By By Meg Sanders,The Berkshire Eagle

Copyright berkshireeagle

Running a business in the Berkshires is different from running one in Boston, Denver or New York.

Here the seasons drive everything. They determine traffic, sales, staffing and whether you finish the year strong or fall short. Anyone who has lasted more than a few years in retail, restaurants, hospitality, or cannabis in this region knows this reality. And it’s a reality that is founded on a key principle: You prepare ahead of time, or you fall behind.

The most dangerous words for an operator are: “We’ll figure it out when we get there.” By the time “there” arrives (ie: foliage season in October, holiday shopping in December, ski season in January) the chance to prepare is gone. The opportunity is either captured or is missed. And unless someone has a secret sauce I’m unaware of, exactly zero Berkshire businesses can afford to miss it.

At Canna Provisions, our holiday season starts in July. That is not a choice, it is a requirement. We order our holiday glassware months in advance. We start mapping gift bundles while most people are still enjoying summer. That way when November arrives, our focus is not scrambling to catch up but executing what we already planned: greeting customers, training staff, and making the shopping experience worth remembering.

Every customer counts. I reminded new staff of that this week during training. The sales floor is the show, and when you’re on shift, the show is live. That means energy, focus and readiness. Walk in tired, unfed or unprepared, and the customer notices.

Two poorly served customers in a single day may sound minor. It isn’t. Those are two people you spent money and effort to bring into your business. If they don’t return, you didn’t just lose a single sale. You wasted the investment it took to get them there in the first place.

That lesson is not unique to cannabis. Any Berkshire business that pays for advertising or social media knows how expensive it is to bring new people in the door. Letting them leave disappointed is a waste, and it costs far more to win them back later than to serve them well the first time.

Planning also applies to staffing. We have blackout dates around the holidays when vacations are not allowed, because that is when we need everyone available. Instead, we encourage our team to take time off in the springtime. That is when the county is slower, and the pressure eases.

Even our holiday party happens in January after the holiday rush. And those crucial holiday months are when your business should be locked in on customers. You’ll have time to celebrate when the snow piles up and the traffic thins out.

This approach matters because the Berkshires don’t run on a steady 12-month cycle. We live on pulses: fall foliage, holiday shopping, ski season, summer tourism. That is what makes our economy unique, and it is also what makes it fragile.

In the chambers of commerce we are part of (we are proud active members of four and counting), one topic comes up again and again: the fear of becoming a two-season county. Imagine a Berkshires that thrives in July and August, again in October, and struggles the rest of the year. That is not just an idle question. It is a warning. And it demands preparation now, not later.

Cannabis operators feel this pressure even more sharply. We work in one of the most difficult retail environments in the country, with margins under attack, heavy taxes and regulations that add layers of expense. That means every customer interaction is critical. Holiday bundles, seasonal promotions, community outreach, and partnerships are not extras. They are the difference between survival and collapse.

But this lesson extends well beyond cannabis. Every business in the Berkshires should be reviewing its partnerships, strengthening ties in the community, and making sure people have reasons to return. Your neighbor down the street is talking to customers you may never see.

If you are not staying present and visible, you risk being forgotten. And in a seasonal economy, being forgotten can be fatal.

The Berkshires are remarkable in every season. But natural beauty and reputation alone will not sustain a business. Leaves fall, tourists leave, and the peaks fade quickly. Turning those moments into long-term strength requires advance work and discipline.

For cannabis retailers like us, the planning has already started. For restaurants, holiday staffing will already be sorted. For hospitality, winter packages are built before the first frost. This is what preparation looks like. We talk often about the Berkshires as a four-season destination. That only matters if we run our businesses as if that is true. The county will only avoid sliding into a two-season economy if its business and arts community accepts responsibility for making it four.

The holidays are coming. Tourists are coming. Our neighbors are counting on us. We don’t get a second chance. If we want to thrive, if we want to stay four seasons strong, then we need to act like it — together.