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 Holding onto an outdated positioning or resisting change out of fear can feel safe, but at what cost?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.