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The Reality of Reaching Six Figures in Sales: New Levels, New Devils

So, here’s a fun fact that might date me a bit, but here goes: I’ve been an entrepreneur since 1990. Out of those 34 years, the first 20 were spent on just one business. And from the outside it probably looked like I was doing pretty well. The business grew so quickly, I hit a million in sales by the second year.

But what if I told you that for almost that entire time, I felt like I was standing on the edge of a cliff? Just waiting for the other shoe to drop. For the next big disaster to take me out completely, and I’d be left with just the ashes of what I’d built.

At that point the only people I had to talk to about it were my accountant, my bank manager, my lawyer, and my husband—who usually just asked about the sales figures. None of them were deeply invested in the nuances of my day-to-day challenges. My employees were encouraging, but it seemed like each of them only saw a small slice of the whole pie. Plus, I had made the mistake of surrounding myself with yes-men who never challenged any of my ideas.


It often left me feeling as though the entire weight of the business rested on my shoulders. I carried not just the operational burdens, but also the emotional weight of potentially jeopardizing my family’s security with a single wrong decision. This fear drove me to keep pushing myself beyond limits, year after year. I thought if I could just get over myself, put my head down and work harder, it would be ok eventually.



I know that so many entrepreneurs feel this exact same way – terrified, overworked, burned out. But all these years later I realize that while it might be normal, it’s not healthy, for you or your business.

With some time and distance, I came to understand that all of that stress was due to three primary factors, and now I’m determined to help others avoid these same pitfalls.

1) Managing Money

The primary source of my stress was money, of course. Despite everything looking great on paper (after all, the bank kept giving me money) I constantly struggled with cash flow. I’d stay up at night, tallying up expenses in my head against what remained of my credit line.

My default solution was always to aim for higher sales the following month. For example, if sales were averaging $50,000 or $70,000, I’d set a new target of $100,000, believing that just one more bump in sales could right the ship.

I also never saw the value in investing in administrative services that didn’t directly generate sales, which often led to me screaming into my accountant’s office at the last minute with disorganized records stuffed into envelopes and chaotic spreadsheets. He would patiently go through it with me, and while I was sitting there I could grasp the numbers but by the time I got back to my car, my understanding would evaporate.

Since then, I’ve realized two things: first, I was probably afraid of truly understanding the financials of my business, and second, I really needed an accountant who specializes in physical product businesses. Because the “profit” on your P and L sheet is often actually tied up in inventory, an accountant who doesn’t understand product finances won’t be able to solve your cash flow troubles.

2) Managing People

The second major source of stress for me was managing the people in my business. We had some fantastic employees, but it was always something. Someone had found a better job, someone else needed different hours, or was going on maternity leave—which in Canada could last up to four months for key personnel.


I often felt vulnerable because I needed these people to operate my business, and the uncertainty turned into a constant source of frustration. It seemed like everyone else’s needs came before my own. And because I wasn’t on the regular payroll, I was always last to get paid too, assuming there was enough left over to pay myself.


3) Managing Growth

The third big stressor in my business was achieving sustainable growth. Every year, it felt like I had to dig deeper, come up with more promotions, and find new ways to boost my sales. And it only got tougher and more expensive over time. Why? Because my overhead costs were climbing. Each step I took to grow—hiring more staff, buying more equipment, signing more leases—just piled on more fixed expenses each month.

Chasing after sales became a never ending cycle. It was like constantly trying to outdo myself—last year I hit $1.1 million, so this year I needed to make $1.5 million just to keep up because my daily starting cost was now $4,000.

All of this combined—the money, managing people, and figuring out how to keep the business viable—created a ton of stress. It made me constantly question my end game: How would I sustain this? And what was my exit plan if I decided I couldn’t keep going?

Learning from Mistakes and Finding New Perspectives

The rollercoaster of wins and challenges often left me feeling like a bit of a fraud, or at least like I was only good at certain aspects of my business. I used to brag about my sales skills , but when it came to finances and organization, I’d convinced myself I was terrible.

And that mindset spilled over into how I viewed my role as an entrepreneur: I was the sales driver, nothing more. I’d say things like, “I can only take the business this far and no further,” which really boxed me in. But looking back now, years later, I realize it didn’t have to be that way.

I was largely writing my own narrative. Just working harder and doubling down on effort wasn’t the answer—it only added to the feeling of teetering on the edge of a cliff.

What I needed, and what anyone in a similar position needs, is education. Back then, if you’d told me that my struggles with finances, managing people, or sustaining growth were due to a lack of knowledge, I might have resisted the idea. But now, I clearly see that it’s  not about working harder; it’s about learning the aspects of business management that you don’t know yet. Understanding this can completely change the way you approach challenges and lead your business toward a more controlled and confident future.

Moving Forward with Less Stress and More Knowledge

There are tons of us online, myself included, who can show you how to set up ads or leverage social media. That knowledge will take you a good distance in business. But the real game starts when your sales hit around $100,000, you begin hiring staff, and managing inventory becomes a daily task. That’s when deeper challenges emerge.

Unfortunately, there isn’t much out there about managing the team dynamics or the operational hurdles of a growing business. But I’m fortunate to have figured a lot of this out, and now I’m in a position to pass on that knowledge. I don’t claim to know everything, but I can pinpoint the problems and suggest ways to tackle them—although it takes time to iron these issues out.

In the coming weeks, I’m going to start discussing these critical areas—like understanding finances better and managing people effectively—that aren’t often covered in our industry. I’ll dive into how to foster sustainable growth and set yourself up for success beyond just making do.


We often think our options are limited, especially when just starting out. Yes, it’s crucial first to secure consistent sales, but once you hit that $100,000 mark, it’s time to strategize differently. You could work hard and still end up stressed and unprofitable, or you could learn how to work smart and build a valuable asset.


If you’re interested, sign up to receive weekly emails where I’ll share more about these solutions—not a course, just sharing what I’ve learned to help others in similar spots.

So, if you’re feeling the pinch or just want to prepare for future challenges, sign up for these emails. Let’s make your business journey less stressful and hopefully, a lot more enjoyable.



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What To Do When You’re Short Of Cash, Episode 222

What To Do When You’re Short Of Cash, Episode 222

No time to listen now? We'll send it to your inbox. No time to listen now? We'll send it to your inbox. or scroll down to get the highlightsMastering Cash Flow for Six and Seven-Figure Ecommerce Stores Before we dive in,...