The Entrepreneur’s Holiday Season Survival Guide

Sherri Douville
5 min readDec 1, 2019

This seems like the time of year that we are supposed to do it all, which entails apparently propping up a good portion of the economy while entering the “rat race” I call the “holiday season.” After somewhat rebelling for some years against the expectations and pressures of the holiday season, partly out of entrepreneurial survival and necessity, we’ve come to at least what I consider to be a nice compromise. Why is this time of year so difficult for professional women especially in my view? The things that many professionals might have grown up with and expect even subconsciously, are predicated on the availability of a full time, dedicated human resource. Through either necessity or choice, this family configuration is becoming less common. Even so, the demands and guilt don’t seem to be receding to the proportional availability.

Allocating time and money when it comes to requests from friends:

“Is this a friend you can call at 3AM?” This was my answer to the question for advice I was asked about whether or not to go out of one’s way. This was to fulfill a time consuming, very expensive request by a friend of a friend (but not one of this person’s best friends). This person seemed to feel torn or guilty about potentially declining this request. Can I call this person at 3AM if needed? That’s the decider on extraordinary requests.

It’s OK Not to be Martha Stewart

After numerous discussions with my better half and acknowledging that friends and family were probably sick of me pretending like the holidays don’t exist; we came up with a game plan that works for us. No, I will never be Martha Stewart. I’m sure many women in my life will disapprove of my lack of interest in baking, decorating, and other peripheral traditions that are ignored in my world. I accept this and any resulting disapproval.

Managing requests for time:

A recap on a couple of ways I always manage requests for time but that become even more acute during the holiday season.

  1. I separate out requests for advice or time that either takes away from energy and time budgeted or has no productive impact on my business. This takes place mostly exclusively on Saturday afternoons. This is the time I have the least amount of energy; therefore the lowest tradeoff exists for loss of business and personal productivity. This is a likely time I might meet with a NonProfit on our “green light list” that wants to discuss something with me, for example. We had previously outlined in this post how we prioritize our Nonprofit “green light list” requests for time and resources: https://medium.com/@SherriDouville/how-we-set-community-service-priorities-the-personal-spiritual-parts-of-life-c91c85e1a603
This is a great, simple to implement idea by Isa Walton to save time and focus people’s requests for your time

2. Being extremely clear on my priorities, I can tell people genuinely that I’m happy for them to have their own priorities which could likely be very different from my priorities. If our priorities differ, that’s great but then I also ask them to recognize when they seem to try to impose their priorities onto me; I ask them to reconsider; typically they’re not doing this deliberately or even consciously, they’re kind of “sleep walking” their frequently legacy assumptions and are happy to reconsider. This is when it’s diplomatically pointed out how I may be completely different from them.

One example of leveraging defined personal/household priorities is that I do like and check Facebook almost daily but for an extremely defined and limited scope of time such as 15 minutes, max per day. It’s amazing that even in this limited time both in Facebook as well as real life, the number of charity requests people will make. If you’re deliberate on what you’re willing to do for charity every year ahead of time and it’s allocated in advance based on your household’s priorities and capacity, then you can alleviate pressures. This can include others’ subconscious pressures to have you conform. That would be impossible for a professional to do when there’s seemingly endless requests for your time and resources. At least this works for me.

Budgeting time and resources for the holiday season. On Sunday, November 24, we had a holiday priorities meeting to determine:

1. Overall holiday budget

2. Holiday gift checklist both people and items

3. List of items to be done from end to end to make shipping and other deadlines: stamps, shipping, travel

4. High priority events listed through February based on:

A) Family

B) Closest friendships

C) Business obligations/opportunities.

5. Wardrobes were assessed and gaps were addressed that day online. This is all staged by calendar sequence.

6. Any relevant Host/Hostess gifts ordered that day

7. Holiday card design and quantity decided and ordered

8. Both agreed to what we’re NOT doing (which is plenty); listed what we’re not doing

9. Dedicate one hour every subsequent Sunday during the holiday season to review the checklist for the week ahead on meetings etc.

I was excited for Thanksgiving and was happy to have experienced it. We look forward to a relatively sane, yet still productive season despite the holidays. We’re also working on enjoying the holidays more instead of thinking of them as just another job to manage. We hope this post frees you to be deliberate about what you will prioritize this holiday season.

By: Sherri Douville CEO & Board Member at Medigram, Inc. https://www.linkedin.com/in/sdouville/

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