From Employee to Business Owner: Lessons From A Work-Life Journey
To Quit or Not to Quit
Leaving a stable job with no safety net goes against all conventional wisdom. But for me, staying put felt riskier.
At the time, it wasn’t an easy decision to leave my job, but I knew deep down that life is short, and I’d outgrown my role. Over the years, I’d worked hard to make myself redundant by recruiting and supporting an incredible team—one that was more than capable of climbing the ladder on their own.
But even though I was ready to move on, there was one thought that kept creeping into my mind, my dad’s wise advice:
“Don’t ever leave a job without having a job to go to.”
It’s solid advice, and for good reason. But in my case, I felt something bigger at play.
It was only after I’d experienced cancer (a gift wrapped in barbed wire) that I truly understood the importance of trusting your instincts and taking leaps when they come. That pivotal moment taught me that if you don’t stretch beyond your comfort zone, you may find yourself living with regrets. And that was something I wasn’t willing to accept.
What gave me the final confidence to make the leap was reading Seth Godin’s The Dip. It gave me clarity and helped me see that quitting wasn’t a sign of failure—it was a strategic move that would allow me to do what I truly wanted to do: become my own boss and entrepreneur.
The same is true for brands. Holding onto an outdated positioning or resisting change out of fear can feel safe, but at what cost? Sometimes, the boldest move a brand can make is knowing when to let go and embrace a new direction.
Just Start
Armed with nothing more than a loose business plan, one of my guiding mantras has always been: Just Start. I’m no stranger to procrastination, that voice of self-doubt that whispers, “Do you really think you can pull this off?” But I’ve learned that sometimes the most important step is simply to begin.
For the past decade, that phrase has been pinned to my inspiration wall as a constant reminder to take risks and try new things. It was this mindset that pushed me to kickstart a speaking career, train at UMASS Medical School, attend 10-day silent retreats, introduce mindfulness to schools and corporations, work with Ontario Superior Court Judges and homeless communities, and co-found a branding and design agency.
Curious about adopting a 'Just Start' mindset? Check out the video below:
Brands need this same mindset. In a rapidly changing world, waiting for the perfect moment to launch, refine, or reposition can leave you behind. Just start. Experiment. Put ideas out into the world and refine them as you go. The best brands don’t wait until they have every answer—they learn by doing.
The Safety Net
If you’re considering a leap from your day job into entrepreneurship, there’s one thing I’ll stress: build yourself a safety net. I didn’t dive in headfirst without making sure I had a cushion to fall back on.
Whether it’s saving funds, cutting unnecessary expenses, or waiting for the right time, make sure you have a safety net in place. For us, that meant making the bold decision to sell our big house, downsize, and live with less. We cleared out rooms we never used and sold items we didn’t need. It was liberating—and practical. It allowed us to focus on what mattered and gave us the financial stability to pursue our entrepreneurial dreams.
Similarly, brands need foundational stability to take risks. You can’t pivot effectively without a strong brand core—your purpose, audience, and values. Get those right, and you’ll have the confidence to take bigger creative leaps.
You Don’t Need a Lot of Start-Up Money to Start Making Money
I’ve learned that you don’t need a huge investment to get started, especially if you’re in the service industry. With the rise of AI and other tools, it’s easier and cheaper than ever to start a business.
When I launched my first business, Wake Up Kate, I spent a total of about $350. I had a laptop, designed my own branding, built my own website, and handled my own business registration and hosting. It wasn’t glamorous, but it worked. The point is, you don’t need a lot of capital to begin—just a clear vision and the willingness to do the work.
The same applies to branding. You don’t need a million-dollar budget to build a strong brand. What you do need is clarity—on who you are, what you stand for, and how to communicate it.
When to Pivot
One thing I’ve learned over the years is that knowing when to pivot is just as important as knowing when to stick with something. Pivoting isn’t something you need to do every day, week, or month, but it’s crucial to remain nimble and open to change.
Seth Godin talks about this in his work: there’s a strategic moment when it’s time to walk away from something that isn’t working, and a time when it’s necessary to dig in and continue building. There’s no shame in either choice—it’s just about recognizing what’s best for the situation.
For me, it took time to realize that branding, something I had initially moved away from, was calling me back. After five years of running a successful mindfulness consulting business, it was time to pivot and launch our branding and design agency.
Brands, too, must know when to adapt. Markets shift, audience expectations evolve, and what worked yesterday may not work tomorrow. A willingness to pivot—strategically, not reactively—is what keeps a brand relevant.
The Next Chapter
And so here I am, in this next chapter of my journey. It’s been a wild ride, and I wouldn’t change a thing. Every step—planned or not—led me here, shaping the lessons and perspective I carry today.
Leaving a steady job without a set plan was terrifying—but necessary. The best decisions often are.
The same applies to brands. Playing it safe rarely leads to impact. The brands that make a difference are the ones that start, adapt, and evolve—the ones that have a clear vision yet remain flexible enough to meet the moment.
Have you ever taken a leap in your career, business or brand? What gave you the push?
And if you’re at the stage where you need to define what sets you or your brand apart, we can help.
Words That Changed My Life
The Words That Stay With You
"Don't come to me with problems—come to me with solutions."
When my boss first said those words, they rewired how I approached challenges. Years later, I still carry them with me.
It's fascinating how certain pieces of advice stick, even when their full meaning doesn’t sink in right away. Looking back, I can see how those words shaped my approach to life, business, and leadership. It’s almost like our brains quietly store these lessons, waiting for the right moment to resurface.
Early in my career, I had a habit of regularly updating my boss on the businesses I was working on and sharing the challenges we were facing. Until one day, as I walked into his office, he stopped me:
“Kate, don’t come to me with your problems; come to me with your solutions.”
I can still feel the weight of those words. From that moment on, I never entered his office again without first thinking through a solution. That shift in mindset changed how I lead, collaborate, and make decisions—less reactive, more intentional.
Why It Matters
Words are powerful, often more so than we realize. A passing comment or a remark made during a stressful moment can stay with us for years. I’ve come to understand that it’s not just the words we remember, but also the ones we choose to use—or not use.
For example, I’ve started to avoid the word “busy.” It’s a lazy placeholder, an easy answer when we don’t take the time to reflect on what we really mean. Instead, I try to be intentional—am I fulfilled, overwhelmed, energized? The words we use shape our perspective, our brand, and how others perceive us.
In this video, I dive into how the words we choose shape our lives and brands. Have a watch:
The Ripple Effect of a Few Words
Sometimes, it’s not just one phrase but a recurring idea that has a profound impact. One of my mum’s favorite expressions has always been:
"Sleep is the biggest healer!"
Did I pay attention to this in my twenties? Not really. But now, as a business owner, I see the truth in it. Rest fuels clarity. And clarity fuels better decision-making, sharper thinking, and, ultimately, stronger creative output.
Words don’t just shape individuals—they shape brands, too. The right words can sharpen a company’s message, making it unmistakable and memorable. And just like in life, it’s often the simplest, most intentional phrases that leave the biggest impact.
Me and my mum.
The Words That Show Up When You Most Need Them
What fascinates me most are the words that show up exactly when we need them. Some, like my mum’s advice, have been with me since childhood. Others, like my boss’s challenge, arrived at pivotal moments.
Then there are the unexpected ones. Like the time I was feeling stuck in my business—when a key client didn’t renew, and doubt started creeping in. At that precise moment, I picked up my phone and saw a post from a female business leader I admire. It read:
"You never know what’s around the corner."
Those words were a lifeline, a reminder to stay curious, to keep going even when the path isn’t clear. They reaffirmed what I already knew but needed to hear again: the best ideas, the right clients, the next big opportunity—it’s all ahead.
Pass It On
Words shape us. They push us forward, hold us back, and define our paths. They also define brands—what they stand for, how they connect, and the impression they leave behind.
What’s one piece of advice that’s stuck with you through the years? I’d love to hear your stories.
If you’re searching for the right words to define your brand, this might be the conversation you need.
P.S. One of my all-time favourite phrases to share: 'When someone inspires you, don’t wait to tell them. Tomorrow is never promised.'
How I Landed My First Job (and lessons learned along the way)
Jones Knowles Ritchie’s former offices at 128 Albert Street, Camden Town, London.
Sometimes, The Breakthrough Comes Just After You’re Ready To Give Up.
Having graduated from a top UK university, I had a clear vision: a career that combined my passion for creativity and consumer behavior. I also needed to make a decent salary with real career prospects—enough to afford a bachelor pad in London, even if it was just a tiny room with a fridge, bathroom, and kitchen sink. Advertising checked all the boxes.
Freshly graduated, I was ready to take on the world. I researched the top agencies (JWT, Saatchi & Saatchi, etc.), identified graduate account coordinator roles, and started applying.
But competition was fierce. Each agency had only 2–4 graduate positions, with hundreds of applicants vying for them. After the first round, only 15–20 hopefuls were shortlisted for interviews, and fewer still made it to the final rounds.
Watch the video below to see how I turned my early setbacks into the start of my branding career.
I sent out 20 applications and got just one interview. The odds weren’t in my favor, and I knew I needed a new approach.
Fighting for a Foot in the Door
A year before I graduated, my mum bought me a book on How to Get Into Advertising. At the time, I brushed it off—I thought I had everything figured out. But as my options dwindled, I found myself reaching for that dusty book.
One recommendation stood out: contact recruitment consultants. However, there was a catch—they typically only worked with candidates who had industry experience. Despite the slim odds, I decided to give it a try.
The book suggested purchasing a directory listing of advertising recruitment agencies and cold-calling them. That’s exactly what I did.
Photo of my mum in her twenties.
Breaking Recruitment Rules
I spent hours calling recruitment consultants, repeating the same pitch:
"I’m looking for an entry-level account coordinator position in an ad agency. Do you have any openings?"
The responses were identical: "Sorry, we only recruit for candidates with actual experience."
Each rejection stung a little more. Until the 25th call.
The 25th Call
That call was to Wendy Braverman and Associates, and it’s one I’ll never forget.
I delivered my usual pitch, and the woman on the other end politely replied, “I’m sorry, but I don’t think we have anything that will work...” Then she paused.
In the background, I heard someone mention something to her. When she came back on the line, she said, “Actually, my colleague just flagged an entry-level account coordinator position at a branding and design agency. Are you interested?”
I had no idea what a branding and design agency was. It wasn’t the advertising world I’d envisioned, but I didn’t hesitate.
"Yes!"
After interviewing with Wendy’s team, I was off to 128 Albert Street in Camden Town to meet the agency.
Years later, I learned Wendy had become known as the “ultimate advertising yenta (matchmaker)” in the industry. It gave me goosebumps—it felt like fate had led me to her.
Recently, I read a tribute to Wendy, who had sadly passed away, and was struck by the impact she had on so many lives—mine included. Wendy didn’t just help people find jobs; she helped them find their place. Her ability to connect people to opportunities they didn’t even know existed was a true gift.
The Interview That Almost Wasn’t
Let’s recap: I was about to walk through the door at 128 Albert Street in London and interview with a firm who would become the top branding and design agency in the UK, having no clue what branding and design was.
(Note to future graduates: Please, do your research on the industry and the company before an interview. It’ll help.)
The interview was a blur of questions, many of which I had no idea how to answer. When I was asked about my thoughts on corporate identity, I thought it was something B2B-related!
It wasn’t going well.
Then, I was asked one last question:
"What’s your favourite quote?"
That one, I knew. I answered immediately:
"It’s a far, far better thing that I do, than I have ever done. It’s a far, far better place I go, than I have ever been."
— Charles Dickens, A Tale of Two Cities
The man who interviewed me smiled. Dickens was one of his favourite authors.
I got the job.
Some Things Aren’t Coincidence
It wasn’t just a job—it was the job. I’ll share more about it in a future post.
Looking back, I know these moments weren’t random.
My mum giving me that book.
Calling Wendy Braverman.
Being asked about my favorite quote.
Landing in the branding and design industry.
I was meant to be here.
Lessons From the Journey
That first job changed everything.
And here’s the thing: businesses go through the same journey.
Just like job seekers, brands often start with a vision, apply the conventional wisdom, and hit a wall. They struggle to break through, not because they lack potential, but because they haven’t refined their message—their true differentiator.
In the same way that Wendy connected me to the right opportunity, brands need clarity to connect with the right audience. They need to distill their core identity and communicate it with impact.
That’s what we help businesses do today—cut through the noise, refine their story, and position themselves for the opportunities they’re meant for.
If you’re feeling stuck in your brand’s journey, maybe you’re just one insight away from the right breakthrough.
Have you ever had a career moment that, in hindsight, felt like fate? I'd love to hear it!