3 Things I’m Doing In My Business Right NOW To Prep for The Holiday Season

On Saturday, October 1st, three individual messages popped up on my phone from three separate people:

  • My sister
  • My best friend
  • My husband 

No, they weren’t making plans to bob for apples, pick pumpkins, or go Trick ‘Or Treating as you might expect in October

Oh no– my crew is already ten steps ahead!

They were all reaching out to claim time on my calendar come December. 

Sounds crazy, I know.

In fact, every single one of them said, “I know you’re going to think I’m nuts and this is super early, but…”

And I did think it was early until I looked at my calendar and realized how much time was already claimed and thought through all things I like to do over the holidays.

Ya see:

In my world, the holidays are always busy! 

Maybe you can relate!

Personally, there are get-togethers with friends, family traditions, and, to top it all off, my son’s birthday! Plus, this year, there will be even MORE to celebrate because both of my nieces are turning one and we have a family wedding!

It also tends to be a busy time business-wise. The pre-holiday season is often filled with business planning and wrapping up the financials for the year (hello, tax prep!), closing up or renewing contracts, accounting for team members’ time off, the list goes on and on!

And in both spaces, I use this time to celebrate all the amazing people I have in my life and remember to show them how special they are to me!

Those three (unexpected) text messages were the reminder (and kick in the butt) I needed to start my end-of-the-year prep!

For me, the holidays are all about being together and creating memories with family & friends. But you can’t create the truly magical moments we all crave if you’re stressed, distracted, and running around feeling overwhelmed.

Because I value quality time with family and friends SO MUCH, I’ve become really intentional about how I prepare for this season. 

I’m thrilled to share three of my best strategies and tips with you so that you can support your business while also carving out the precious time and space you need to be present and enjoy the holiday season on your terms!

# 1 Blocking Off OOO Time On The Calendar

Believe it or not, come October, I am already flipping my calendar ahead to December and blocking time off. 

For me, it’s essential that I intentionally decide when I will and will NOT be working. Otherwise, it’s amazing how quickly my calendar will fill up with meetings and projects. If I’m not careful, there’s no time left for me and my personal life!

Blocking time off on my calendar prevents me from accidentally booking anything I need to show up for and reminds me there are limits to what I can “squeeze in,” especially in such a whirlwind season

Once I know WHEN I plan to be off, I can select which boundaries I will need to implement and enforce around that time to make my goals a reality. 

This upfront planning makes it easier for me to communicate my OOO schedule and the boundary expectations around it to my team and my clients. I always strive to communicate my boundaries and scheduling needs EARLY AND OFTEN so that once the time comes, no one is surprised or taken off guard! 

The beauty of it is you have total control over your availability during the holidays as the CEO of your creative business

This means you can absolutely have different boundaries throughout the holiday season! 

For example, this is how I’m setting up my holiday calendar this year:

  • On both Christmas Eve and Christmas Day, I will be MIA from my business. Same with New Year’s Eve & New Year’s Day. The week between, I will sign off and put an OOO message up. I will not check email, but I will keep an eye on Voxer once per day for emergencies only. 

  • I’m also taking a few days off for my son’s birthday earlier in the month for some party and holiday prep. The event happens on the weekend when I’m already off, so on those prep days, I won’t take meetings, but I’ll still be reachable for my team via certain channels because I know that they’ll need me in order to prep for the holiday time. 

It’s okay to have different boundaries for different times and with different people. What’s important is that you clearly communicate your schedule to whoever needs to know it, such as (but not limited to) clients, team members, and vendors.

# 2 Holiday Gifting

Gifting isn’t just for friends and family. 

I know, I know. 

This may sound overwhelming at first. 

Yet ANOTHER list of people to buy gifts for?!

But hear me out.

I wholeheartedly believe intentional gifting can and should be a big part of any business model. Gifting doesn’t have to be elaborate, expensive, or daunting. It truly is the THOUGHTFUL thought that counts. 

Taking the time now to be intentional about who you’re going to give gifts to, what you’d like to give them, and specifically why you have chosen that particular gift can help reduce your stress levels come December while helping you maintain strong bonds with your people. 

It can… 

  • significantly improve your overall client experience 
  • boost team morale and culture, leading to improved retention rates
  • and build community across the board with other stakeholders, vendors, and business partners

In turn, allowing you to nurture and cultivate relationships with all the people who make your creative business POSSIBLE!

Right now, I’m making lists (and checking them twice) of who I want to gift to. I’m also establishing a budget so I can plan for the holiday season financially. 

I prefer to shop early for all of my holiday gifting needs, both personal and business related. Between shipping delays, a kid with an early December birthday, playing host to multiple holiday parties, AND being married to the equivalent of Clarke Griswold, makes for a hectic time…and chaos stresses me out. 

So, I try to get ahead of the craziness and shop on the earlier side of November. I don’t always succeed, but I set it as a goal. I always aim to ship my gifts the 1st week in December, so people receive their packages BEFORE the holiday and nothing gets lost in the shuffle (I speak from experience…).

I don’t put pressure on myself to get the perfect gift and one up myself every year because that can spiral out of control real fast and I know I’ll never feel completely satisfied year after year if I let myself go down that road! Instead, I focus on being thoughtful and intentional, and I go from there. All in all, this helps me take the pressure off of myself, so I can enjoy the process of gifting instead of letting it consume my time and energy!

COO Tip: Holiday Gifting is something I’m really passionate about in business. In fact, I’ve created an entire Holiday Gifting Guide to help you get the answers to all your who, what, where, when, and why questions of gifting in your business so you can nail your gifts this year! Snag the freebie here!

# 3 Year-End Review and New Year Planning

Last but not least, it’s time to prep for my end-of-year review and new-year planning!

I really like carving out time for this AFTER I’ve established my personal time off. After all, our businesses should support our personal lives, we shouldn’t have to build our lives around our businesses. This ensures that my family time comes first, and then I can build out my December business needs around those priorities!

In addition to carving out time to be OOO with family and friends, I also reserve CEO time on my calendar in December to tie off any loose ends and begin to set my vision for the year ahead! This also helps me start to gather all the things I need for my year-end review and new year planning session.

My end of year review and planning is vital to staying dedicated to my work. It allows me to continuously improve as the strategist and visionary of my business. 

To sum it up: this work ensures I’m able to run my busines in a way that feels aligned– instead of allowing my business to run ME!

My end-of-year review includes:

  • Looking at my numbers, such as finances, client retention, and current offer pricing.
  • Getting a pulse check of how things are feeling in my business so I can evaluate what is and isn’t working.
  • Reviewing my past goals to track and assess my progress.

This information prepares me to reset or revise my goals for the year ahead!

My new year planning session involves:

  • Creating a vision board to get clear on my aspirations!
  • Setting S.M.A.R.T. financial and big-picture goals (S.M.A.R.T. stands for specific, measurable, attainable, relevant, and time-based).
  • Setting or updating my strategies accordingly.
  • Auditing my systems and content, including…
    • Public-facing platforms: website, social media, branding, etc.
    • Materials and collateral: templates, contracts, welcome packets, nurture sequences, etc.
    • Plans: content, marketing, sales, etc.
    • Software: Client Relationship Management (CRM) System , Project Management (PM) system, email platform, subscriptions, etc.
    • Systems and SOPs: onboarding, offboarding, training, etc.

COO Tip: Looking for more support as you assess the previous year and prep for the year ahead? Be sure to check out my blog post, “What We’d Be Working On If I Were Your COO Q4 Edition,” to get the full scoop with step-by-step actionable guidance

Start Prepping YOUR Business For The Holidays!

Now it’s your turn to take these suggestions and make them your own. 

While your holiday priorities, schedules, and goals may look different than mine, taking the time to get clear on what you want the upcoming season to look and feel like in your life and business will make all the difference!

I hope this blog has served as a reminder to you that YOU are so incredibly in charge of building the business of YOUR dreams. A business that allows you to do what you love while also supporting the other aspects of your life so that you can find and maintain your version of success for many years to come!

Build Your Business Beyond The Holidays

In fact, I am on a mission to debunk the starving artist myth and teach creative entrepreneurs like you all the things about running a business you didn’t learn in art school. If you’d like to come along for the ride, I invite you to add your name to the no-obligation waitlist for my upcoming online course so you can build your business in an approachable, sustainable, and profitable way.


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