A B2B Entrepreneur’s Guide to Coping with Holidays

Aaron Dinin, PhD
3 min readNov 28, 2019

In honor of Thanksgiving, I’m going to make an assertion that’s sure to get me some angry comments:

Entrepreneurs with businesses that sell to other businesses (B2B entrepreneurs) hate holidays.

I realize I can’t speak for all B2B entrepreneurs. I’m sure some of them love holidays… particularly the few whose sales increase as a result of consumer holiday spending. But, for the rest of the B2B entrepreneurial community, holidays represent two things they don’t like.

First, holidays distract potential customers. They leave work early. They have holiday parties where they’re enjoying potluck lunches instead of sitting through your product demos. They often take vacation days surrounding holidays. Simply put, whether it’s Thanksgiving, July 4th, or even Valentine’s Day, potential customers get distracted during holidays, and that makes them less likely to buy.

Since making sales is already hard enough, it’s little wonder entrepreneurs have trouble getting into the “holiday spirit.” Everyone else’s day off makes it harder for B2B companies to hit their revenue goals.

The second problem B2B entrepreneurs have with holidays is they usually prevent the entrepreneurs themselves from working, and that creates frustration and anxiety. Entrepreneurs don’t see building and running their companies as “work” in a derogatory sense. It’s something entrepreneurs get deep enjoyment from (even when it’s not going well). Building companies is their passion; their companies are often their “babies.” Being told they can’t work is like telling a painter she can’t paint for a day, or a violinist he can’t play for a day. Sure, sometimes this can be a welcome respite. But, often, not being able to work on their companies can feel less like a celebration to an entrepreneur and more like a punishment.

If all this discussion about entrepreneurs hating holidays and loving work sounds crazy to you, you’re probably not the audience for this post. But if you’re nodding your head in agreement — perhaps while sneaking a peak at your favorite entrepreneurship-themed website during a trip to the bathroom between Thanksgiving dinner and Thanksgiving dessert — then you know exactly what I’m talking about, and this post is for you.

Aaron Dinin, PhD

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @ aarondinin.com

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