November and December aren’t your typical months in the creative business world. It’s the time when many of us are hustling to wrap up projects or ship holiday orders while also trying to squeeze in some moments on our already overextended calendars for family, friends, and all the fun holiday festivities. 

Have you ever felt torn between the pressures of running your business and the longing for quality family and personal time?

I certainly have.

Early in my business, I found myself trying to be an entrepreneurial superhero.

I had some unmet goals looming over me, and my perfectionist tendencies kicked into overdrive. I somehow managed to accomplish everything I set out to do, but it came at a cost.

I, admittedly, wasn’t fully present for my loved ones, and I even had to bow out of a few get-togethers with friends. While it might be okay occasionally (there are absolutely seasons for hustle and rest in business) those moments were crucial to me, and I felt like I had compromised my core values.

That experience taught me a valuable lesson. 

I swore never to prioritize my business goals so much that I’d let my personal goals be sacrificed again. 

Since then, I’ve realized that November and December are more than just a season of year-end business rush; they’re an opportunity to wrap things up intentionally, re-evaluate what’s working (and what’s not) in my business, and prep for the new year in a way that feels aligned with my values and my goals.

Over the years, I’ve learned through a fair share of trial and error what works for me during this unique season. I’ve also had the privilege of helping my clients find their own paths because, let’s face it, what works varies for every entrepreneur. 

No matter how you want to approach the holiday season ramp-up and year-end cool-down in your business and life, I’ve collected helpful tips and strategies you may consider. I hope this blog will help you focus on the business tasks that will be most impactful for you in the long run while also giving you the time and space you need (and deserve) in your personal life. 

Ultimately, these actions will be something your future self will thank you for in 2024. They will set you up for a successful wrap-up of 2023 so that when January 1 arrives, you can feel at peace with where you stand in your business and know that you were able to savor the holidays to the fullest.

Tips for Balancing the Holiday Season and Year-End Goals

Ending Strong

The first step in conquering the challenge of the year-end season is to define what “ending strong” means to you. This doesn’t necessarily mean hustling relentlessly into the new year (although it CAN depending on your priority). No matter how you go into this season, it’s about being intentional and proactive in your approach.

For example, if you are a service-based business, you might decide to wind down some of your business operations (“ops”) in November and take most of December off. 

Now, in full transparency, this won’t work for all creative businesses depending on how you’re business is set up, but absolutely CAN work for many!

During this time, you could meet with clients or fulfill essential commitments, but you intentionally avoid diving into other work-related tasks like logging into social media, crunching numbers, or manually sending invoices. This kind of break can provide you with the mental space you need to be productive in your work and present in your personal life.

For context, I’ve done things a few different ways in my business over the years.

A few years ago I made the decision to wrap up all my heavy-lift ops by the end of November and essentially take a break from them throughout December. During the first two weeks of December, my only commitment was meeting with my clients. Then, I took the entire last two weeks of December off completely.

It was magical and what I fully needed that year.

I enjoyed having time off in December so much that I decided to lean into it! Today, I continue to take the last 2 weeks of December off every year to enjoy Christmas and New Year’s.

To make this happen, careful preparation is key. 

Here’s how I do it and how you can too!

• Utilize tools like a CRM system to automate essential tasks (like sending those invoices so you can still get paid while you’re enjoying your holiday!). Set up an out-of-office message, and schedule your social media posts, emails, and blogs in advance.
  
  
• Communicate your plans with your team and clients early and often. This way they will know what to expect during your break. By working ahead, setting clear expectations, and preparing well, you can enjoy a relaxing holiday season without feeling overwhelmed by work.
  

It’s important to note that there’s no one-size-fits-all approach. Some creative entrepreneurs prefer to work through the holidays, while others take the entire month off. I have clients who take the whole month of December off, some who use this time to pour into their creativity, and others who work through without skipping a beat.

The key is to do what works best for you and your business while being proactive in planning and facilitating it.

Re-evaluate Your Goals

As the holidays approach, take some time to re-evaluate your current priorities and even reflect on those big goals you set way back in January. Are those goals still important and meaningful to you and the current state of your business? 

For the goals that are still relevant and of priority to you, consider whether the holiday season might impact your ability to reach those goals before the new year. 

• Are you on track to achieve what you set out to do at the beginning of the year? 
• Do you need to adjust, pivot, or realign your expectations?
• How will those adjustments impact your goals?
• Will you be able to realistically achieve them?

If your plans need to shift, please don’t be too harsh on yourself. 

Don’t set yourself up for a negative start to the new year by heading into the year surprised or frustrated with yourself for not achieving something in the previous year.

Give yourself the flexibility to recalibrate your expectations and, if needed, reset your goals and plans accordingly. While calendars can serve as powerful sources of motivation, they can also trigger unwarranted, unnecessary stress. 

There are times when it’s wiser to take a step back and pursue your goals at a more sustainable pace, rather than rushing to knock them out at the last minute and sacrificing other essential aspects of your life.

Consider Buyer Behavior

In addition to doing a pulse check with yourself and your capacity, be sure to consider your audience and how their tendencies may influence your goals, tasks, and priorities this season.

How customers act can change a lot during the holiday season and may impact which goals you focus on and your ability to achieve them during this specific time of year. 

Depending on your type of business, you might see sales skyrocket or slow down temporarily as people shift their focus to holiday spending or budgeting.

If you’re selling products or your offerings are related to the holidays, you’ll definitely feel a change in your priorities towards the end of the year and an uptick in activity.

But, if you mainly offer services, you might notice things quieting down as clients take time off for travel and holiday plans. When it comes to your current clients, it might not even be worth squeezing in meetings; it could make more sense to regroup in January.

For those who run workshops or courses, you may notice that most people aren’t looking to start a new learning adventure in the midst of holiday craziness. They’re more likely to get interested in your offerings in the new year. So, this season might be a bit slower for you.

Pay attention to how all of this affects your business and the viability of your plans so you can adjust your goals and strategies accordingly.

Intentionally Schedule Time Off

The holiday season can be hectic, which means it’s even more crucial to schedule some much-needed rest and time to fill up your cup. 

But, if you don’t make it a priority, I can just about guarantee other things will creep onto your calendar and eat up your time. 

I highly recommend you block off time on your calendar for personal activities and family gatherings. Add it like an appointment and do not cancel on yourself! 

This can help you avoid overcommitting to work-related tasks and ensure that you don’t double-book yourself. 

Setting and holding boundaries is essential to achieving a balance between your business and personal time.

COO Tip: Don’t forget to proactively communicate your out-of-office (OOO) schedule to both your team and clients well in advance! Ensure that your clients are aware of who to contact (if necessary) during your absence, and make sure your team is fully prepared to manage things in your absence if they’ll be working during that time. Better yet, consider granting them some time off and demonstrate that you’re a boss who appreciates their well-deserved holiday time!

Your End-of-Year Celebration

No…it’s not a party, per se. 

But carving out an annual review or year-end celebration to reflect on your accomplishments and set the stage for the year ahead can be a great way to bring the year to a close on a high note. I find that November and December can be a great time to work on your business instead of just working in your business. 

To prepare, pull your data and set aside some CEO Time (get it on the calendar, treat it like an appointment, and keep it) to assess your key performance indicators (KPIs), review financials, assess market research, and consider customer feedback. 

I recommend a three-part process that should include an annual review, visionary goal setting, and tactical and strategic planning.

Part 1: Annual Review

Start with a big-picture look at your year. 

Think about… 

• what went well
• what didn’t quite work out
• and what you achieved

Take some time to consider why some things were successful while others weren’t. Dive into the details and take a good look at your data to understand where you stand right now. 

This self-reflection is the foundation for setting goals moving forward so you always start from experience, not from scratch!

Part 2: Vision Setting

Once you’ve taken a look back at the past year, it’s time to unleash your inner dreamer and start thinking big!

Let’s set some clear goals, not just for the year, but also for the near and distant future.

Short-Term Goals: Think about what you can achieve in the next few months. Maybe you’ve got an exciting new product you want to launch in the first quarter. It’s a great way to kick things off and spark some excitement.

Annual Goals: As you plan for the year ahead, the possibilities are endless. You could aim to double your revenue, or maybe it’s time to finally commit to that 2-week vacation you’ve been daydreaming about. Make sure your business can keep humming along even when you’re away!

Long-Term Goals: Looking even further down the road, consider where you want to be in 3-5 years. Plan for growth by thinking about team expansion, creating new roles, crafting competitive job offers, and setting clear goals with key performance indicators.

And to make these goals even more solid, take a moment to clarify your dreams, outline your vision, define your mission, and jot down your core values. This will give your goals a strong foundation and keep you on track.

So, have some fun with this! Your imagination is the limit. Whether it’s short-term innovation, annual personal milestones, or long-term growth, the possibilities are wide open, so choose your own adventure!

Part 3: Strategic Planning

Now, it’s time to roll up your sleeves and dive into both the tactical and strategic stuff. This is where you’ll craft or update your solid business plan with all the specific, actionable details for the year ahead so you can make sure all the pieces of your business add up to allow you to achieve the goals and vision you just set. Set KPIs to track your progress and work out a budget to keep your finances on point. 

Then, you can start to get your key strategies in place, from marketing to sales and operations. This planning process will take you from the big dreams you set to the nitty-gritty, day-to-day action items that will bring it all to life. 

And don’t forget, this plan can also include your personal development roadmap so you can be sure you’re pouring into your continuous growth (after all, you are your number one asset).

COO Tip: If any of this feels overwhelming or you’re not quite sure where to start, I break it all down in my new course, Business Building for Creatives. 

Keep on Learning!

Speaking of continuous growth, this is a perfect time to learn something new that you can carry into the new year! 

Embrace a beginner mindset, and jump into a topic or skill that’s always intrigued you. 

Maybe it’s related to your creative work, or maybe it’s something else entirely. Whatever it looks like for you, let this time spark your curiosity and stoke your creativity. 

The Holiday Shuffle

Balancing the busy holiday season with year-end goals can be challenging for any creative entrepreneur. But, with a proactive approach, intentionality, and a willingness to adapt, you can navigate this time successfully. 

Remember, it’s essential to prioritize self-care and embrace the magic of the holiday season. By setting boundaries, scheduling time for relaxation, and celebrating your achievements, you can wrap up the year on a high note, and enter the new year with renewed energy and enthusiasm. 

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