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Handling Your "If Only I Had Known" Moments

Wedding pros share what they regret not doing in their first five years of business

Defining your brand, acquiring funding, identifying your audience, and perfecting your offerings—the first five years of a business are no cakewalk! Most entrepreneurs experience a rollercoaster of highs and lows during the startup stage, with nearly half of all small businesses folding before their fifth anniversary.

There are many reasons companies fail: lack of industry knowledge, poor marketing, and rapid growth, just to name a few. But on the other side, more than half of all small businesses do hit the five-year mark and, for some, survive far longer. 

If you’re in the early stages of a business and struggling more than anticipated, you’re in good company. But that doesn’t mean you’re destined to go under! New entrepreneurs should take notice of their tenured counterparts who have 10, 15, and 20 years under their belt to learn best practices and avoid common pitfalls.

Here are eight things experienced wedding pros regret neglecting when starting out.

Figuring it out on the fly

Some things can be made up along the way, like a new smoothie recipe or a morning workout. However, a business doesn’t fall into that category. While there are certain elements you’ll need to figure out over time, every new entrepreneur should enter the process with a business plan that lays out how it will generate revenue.

It’s easy to dive into the work side of a business, but without a big-picture plan, it’s just as easy to lose track and experience unnecessary setbacks. 

That’s what happened to Cathy O’Connell when she started COJ Events. “We launched with a client asking for help, jumped into it, and just took off so fast that we never really sat down and did a full business plan,” she shares. “Our only goal was to grow and sustain ourselves! This lack of planning hindered us later on.”

O’Connell isn’t the only one who overlooked the importance of a plan in the beginning. “I wish I had sat down to write out a 3-5 year plan,” reflects Samantha Leenheer of House of Joy. “Having a long-term plan in place would have put me in the position to work on relationships and build skills to get closer to those goals and give me something larger than myself to work towards.”

“Putting a plan into action makes a difference and is your blueprint for progress,” agrees Maria Romano of True Love Knots. “You need to create a business plan or find someone to help you, especially if you are not numbers-oriented or marketing savvy.”

At first, it’s hard to dedicate time to dreaming about the future and writing plans when you’re laser-focused on turning a profit. However, event planner Penny Haas cautions that focusing on making money can lead to short-term gains at the expense of long-term sustainability. “Understand when and where to play the long game,” she says. “Being mindful of the scope of your business and if you want to grow it or maintain it and your lifestyle is something I learned along the way.”

The good news is that it’s never too late to create (or update) a business plan! It’s always worth having a solid plan to lean on, even if you’re several years in and making a comfortable profit. A business plan serves as your North Star, guiding you in the right direction during slower periods.

Pigeonholing their offerings

You start a business, produce successful results for your first client, decide you’ve found your niche, and lean into it — it’s a tale as old as time. But avoid giving too much credence to where you think you belong in the early stages of your business. Otherwise, you may tie yourself to an offering or audience, limiting your growth potential.

Instead, Rajbir Grewal of Lux Affairs urges new event pros to avoid her mistake of focusing solely on one style of event. “Keeping an open mind can lead to unexpected opportunities,” she says. “Exploring other industries or creative areas can be highly beneficial.”

The first years of a business are for experimenting. Try new things, explore what you love (and hate), learn what the market wants (or doesn’t), and stay curious! Many entrepreneurs find their businesses evolve as they gain experience and refine their business plans. Treat detours as opportunities, not failures!

Scrimping on business expenses

People love to hear inspirational stories about entrepreneurs pulling themselves up by the bootstraps and turning startups into empires. But you’d be hard-pressed to find a successful executive who didn’t invest money into their businesses, even at the risk of personal financial loss.

You might be able to get by with the bare minimum of expenses, but what you save in your bank account will drain your time and energy—two vital factors for success. You may also unknowingly lose potential leads by appearing cheap or unprofessional.

“I cannot believe I did not invest in tools that would make my life easier and look more professional,” shares Jordan Heller of Suncoast Wedding and Event Leaders. “E-mail service providers, CRM software, accounting tools, and social media apps have all changed my business but would have saved me a lot of time and closed more leads if I had them from the beginning.”

You might think you’re saving money by passing up on valuable business resources, but your lost time and energy likely mean you’re missing out on profitable opportunities. So instead of worrying over every cent, learn to separate investments from expenses. Financial investments provide intangible returns for the good of you and your business. The saying is true: You have to spend money to make money.

Undervaluing and undercharging

Most of the time, entrepreneurs must scrimp because they aren’t producing enough revenue to invest back into the business. Unfortunately, that’s often because they undercharge due to low confidence and poor market understanding.

“It is hard to figure out what other people are charging and where to start,” explains event planner Keith Willard. “I thought I needed to be affordable to get events under my belt, but zero idea of what other people considered affordable versus giving it away. Know your value and the value of the services you provide.”

Wedding photographer Colton Simmons shares Willard’s regret. “I undervalued myself far longer than I should have in the first five years of my career,” he says. “I worked far too many weddings and did not charge enough. This led to burnout in my fifth year, and I almost walked away from the industry altogether. Incrementally increase your pricing as you work three to five weddings, and you’ll avoid the same mistake I made.”

While new event pros shouldn’t expect to charge Mindy Weiss-level rates, accept that value is in the eye of the consumer. Low self-esteem has no place in a business’s pricing, so focus on data-backed numbers from your market instead. For example, if you’re a new florist, look at what experienced florists charge and use incremental adjustments to work back to a reasonable starting point that lays the groundwork for growth.

Not getting the word out sooner

It’s scary to put yourself out there as a new business owner. Your company is your creative brainchild, and exposing it to the world requires vulnerability and risk. But nobody will know your brand is wonderful if you keep it hidden!

That’s where marketing comes in. Building brand awareness is critical to success whether you’re a venue owner, caterer, DJ, or otherwise.

When Samuele Gallorini launched Gallorini & Giorgi Events, he felt like funding stood in the way of an effective marketing strategy. But looking back, he wishes he had chosen to “apply for a business loan to start up the company and immediately hire a marketing and business expert in the wedding industry.”

People can only buy from companies they know exist, so you must position your brand to reach them through social media, press, digital ads, podcasts, and emails. 

In this case, Wedding Venue Map’s Shannon Tarrant notes that quantity is sometimes better than quality. “I spent a lot of time perfecting each funnel before adding the next one,” she shares. “The better time would've been spent investing a little in more places so they would have had time to grow.” By putting out feelers in multiple channels, you can spread awareness faster, evaluate performance, and improve the strategy as you go.

If marketing has produced disappointing results, Bite Catering Couture’s Vijay Goel suggests it may be a matter of “clarifying and communicating a unique perspective.”

“It's easy to copy others,” he says. “It's harder to find your voice and make the best ideas your own! But this is what great businesses and artists do.”

Startups are messy and ever-changing, but entrepreneurs pour so much passion and grit into them. They deserve recognition, which starts with a sound marketing strategy.

Overlooking the value of networking

From client referrals to brand partnerships, a broad network offers a wealth of opportunities at every stage of business. 

“I was unaware of how powerful relationships with other vendors would be when their clients need your service,” Simmons notes. “You can build a synergy that becomes massively beneficial for your shared clients.”

But beyond growth potential, industry connections also provide support and friendship on a journey most people don’t understand.

Wedding photographer Tracy Autem admits she didn’t network for the first two years in business. “I thought it was all about an elevator pitch and giving out business cards,” she recalls. “Networking, when done authentically and from the heart, could not be further from that. It is a way to grow friendships, find your tribe to call on when you have a difficult client, and eventually refer each other business."

Start small with local industry groups and professional networking events. As you build confidence and experience, attend national conferences and retreats to expand your network to a national or global level.

Navigating entrepreneurship alone

Starting a business is not for the faint of heart; many discover that entrepreneurship can be lonely. But it doesn’t have to feel that way! Mentorships are rewarding opportunities to establish a meaningful connection and learn from a seasoned veteran.

For Chandai Raghunauth, it took a few years before deciding to hire a mentor after starting Chandai Events. “I wish I had sooner,” she states. “It was the best investment. It has made me see a bigger picture and broaden my horizons.”

Jen Sulak of Weirdo Weddings agrees, wishing she had found “someone who could guide me through the first steps of the mental and emotional aspects of running a small business tailored to my goals and dreams. I think I would have leaned in a little more to who I was rather than just what I did.”

Only a few lucky ones naturally stumble upon their ideal mentor; most have to go out looking until they find the right one. If you’re unsure where to start, revisit the last tip and dedicate more time to networking!

Ignoring self-care and well-being

Last but certainly not least, many event pros regret prioritizing their businesses over their health and happiness. Getting stuck in the hustle-and-grind mentality is common, but humans need time to rest and recharge—including you.

“No one needs to work 24/7, and unless you are saving a life, nothing is so important that it can't wait a few hours,” confirms Megan Lentz of Vida Events. “Respect your home life, as well as your work life.”

Mangia and Enjoy!’s Sarah Chianese adds that she wishes she had “established clear boundaries with clients and other wedding professionals and had clear and robust contracts with anti-abuse and anti-harassment clauses.” She also regrets “not sleeping more or practicing block scheduling allowing for self-care practices.”

Remember: Your business’s health aligns with your personal health! Investing your energy is impossible when burnt out, so take care of yourself first.

As you navigate the early years of a business, expect to go through some growing pains. They’re perfectly normal and will build resilience to overcome future hurdles. Treat them as learning lessons, and don’t let them steer you away from pursuing your dreams!

Meghan Ely is the owner of wedding PR and wedding marketing firm OFD Consulting. Ely is a sought-after speaker, adjunct professor in the field of public relations, and a self-professed royal wedding enthusiast.

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