How Professional Web Designers Prepare for the Holiday Season
It’s no secret that the holidays can be a stressful time for freelancers. There are plenty of ups and downs: business development emails to send, discovery calls to book, and looming seasonal website updates on the horizon. Plus, in between all that stress, freelancers need to balance their own projects and family obligations—not to mention attempting to achieve any lingering goals set for the year and prepping for tax season.
But, not everyone’s holiday experience is the same. On one hand, some web designers may feel the crunch of end-of-year deadlines with clients trying to wrap big projects in time to hit last quarter goals. On the other hand, some might face an empty calendar and an inbox full of out-of-office messages as their clients take time away ahead of the new year.
No matter what end of the holiday-season-stress scale you’re on, you’re not alone. Whether you’re juggling more projects than you can count on both hands or staring down at the empty space under the tree, there are still ways to make the most of the season.
For tips on conquering the holiday crunch, we interviewed several successful members of Circle, Squarespace’s partner program and professional community of web designers, developers, entrepreneurs, and other freelance creatives. In addition to their roles as Circle members, they are Community Leaders, an opportunity that exists to honor members who have made significant contributions to the community.
Meet the pros
With over a decade of collective experience, Risha Chesterfield, Omari Harebin, and Kwame know what it takes to both survive and thrive during the holiday season. Whether they’re handling the holiday drought, re-engaging past clients, keeping projects on track, or budgeting “me time,” they have tips to help freelancers going into their first, or hundredth, winter in web design.
We sat down with Kwame, Risha, and Omari for a Q&A session on how they prepare for the holiday season and set themselves up for success.
How does the holiday season impact your business as a web designer?
Kwame: It really varies year to year. Sometimes it's a quieter period with a focus on maintenance/updates for existing clients, especially those with ecommerce offers. Other times, I'm super busy with an influx of new clients hoping to capitalize on the extra interest and traffic.
Risha Chesterfield: Usually, the holiday season is a VERY busy time with clients who are ready to make changes or build new sites for the new year. I’ve also had times where things slow down on the client side, but that makes room for me to create strategies and new business offerings for the new year.
Omari Harebin: The holiday season used to really hurt when I first started working as a web designer. I was never prepared for the slowdown, so I was always scrambling for work and had several cold winters as a result.
How do you prepare your business for the holidays?
Kwame: I try to book clients for larger builds/branding projects early so I can easily manage my time. I pre-write a few emails and schedule them to send to existing clients (e.g., Happy New Year, etc.), on top of more personalized outreach if I'm looking for new ones. I also really go through my schedule and work out when I want time off and make sure I have space for it.
Oh, and I check the Circle Release Tracker and general updates to see if anything big is coming up that I can make use of.
Risha: I start assessing what projects are currently in motion, what needs to be finalized by the end of the year, and what needs to continue into the new one. For example, if there’s a client that I’ve worked with for a while but our time for the project scope is coming to an end, I make sure to communicate all that’s needed so the ending doesn’t feel abrupt.
When it comes to what I’m marketing or selling for the holidays, I know I need to have my offers ready for Thanksgiving and Black Friday. This year, I’m prepping to have a template store open and major discounts available for customers.
Omari: When I’m in prep mode for the holidays, I ramp up. I’ll make more offers to existing clients and potential new ones. I’ll especially zero in on where I can be of most value and hone in on how I can deliver for their businesses.
When do you start preparing for the holidays?
Kwame: As soon as possible! For me, the cold marks the start of the holidays (around October or November), so I start thinking in summer and making plans for August and September. It’s usually nothing big, just a skeleton plan that I slowly build upon as we get closer to the season.
Risha: I probably could start thinking a lot earlier, but I begin working through ideas in September. Then, in October, I begin putting things in motion.
Omari: For me, August and September is a good time to start planning my campaigns and promotions.
What is the best way to reconnect with clients during the holidays?
Kwame: The best way is to ask what they're doing and if/how you can support them. I focus on building a rapport and collaborative relationship with clients from the get-go. They appreciate your interest in their business, and usually more work can come from simple conversations. I find it's also often a case that many clients might want or need help but simply haven't thought about reaching out and seeing if you can. I start by spending a bit of time looking if there are specific reasons to reach out to each client and go from there.
Risha: This season is a great way to just touch base with past clients. I reconnect by sending an email to see how they’re doing and how things are going with their website. I’ll also offer them first dibs on new projects for the new year to get them to commit.
Omari: The best way to reconnect is by simply reaching out to update them on your work and find out if you can be of service. In my outreach, I’ll take initiative and pitch something that would be valuable to them and then offer it as a gift. For example, if you have a client with an online store, they may not have any promotions in place. You could send them a mock-up landing page for a holiday promotion, and then go from there with other holiday updates.
How do you balance taking time for yourself while maintaining your business?
Kwame: I'm a workaholic so it's hard. But, having plans well in advance creates a hard limit to what you can or can't do so you can let clients know when you're unavailable.
It’s also helpful to give clients the tools to self-manage their website so they’re empowered to not be totally dependent on you for every little thing. A big reason I chose to work with Squarespace…was because I don't want to be in an ecosystem where the client is completely reliant on you to make any changes or updates on their site—not just because it feels unfair, but because it means I'm also not constantly dealing with emails to make small changes.
Squarespace makes it easy for clients to run their business without a ton of expertise, and if I support them using that platform, I find they can be less demanding and needy—especially during the holiday season. I even have clients that’ll pay me for videos, tutorials, or even calls to teach them how to manage their business and DIY things on their site more efficiently and effectively, which often means I can enjoy the holiday without stressing too much about running things.
Risha: I find balance by creating clear boundaries with myself and with my clients. A big part of that is letting them know my time out of office well in advance. It’s also important to make space for prepping strategies for the upcoming year, even in the holiday season.
But, you also need to have days where you don’t open your laptop. They’ll make you miss the work and get excited about getting back to it!
Omari: I'm not necessarily good with balancing time for myself while maintaining my business in a conventional sense, but I've been paying more attention to my energy levels and capturing them when they are at their peak but not forcing it when they are not.
What advice do you have for a newer web designer going into their first holiday season?
Kwame: I’d recommend that they start by reaching out to existing and past clients, being genuine in how they can help them and really personalizing the emails and calls if they have the time.
Also, be sure to take some “me time.” Seriously. There’s no pouring from an empty cup, so make sure to refill through spending time with family, friends, and loved ones. Budget for it in terms of time and money—it can be really easy to let yourself work too much and then you suffer. Set hard boundaries on days and times you won't work and make sure to respect them.
Lastly, don't be afraid to outsource and collaborate. We have a great community in Circle, so consider looking to work with others to ease your workload and enhance your offerings. Things like plugins and courses might be a financial investment but can reclaim a lot of time and stress too. Oh, and use the forums!
Risha: If you’re doing this work full time, this may be a busy season—and that’s totally okay. It may feel like you’re working through the holiday season to make ends meet without having any time for yourself. If your workload has you stressed out, really assess what got you to where you are and make more time next year to plan for this season.
Also, if you are running sales, invest in ways to better connect with the people that are buying from you, like adding them to your mailing list. They tend to make a purchase from you just because it’s at a lower rate, but take full advantage of them coming into your ecosystem. They could become a high-ticket purchaser in the future!
Omari: Going into your first holiday season as a new freelancer can be hard, so sometimes being realistic with yourself is the best approach. If you aren’t hearing back much from your client outreach, expect things to slow down after November and plan accordingly. It won’t always be like that, but sometimes your first few holiday seasons can be tough.
How do you ensure you meet end-of-year deadlines?
Kwame: Grind! In all seriousness, plan and try to predict issues while keeping clients aware of your time boundaries so that they make sure they're not causing delays and missed deadlines. You may also want to include something about late delivery of content in your contracts to keep things on track.
I also always factor in extra time for the unforeseen and aim to finish projects well before I'd like to stop working so that I have leeway to fit in extra hours or days.
Risha: I usually set deadlines that are earlier in December to ensure that if I need an extra week, I have that time baked in so I’m not going into the holiday break with incomplete projects. Last year, I had a project go past the end-of-year deadline, and I didn’t like how that loomed over me during the holiday season.
How are you preparing for the new year?
Kwame: Pretty much the same way as the rest of the holiday season! One thing I will do, though, is run through my expenses and earnings so I'm ready for taxes. It's never worth letting them sneak up on you.
Risha: I’m BIG on assessment. So, I’m going into the new year looking at what projects I really enjoyed this year and thinking about how I can create more of those for 2024. Also, I’m giving incentives to clients that are open to pushing their project into the new year. That’s going to help me have guaranteed work when I return without having rush projects before the end of the year.
Omari: I find that closing out any loose ends and unfinished intentions for this year frees me up for the new year. It’s nice to go into January feeling open and untethered so I can focus on what’s ahead.
Finding success during the holidays
While the holidays can be a whirlwind for professional web designers, the season doesn’t have to be a time of stress. If you’re facing a heavy workload, budgeting time, managing deadlines, and level-setting with clients can make for a relaxing, productive, and rewarding season. If you’re staring down a quiet calendar, reconnect with past clients, manage expectations, and focus on future growth for success in the new year.
With the support of the Circle community and members like Kwame, Risha, and Omari, you’re ready to build your business with Squarespace. As a member of a global group of creative professionals, you have everything you need to conquer the holidays–and beyond.
Special thanks to our interviewees for sharing their expertise.
Kwame has been a Circle member since 2018. He is the principal designer, developer, and owner of Kwame & Co Web Design and Branding Studio. His London-based creative agency specializes in working with brands and startups looking to carve out their niche and establish themselves online.
Risha Chesterfield is the owner and designer at Sow Good Creative, a web design agency based in Nashville. She’s been a member of Circle since January 2019 and focuses on website builds and digital strategy for brands.
Omari Harebin is the founder of SQSP Themes, a revered resource for professional web designers. He is both a marketing and mindset coach for Squarespace professionals. In addition, he runs a performance marketing agency for Squarespace professionals, Vizier Media. He’s an original member of Circle and has been part of the partner program since its inception.
Want more?
Check out Squarespace Circle, Squarespace’s program for professional designers. Along with exclusive content, discounts, and other perks, Circle brings professionals together from all across the globe to exchange advice while connecting with new clients and collaborators.
