Jessi’s Holiday Week Musings, Part 1

by Jessi Burg and Kelly Sullivan

Today’s blog post is the first in a new series at Outgrow Your Garage about the unique relationship that entrepreneurs have with holidays. 

Starting in September, we have a nationally recognized holiday in the United States roughly once a month until the end of the year. September brings Labor Day, October gives us Halloween, then Thanksgiving, and of course, that weird week between Christmas and New Years where a lot of businesses are quiet. 

One of the things about owning a business that I have recently come to terms with is the way in which holidays become a sort of refuge from your regular loud, chaotic workflow. While most use their holidays to relax and recharge, many of us entrepreneurs will use quiet holidays to catch up on emails, prep, or plan for the future. When clients are busy and your staff is off, you end up with extra time to get stuff done without any immediately pressing tasks.

As business owners, this inherently means that we navigate holiday times differently than most of the other people in our lives. I don’t always feel like I’m actually part of the workforce. It is my responsibility to make sure that everyone else gets paid, and my hours are much more erratic than the rest of my team. 

I personally find that my best work happens in the late morning to early afternoon. I take a break, and then do another few hours in the evening. Sometimes I work weekends or take half days off. If I travel (for work or for pleasure), I do it during the week. Having the freedom to control my schedule is part of what I love about entrepreneurship, so long as it’s compatible with the rest of the team.

Since our team is small, I handle a lot of the day to day operations, like overseeing the company and managing staff, while simultaneously doing the long term planning and strategization. I have to balance the “how can I be available for my staff” with “what are the basic needs that need to be met for me to be able to manage a growing business?”.

One of the ways I handle this juggling act as a manager is to set clear metrics and expectations for everyone. The Outgrow Your Garage team works on a project-based calendar, which means my staff is free to set their own hours as long as deadlines are met. We focus more on the quality and completion of projects, rather than obsess about the timeclock. 

As a business owner, Labor Day is just another day for me. I spent the holiday learning our new project management system (Airtable) and getting ready for our Quarter 4 planning session. Having a day with no meetings and no interruptions was a key part of my success, which is why I tend to do this type of work on the weekends. 

Even though my staff sets their own schedules and have more days off than a lot of other workers, I still feel the need to reinforce the holiday practice. Labor Day itself is a neat holiday – celebrating workers by taking a day off of work. Three day weekends are great for group gatherings, family visits, and travel. My personal favorite part of cultural holidays is how they’re a collective day off, so it’s easier to get together with friends and family. 

In theory, anyone can take Labor Day off at Outgrow Your Garage. In practice, I chose to work because it was a great time for planning and professional development. It made me stop and think about what a unique relationship I, as an entrepreneur, now have with holidays. As an employee, holidays were a bonus day off and something I didn’t think much about. Now, I appreciate the quiet time to reflect on my priorities for the coming months.

This OYG holiday blog series is dedicated to presenting the different ways for you to think about how to manage holidays in your own business. If it means you work, then enjoy the productivity and extra time. If you take it off to relax, enjoy that too. There is no right or wrong answer! Do what works best for the health of you and your business.


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