Featured NOLA Entrepreneurs

My Biggest Mistakes from 10 Years in Business

Picture this: It’s 2013, an art major turned accidental entrepreneur, armed with a passion for graphic design and web development, jumping headfirst into the chaotic world of business. I mean, what could go wrong, right? 

As I dabbled in building websites with my husband while producing ad campaigns for colossal global brands, I couldn’t help but notice that the satisfaction of working with small business owners was significantly more palpable. So, despite my almost complete lack of managerial skills and barely-there business acumen, I decided to take the plunge into the wild world of entrepreneurship full-time.

You’ll not be surprised to learn that I’ve racked up quite a collection of blunders on this wild journey. As I look back on a decade in business, I figured it might be both amusing and enlightening to share some of my most epic missteps along the way. 

Refusing to take time off 

Yep, I was the crazy lady in the maternity ward taking phone calls and adjusting website copy. Was it necessary? Absolutely not. Did it bring any long-term benefits? Doubtful. But in my quest to prove my invincibility, I treated time off as if it were shameful.

Let’s face it, overworking, especially when you’re already feeling a bit vulnerable (hello major abdominal surgery!), is a recipe for mistakes, shoddy work, and the dreaded burnout. Yet, there I was, fearfully convinced that taking a breather, even for an excellent reason like childbirth, would signal weakness.

I admit, that I still occasionally struggle to distinguish between my personal life and business (hey, it’s a work in progress), but now I’ve learned to set that trusty “Out of Office” message when I’m on vacation. And guess what? My employees enjoy the same perks. Embracing flexibility and permitting ourselves to hit the reset button has done wonders for our team’s happiness and productivity. Who would’ve thought?

Trying to do it alone

Do you know what would have made maternity leave possible? Bringing a trusted right-hand person on board. I knew it at the time but fear (there’s that word again) stopped me from making the investment. What if I couldn’t pay her? What if, heaven forbid, we lost all our clients overnight? I won’t deny it; these were legitimate worries. However, that age-old saying, ‘you have to spend money to make money,’ has stood the test of time for a reason.

When I finally brought on my first employee, I was freed up to concentrate on growing the business. Not to mention, having a colleague, thought partner, and coffee buddy all rolled into one was a delightful bonus.

Over the years, I’ve brought lots of talented people onto the team. They’ve all contributed something valuable to the team, and I’ve learned from each and every hire. And more often than not, they’ve paid for themselves and then some. 

Not celebrating the wins 

Y’all, let’s face it, Business ownership can be hard. Sure, I get to make my own schedule and be my own boss but that comes with a hefty dose of responsibility. The anxiety of meeting payroll or the thought of losing a major client can be nightmare-inducing. And don’t get me started on diving into the exciting world of insurance paperwork and tax filings. It’s a grind, plain and simple.

But the thrill of receiving a glowing review, snagging an award, or seeing a small business blossom because of our efforts is worth savoring. Far too often, I’ve blitzed past my achievements, laser-focused on what’s still left on my endless to-do list, or worse, dwelling on my missteps. Self-reflection has its place, but as a small business leader, it’s equally vital to take a moment for a little self-congratulation.

My dear friend and occasional coach, Lelia Gowland, has a brilliant suggestion: instead of fixating on the never-ending to-do list, occasionally set it aside and create a ‘Ta Da’ list. She wisely reminds us that “even under the best circumstances, we’re better at recalling unfinished tasks than completed ones.” So, let’s celebrate those victories, big and small, and give ourselves a well-deserved pat on the back!

Squirreling away company knowledge

Deep into Get Online NOLA’s journey, I found myself juggling every task in the business, albeit not always with the greatest finesse. However, as our company expanded, it became clear that my brain could no longer contain the intricacies of every single operation – nor should it have to. That’s when the importance of establishing streamlined processes that could be easily shared and duplicated truly hit home.

In the early days, we began by crafting simple process documents. Later on, we embraced the magic of project management software to achieve the same goal. The sheer delight of clicking a single button that unfurls a well-defined roadmap to success is, for lack of a better term, nerdy nirvana. Clear-cut processes not only save precious time and money but also preserve our collective sanity.

Ignoring the numbers

Like I said up top, I never considered myself a numbers gal. Initially, my skill set was firmly rooted in the creative aspects of the business. So poring over P&L statements and cash flow projections was not my idea of a good time. I’m embarrassed to confess that for the first couple of years, I didn’t even know what those financial documents were! 

Fortunately, about two years into my business journey, a fellow female business owner urged me to interview for the Capital One Getting Down to Business program. That’s when things truly began to take off. This four-month program covered a wide range of topics, from legal contracts to human resources. But the part that really struck a chord with me was the financial coaching. For the first time, I grasped where our business was thriving and where it needed improvement. I learned how to structure our pricing and make predictions about future sales. It was truly a game-changer. I’m not planning to switch careers to finance anytime soon (see my next mistake), but I can honestly say that financial reports are exciting now! I pay attention to the books and consult them before making any significant decisions. 

Not knowing when to outsource

Armed with my newfound bookkeeping knowledge, I upgraded my accounting software and established some financial processes. I diligently managed accounts payable, sent out invoice reminders, and even downloaded monthly statements. But all the time I spent with my nose in the books was time I wasn’t devoting to looking for new business and effectively leading my small team. Eventually, these tasks turned into mundane chores that risked being overlooked. Moreover, my brief training left significant knowledge gaps.

Cue the alarm bells, fellow entrepreneurs! That was the clear signal that it was time to consider outsourcing. Of course, hiring an in-house accounting department was out of reach. After procrastinating for far too long, I finally decided to outsource our financials to an expert, and I’ve never regretted it.

This valuable lesson prompted me to recognize that outsourcing is essential in other areas as well – particularly for tasks that demand specialized skills that fall outside of your core competencies and are too costly to handle in-house. Before long, we had enlisted the help of an outsourced HR consultant, a bookkeeper, and a small business attorney. For most businesses, marketing is another one of those “must outsource” categories, but luckily we have that well in hand.

Working in a Bubble

Louisiana is home but when I moved back to the South after stints in London and Los Angeles, I felt like an outsider in New Orleans. I confined myself to my little home office, which was essentially a glorified closet, relying solely on word-of-mouth referrals from friends and family to drum up business. 

I was too scared to venture out into what I later learned to be the balmy world of the New Orleans business community. Eventually, I plucked up the nerve to attend a Stay Local event, and I immediately recognized what I had been missing. As former New Orleans Chamber CEO Ben Johnson liked to say, “Networking is an excuse for grown-ups to talk to each other.” All of a sudden I felt as if I was part of a community. Not only did I (eventually) gain new clients, I also found a group of people who understood the ups and downs of running a business, and some of those people even became treasured friends. 

Letting Fear Hold Me Back

You may have noticed a recurring theme in many of my past mistakes – fear. Honestly, fear still lurks around the corners, but a decade in business has taught me the importance of being brave. I’ve come to understand that effective leadership means discerning when fear is justified and when it’s impeding my growth.

The Next 10 Years

It’s clear that every mistake has been a stepping stone toward growth and self-discovery. From those early days of refusing to take time off to the moments of isolation working in a closet/home office, I’ve learned that fear can either be a hindrance or a motivator, depending on how we choose to confront it.

No inspirational blog post would be complete without a dubious quote, so here goes. Mark Twain once said, “Courage is resistance to fear, mastery of fear, not absence of fear.” So as I move into the next decade of Get Online NOLA, I’ll aim to do it with courage. 

I hope that by sharing these lessons and insights, I can help other scared business leaders embrace their own journey with newfound courage and enthusiasm. Here’s to the next decade of growth, innovation, and learning from my mistakes. 

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