Hiring and Growth

3 Ways Entrepreneurs Can Escape the ‘Sunday Scaries’

Jeff Haden Inc. columnist and small business management expert 
sleepy woman who doesnt want to get out of bed representing the sunday scaries

I always liked Fridays. But as my business grew, so did my dislike for Sundays. At some point, usually just after lunchtime, I stopped enjoying the weekend and started worrying about Monday. I couldn’t stop thinking about projects I needed to complete, calls I needed to make, conflicts I needed to resolve…

Call it worry, call it anxiety, call it stress—whatever you call it, Sundays started to suck. 

It turns out I wasn’t alone.

One study found that 88% percent of respondents experienced anxiety on Sundays when they thought about Mondays (aka the Sunday Scaries), and the feeling was most likely to strike at 3:58 p.m. That may seem hyper-specific, but it also makes sense. As day turns into evening, thoughts naturally turn to tomorrow.

A LinkedIn survey found similar results, determining that every Sunday, four out of five people worry about the workweek to come. Interestingly, the younger you are, the more likely you are to experience the Sunday Scaries. 

What do most people worry about? In this order:

  1. Workload
  2. Balancing professional and personal tasks 
  3. Unfinished tasks from the previous week

The key word is “worry.” According to clinical psychologist Jonathan Abramowitz, “… it’s a response to the perception of some sort of threat. We jump to conclusions,” he says, and “underestimate our ability to cope.” 

We start to dread Mondays on Sundays because Mondays feel threatening. Monday is unknown, and at least for me, the most paralyzing fear is that of the unknown—even though few things turn out to be as scary or hard as I imagine.

So how did I overcome the Sunday Scaries?

3 ways to fight the Sunday Scaries

1. Make a plan.

Jim Whitehurst, the president and CEO of Red Hat, sits down every Sunday evening to map out his week. He reviews monthly and yearly goals, checks his calendar, and creates to-do lists. According to Jim, creating structure and discipline for the week keeps “urgent” from taking precedence over important.

That works for Jim. It didn’t work as well for me. I dreaded my Sunday evening planning sessions almost as much as I dreaded Mondays.

Instead, I extended my end-of-day routine on Fridays and created an end-of-week routine. 

The first thing you do in the morning is the most important thing you will do that day, because it sets the tone for everything that comes after. So I always prepare for that “first thing” at the end of the workday.

I set out the materials I need, make sure my notes are handy, and double check that I’m clear on what I need to accomplish. That way I can sit down and start.

I use the same approach to prepare for the following week. I know what I haven’t gotten done, and I know what I need to get done. I prioritize, decide what is most important, and create a short-list of those tasks.

While that process doesn’t make accomplishing some of those things any easier, it does help reduce any fears of the unknown. 


2. Write down your concerns.

As David Allen, the creator of the “Getting Things Done” productivity system, once told me:

“Most people try to use their psyche as their systemic process, which means issues gain importance based on your emotions. I’ve never met anyone who said they didn’t feel a little better if they sat down and made a list. Nothing changes when you write things down except how you engaged with your issues. Then you can be objective and also be creative and intuitive.

Your head is for having ideas, not holding ideas, and it’s certainly not for filing them away. Without exception, you will feel better if you get stuff out of your head.”

Worried about revenue? Write it down. Worried about an interpersonal issue between two employees? Write it down. Worried about a critical sales call? Write it down. 

List possible challenges, roadblocks, and potential negative outcomes.

Do that, and you’ll switch from worrying to problem-solving. You’ll start to think of ways to overcome challenges, bypass roadblocks, and mitigate any adverse outcomes.

Best of all, you’ll realize things aren’t as bad as you think. And you’ll realize you have the skills—and determination—to deal with whatever does happen.

3. Write down your positives.

Small business ownership can be all-consuming. (I know: Tell you something you don’t know.) Problem-solving, firefighting, conflict-resolving… it’s easy to get hung up on the less appealing aspects of running a business.

Yet you also love what you do—that’s why you started your business. You love the work, and you love helping and watching other people succeed. Nothing feels better than enjoying the fruits of your labor.

There are some things about your job you absolutely love.

But do you look forward to doing those things? Probably not, because you’re too busy thinking about all the other things you need to do. 

Retired NASCAR driver Kasey Kahne taught me that lesson. He started a dirt track team mostly because watching his team race gave him something to be excited about.

“Every single week, I have something to look forward to,” he told me. “It doesn’t feel like work when you’re having fun and looking forward to seeing what happens.”

Sounds too simple, right? But after Kasey and I talked, I thought about what I look forward to professionally. I was good at working hard, staying focused, delaying gratification—in short, grinding. But was I actively creating a steady stream of things I couldn’t wait to do?

And did I remind myself of those things on a regular basis?


Which is why the last thing I do every Friday is list the things I look forward to doing the following week: people I’ll talk to, projects I’ll start, projects I’ll complete, and interests I’ll pursue. 

I’m writing this on a Friday, and next week I get to interview David Beckham, retired soccer superstar and one of the owners of a new Major League Soccer franchise in Miami.

It’s hard to dread Monday when there are things you can’t wait to do next week.

Jeff Haden
Jeff Haden Jeff Haden is a writer, speaker, small business management expert, and Inc.’s most popular columnist. He's the author of The Motivation Myth: How High Achievers Really Set Themselves Up to Win.
Back to top