’ve been thinking about how often that applies to branding.

When you’re deep in your business — juggling the to-dos, responding to the fires, making things work — it’s easy to lose the bigger picture. To start doing things simply because you’ve always done them. To make decisions based on convenience instead of clarity.

And that’s where things can start to feel off.

Not broken. Just misaligned. A little flat. A little meh.

But sometimes, all it takes is a shift in perspective.

Not a full rebrand. Not a big dramatic overhaul. Just a step back. A fresh look. A moment to ask:

Is this still true?
Is this still me?
Is this still working?

Good branding isn’t always about reinvention — it’s about realignment. It’s about making sure what you’re putting out into the world still feels connected to what you care about, who you’re here for, and what kind of experience you actually want to create.

Sometimes that means changing the story you’re telling.
Sometimes it means changing how you tell it.
Sometimes it just means remembering why you started.

Perspective doesn’t always shout. It nudges. It gently reminds you that your brand isn’t just how you look — it’s how you show up. And when you start showing up with more clarity, more honesty, more you — people feel it.

So if things have been feeling a little off lately, maybe don’t force it. Don’t scrap everything.

Just shift the angle. Take a breath. And look again.

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Jason Caldeira Jason Caldeira

Why I Say “We” (Even Though It’s Mostly Just Me).

I’m a designer. And for the most part, I work alone.

There’s no bustling office behind the scenes. No team of minions handling the emails, or polishing pixels, or dreaming up strategy in a neon-lit war room. It’s mostly just me — sketching, designing, typing, overthinking, tweaking. Then overthinking again.

And yet, when I write about Caldeira Co., I often say “we.”

Why?

Well, first, because there is a “we.” My lovely wife Erin is an essential part of the team. She’s the voice of reason, my second set of eyes, an amazing brainstormer, the one who gently reminds me that yes I should probably get up and go for a walk. And she brings to the table retail knowledge and experience that I simply do not have.

But there’s more to it than that.

I say “we” because it sets the tone for how I work. Because even when I’m technically “the hired creative,” I’m not working for my clients — I’m working with them. What we’re doing is a partnership. A collaboration. A conversation. A we.

I don’t believe in client relationships where you just hand over a brief, walk away, and come back to a shiny new brand three weeks later. That’s not how good work gets made.

The best design comes from co-creation. From listening deeply, asking questions, trading ideas, making a few wrong turns, and finding our way together.

The we isn’t just semantics — it’s branding. It’s a quiet cue to my clients (and to myself) that this isn’t a solo sport. It’s a team effort, even if the team is small. Sometimes it’s just me and you and Adobe. But we’re in it together.

So yes, I’m sorta a one-man design studio. But when you work with me, we’re we from the start.

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Jason Caldeira Jason Caldeira

AI for Your Small Business: Helpful, Harmful, or Hype?

Some honest thoughts on when to keep it human, and when it’s probably okay-ish.

If you run a small business, chances are you’ve dabbled in AI. Some people swear it’ll save you hours a week. Others say it’s coming for your job. And most of us running small businesses are just trying to keep up without losing the thread of what we’re actually here to do.

So I wanted to slow things down and talk honestly about AI — what it’s good for, what it’s not good for, and how to think about it if you’re building something small, thoughtful, and personal.

Let’s start with the good.

As much as I hate to admit it, AI can be useful.

It can help you brainstorm when you’re stuck. It can tidy up your messy draft, summarize your meeting notes, or auto-generate content ideas when your brain feels fried. When used well, it can give you time back — and if you’re doing everything yourself, you know how valuable that can be.

But here’s the thing: the best parts of a small business simply cannot be automated.

That voice you’ve spent years developing? That sense of trust you’ve built with your customers? The gut decisions that don’t always “make sense” but end up being exactly right? AI can’t replicate any of that. And if you try to replace those things with a robot, your business will lose the very thing that made it worth building in the first place.

This includes branding & design, btw.

Branding is more than a color palette or a quirky font. It’s the emotional layer — the thing people feel when they interact with you. It’s the way you make decisions, tell your story, and show up in the world. And design? Design is how you communicate that story even when there are no words at all.

Sure, AI can spit out a logo in seconds. It can pair fonts and suggest color palettes. But it can’t understand nuance. It doesn’t know what your business stands for. It doesn’t feel your story. It doesn’t care about how your audience sees you. It’s only there to deliver on your prompts, whether they’re the best direction or not.

And when you let it take the reins on your brand, it shows. The result may be passable-ish, but it often lacks soul. Character. Personality. It blends in, not because it’s subtle, but because it’s empty.

So here’s my take:

Use AI as a tool, not a crutch. Let it help you brainstorm, organize, automate, tidy. Let it handle the things that drain your energy so you can focus on the parts of your business that require real heart.

But don’t let it near the things that make you you. Your voice. Your instincts. Your taste. Your weird ideas. Your sense of humor. Your story. Your brand.

Because no matter how advanced the tools get, what people are still drawn to — what they remember — is something that feels legit. Real. Human. Thoughtful. Honest.

And that? That’s still your edge.

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Jason Caldeira Jason Caldeira

Why Small Businesses, You Ask?

Because they’re everything to me.

There’s something about small businesses that gets me every time, and always has.

Maybe it’s the hand-painted sign hanging slightly crooked in the window. Or the way the barista knows your order before you open your mouth. Maybe it’s the way the owner waves goodbye like they actually mean it — because they do.

Small businesses are just different. You can feel it. They carry stories in their walls and pride in their details. They’re built on people’s dreams, not investor decks. And that difference? It matters. At least to me.

What I admire most is how deeply personal they are. Every small business starts with a decision — often a scary, risky, against-the-grain kind of decision — to make something of your own. To not follow the conventional path. To trust your gut when everyone else tells you to play it safe.

I have deep respect for that kind of person. The ones who’d rather build something slowly and honestly than chase someone else’s version of success. The ones who figure it out as they go. The ones who say, “I think there’s a better way to do this,” and then go do it.

I love people who think differently. Who carve their own lane. Who care deeply about what they’re putting out into the world. And small business owners — the good ones, the scrappy ones, the ones still holding the reins — do that every single day.

They don’t just open shop. They open up space — for community, for connection, for care. They remember your dog’s name. (Although admittedly it’s hard to forget ours.) They sponsor the local soccer team. They hang handmade flyers in their windows. And all they ask in return is a little bit of your time and attention.

It’s easy to overlook those things. But they add up. They turn neighborhoods into homes. They make our uneasy, oftentimes depressing as hell world feel a little more human and a little less heavy.

And that’s why they will forever have my support. Not just because they’re the underdog. But because they remind us that business can and should be personal. That success doesn’t have to come in one shape or size. That it’s still possible — and powerful — to do things your own way.

So to the people building something of their own: I see you. I believe in what you’re doing. And I’m proud to be in your corner.

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Jason Caldeira Jason Caldeira

This Isn’t Just Branding.

We believe small businesses do more than keep the economy moving. They carry something deeper — a sense of place, of personality, of purpose. They shape the character of the neighborhoods they’re in. They give people something to root for. They make the everyday feel a little less ordinary.

Look closely and you’ll see it: the coffeeshop where regulars are greeted by name. The florist who slips an extra stem into the bouquet. The repair shop that fixes what’s broken without making you feel foolish for not knowing how. These businesses aren’t just transactions. They’re an essential part of the fabric of our communities.

We believe everyone deserves the chance to build something meaningful — something that reflects who they are and what they stand for. That opportunity belongs to all of us, regardless of race, gender, or sexuality. The right to show up as yourself and be taken seriously shouldn’t be up for debate.

We believe that how you succeed matters just as much as if you succeed. That there’s no prize worth winning if it means compromising your values or stepping over someone else to get there.

We believe in community over competition. In curiosity, not cynicism. In doing the right thing especially when nobody’s watching.

And yes — we believe in branding & design. But not because it helps you shout louder or sell faster, but because it helps small businesses get clear on what they stand for and who they stand with.

That kind of clarity is powerful. It draws the right people in. It gives your business a center of gravity. It becomes a quiet kind of confidence.

If that resonates with you, we’d be proud to help you build it. To design a brand that doesn’t just look good, but feels honest. One that reflects your values and earns people’s trust — not with noise, but with meaning.

And if that’s not what you’re after, we understand. There are plenty of people who can make things look nice. But if you want to build something that lasts — something that matters — we’re right here.

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Jason Caldeira Jason Caldeira

The Field Notes Film Festival.

How Draplin & Coudal turned sheets of paper into a cultural movement

Last night, I walked the few short blocks from my house to Chicago’s historic Music Box Theatre to attend the inaugural Field Notes Film Festival: a charming, low-key, and surprisingly moving celebration of the quirky, romantic, and unexpectedly inspiring promotional videos that have accompanied Field Notes editions over the years. Or, as co-founder Jim Coudal put it, “I can’t believe we got you all to pay good money to come out and watch our ads.”

The evening was more than just a retrospective of branded content — it was a love letter to the creative process. A joyful gathering of people who obsess over things like mid-century typefaces, vintage printing presses, and the satisfying snap of a well-made notebook. It was a room full of people who get it. And as someone who’s spent most of his design career flying solo, it felt quietly meaningful to be surrounded by fellow travelers — the kind of folks who see the same beauty in proper kerning and Futura Bold as I do.

What Field Notes has built over the past decade is something rare. Yes, they make notebooks. But more than that, they’ve cultivated a culture — one that celebrates curiosity, reveres craft, and somehow makes you care deeply about things you didn’t even know could be cared about. Self-proclaimed “junker” Aaron Draplin doesn’t just talk about old things — he converts people. With unapologetic enthusiasm, he makes a case for every rusted tractor logo, every defunct hardware store sign, every dog-eared manual pulled from a barn sale. And damnit if he didn’t make me want to spend the rest of the week hunting for mid-century ephemera in a dusty corner of the Midwest.

By the end of the night, I wasn’t just entertained — I felt recharged. Reminded that design doesn’t have to chase trends or bend to algorithms. It can be personal. It can be obsessive. It can be weird and specific and full of heart. And maybe most importantly, it can bring people together — even if just for a night, in an old theater, watching ads that don’t feel like ads at all.

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Jason Caldeira Jason Caldeira

Human Made by Human Made Humans.

Why would anyone want to use AI for the fun stuff like creativity, writing, design, and making music? Let’s use AI for organizing spreadsheets and doing the dishes instead.

If you’re committed to keeping things human-made, get yourself one of these stickers for FREE. Yes, you read that right… send me your address and I’ll send you a sticker. No other sign-up necessary. No tricks. No ulterior motive. Just a sticker.

Continental US addresses only, please!

 
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Jason Caldeira Jason Caldeira

Industry spotlight: giving a little TLC to THC.

It’s not often that we witness the rise of an entirely new industry—one that requires both consumer education and a warm invitation in. In the early 2000s, we saw the dot-com boom, followed a decade or so later by the explosion of microbreweries and independent craft beer. Now, it’s time to welcome the cannabis industry into the mix.

 

From a branding perspective, cannabis is undergoing a fascinating transformation. Gone are the days of tie-dye tapestries and dancing Grateful Dead bears. The modern cannabis landscape is sleek, sophisticated, and devoid of the shame-inducing baggage that we ‘80s kids have struggled to shake. (Thanks a lot, Nancy Reagan.)

As younger generations—and society as a whole—move away from alcohol in increasing numbers, cannabis in its many forms has found itself the welcome newcomer; a less toxic, hangover-free way to unwind, socialize, or simply enjoy a tasty little buzz. And with legalization spreading, the industry has gone from underground to ubiquitous, transforming city streets with a Starbucks-level presence seemingly overnight.

This rapid shift means designers are rethinking the visual identity of cannabis, moving away from the burnout-era aesthetic and into something more refined. While beer packaging has evolved from nostalgic, grandpa-approved labels to a playground of wild, anything-goes creativity, cannabis branding is still finding its footing. But one thing is clear: it no longer belongs in the realm of head shops and incense-filled thrift stores.

 

Today’s cannabis consumers are more mindful, sophisticated, and looking for an experience that seamlessly fits into their Instagram-worthy lives. They also need guidance through the oftentimes-overwhelming process of choosing the right products in this new era of THC. This is where visual branding and consumer-focused design play a crucial role—not just in capturing attention in a competitive market, but in guiding consumers toward the products that best suit their needs and lifestyle.

With beer, the main job of branding is to hint at the flavor and experience. But cannabis—especially in the form of edibles and beverages—requires a different approach. Consumers aren’t just choosing between flavors; they’re navigating potency, effects, and an entirely new way to consume. So branding isn’t just about aesthetics—it’s about building trust, easing uncertainty, and making the experience feel intuitive, inviting, and seamlessly integrated into modern lifestyles.

 

Images used for editorial purposes only and were not designed by Caldeira Co.™

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Jason Caldeira Jason Caldeira

Who’s going to push boundaries if not for us?

There’s no getting around it. Design has devolved into a sea of sameness. Same templates, same sources of inspiration, same blind allegiance to the trend du jour. Don’t believe me? Just scroll through Behance or BrandNew and look at where things have been headed over the past several years.

It seems to me that a few things are at play here: 1) Designers have gotten themselves so worried about following rules of engagement (I’m looking at you, web design) that anything even slightly veering off course is viewed as a radical departure. 2) Designers aren’t designers anymore. They’re hobbyists. Canva fanatics. Wannabe influencers following in the paths of their digital heroes. 3) The world moves too fast and budgets have gotten too chopped for any of us to have the luxury of thinking. And that’s really at the core of successful design: thought. Problem solving. Turning ideas into something tangible. But without the time needed to flesh out a given idea, what are we left with? Cranking out stuff that looks… nice.

I’ve certainly been guilty of this myself on occasion. Clients short on time or money or both force me to move at a pace that doesn’t always result in the strongest work. But having done this for nearly 30 years, even my “crank it out” is at least rooted in some deep knowledge of what works and what doesn’t. But I for one want more out of my profession that just executing what I know the client will approve then moving on to the next thing.

Design should be collaborative. It should be thoughtful, ripe with opinions and intellect. It should make users stop in their tracks (or in their scroll, as it were) and actually think. Anything else is doing a disservice to our clients, and subsequently to their customers.

All this to say… designers, take the time to do things right. Work through the problems. Insist that your clients let you. And clients, do your best to understand that you’re hiring us for our brains not just our hands. Because someone needs to push the boundaries, and it’s not going to be a Canva template.

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Jason Caldeira Jason Caldeira

The power of protest graphics.

Graphic design isn’t just for coffee packaging and concert posters. Design has long been used as a form of social commentary and awareness raising. The ability to distill complex thoughts into succinct visuals is at the heart of every good designer, and nobody is doing that better right now than Gary Taxali.

Now to be fair, I don’t know Gary nor do I know if he categorizes himself as a designer, an illustrator, or an artist. But that’s not the point. Just look at these examples. If a picture is worth a thousand words, these works are a full-blown dissertation. At their core the visuals are simple, but the message they’re broadcasting is anything but.

In a world of disinformation, media bombardment and endless scrolling, the ability to stop someone in their tracks and get them to actually think is more valuable than ever before. Design can do just that. You don’t need to be edgy, and you certainly don’t need to be political. All you need is a perspective and a visual that broadcasts that perspective quickly and clearly. And that’s something you simply won’t find in a Canva template.

 
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Jason Caldeira Jason Caldeira

Where do we look for inspiration?

As a design team working with small businesses we’re often tasked with finding sources of inspiration that align with the everyday lives of our clients’ customers. Whether it’s a yoga studio, a brewery, or a furniture designer, each and every category speaks its own very specific language, and it’s up to us to learn that language before we can speak it ourselves. So how exactly do we do that?

To an extent it comes naturally to us. We have a tendency to take on clients that are in spaces we frequent ourselves. We live in Chicago after all, and are borderline obsessed with the small businesses in and around our neighborhood. We know their clientele because we are their clientele. But every now and again we work with clients that push us into completely new territories, and that’s where sourcing inspiration becomes paramount.

A glimpse into our process.

The first thing we do as part of our process is interview our clients. Over the years we’ve refined a proprietary “get to know you” exercise that not only teaches us what our clients are all about, but oftentimes shows the clients a side of themselves even they didn’t know. It’s amazing how much information we walk away with. And we use this information as our basis for creative exploration and inspiration gathering. That’s where the fun begins.

Inspiration vs. research.

We like to look at creative inspiration from a few angles: ➊ Literal design inspiration. Logos, color palettes, graphics… imagery that feels like the world we want to be in. ➋ Experiences. What is the experience like for your customers, whether it’s a physical location or a digital one? And ➌ how can we “stand out while fitting in”, meaning… what aesthetic does the category lean toward, and how can we create something that’s ownable but not necessarily a radical departure from what customers expect?

And last but certainly not least, we consider the overall vibe and energy of our clients’ typical and/or ideal customer, which helps us further define the language we’re trying to speak. So it’s a bit of a design research/inspiration gathering double feature.

Our go-to resources.

We have a pretty substantial design book collection (thanks in part to the fine folks at Counter-Print and viction:ary) and are scrollers of Pinterest on the regular. We also love hand-painted signage, vintage matchbooks, pre-1960s album cover art, old menus… there’s really no shortage of visual resources - both analog and digital - to get the creative juices flowing. And we dip our toes in as many as we can.

More than anything else, inspiration comes to us by walking in the shoes of our clients’ customers and taking the time to look around and smell the proverbial roses. Because when it comes down to it, we want our clients to become a part of their customers’ daily lives. That’s when we know we’ve done our job.

 
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Jason Caldeira Jason Caldeira

So anyway… have I told you about my podcast?

 

Yesterday was the longest year ever. I’m not entirely sure how to find my way back to “business as usual” right now, but hey… I have a podcast! I don’t promote it much and I should probably do that. So that’s what I’m doing here. Look up Launch Breaks on the podcast app of your choice and listen in as I fumble my way through 10 minutes of unfiltered, unedited small business-focused inspirational ramblings designed to help you launch your product or business out into the universe. That’s it. Now if you’ll excuse me I have some doomscrolling to avoid.

 
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Jason Caldeira Jason Caldeira

Entering the era of uncertainty.

Only 4 days left of democracy as we know it. Is that hyperbole? I’m honestly not sure. But I do know that none of us know what the next 4 years are going to bring for small businesses.

 

Photo by Tim Mossholder on Unsplash

We can take educated guesses about big business: tax breaks, price gouging, billionaire CEOs… same ol’ same ol’. But for small, independent businesses the future is much less certain and much, much scarier. So what can we do (other than the obvious rage-venting on social media)? The way I see it, now has never been a better time to build a support group: friends, family, like-minded businesses in your area, happy customers et al. We’re all going to need to proactively be a part of a bigger community if we’re going to weather this storm. And the key word here is “proactively”. Get out there, build your groups, reach out to your neighbors. It’s going to be a bumpy ride.

 
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