Managing Productivity and Time-off Around the Holidays

Looking to take time off during the holidays but afraid all of the distractions will lower your productivity? Here's some tips to help you benefit on both ends of the spectrum.

Managing Productivity Around the Holidays on JonathanMillsPatrick dot com
Taking time off is important. But so is staying productive this time of the year.

The life of an entrepreneur definitely has its ups and downs. For small business owners and freelance professionals who set their own schedules, the appeal of working untraditional hours can feel like freedom for those who have been unhappily confined by a 9-5 schedule. But for those who are new to managing their own off time or businesses with small teams, coordinating time off can be difficult, and all the distractions can lead to lost productivity.

Taking some time off for the holidays? Here are a few tips to keep productivity and relaxation at the max this season.

Coordinate Time off Requests

Managing competition for those premium days before and after major holidays can be a stressful, strenuous process. While some have the luxury of closing for multiple days, that may not be feasible for those with smaller teams, freelance professionals or those whose businesses depend on holiday demand.

Coordinate time off requests with your team as early as possible. Touch base with your team and/or clients at the start of the season and make a plan through the end of the year.

Small business owners should set clearly defined rules for time off requests so no one is caught off-guard. A good system should be fair for all employees, not based on merit, team or tenure. You can even automate the process if you want to be as impartial as possible.

For freelance professionals without PTO, be attentive to your clients’ holiday availability. Unless you work with clients whose businesses are dependent on holiday sales, plan your projects around the days they are out of office so that you too can take time for yourself.

Clear Communication with Team and Clients

Organization and communication are the foundation of any successful business. That goes triple around the holidays. With so many people traveling and out of office, it can be difficult to close on deals or ensure your team will have projects completed on time. Avoid the holiday communication confusion by being upfront with your team and clients about time off requests, project expectations and/or days you may be harder to reach.

Be mindful of people’s time off and let them detach from thoughts about work. Try to limit the number of texts, emails and Slack messages to emergency-only situations for those taking time off.

Set Realistic Expectations

For a lot of small businesses and freelancers, the holidays are a slow season. With so many things going on at once and less purchase behaviors around non-commercial products, it’s natural that many workers find themselves in a lull. For others, it’s the busiest time of the year. Wherever your business may stand on that spectrum, setting realistic timetables for when projects should be delivered around the holidays will help keep productivity to the max while minimizing thoughts of work when it’s time to relax.

Project management or content management software like Monday.com or Asana can help you organize your days and set expectations for when things should be completed. If you don’t find CMS helpful, you can use your Notes app, Slack or Google Suite for communication and organization.

Plan ahead for Variants

I’m sure I don’t have to remind you how hectic traveling during the holidays is. Packed airports. Packed roads. Large parts of the country are covered in snow. It’s no wonder why so many people loath going home for the holidays. And for those with less-flexible schedules forced to travel on some of the busiest days of the year, a lot of things out of your control can happen to throw off that perfect schedule you made before leaving.

Plan ahead for variants in your travel plans. This includes weather, cancelations and other travel delays. If you have the flexibility, schedule a day or two after your return to rest in the event your travel plans are altered.

Be Mindful of the Season

The holidays are a busy time for everyone. Be mindful of the season when planning your productivity and KPIs for the end of the year.

Unless your industry is specifically geared towards the holidays (e-commerce, food & beverage, etc.), it’s likely to be slow. Most people are worried about recipes and gifts, not cybersecurity tools or marketing campaigns. Don’t try to do too much. Strategize for what you want for the New Year. Refine your plan for how you want to attract new eyes to your business when everyone returns to work.


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