The Entrepreneur Holiday Checklist

Planning Ahead for a Lucrative and Stress-Free Holiday Season

Published Date: Nov 5, 2021 | Blog Category: eWomenNetwork
Nicole Caliro

The holidays are a perfect time to take a beat, be thankful, and embrace tradition and cheer as we march on toward 2022.  The reality is, of course, that the holidays are stressful. Navigating travel, family plans, work commitments, holiday events; and the only way to get through it is to plan ahead. Especially when you're an entrepreneur.

Send Holiday Cards. Family expects them, but clients often do not. Isn’t it lovely to get mail that isn’t a bill? For some the idea of whipping out the old rolodex and handwriting cards is a delightful blast from the past, a soothing task that brings repetition and order to a chaotic time of year.  If you don’t fall into this category however, no worries, there are plenty of services that do it all for you. If you fancy physical cards, take a look at postable.com, simply select your design, hand over the names and addresses, and you’re good to go!  

Plan time off. For the workaholic, this one can be hard. But remember, with so many people celebrating the holidays, many of your clients will be MIA, so it’s okay to take a breather. Consider when you anticipate clients will go into holiday mode and follow suit. And when scheduling days off for your employees or contractors, remember that not everyone celebrates the same holidays or even celebrates at all.  While some may prefer Christmas Eve as a day off, others may favor the last night of Hanukkah. Provide them with options when you're able.

Overcommunicate with your customers. This is a biggie. Entrepreneurs are some of the most plugged in, on-call people in existence, and when that changes it can be confusing for clients. It’s nothing overcommunication can’t fix. Plan those out of office messages, send out mass email communication, and update your social media. Even before the holidays are in full swing, it’s a good idea to double-confirm every call and meeting. The holidays are hectic for everyone, so it’s possible your clients may have some things fall through the cracks as well.  

Think ahead when it comes to decorating. When to decorate is a hotly contested issue of the last several years.  Many brick and mortar retail stores begin the day after Halloween, prompting some to shout “too soon!”, but it’s not consumerism that drives this timeline, it’s managing the workload early on so employee hours during the holiday season are focused on customer service. So when you’re looking at when to decorate, whether it be your home or your business, think about what makes sense for your schedule. If December is a busy month, get everything out of the way in November so you can drive your year-end goal 100% without distraction. And remember, if you prefer to hire someone or (gasp) not decorate at all, THAT’S OKAY.  A mini pre-lit tree from Target is totally acceptable when you’re focused on building an empire!

Shop early. It can be tempting to take advantage of those last-minute sales, but anything big or important should be taken care of before Thanksgiving. Not only is it a nice feeling to be finished, but availability will always be an issue at some point. Big or small, things run out. When I was 25 and working on the sales floor at Barnes & Noble, a woman shouted at me something fierce on Christmas Eve because we were sold out of The Lovely Bones. “How can you be sold out? It’s the number one book in the country!” Exactly. Everyone wants it. The shipping and manufacturing issues that lead to hot items selling out are usually less of an issue prior to Thanksgiving. 

Buy a few emergency gifts. We’ve all been there, the unexpected gift is handed to you from a client or coworker, and you have, well…nothing. Having a few emergency gifts on hand can be a life saver for that unexpected client, or even when a family member brings home a new girlfriend or boyfriend with no notice.  No need to break the bank, a few $10 gift cards or bath bombs will do.    

Double check all travel plans. This is a given, but in times of COVID, it can be a game changer. If your heart is set on travel, be sure to check flight statuses as well as your destination’s regulations for COVID tests, masks, and vaccinations, especially for international travel. Expect the unexpected and always have a backup plan. 

Plan at least one day for yourself. As entrepreneurs it’s easy to focus so much on your clients’ and family’s holiday experiences, that you forget to enjoy the holidays yourself. And let’s face it, sometimes the things that are supposed to be fun are clouded by stress. Give yourself one day. One day where you can enjoy the holidays. What you say goes. No asking for the opinions of the kids or spouse, you do exactly what you want. If you want to be Christmassy and make snow angels, go for it.  If you want to have martinis and get a massage, do it.  Take one day that’s all about you and celebrate your hard work and success.



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