It’s always a challenge to stay motivated when the seasons are changing, but the transition to winter, with its colder, darker days can make being productive feel especially challenging - particularly for freelancers, entrepreneurs, or anyone else working outside of a traditional office setting. To help you brave the winter months, we’ve rounded up eight time-tested methods for staying motivated and productive this time of year. Whether you’re working from home, sharing a co-working space, or keeping cozy at your local coffee shop, take these tips as a starting point for developing your own battle plan for working through the coldest season. You might just find they work so well, you apply them in the summer, too!

As the days get colder, it can be hard to stay motivated ( source image )
As the days get colder, it can be hard to stay motivated (source image)

Start Your Day Right

For most  independent workers, developing a regular sleep schedule is key. It introduces a measure of discipline that will get you on track and help keep there over the course of the day. Getting up early and at the same time everyday — as if you had a conventional office job — tends to jumpstart productivity because it allows a little time for transitioning to your workday in whatever style suits you best, whether that’s exercise, mediation, or getting caught up on the news. Don’t forget, when you get an early start, you’re better able to reward yourself by knocking off early enough  to spend a few precious winter daylight hours however you see fit.

Plan Your Day Ahead of Time

It pays to schedule a regular part of your work routine in advance. Start with any upcoming deadlines and work backward, allowing enough time to complete your tasks without  stress. Give yourself personal short- and long-term goals and build them into your schedule, too. If you need help, learning to use scheduling and task-management apps might be the answer. In recent years, they have become flexible and sophisticated ­— and can keep you on track in ways traditional calendars cannot.  

When you know your schedule, you never feel lost ( source image )
When you know your schedule, you never feel lost (source image)

Dress for Success

“Clothes make the man,” says the age-old proverb, everyone is judged by their appearance. But the way we dress also affects how we feel, think, and perform. Pajamas may be comfortable but they also put you in a mindset best suited to slacking off. Getting appropriately dressed for the workday helps keep you motivated and focused on the tasks at hand. A suit and tie may be going too far — start within the “casual Fridays” range (a warm sweater fits the bill in winter) and watch your productivity grow.

Create a Dedicated Workspace

Like your attire, having a dedicated workspace is crucial to your state of mind. Even a small workspace within a bedroom or family room can help set psychological boundaries, and long-term, home-based workers often find a full-fledged office to be worth the added expense.  You may also want to consider purchasing a sun lamp, which may enhance your mood throughout the long winter and help regulate the circadian rhythms that govern sleep cycles and digestion. And if you just want to get out of the house, co-working spaces catering directly to independent workers have sprung up everywhere. There’s another potential benefit to creating office space at home: You may be able to write off a portion of your rent or house payment from your taxes. Check with a professional tax preparer for the latest IRS guidelines.

Manage Your Distractions

The computer you almost certainly use to do your work also should be recognized as the single greatest sources of work distractions ever devised. For many, the temptation to respond to social media notifications is overwhelming, so get familiar with how to turn off those pings and visual cues from Facebook, Instagram, Twitter, or whatever other apps  call your name. The same goes for your favorite websites — remove key bookmarks from your line of sight if you can’t resist the urge to click. By the same token, remember to build regular breaks into your workday. Reward a few hours of focused work with a 10-minute break to watch a video, play a game, or just go outside, any of which can clear your head and renew productivity.

Small rewards help you feel renewed ( image source )
Small rewards help you feel renewed (image source)

Eat Healthy and Smart

Temptations can also be found in your fridge and pantry when working at home. It’s crucial to keep junk food at bay — don’t underestimate the importance of eating right to your general well-being and ability to perform your work. For many, the key  element is planning meals in advance. Make shopping lists and allow for time at the grocery store, treating these tasks as part of your work schedule. Find at least one core dish you enjoy to make in a large batch each week. That way you’ll always have a sustaining meal ready to go, even when you’re in a deadline crunch.

Keep Yourself Connected

All independent workers have days in which they communicate with others only through their computers. Yet for most people, maintaining non-digital human contact is essential to a happy work life. So consider finding a work buddy, a friend or colleague you can meet at a coffee shop or library once a week to work together (a primary reason for the increasing popularity of co-working spaces is the human contact and camaraderie they offer). And instead of writing yet another work email, pick up the phone and actually talk to that supervisor or team member you haven’t spoken to in ages. Independent workers are more likely to start feeling isolated during the winter months, so plan accordingly.

It’s important to stay connected with friends and colleagues IRL ( source image )
It’s important to stay connected with friends and colleagues IRL (source image)

Try Productivity Apps and Courses

There’s a great variety of useful (and typically free) productivity apps available today beyond the scheduling software mentioned above. Widely recommended apps will keep your ideas organized (Evernote); monitor your daily use of websites and apps (RescueTime); reward you for not allowing your phone to distract you (Forest); and help you find work-friendly environments outside your home (Work From). Whatever component of your work life may be holding you back, there’s an app for that

Whatever challenges you experience when developing your independent work life, keep in mind that one size does not fit all when it comes motivation and productivity. Be sure to experiment with different techniques and learn what works for you. Take regular breaks in your workday and occasional days off, and generally try to cut yourself a little slack. It’s not easy inventing the future.


Need more tips and tricks? Skillshare offers dozens of classes on how to manage your time, energy and attention so that you stay motivated and productive through the winter - and beyond!

Written By

Ken Korman

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