It’s started again. It happens every year, and even when I know it’s coming, I’m never quite prepared for it.

The Holidays.

The “What are your plans? Where will you be on these dates?”

They come from both sides of the family. The asks are always slightly different, always with a pause where you know if you don’t answer exactly how they want you to, you’ll get the protest. So we sit and don’t answer.

But I know we’ve brought it on ourselves because we haven’t set a schedule and stuck to it. It’s not that we don’t want to necessarily. It’s more about what the weather will be like, what sicknesses we’ll have or not, what siblings have plans, what work has to happen, whether we’re going skiing, and on and on.

Every year we end up saying “We’re never doing that again.” And then we don’t do exactly that, but we do some other version of it that leaves us just as miserable.

And every year at this time I say, we really need to come up with a plan.

And we don’t.

Why?

Well, I think it’s because we don’t want to disappoint anyone. Generally Nic and I are people pleasers and we want to keep everyone happy. But in doing that, we often find ourselves not so happy, things are left unsaid, and frankly, tension grows.

The Unique Pressure of Managing Holiday Stress as a Small Business Owner

The amount of pressure society puts on the holidays is truly not sustainable. The holiday season should be about spending time with the people you love. It shouldn’t be about one specific day—it should be about the season.

The way I see it, the problem is about the expectation of celebrating a holiday on one specific day. People get off work for one specific day. And when you have families, you can’t always spend that one specific day with everyone. But instead of embracing the season and celebrating on different days, we put all the pressure on this one day. And that sets us up for disappointment.

It’s kind of like in your business when you put all your expectations on your email marketing selling your product instead of diversifying how you reach your audience. Or expecting your home page alone to sell your services.

Or, as a solopreneur, putting all the pressure on yourself to run every aspect of your business—from bookkeeping and sales to design and marketing to service and fulfillment.

You can’t do it all.

Somewhere, something will fail. The very precarious system you built will fall, and you’ll be overwhelmed and scrambling, trying to pull something together.

This is exactly why managing holiday stress as a small business owner requires a different approach. It’s not just about family logistics. Add in client gifts, year-end planning, tax prep, holiday cards, and regular business work, along with family shopping and school activities, and you’ve got a recipe for an overfull plate.

Sometimes that 24-hour answering of emails just isn’t possible.

Why We Get It (And How We Help)

It’s why we’ve been really good at helping other small business owners manage their stress by taking their company vision and creating a website with the right technology to support their business—because we get it. We live it too.

With our experience, systems win every time. It’s why we do what we do: to help businesses like yours set up for success, even during the most hectic times.

When we design and build websites, we’re not here just to make your website look pretty. You could buy a template, flow in some copy, and boom—you’ve got a pretty website. But that doesn’t excite us.

We’re here to build a website that gives you TIME back.

What does that mean? It means we talk to you about HOW your business actually works. We figure out your pain points, and we find tools and technology solutions that work together to make your life easier.

Managing business stress during the holidays starts long before November. It starts with building systems that support you year-round so you’re not scrambling when things get busy.

What We Believe About Your Website

When we build you a website, we believe 3 things:

1. Your Website Should Look Good AND Function Well

It should be easy to navigate, speak clearly to your ideal client, build trust, and capture the information you need from potential clients in a simple way. No friction. No confusion. Just clear paths to connection.

2. Your Website Isn’t a Stand-Alone Piece of Your Business

Your website should be integrated with your systems. Your email marketing, CRM, product management—it should all talk to one another and make it easier for you to do your job. When everything works together, you spend less time on manual tasks and more time on what actually matters.

3. Your Website is Your Storefront

It shouldn’t look like everyone else’s. Each website we build is designed for YOU with your ideal client in mind. We believe unique is truly better. Your clients should recognize you in your website, not see another cookie-cutter template.

The Creare Difference: Partnership Over Vendor Relationship

When you work with Creare Web Solutions, we work with you as a partner, not a vendor. We’re an extension of your team, there to save you time and money through implementing technology that works for your business.

We price our work fairly. We’re transparent. And there are never any surprises—because that’s what we want when we’re looking for help.

What our clients probably love most? We respond.

Send an email? You’ll hear from us within 24 hours. Call us? We answer. We get it. We know when a quick fix is needed, and we’re there to help.

Because we’re small business owners too, we understand what managing holiday stress as a small business owner actually feels like. We know the guilt. The overwhelm. The pressure to keep everything running smoothly while also trying to be present for your family.

Your Permission Slip for This Holiday Season

So as the holidays hit and you’re overwhelmed with questions and decisions that start weighing on you—don’t let them bring you down.

Look for where you can get the help you need to managing holiday stress as a small business owner.

Maybe it’s time for some system implementation and a new website. Maybe it’s time to hire a bookkeeper. Maybe it’s time to stay home and relax, even if that means disappointing some family members.

Whatever is causing you stress, try to let it go. The holidays should bring joy, not just more to-do lists (although they always do).

And I invite you to reach out if one of the things on your plate causing you stress is your website, technology, or online presence. We can help you take that stress away.

Start by booking a call with us.

Remember, the best gift you can give your business (and yourself) is permission to do less, be present more, and ask for help when you need it.

Frequently Asked Questions: Managing Holiday Stress as a Small Business Owner

Why is managing holiday stress harder for small business owners than employees?

Small business owners face unique holiday pressure because there’s no separation between personal and professional stress. Unlike employees who can clock out, business owners carry financial responsibility, client obligations, and operational concerns home with them. Your small business stress is personal stress, and the holidays amplify both making it especially hard to manage.

How can I take time off during the holidays without my business falling apart?

Start by communicating your schedule to clients by November 1st. Set up automated responses explaining your availability. Block specific days as non-negotiable and build everything else around them. Most importantly, implement systems and tools that can handle routine tasks while you’re away—your website, email automation, and CRM should work even when you’re not.

What are the biggest sources of holiday stress for small business owners?

The main stressors include: trying to close Q4 strong while planning for Q1, managing client appreciation and gifts, attending networking events, handling family obligations, maintaining regular business operations, and feeling pressure to be “grateful” while feeling overwhelmed. The guilt about not doing enough in any area often creates the most stress.

Should I send client gifts if I’m overwhelmed with holiday tasks?

Client gifts don’t have to be elaborate to be meaningful. A heartfelt, personalized email thanking specific clients for their partnership often means more than expensive swag. If gifts matter to your business relationships, batch the task: dedicate one afternoon to all client appreciation, whether that’s writing notes, ordering simple gifts, or sending digital gift cards.

How do I set boundaries with clients during the busy holiday season?

Communicate early and clearly. Tell clients your holiday schedule by early November, not mid-December. Use auto-responders on email. Adjust your service level agreements temporarily (respond within 48 hours instead of 24). Most clients will respect boundaries if you set them proactively rather than reactively.

What business systems can help reduce holiday stress?

Website systems that capture leads 24/7, email automation for client communication, scheduling tools that let clients book without back-and-forth, integrated CRM systems that track client information, and payment processing that doesn’t require manual invoicing. The goal is to reduce manual tasks during your busiest season.

Is it normal to feel guilty about holiday decisions as a business owner?

Absolutely. Small business owners are often people-pleasers who struggle with disappointing anyone—clients, family, or business partners. Remember: guilt about not doing it all isn’t a sign you’re failing. It’s a sign you care deeply. The solution isn’t doing more; it’s being intentional about what matters most and protecting those priorities.

How far in advance should I plan for managing business stress during the holidays?

Start planning early. Sometimes reviewing last year’s pain points, and deciding on one non-negotiable priority for the season is helpful to do in January, right after you’ve gone through the holidays. Then, communicate boundaries to clients (and family) by early November and implement any systems or automation before Thanksgiving. The earlier you prepare, the less reactive you’ll be when December chaos hits.

What’s the most important thing I can do to reduce holiday stress as a business owner?

Ask for help. Whether that’s outsourcing tasks, implementing technology to automate routine work, hiring temporary support, or simply telling your family what you actually need—accepting that you can’t do it all is the first step. The second step is taking action to get support in the areas causing the most stress.

Should I focus on business growth during the holiday season or just maintain?

Give yourself permission to maintain rather than grow during November and December. Most businesses experience slower decision-making from clients during this time anyway. Focus on closing out the year well and positioning yourself for January growth. Strategic planning feels nearly impossible when you’re in crisis mode—save it for January when you have bandwidth. And next year, start it in August!

Ready to take website stress off your plate? We help York County Maine and Seacoast NH small business owners build websites and systems that work for them, not against them. Book a discovery call today and let’s talk about how we can help you start 2026 with one less thing to worry about.