5 YEARS IN BUSINESS: NAVIGATING BRAND GROWING PAINS
- Jenny Henderson
- Apr 28
- 5 min read
Updated: Apr 29

Earlier this year, I celebrated my fifth year in business. It’s safe to say, I am not the same business or business owner I was when I first started in 2020. So here I am, five years in, and I’m feeling this nudge to reevaluate my brand and positioning. Maybe you’re feeling the same way in your own business.
This is a sign your business is maturing and evolving.
So, how do you navigate the twists and turns of an evolving brand? When is the “right time” to rebrand and how do you know if your business needs to rebrand or just reposition?
These are just a few of the areas we’ll explore in this blog.
CONTENTS
THE BRAND LONGEVITY MYTH
Don’t believe the myth that a brand has to be forever. The best brands are those that evolve with the times and the needs of their audience.
Even the brands we commonly think of as “forever” brands—they’ve all experienced their own phases of reinvention.
Look at Apple. They started as a computer company. But today their range of products have expanded to meet the needs of modern consumers and convenience.
Imagine if Netflix had maintained their original business model as a DVD rental company. They'd be obsolete. Instead, their business evolved to spearhead a movement for online streaming services.
Starting a business does not mean you need to know on day one what your brand will look like in five or ten years. One of the greatest privileges of being an entrepreneur is how you, your business, and your brand will evolve over time.
THE FORMATIVE YEARS OF A BRAND’S LIFECYCLE
Rarely is the brand you first launch the one that endures for decades to come. Consider those first few years of business your formative years. This is where you’re experimenting in business and finding your way. Typically this looks like:
pivoting or refining your offer suite
finding and honing in on your ideal target audience
brand messaging trial and error
As a brand during your formative years, you’re in a perpetual state of reinvention. This is why I encourage anyone just beginning their entrepreneurial journey to DIY their brand with a simple typographic brand identity. Starting simple allows for a natural evolution of your brand.
Years one through four are important for discovering the type of business you’re truly meant to be. You’ll refine your offers, fine-tune your mission and messaging, and start to claim pieces of your identity that feel true.
Experimenting in entrepreneurship is how you find alignment and authenticity as a brand. These are the keys to brand longevity.

Signs You Might be Having a Brand Identity Crisis
During your formative years, you may experience a brand identity crisis. What this means is your business has evolved but your brand has not. This misalignment will show up in different ways.
Here are a few signs you may be going through a brand identity crisis:
you’re always changing your brand colours and fonts
you’ve rewritten your website copy more times than you care to admit
you keep attracting the wrong type of clients (or not enough clients)
you’re always borrowing ideas from other brands you like
you get requests for services you don’t actually offer
you waste time reinventing your brand aesthetic with every new offer you have
When your business and brand are out of sync, it will hinder your growth by muddying the narrative surrounding your business. Keep reading to figure out how to navigate this awkward phase.
NAVIGATING YOUR FIFTH YEAR IN BUSINESS AS A BRAND
Following your formative years, you’ll typically find yourself in one of two places:
Confident and clear about the direction you’re heading and ready to make it official.
Confused and uncertain about how to shape your brand from here on out.
Rest assured, these are both signs of a maturing business.
For some, your years of trial and error have cleared the fog and you completely trust the direction you’re heading in.
For others, the fog is still clouding your vision. You’re struggling to see past certain parts of your identity which is stopping you from moving forward at all.
Owning Your Brand Evolution
If you’re ready to step into your power as a brand, investing in brand strategy at this phase provides you with the foundation for your brand, allowing you to commit to those parts of your brand identity that will support your business growth long-term.
I want to be clear, this brand commitment isn’t about limiting your evolution. It’s about identifying your brand purpose so your business will continue to strategically evolve and adapt to the changing times without ever sacrificing who you truly are.
Strategizing the Way Forward
If you’re at a standstill, working with a brand strategist will provide you with the clarity you’re seeking. Why? Because just like a good therapist, a brand strategist is able to hear what you’re trying to say while recognizing opportunities for brand distinction and direction.

REPOSITIONING VS REBRANDING AN EVOLVING BUSINESS
As your business evolves, you may be feeling a nudge to shift something about your brand. Before you can decide whether to reposition or rebrand, it’s important to understand the difference between rebranding and repositioning.
Repositioning Your Brand
Repositioning happens when your business is fundamentally the same, but you need to shift how it’s perceived. Maybe your ideal client has evolved and you’ve refined your offers to align with this new target audience. To better articulate the transformation you provide, repositioning your brand will help amplify this shift across your messaging and marketing.
Repositioning will help breathe new life into your brand without needing a complete visual overhaul.
Rebranding Your Business
Rebranding makes sense when the foundation of your business has evolved. Maybe your services have completely shifted, you're entering a new market, your business model has changed, or your brand no longer reflects your long-term vision.
It’s not uncommon at the five-year mark for a business to outgrow its original brand identity. A strategic rebrand will realign your visual identity and brand experience to reflect the business you are today, while continuing to attract new clients and aligned opportunities.
RECALIBRATING YOUR BRAND FOR YOUR BIGGER VISION
Hitting the five year mark is an important milestone in business. It means you’ve experimented, learned, adapted, and grown. Sometimes we feel stuck while other times we feel a renewed sense of clarity. In both cases, it’s natural for your brand to need a recalibration to reflect the business you’ve become and the bigger vision you’re stepping into.
Whether you're ready to formalize your evolving identity or you're seeking clarity on how to move forward, investing in your brand at this stage will set the foundation for sustainable growth in the years ahead.
Ready to bring your next evolution to life? Learn how we can work together to position your brand for the business you’re becoming—or join me for an intro call to learn what path forward is right for you.
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Jenny Henderson Studio develops memorable brand experiences and strategic brand foundations to improve recognition and revenue for service-based small businesses.
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