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7 Reasons Entrepreneurs Deserve to Rest this Holiday This Year

The Radical Connector Blog: 7 Reasons Entrepreneurs Deserve to Rest this Holiday This Year

It’s been a doozy of a year and we need to talk about why entrepreneurs deserve to rest and how to take advantage of the upcoming holiday season to go from burnout to balance … are you with me?

I often get the strangest comments from people about how I need to take time off, slow down, or stop working so hard. The funny thing is, I do all three of these … take time off, slow down, and stop working so hard.

In fact, I used to burn out All The Time because I didn’t do this in the past. I have learned (the hard way) that it is essential to my business and my life to set up lots of rest, space, and time off because friends, burning out is becoming way too common … and I’m over it.

I have a sneaky suspicion that what's really happening is these kind friends and community members have also experienced the exhaustion of burnout and want to make sure I and others don't fall into the entrepreneurial burnout trap!

Friends, I’m officially giving you permission to slow down, take time off, and stop working so hard in your business with 7 reasons why you absolutely deserve an extra-long holiday this year.

1. Avoid Burnout

This is one of the most common complaints I hear from entrepreneurs in their first three years. There is a misbelief that if they don’t think about, talk about, and attend to their business 24/7 it will crash and burn.

Add to that FOMO, fear of missing out, and the pressure of keeping up with others’ success plastered all over social media and before you know it, y’all have worked yourselves into the ground.

Your energy and passion are depleted. You lose the connection to why you are doing all of this in the first place. Your joy is gone.

Taking an extra-long holiday this year is not so you can recover from burnout … it’s so you can prevent burnout in the first place!

2. Spark Your Creativity

As you move from burnout to balance, you’re going to notice a fabulous thing happen with all that lovely space and rest you’re giving yourself … creative solutions and new ideas will start bubbling up.

This might sound strange, but some of my best ideas come when I’m binging YouTube videos.

(I’m currently binging to The Icing Artist and Forrest Valkai)

There’s something about letting my brain enjoy learning something new and NOT thinking about work that gives it the space to play without me overthinking … and I always get my best creative ideas in that space.

Are you tapped into where and when your creativity gets sparked outside of work? Yeah, do more of that!

3. Get a Bird’s Eye View on Your Business Activities

When we are getting our hands dirty and are up close and personal with our business all day, every day, it’s hard to have perspective on what’s working and what's not.

When you give yourself an extra-long break it allows you to get back into balance and reflect on what you need to stop, start, and continue as you head into the new year.

I have an annual tradition where I go away somewhere snowy and pretty all alone for five days so that I can just … think.

I don’t do any official work. No blogs or social content. No client meetings or podcast guest speaking.

It’s all about slowing down, journaling, thinking, and reflecting on where things are at in my business from a, “Do I like what I’m doing?” perspective.

I get real with myself on what I may need to stop (or phase out), what I want to start, and what’s been working and will absolutely be continuing.

It’s like my own private conversation between Whole Lindsay and Entrepreneur Lindsay. We check in and make sure my business life is still aligned with who I am, what I value, and what I want.

When you take your extra-long holiday this year, I want YOU to carve out time to have that conversation with yourself. Ask yourself, “Do I like what I’m doing?”

4. Enjoy Yourself!

This year has been one helluva rollercoaster and I have a pretty strong feeling that next year is going to be more of the same.

You’ve come through many (many) wildly stressful moments in history and you absolutely deserve to indulge in extended rest and all the self-care and play you can handle.

🥰 Set up virtual gatherings with your friends, put on something sparkly, and spend an evening laughing together.

🥰 Grab that book you’ve been meaning to read and indulge in an afternoon all to yourself of reading, sipping tea, and heck … let yourself fall asleep for a mid-afternoon nap.

🥰 Bundle up the family and head outdoors for some hiking, snowshoeing, or sledding. Enjoy the season and let the deep belly laughs ensue.

🥰 If you’re like me, slip away for a solo, social-distancing spa day (if it’s safe) and enjoy a day of being pampered.

🥰 Try a new recipe, volunteer with an organization you love, dive into an adult colouring book, binge terrible holiday movies on Netflix …

It’s your time, baby, do what you love!

5. Prove That You Can Take a Break and Your Biz Won’t Fall Apart

Ok, if you are inside of three years in your business this is an important one. You need to prove to yourself that you can take an extra-long holiday and that your business will still be there when you come back.

In fact, you’ll be a better business owner when you come back … bonus!

I take a full month off every December and August and I’ve been doing this for over 10 years. How? I set up my business to be able to function without me in October and June so that I can fade into the background and nobody knows I’m gone.

Also, December and August tend to be slower months because people are out doing #4 … enjoying themselves. And you can be too!

If you’ve ever heard the phrase, sleep when the baby sleeps, you know what I’m talking about. The best time to get some rest and recharge your batteries is when your business is sleeping.

When is your business slowest?

Take an extra-long break during that time. Just make sure you set yourself up BEFORE you go so that your business is primed and ready for your return.

Tip: Start small! Start with taking 5 days all to yourself and every year extend that time further and further until you reach your sweet spot

6. The World is on Fire …

Ok … I mean ... does this even need an explanation? We’re tired. We’re worried. The future is uncertain and holy smokers we could all use a break.

Take the pressure off yourself to be anywhere, do anything, and show up for others.

(This includes social media)

Shut it all down, shift from burnout to balance, and enjoy a long, luxurious, self-care holiday.

You’ve earned it!

7. Play In Your Business

This is the best time of year to slow down and catch up on all the cool things you’ve been saving all year.

You can finally dig into:

  • The latest tech and apps to help you run smoothly and automate

  • The articles, blogs, thought pieces, and books you’ve been collecting

  • Optimizing your SEO, nurture sequences, and automation (am I the only one that finds this fun??)

  • The latest trends and functions on social media (I'm coming for you, Instagram Reels)

  • Setting up your YouTube channel or podcast.

  • The courses you keep buying but never actually open

  • All the Nonessential Busy Work you’ve been diligent at putting on the shelf to focus on Revenue Generating Activities and Essential Busy Work all dang year!

This is the time when you get to slack off, play around, and do all the learning, researching and practicing with what’s new and possible in your business ... but only if you want to and not if it comes at the cost of shifting from burnout to balance!

So there you have it. 7 reasons why you absolutely deserve and need an extra-long holiday this year. What will you do with your time?


You’ve been working your buns off all year while also navigating a flipping pandemic … you deserve to take an extra-long holiday this year!

👉 Avoid Burnout: Rest is essential to your growth … not a reward for working yourself into the ground.

👉 Spark Your Creativity: Rest, space and free time allow your brain to bubble with creative ideas and solutions.

👉 Bird’s Eye View on Your Business: How did you feel this year and how do you want to feel next year? What do you want to stop, start, and continue?

👉 Enjoy Yourself: Celebrate your persistence, resilience, and tenacity with unadulterated fun with your favourite people … including yourself!

👉 Prove to Yourself Your Business Won’t Fall Apart: Trust me, taking a few days off from eat-sleep-breathing your business won’t kill it … you need to get comfortable taking time off and walking away from the laptop for days (or weeks) at a time!

👉 The World is On Fire: Take some space to rest, talk it out, get involved, and refuel.

👉 Play In Your Business: Now’s the time to play with all that NonEssential Busy Work you’ve been putting on the shelf all year! (I’ll be catching up on all the fun courses I bought and never actually opened, muahahaha)

Start Small: Can you take 3-5 days off and not look at your phone or laptop and just … breathe?

Start there and work your way up to more and more extra-long holidays every year.

Wishing you oodles of rest, play, and wonderful connections this holiday season!



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