After years advising entrepreneurs, launching my own Connecticut cottage food business taught me unexpected lessons about farmers markets, customers, inventory, displays, sampling, and more.
This past summer, I launched my cottage food business, Storyline Chocolates.
For those unfamiliar with the term, a cottage food business produces approved foods from a licensed home kitchen for direct sale to consumers. In Connecticut, cottage food operators must follow regulations governing which foods can be produced, how they can be sold, labeling requirements, and annual sales. The current gross-sales limit is $50,000 per year, and cottage food products cannot be sold wholesale.
I was hardly new to small business when I started.
For more than six years, I have worked as a Business Advisor with the Connecticut Small Business Development Center, advising hundreds of entrepreneurs across industries ranging from food and retail to ecommerce, manufacturing, professional services, contracting, and transportation. I have helped clients work through business plans, financial projections, marketing strategies, operations, and the countless decisions involved in starting and growing a business.
And none of that fully prepared me for my first month on the other side of the table.
Storyline Chocolates itself was nearly two years in the making. During that time, I rewrote stories, attended online chocolate school, developed the brand, reformulated chocolates, built the business infrastructure, refined the concept, and eventually brought my brother into the business as my partner.
By June 2026, we were ready to launch—or at least as ready as entrepreneurs ever seem to be.
Despite all that preparation, we were still scrambling the night before our first market: building inventory, finalizing processes, organizing the display, packing supplies, and dealing with a dozen details that had somehow escaped the plan.
That first month reinforced what I have told many clients over the years.
The underlying fundamentals of business are the same. The execution is not.
Here are 10 lessons my first month running a cottage food business taught me.
Connecticut has an abundance of farmers markets, and during our first season we participated in markets in Old Wethersfield, Glastonbury, Litchfield, and Stafford.
Before becoming a vendor myself, I underestimated everything that goes into creating a good market. Market managers carefully curate the vendor mix, coordinate local organizations, arrange entertainment, promote the event, handle logistics, and create an atmosphere that gives people a reason to spend part of their day there.
Some of my favorite moments had very little to do with selling chocolate. I loved watching families spread blankets on the lawn, enjoy food they had picked up from vendors, and listen to live musicians nearby.
A good farmers market is a community experience—and vendors are part of creating that experience.
Farmers markets offer an opportunity to learn about your customer.
Traffic alone does not determine whether a market will perform well for your business. We saw significant differences from one market to another.
At some markets, customers were primarily shopping for weekly staples: fruits, vegetables, bread, dairy, meat, and other products they regularly replenish. At others, shoppers seemed more inclined to browse, discover something unusual, purchase a gift, or indulge themselves.
Those are very different shopping missions. That is why testing multiple markets can be so useful, particularly when you are launching something new.
Pay attention to more than sales. Notice:
Markets offer an opportunity to observe customers in real time. Use that information to refine both your product and your value proposition.
A market tent may only be 10 feet wide, but it is still retail space.
Your booth is a physical expression of your brand, and thoughtful merchandising matters.
Your business name should be easy to see from a distance. Signage, brand colors, packaging, and table coverings should feel cohesive. Products displayed at different heights create visual interest, while featured items give shoppers a focal point.
Most importantly, your display should give someone a reason to pause.
At a busy farmers market, people are constantly scanning dozens of tents. If nothing catches their eye or sparks curiosity, they can easily walk past without ever realizing what you offer.
For Storyline, that means our display has to communicate quickly that we are not simply selling chocolate bars—we are offering chocolate paired with stories and guided tasting experiences.
Market managers notice presentation too. Each vendor contributes to the overall atmosphere and is a reflection of the market.
If you sell outdoors in New England, weather becomes part of your operations plan.
A market season can stretch from May into late October or early November. During that time, you may encounter cold mornings, pouring rain, strong winds, oppressive humidity, and 90-degree afternoons.
I once watched another vendor's tent blow across a market like a tumbleweed because it had not been properly secured.
Your tent needs adequate weights. Your signage needs to withstand wind. You need layers for cold mornings, protection from rain, and a plan for extreme heat.
For us, heat management is especially important. Chocolate and 90-degree summer days are not natural partners. A portable power station and refrigerator have become essential equipment for protecting inventory when temperatures climb.
Weather isn't an inconvenience you deal with after it happens. It is something you plan for before you leave home.
One of the least glamorous lessons I learned is how difficult it can be to step away once a market begins.
Customers may start browsing before the official opening time, and once traffic picks up, leaving the booth for food, water, or a restroom break can become surprisingly complicated.
I quickly developed a routine: eat before the market begins, use the restroom just before opening, bring water and snacks, wear comfortable shoes, and be ready for early shoppers.
If you have someone working with you, decide ahead of time how you will cover breaks.
It sounds simple, but market days are physically demanding. You're standing, talking, lifting, restocking, answering questions, processing transactions, and staying attentive for several hours at a time.
Once the market opens, it's go time. Plan accordingly.
To sample or not to sample? I quickly learned there isn't one universal answer.
Some customers seem to arrive at farmers markets determined to sample everything available. Some vendors use enthusiastic calls of "free samples" as their primary way of drawing people toward the table.
For certain products, that strategy works extremely well. For others, it can become expensive very quickly.
We've had markets where we offered no samples and sold well. We've also had markets where sampling clearly helped customers understand the product and led directly to purchases.
The better question is not simply, "Should I offer samples?" It is:
Does sampling improve conversion enough to justify the cost?
Consider the cost of the product you are giving away, the labor involved in preparing samples, serving supplies, and any additional market or health-department requirements.
In Connecticut, cottage food operators may offer free samples with local health-department approval, and individual markets may have additional requirements. Always check before the event.
Sampling should be a business decision, not an automatic habit.
You need a reliable system for tracking what you bring to the market and what you sell.
Your POS system can provide valuable reports, but I have found that technology alone doesn't capture everything I want to know.
Surprisingly, pen and paper have become one of my most useful tools.
Alongside our sales data, I keep space for observations:
Sales data tells you what sold. Your field notes often help explain why.
Together, they give you much better information for planning production, choosing future markets, refining products, and adjusting your marketing.
There will be markets where you sell very little.
That can be difficult especially after spending hours producing inventory, packing the car, setting up the tent, and standing at the market.
But a slow sales day is information.
Sometimes the product, audience, event, price point, weather, or shopping mission simply isn't the right match.
Instead of asking only, "Why didn't we sell more?" ask:
What did this market teach me about where my customer shops?
Perhaps your product performs better at a craft fair than at a produce-heavy farmers market. Maybe a winery, bookstore, boutique, or other business collaboration creates a stronger environment for your offer.
And slow periods don't have to be wasted time. During the years I waitressed my way through college, my boss used to remind us that there was always something useful to do when business was quiet.
I still follow that advice.
At slow markets, I have planned marketing content, organized inventory, labeled boxes, taken notes, and observed what other vendors were doing.
There is almost always something to learn.
Introduce yourself to the people selling around you.
Ask about their businesses. Learn their names. Follow them on social media. Buy something from them when you can.
Do not automatically view neighboring vendors as competitors.
Markets develop their own communities, and experienced vendors can be incredibly generous with what they know. They share recommendations about events, market managers, weather strategies, equipment, and other lessons they've accumulated over years of selling.
They may purchase from you, refer a customer, or simply provide encouragement during a difficult market.
And you can do the same for them.
No single vendor makes a farmers market successful. Much of its appeal comes from the collective energy created by everyone participating.
No matter how organized you are, there will eventually be a morning when you're running late.
That is precisely when you will forget something important.
A chair. Your cash bag. A sign. Your tent canopy. Your phone charger.
After enough markets, packing may start to feel routine. Don't let that convince you to rely on memory.
Create a checklist and use it every time.
Mine includes categories such as:
A checklist may be one of the least exciting tools in your business. It can also prevent one of the most stressful mornings of your week.
After years of advising entrepreneurs, launching Storyline Chocolates has given me a new appreciation for the distance between knowing what a business should do and experiencing what it takes to actually do it.
I still believe deeply in planning.
A strong business plan, financial model, marketing strategy, and operating plan give you a foundation. But eventually customers arrive. The temperature reaches 93 degrees. A market performs differently than you expected. You forget a chair. Someone asks a question you have never considered. And suddenly the neat assumptions in your spreadsheet meet the wonderfully messy reality of running a business.
That's where another kind of learning begins.
My first month as a cottage food entrepreneur didn't make me question the fundamentals I have spent years teaching. It made me respect the execution even more.
And we're only at the beginning of the story.
Be sure to sign up for our Storyline Inspires Newsletter to receive new story teasers, inspirational vignettes about travel, food, and reading, community impact, and upcoming events before they are promoted. We send our newsletter once per month at the beginning of the month. Join the Story!
No one wakes up one day with a fully formed business, unwavering confidence, and all the answers. Every entrepreneurial journey is a story in progress—one shaped by uncertainty, learning, and the people who walk alongside us.
For me, mentorship has been one of the most constant and grounding forces through every chapter of my life: my career, my education, moments of personal struggle, and now, the journey of building Storyline Chocolates. It’s why this month matters so much to me.
Escape into the flavors of fall with Byways to Montague, the debut Chocolate Story from Storyline Chocolates. You’ll be whisked away on an adventure through the Pioneer Valley of Massachusetts during New England’s most spectacular season — autumn.
