Is Rebranding Your Business Self-Sabotage? How to Build a Brand That Lasts with Diana Jakubcova
Dear Creator,
Is rebranding always a way for your business to grow into a newer, higher version of itself? Or is it sometimes a way to avoid a real problem? Is it self-sabotage? In this episode of Dear Creator, me and Diana, brand director and founder of Deeply Rooted Studio, talk about when it’s actually supporting your brand for the long term vs. when it’s an act of avoidance and staying in the cycle of constantly chasing the next new best thing.
Diana is a Brand Director and the founder of Deeply Rooted Studio. She helps established founders stop showing up as the 'safest' version of themselves and instead build a brand that actually reflects the full, intentional spectrum of who they are and what they’ve built.
Key Highlights of the Dear Creator Conversation
Rebranding: Evolution or Self-Sabotage?
We opened with a question I’d been sitting with for a while. Is rebranding your visual identity over and over again, an act of evolving, or is it a form of self-sabotage?
Diana’s answer reframed the entire conversation for me. The problem isn’t rebranding itself, it’s that most founders end up evolving the same version of themselves. They reach for a visual refresh because it feels safe, because it’s the version they’ve seen work for other people on Pinterest and Instagram. But if the foundation underneath hasn’t actually changed, a new logo won’t fix anything.
The signal that it’s actually time to rebrand, according to Diana, is when you can feel a new version of yourself already taking shape. When you know who that person is, even if you can’t fully articulate it yet. The signal that it’s not time is when you’re still unsure, still testing, still asking “do I even want this?” Rebranding into uncertainty just creates more uncertainty.
The “In-Between Era” Problem
So many of us get stuck in this middle stage of not knowing if we need a rebrand, a new offer, a new business strategy, or just… time. Diana’s advice was that before you hire a designer, do the work of figuring out your own vision first. You don’t need a polished way to articulate it yet. You don’t need a full mood board of all the “right” words to describe it. What you need is conviction about the direction you’re heading because a designer’s job is to translate that vision, not manufacture it for you. When founders come in without that clarity and keep shifting direction mid-project, that’s when the whole process gets shaky and miscommunication can creep in.
It’s a good reminder that a rebrand is a reflection of a decision you’ve already made internally. Not a substitute for making it.
Why “Safe” Design Trends Are A Trap
One of my favorite parts of this conversation was Diana naming the actual design trend cycle we’ve all been going through. First it was the clean, editorial “luxury” aesthetic, soft serif fonts, white space, the “editor’s note” font everywhere. Dominant around 2020-2022. Now we’re swinging hard in the opposite direction… bold, saturated, almost over-stimulating “color-maxing.”
Her point wasn't that either style is bad. It's that chasing whichever one is currently trending makes brands blend together. When you open ten different websites and think, "wait, haven't I seen this exact site before?" that's the safe option winning. And in a world where AI-generated design is only getting more common, standing out increasingly depends on how much of your actual personality and quirks you're willing to put into your brand, not how well you can replicate what's popular.
Design Built To Stretch, Not Shrink
This one surprised me. The typical branding advice is to limit everything… fewer colors, fewer fonts, fewer logo variations — to keep things "cohesive." Diana pushes back on that, especially for founder-led businesses.
Instead, she intentionally builds her clients a wider range. She includes more colors to draw from, more fonts to create hierarchy. And the reasoning is pretty simple… founders aren't static. Some seasons call for a bold, energetic push (like a launch), others call for something calmer.
A brand system with room to flex across those seasons doesn't need a full redesign every time the founder's energy or offers shift. It's future-proofing by design, not by restriction.
A Trend Is Not A Personality
We had a fun tangent here that's worth including, which is the idea of jumping on a design trend that has nothing to do with who you actually are. Picture someone who wears all black, has tattoos, and leans edgy and artsy — suddenly adopting a bright, playful, candy-colored aesthetic because it's having a moment online.
It doesn't need to be said twice why that wouldn't land. Trends can be fun to look at, but adopting one that contradicts your actual personality reads as inauthentic almost immediately — audiences can feel the mismatch even if they can't articulate why.
Diana’s Own Pivot: Closing Her Group Program
Diana shared that over the past year, she launched a group program and multiple templates, all while her core business was one-on-one, done-for-you design work.
Looking back, she realized she wasn't launching those things because they served her business. She was trying to escape something. Specifically, difficult client dynamics that were draining her. Social media had also convinced her that "passive income" was the responsible next move, even though her actual strength and preference was going deep with individual clients, not managing a group.
Eventually, she closed the program and pulled those clients back into one-on-one work. She reflected that she'd spent months solving the wrong problem, and it cost her time and energy she could've spent doing the work she actually loves.
Fixing The Root Cause Vs. Escaping Through Strategy
The reframe that ties this whole section together is that the issue was never really "should I have a group program or one-on-one offers." It was why Diana was reaching for a new offer in the first place.
She traced it back further and noticed that she wasn't fully valuing or seeing her own work, which led to over-delivering, which attracted client dynamics that left her feeling unappreciated no matter how hard she worked. She was trying to escape those dynamics by building something new, instead of addressing the dynamic itself. A pattern worth sitting with is that sometimes the "strategic" fix is actually an avoidance tactic in disguise.
The Shiny-Object Test
We ended on something genuinely actionable — a framework for anyone feeling the pull toward a new course, template, or strategy:
Ask how it felt last time. Have you tried something like this before? What actually happened?
Give it real time before committing — 24 hours at minimum, ideally closer to a week.
Check free resources first. A lot of what's being sold in $500 courses is available on YouTube.
Notice if you're reacting to scarcity. A slow month or a wave of overwhelm often triggers "I need to fix this right now" thinking — which is exactly when a Band-Aid purchase feels most tempting and is least likely to actually help.
Intention Over Imitation
If there's one idea that ties this entire conversation together, it's that business isn't one-size-fits-all, and copying someone else's model — whether it's a rebrand style, a launch strategy, or an entire business structure — without checking in on why you're doing it is a fast track to burnout.
Experimentation isn't the problem. Doing it on autopilot, reactively, because everyone else seems to be doing it, is. The most future-proof thing you can, build in your brand or your business model, is one rooted in who you actually are, not who the algorithm is currently rewarding.
Thanks For Tuning Into Dear Creator!
You can listen to the full conversation to hear what didn’t make it into this recap on YouTube, Spotify, Substack, and Apple Podcasts. If you enjoyed the conversation or the podcast, please leave a review or rate it! It’s greatly appreciated and it helps others who need to hear these conversations, find them.
