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Sleigh Your Tasks: 20 Productivity Tips and Gifts for Entrepreneurs

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20 oproductivity tips to balance holiday hustle with time management tips and gift ideas for entrepreneurs.


As the holiday season rolls around, I often find myself caught in a juggling act that would make even the most seasoned circus performer sweat. Balancing the demands of running my own business with the festive cheer and family commitments is like trying to string Christmas lights in a blizzard. (I just did that – and yeah, it was just like that)

clear glass jar - productivity tips that will save you time and make you money
Photo by Sam Dan Truong on Unsplash

It’s not just about keeping the business ball rolling; it’s also about not missing out on those priceless moments that make the holidays special. I’ve learned, sometimes the hard way, that the key to surviving (and thriving) during this time is all in the art of time management.

So, I’ve reached out to my small business entrepreneur community and asked them how THEY keep it all together during the holidays. And 20 of them came through with time management tips that have helped me keep my sanity intact while wearing my entrepreneur hat.

And because ’tis the season of giving, I’m pairing each tip with some fun and thoughtful gift ideas to spread that holiday joy a little further. So, grab a cup of hot cocoa, get your shopping clicker ready and let’s dive into turning this holiday season into a masterclass of efficiency and cheer!


Prioritize and Delegate Tasks

As an entrepreneur, the art of prioritization and delegation becomes crucial during the holidays. It’s about identifying what you absolutely must do and empowering your team to handle the rest. This strategy creates breathing space for holiday enjoyment without compromising business efficiency.

One of my favorite ways to decide on what I can delegate is to make a list of all the tasks that ONLY I can do. Anything else can be delegated.

Here’s another thing, you don’t have to have employees or a team. You can head over to Fivrr or Upwork and hire a freelancer to take care of that project that you’ve been putting on the back burner for months!

Besides reducing the workload, delegation empowers my team to accept more task responsibilities.

Darren Graham, Company Director, 408 Media Group

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03/11/2024 04:09 am GMT

Employ a Priority Pyramid

Using a priority pyramid means starting your day by knocking out three major tasks. This approach, perfect for the busy entrepreneur, ensures the most crucial tasks are completed first, leaving you with ample time for holiday cheer later in the day.

A priority pyramid is a tool used by entrepreneurs to prioritize tasks and identify which items should take precedence in their business. The pyramid is typically divided into four levels: Primary goals (or ‘big rocks’), Plans & Strategies, Specific Tasks, and Daily Activities. Primary goals are the most important and should be addressed first; they represent the long-term success of the business. Plans & Strategies are more detailed plans that may need additional research or resources to accomplish. Specific Tasks are actionable steps for implementing plans while Daily Activities consist of smaller tasks that make up larger projects. This framework helps entrepreneurs remain focused on the most important priorities while still making progress towards bigger goals.

 It is important to maintain a clear separation between work and personal life; set aside specific time slots for each, avoiding the temptation to combine the two.

Jason Tebeau, President and CEO, Da Vinci Medical

  • Desk organizer
  • Daily goal setter
  • Team-building workshop passes
Mastering the Rockefeller Habits: What You Must Do to Increase the Value of Your Growing Firm
$10.44

In his book, The Rockefeller Habits, Verne Harnish provides an insightful look at the key habits that have helped propel John D. Rockefeller and other successful business leaders to the top of their respective industries. Through clear and concise advice, Harnish emphasizes the importance of focusing on doing the right things in order to achieve success. He argues that by honing in on what truly matters and efficiently executing these tasks, businesses are more likely to reach their desired objectives. The book offers a step-by-step guide on how to develop focus and discipline while still leaving room for innovation and creativity.


Overall, The Rockefeller Habits is an excellent resource for any business professional or entrepreneur wanting to hone their focus and reach higher levels of success. By providing practical steps on how to prioritize tasks and simplify decision making processes, Harnish’s book serves as a roadmap for anyone looking to maximize their potential for growth. With its emphasis on doing the right things right, The Rockefeller Habits is definitely worth a read!

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02/18/2024 10:34 pm GMT

Set Priorities and Make Plans

Drawing a clear line between work and personal time is vital. Plan your schedule with this balance in mind. This method not only improves focus during work hours but also guarantees quality time with family and friends during the holidays.

Establish a holiday timetable that incorporates significant obligations alongside meaningful moments spent with cherished ones. Assign duties at the workplace to reliable members of the team to guarantee the continuity of operations in your absence.

  • Customized calendars
  • Smart watches with scheduling features
  • Online project management tool subscriptions

Avoid Burnout, Learn to Delegate

Delegate to avoid burnout. Trusting your team with tasks can be liberating. This not only helps maintain your energy levels but also fosters a sense of responsibility and growth within your team.

Do the math and realize that burnout costs more than “losing” a few days off work to the holidays. Learn to delegate! This is perhaps the hardest lesson I’ve had to learn as an entrepreneur. Leaving important decisions in someone else’s hands seems impossible, but neither you nor your business can survive without it. You’ve hired people, you’ve trained them, now trust them.

  • Spa day vouchers
  • Meditation app subscriptions
  • Team leadership books
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02/18/2024 08:19 pm GMT

Delegate and Recharge

Delegating tasks allows entrepreneurs to focus on high-impact areas of the business while also finding time to recharge. A well-rested mind is more creative and efficient, making this a win-win for both personal and professional life.

Holidays are about togetherness and remembrance, not burning out. I make sure that I stay sane, focused, and enthusiastic by taking care of my mental well-being, which is equally important as work.

Abid Salahi, Co-Founder and CEO, FinlyWealth

  • Team training courses
  • Rechargeable power banks
  • Weekend getaway packages

Set Firm Work Boundaries

Setting firm work hours and communicating them clearly helps in maintaining a healthy work-life balance. This practice ensures dedicated family time, making the holidays more enjoyable and stress-free.

Last Christmas, I decided to work only until noon. I informed my team in early December, so everyone was prepared. Afternoons and evenings were mine to enjoy with family, guilt-free.

David Kemmerer, Co-Founder and CEO, CoinLedger

  • ‘Do Not Disturb’ desk signs
  • Noise-cancelling headphones
  • Personalized out-of-office message templates

Plan Ahead, Care for Team

Planning your holiday schedule early and ensuring your team is well-prepared shows leadership and foresight. A contented team leads to a smoother operation, allowing you more time to enjoy the holidays.

Always plan ahead. This is a period where employees need and deserve a break, but if you’re not careful, you can find yourself picking up all the slack. So, start organizing your Christmas schedule sooner rather than later. We start this in September. Encourage employees to book their time off well in advance, look for any ways you can minimize workload, and find ways to compensate those who don’t get their desired days off.

Martin Gasparian, Attorney/Owner, Maison Law

  • Team scheduling software
  • Holiday bonus envelopes
  • Company-wide holiday party invitations
Amazon.com Gift Card in a Snowflake Tin
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Surprise your employees and vendors with the ultimate token of appreciation: Amazon Gift Cards in Festive Holiday Tins. Each loaded with $100, these cards are perfect for acknowledging their hard work and dedication. With the flexibility to choose from a vast array of products on Amazon, it's a practical, thoughtful gift that caters to individual tastes. Presented in attractive holiday tins, they're not just gifts but a gesture of gratitude that strengthens business relationships. Gift the joy of choice this holiday season!

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02/18/2024 09:39 pm GMT

Manage Notifications with Focus Statuses

Mobile devices are designed to distract us with constant notifications. But Custom Focus statuses help entrepreneurs manage notifications efficiently. In your settings, turn your “Focus” on and you won’t get any notifications during a time you’re trying to work.

I set custom Focus statuses. It allows me to decide when I’ll accept work notifications and also escalate those from high-priority people.

  • Smart device distraction minimizers
  • Productivity apps
  • Focus-enhancing essential oil diffusers

Schedule Family Events First

By scheduling family events first, entrepreneurs ensure that personal commitments aren’t sidelined. This approach guarantees that work doesn’t encroach on precious family time during the holidays.

If there are work events that conflict with something you have scheduled with family, see if you can reschedule or delegate the work event. Protecting that quality time with loved ones should be the priority whenever possible.

  • Family event planners
  • Ticket vouchers for family activities
  • Custom holiday photo albums

Protect Your Downtime

Downtime is crucial for mental and physical health. Entrepreneurs should protect this time zealously to avoid burnout and maintain productivity in the long run.

If you are truly focused on success, then achieving a balance between work and personal life is not just a short-term goal; it’s a strategy for the long-term wellbeing of your business.

Katharine Gallagher, Professional Growth Specialist- Education, Career, Recruitment, Productivity, Business, katharinegallagher.com

  • Relaxation kits
  • Digital detox retreats
  • Hobby-related gift sets
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This luxury coloring book is the perfect gift for an entrepreneur who needs some relaxation and down time. Each page contains intricate and detailed designs that will help bring peace and solace to their mind. The drawings range from whimsical scenes of nature, to abstract patterns, to fun characters that can be colored in whatever color they feel inspired by.

There is even a section devoted to inspirational quotes and motivational messages that can provide extra motivation when needed. This one-of-a-kind coloring book is printed on high quality paper, with archival quality inks so the colors will remain vibrant for years to come. It's guaranteed to give any entrepreneur the break they need from their busy day and help them unwind while still feeling productive.

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02/18/2024 09:04 pm GMT

Plan the Week on Sundays

Planning the week on Sundays sets a clear agenda for the upcoming days. This foresight helps entrepreneurs stay organized and ensures that both business and personal commitments are met.

Keep in mind that when one plans the week in this way is that by understanding the importance of all these areas of life, one is able to perform at their highest level as an entrepreneur. This subtle mindset shift is what truly differentiates those who have balance and those who do not.

  • Weekly planning boards
  • Motivational quote books
  • Gourmet coffee for productive Sundays
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Revitalize your entrepreneurial spirit with the 'Coffee Connoisseur's Delight' Gift Box! Specially curated for the busy, stressed-out entrepreneur, this gourmet coffee selection offers the perfect pick-me-up for those long workdays.

Each box is packed with a variety of premium, hand-selected blends guaranteed to invigorate your senses and boost your productivity.

Whether it's a morning kick-start or a late-night grind, these exquisite coffees provide the ideal companion to your entrepreneurial journey.

Embrace the grind in style and let each sip inspire your path to success. Gift yourself or a fellow entrepreneur the joy of exceptional coffee today!

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02/18/2024 09:14 pm GMT

Forewarn Clients of Holiday Absences

Informing clients about holiday absences in advance maintains transparency and trust. This proactive approach prevents last-minute scrambles and ensures a smooth holiday season.

Automated emails are a great way of imparting this information, reminding clients at multiple intervals of any expected absences over the holidays.

Oliver Savill, CEO and Founder, AssessmentDay

  • Automated email setup services
  • Client gift baskets
  • Branded holiday cards

Take a Pre-Holiday Vacation

A short vacation before the holidays can rejuvenate entrepreneurs, helping them return to work with renewed vigor and focus. It’s a gesture that also shows family the importance you place on spending quality time with them.

It doesn’t have to be that long, or that expensive either. A Thursday-to-Monday break at the end of November is, in fact, my favorite option.

Domenico Trimboli, Freelancer and Business Owner, Domenicotrimboli.com

  • Weekend travel bags
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  • Travel guidebooks
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02/18/2024 09:19 pm GMT

Plan and Delegate Work in Advance

Planning and delegating work in advance allows entrepreneurs to fully unplug during the holidays. This preparation ensures that business runs smoothly in your absence, affording you true peace of mind.

Create checklists or to-do lists for your team, and leave it in your capable second-in-command hands.

  • Advanced project planning tools
  • Leadership development courses
  • Stress-relief gadgets

Prepare Staff for Holiday Operations

Preparing your staff for holiday operations ensures a seamless transition during your absence. This preparation is key for entrepreneurs looking to enjoy a stress-free holiday period.

Make sure you have staff properly trained and given the tools they need to do their jobs with minimal input from you during this time period. The last thing you want to be doing is putting out fires during those most critical times when you should be with your family.

  • Employee training programs
  • Holiday operation manuals
  • Appreciation gift cards

Grant Yourself a Holiday Half-Day

Taking a holiday half-day is a simple yet effective way for entrepreneurs to recharge. It’s a small gesture that can make a significant difference in your overall well-being.

I’m a big fan of the half-day Tuesday. It allows me to shop for holiday gifts on retail’s slowest day of the week, while still having a full day before and after to schedule meetings.

  • ‘Half-Day Hero’ awards
  • Self-care packages
  • Local experience tickets

Hire Seasonal Help for Holidays

Hiring seasonal help can significantly lighten the workload for entrepreneurs during the holidays. It’s a strategic move that ensures business continuity while you enjoy some well-deserved downtime.

For tasks like keeping up with content creation and maintaining your website, it helps to hire outside work for a few months.

Pascal Tatipata, Composer, Founder and Owner, dl-sounds.com

  • Freelancer hiring guidebooks
  • Outsourcing service vouchers
  • Team welcome kits

Keep Work at Work

Keeping work strictly at the office is a golden rule for maintaining a healthy balance. This practice allows entrepreneurs to fully engage in personal life without the distractions of work.

Avoid bringing work home with you. This is the single easiest way to ruin your work-life balance because it blurs the difference between personal and corporate hours.

Michael Nemeroff, CEO and Co-Founder, Rush Order Tees

  • Home relaxation sets
  • Work-only laptops
  • Family board game sets
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Reignite the joy of family time with the Deluxe 15-in-1 Game Center, an entrepreneur's perfect escape from the daily grind. This elegant mahogany-finished wooden chest not only beautifies your space but also houses 15 classic games like Chess, Checkers, and Backgammon. Whether it's a strategic game of Chess or a lighthearted round of Snakes and Ladders, there's something for every age and skill level. Compact and portable, this game center ensures fun is always within reach. Turn off the work notifications, gather your loved ones, and rediscover the timeless pleasure of game night. Ideal for gifting, it's more than a game set; it's a gateway to cherished memories and well-deserved relaxation.

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02/18/2024 09:29 pm GMT

Automate to Go Offline

Automation tools allow entrepreneurs to step away from work without worry. Implementing these tools means your business keeps running efficiently, even while you enjoy the holidays.

Customer support can be fully outsourced to chatbots and AI, so you aren’t in the trenches yourself. You can even let AI do the heavy lifting when it comes to targeted email blasts and social updates.

  • Marketing automation software
  • Chatbot setup services
  • Digital detox guides

Plan, Automate, and Complete Tasks Early

Planning and automating tasks in advance frees up time for entrepreneurs during the busy holiday season. Completing tasks early means you can relax and enjoy the festivities without the shadow of work looming over you.

As an entrepreneur, you know that there are busy seasons and “dead” seasons. Use those dead seasons to get ahead as much as possible so you can afford to take time away for the holidays.

  • Early bird planners
  • AI tool subscriptions
  • Time-saving gadgets

With these tips and accompanying gift ideas, entrepreneurs can not only manage their time effectively during the holidays but also add a touch of fun and relaxation to their routines. Enjoy the holidays without losing sight of your business goals!

Wrap-Up: Stress Less, Achieve More!

As we close this treasure trove of 20 de-stressing and productivity ideas and gifts, remember that the journey to peak productivity is sprinkled with moments of relaxation and joy. Whether it’s savoring a gourmet coffee, strategizing over a classic board game, or jotting down ideas in a specially designed planner, each item on our list is a step towards a more balanced and fulfilling entrepreneurial life. So, embrace these tools and gifts not just as aids, but as companions in your quest for success and well-being. Go ahead, give yourself the gift of productivity paired with peace, and watch as your entrepreneurial endeavors soar to new heights!

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