2ND EDITION | ISSUE #166

I'm no longer sorry for taking the scenic route when it comes to my brand.

Because now that it feels like I am reaching the end of the road - I can look back and see how each stop along the way got me to where I am now.

The only thing I regret?

Is ever calling it a rebrand in the first place.

This time last year, I started to think about just how much the word "Rebranding" had lost its true meaning and how that impacts how we, as founders, evolve the brands we have for the better.

I even created a "Rebrand Diaries" Series on Instagram.

But as each new offer rolled out—from the brand color kit, to my 2D design masterclass, to Brand Brushstrokes, and then The Studio Sesh—I realized that my brand wasn't really changing.

It was evolving. Deepening.

As each piece of feedback came in - with every new beta tester, my understanding of my clients and audience became even clearer.

And then it dawned on me.

The majority of us Online Business Owners don't have a background in Marketing. But here we are—building our own brands and learning how to market them effectively in real time.

We fall into two buckets:

Bucket 1: The marketers—copywriters, designers, social media managers, content strategists—trying to "stay in their lane" and avoid scope creep into someone else's marketing territory.

Bucket 2: Non-marketers who need to market their brands anyway.

What both buckets have in common? Overwhelm. And both buckets end up in the same place—Googling 'do I need a rebrand' at 11pm instead of actually fixing the thing that's not working.

Rebranding is a word that has lost its meaning.

To the point where plenty of people - myself included - have used it or identified as rebranding when that isn't really what's going on at all.

"Rebrand" has become this catch-all solution for any brand "problems". Your services page feels off? Rebrand. Your messaging isn't landing? Rebrand. You're shifting from 1:1 to group programs, and nothing feels aligned? Rebrand.

But rebrands are expensive, time-consuming, and if you do them for the wrong reasons, you'll end up right back here in six months, wondering why your content and offers are still not converting the way you want them to.

Here's what this newsletter will actually give you: A framework to diagnose what's not working—starting with the three questions I ask every single client before we touch a single font or color.

Because most of the time, your brand colors and logo aren't the problem. What you really have are positioning problems, messaging problems, and "I'm not sure who this is even for" problems.

Do you even need a rebrand? Is that what you're really doing here? Let's find out.

Here's what was actually happening behind the scenes of my 'rebrand'—and how these three questions revealed what I really needed.

Early 2025 — I started questioning whether "rebrand" was even the right word. In a reel from February 21, 2025, I broke down the real spectrum: refresh vs. redesign vs. repositioning vs. total rebrand.

That realization came after nearly a year of what I'd been calling a "rebrand." I'd announced it back in April 2024, built around my core belief that you can't build a brand in a day—and that redoing your own brand is hard as hell.

But by August 2024, I was no where near done. Why? I'd spent most of spring doing client work and preparing for a 4-week sabbatical where i’d be living out of a tent. But more importantly, I was going back to basics—redoing Cedar June's entire Brand Strategy for the first time since 2022.

I Haven't "Rebranded" — I Repositioned and Evolved

Current Status (February 2026): My website is launching at the end of February 2026 — just weeks away. I'm currently in the design phase, using my own Signature Site process.

So what did I actually do over the past two years? Let me break it down by category:

Here's a framework to diagnose what's not working behind the scenes of your brand—starting with the three questions I ask every single client before we touch a single font or color to help them determine whether or not they really need a full rebrand or if what they actually need is repositioning or a visual refresh..

What I Actually Did (2024-2025)

• Rebuilt my entire Brand Strategy from the ground up for the first time since 2022—moving from someone else's strategy template to my own framework.
• Repositioned from "brand designer & content marketing expert" to someone who does "brand pivots with personality. I now identify as a brand positioning expert, illustration-based designer, and strategic implementer"
• Developed signature frameworks: The Slow Branding Philosophy, The Chief Creative Office Week Framework, & The Branding Butterfly Effect​

The Issues I Was Actually Solving

✓ Positioning Gap: I called myself a "brand designer & content marketing expert" when my work actually encompasses brand development, design, and strategic implementation. My messaging didn't reflect the full scope of what I offer.

✓ Clarity Problem: When asked what made me different, I didn't have a clear answer. My bio said generic things like "build, manage & grow your brand" — but what does "brand management" even mean? People were confused about whether I did social media, branding, content strategy, or all of the above.

✓ Market Shift: I started attracting multi-passionate entrepreneurs who needed strategic support beyond just pretty visuals—but my positioning still made me sound like a designer who makes things look good.

Strategy Red Flags (That Might Sound Familiar)

🚩 You struggle to explain what you do in one clear sentence

🚩 Your current messaging doesn't reflect who you serve now or what you actually offer

🚩 Traffic arrives but doesn't convert because your messaging doesn't match their search intent

I didn't drastically change my visuals — I just refined them by swapping out a couple colors and refining my fonts.

The Issues I Was Actually Solving

My own design skills had gotten so much better since first designing my brand. So it wasn't that my visual identity changed drastically - I just refined it by swapping out a couple of colors and refining my fonts.

Design Red Flags (That Might Sound Familiar)

🚩 You cringe when sharing your URL or feel apologetic about your site

🚩 Your aesthetic doesn't match the caliber of work you deliver

🚩 You are constantly recreating the wheel when you design for your brand because you don't have any guidelines that make sense to you.

The Issues I Was Actually Solving

✓ Fragmented Systems: I didn't have a cohesive way to explain my offers or how they connected. So I essentially redeveloped my entire offer suite in the last year.

Implementation Red Flags (That Might Sound Familiar)

🚩 Your site is too complex/rigid to maintain or make quick changes yourself

🚩 Brand assets and guidelines are scattered or non-existent

🚩 Current platform can't support the features or integrations you need

Question 1: Can you clearly articulate who you serve and what transformation you provide?

If someone asks "So what do you do?" at a networking event and you launch into a rambling explanation covering three different services, two past career pivots, and somehow leave them more confused—you have a positioning problem, not a visual identity issue.

What this reveals: If you can't articulate your positioning clearly, updating your colors won't fix anything. You need strategic repositioning work first.

Question 2: Does your current brand look and feel match the caliber of work you deliver?

You look at your website and cringe. Your brand doesn't look like you anymore. You have seventeen half-finished Canva files and three different "final" color palettes. Your visual identity feels dated compared to your peers, or doesn't match your personality.

What this reveals: If your positioning is solid but your visuals feel off, you need a visual refresh—not a complete rebrand.

Question 3: Has your business model, audience, or offers fundamentally shifted?

You've pivoted from service provider to product creator. From B2B to B2C. From 1:1 to scalable offers. Your current brand was built for a completely different business than the one you're running now—and nothing makes sense anymore.

What this reveals: If both your positioning AND your visual identity are misaligned with where your business is now, you might need a full rebrand.

The Diagnosis

I had strategy problems masquerading as design problems. I could have redesigned my website six times and it wouldn't have fixed the real issue: I wasn't clear on my positioning, so nothing I created could land with clarity.

So yeah, two years to evolve my brand positioning, test 5 new offers, refine my messaging, figure out what I actually do, beta test with real clients, develop frameworks, consume all the course content, lose a major client, break an arm, plan a wedding, renovate a house, and now finally build the damn website.

The brand evolution? That happened organically through all the testing and client work.

The website? Took forever because I kept pushing it for "more urgent" things until i finally deleted everything else and made it THE priority.

Why This Distinction Actually Matters

When most people say "I need a rebrand," they're actually talking about their visual identity—new colors, new fonts, new logo.

But if your positioning is the actual problem (you're not clear on who you serve, what makes you different, or how to talk about your transformation), then updating your visuals won't fix anything. You'll just have a prettier version of the same confusion.

The real question isn't "should I rebrand my business?" It's "what isn't working at the core—and does fixing it require strategic repositioning, visual updates, or both?"

And if you're sitting here going "okay but HOW do I figure out which one it is"—that's literally what the Studio Session is for. 60 minutes, you and me, we diagnose exactly what's misaligned and map out what to fix first.