We asked the small business community how they keep Sunday dread at bay when they run their own show. From Friday shutdown routines to Monday morning rules, here is what they told us…
I don’t think I have ever experienced the Sunday dread since being self-employed. But there are clear things I do that play a part in this:
1. I review my week on Friday and map out the following week before I log off (noting down any big rocks, meetings, travel and anything personal). This way, when I come to start work on Monday, I am not spending time trying to remember where I left off.
2. Friday celebration of the week. Whatever this looks like, it could be a takeaway or a glass of your favourite beverage – I just make sure that it IS different to all the other days.
3. Morning routine. I’ve created a routine that I can’t wait to get out of bed for. I’m an early riser, so I love getting going as soon as my alarm goes off. I hit the gym or go for a brisk walk as often as I can (and always on Monday) and am usually back before anyone else in the house is up for breakfast.Raimonda Richardson, Let’s grow! …with Events & Expos | Fractional Marketing Consultancy
I usually plan my week either on a Friday or Sunday afternoon so I’m not starting Monday feeling overwhelmed. But I also know that if I feel the Sunday dread, something is usually wrong with my business or the work I’m doing, so I use it as a sign I need to check in and figure out what needs to change.
Fliss Lee, Outsourced Head of Brand for growing SMEs + creative freelancers and founders
I started getting the Sunday night dread about two years into my freelancing career. I noticed I’d basically replicated the same overworking, overdelivering, underearning patterns that I’d created in my 9-5 role. I took on all work regardless of scope out of fear that nothing else would come along, and I underpriced my services because I didn’t want to appear greedy or make the client feel uncomfortable. Basically, I was putting everyone else’s needs ahead of my own health and wellbeing.
What helped me most was getting clear on what I wanted to be known for, who I wanted to work with and how I wanted to help them. That clarity piece around my offer and ideal client was the turning point for me attracting more of the right opportunities, saying no to the wrong ones and feeling confident pricing my services appropriately. And I don’t get that Sunday night dread anymore.
Jane Curtis, I Help Charity Freelancers & Consultants Replace Their Salary Without Working 24/7
The Sunday dread comes with the sense of trepidation of a mandatory management meeting for my fractional project at a start-up on Monday at 8.30am. The early start reminds me of corporate life, but with one critical difference: I determine how I dedicate my hours for the rest of my day and week. I also write a task list for the week, which I enjoy checking off, though never successfully. It does focus the mind though!
Gila Moyal, Leading Marketing Strategist
I’m co-owner/co-founder of Toucan International. Since starting Toucan, Sundays don’t feel as daunting as they used to when working for agencies and other businesses. I’ve found it liberating to be in control of my/our destiny and have full visibility of our commercials, sales pipeline and decision-making. Naturally, things happen in any company that raise your heart rate and stress levels, but I think it’s about channelling some of those concerns into things that benefit the business or bring in new business. The combination of keeping busy and working on things that give you the sense that you’re improving the situation, whether that’s going to generate an immediate return or something that comes a few months down the line, makes you feel like you’re actively doing something constructive. For me, that might be strategy behind our marketing activity ahead of an industry conference or sharing some of our marketing content in a bid to land more new business. Being in that conversation with different brands you’re trying to land throughout the year keeps the wheels in motion and always has new opportunities to explore.
James Dixon, Helping brands deliver record-breaking Organic revenue through award-winning Digital PR
Knowing I don’t have to iron five shirts has removed the Sunday dread for me. More seriously, though, I find you’re thinking about your business all the time when self-employed; I usually focus on the week ahead late on a Sunday afternoon. I try to ensure that the first thing on the schedule on a Monday is fun.
Ralph Cunningham, B2B Writer, Editor & Content Strategist
Yes, I totally do know that feeling. For me, the only way to tackle it is to be prepared and ‘try’ to control the controllables and be one step ahead. I’ll prepare my strategy for what’s on my desk for Monday, get my LinkedIn post ready, and make a plan for outreach or portfolio work if I’m in between clients. It saves me from being thrown around by the currents, and buys me flex for when I need to react to curveballs. Essentially, being as organised as I can helps. I find avoidance just makes things bigger, for me anyway.
Melissa Wheeler, Senior Copywriter | UX Writer | Content Designer | Content Marketer
I used to experience this a lot in the corporate world. It’s less of a loss now as a small business owner working for just myself. But it sometimes creeps in – and it tends to be because I’ve overbooked my week or have some challenging things to tackle. Inevitably, it means I’m in control. So lesson learnt. I don’t overbook my week – I time block. I give myself permission and the confidence to say no if my week already looks a bit hectic. Or I delegate – sometimes there is a task I know I need another brain to help me. I have a great network and know some other great freelancers. Straight away this burden feels lighter. Planning is key. Being honest with yourself is a must. And where I need to, I’m honest with my client about timescales (which is already detailed in my welcome pack/message), what is and isn’t possible, and why.
Penny Gibbs (MSc, BA), Digital Marketing & Media | Helping therapy, treatment and wellbeing businesses get found, trusted and chosen online
As someone who has recently taken the leap into PR freelancing, I’ve found the Sunday scaries have mostly gone – as I try to avoid booking anything on a Monday morning unless it’s essential, so I use that time to plan the week. However, the Sunday scaries have been replaced by smaller, daily ‘scaries’ where I worry I’m not “doing enough” (whatever that actually means!).
Going freelance just before the summer holidays probably intensified that feeling, as prospective clients were either away or reluctant to commit to anything in the holidays. I’ve done plenty to promote myself and my services online and in-person, but because the results aren’t immediate, it is difficult to know where to draw the line and stop.
I’ve found the best way to mitigate this issue is through creating a simple outreach CRM – holding me accountable for prospecting without feeling as though I should be doing it constantly.
Steve Lambert, Freelance PR and Communications Consultant
I’ve definitely experienced the “Sunday dread”, particularly as a self-employed business owner when there’s always something else that could be done. For me, the best way to reduce it is to finish the week organised. On Fridays, I make sure each production station is fully stocked, place any supply orders and ship everything that can go out before the weekend, so unfinished work doesn’t unnecessarily flow into Monday.
I also spend about half an hour on Sunday evening checking business emails. If something is urgent, I’ll deal with it then. Otherwise, I know what’s waiting and can give myself time to think it over overnight. This helps me start Monday feeling prepared rather than blindsided, which is important because Mondays are usually chock-full of printing and customer enquiries.
Katie Lynch, Founder + Director at Katie J Design and Events
Sunday dread is a form of anticipatory anxiety: your brain simulates what’s coming and prepares for potential demands before they actually occur. And I have certainly felt it.
For a small-business owner, Monday can contain a lot of uncertainty, since we wear all the hats!
So here’s a quick tip that leverages behavioural science: reduce Monday’s uncertainty. Before you finish work on Friday, decide exactly what’s going to happen on Monday morning: “At 8:30 Monday, open the webinar deck and write slides 1–5.”
The Friday Shutdown. Before stopping Friday, answer three questions:
1. What is the ONE most important thing I need to accomplish next week?
2. What is the ONE thing I will do first Monday morning?
3. What am I consciously choosing not to think about until Monday?Then close the laptop! This should help.
Howie Chan, Become a Professional of Influence | Keynote Speaker | Strategist
I think you have to see every week as a new opportunity to make a difference and create even more opportunities. When you choose to work for yourself, it’s about balancing the delicious freedom with that persistent need for self-motivation and conscientiousness. If Sunday night overthinking creeps in, I remind myself I’d still rather steer my own path in my own time than be beholden to the inevitable rules, routines and interruptions of being in-house, and I always make a good old pen-to-paper to-do list alongside a week-view paper diary to get circular worries out of my head. Such a simple thing, but it really helps, and it stops you looking at screens for at least five minutes!
Zena James, Freelance PR/writer/comms specialist
The Sunday dread (aka the Sunday Scaries here in the U.S.) is much less intense now that I work for myself. I intentionally avoid booking meetings on Mondays (particularly Monday mornings!), which gives me some breathing room, allowing time to get organised and get a strong start on my work for the week.
Michelle Garrett, PR for B2B Clients
We have a Monday morning date! Bike ride, run, breakfast, and a walk to pick up the paper and read it together. If you kick off your week with a date, what’s there to dread? (And if you’re dreading a date, that’s a whole other question!)
Francesca Baker-Brooker, PR. Copywriting. Marketing
A calm Sunday at home, doing simple stuff with the family, works wonders for me. If I can get some time at the weekend to get my life admin in order, like ordering the food shopping or spending some quality time with the kiddos, I feel much less overwhelmed by the prospect of work on Monday because I know that everything else is ‘done’. When I overschedule myself at the weekends, that’s when the scaries creep in for me.
Sarah Ellis, Website copywriting, editing + brand messaging frameworks for great people doing good stuff | Storyteller + soft seller + SEO
I avoid it by doing some work on Sunday evenings! The world feels quieter, and that makes it easier for me to focus on things that need uninterrupted thinking time.
Fred Hicks, LinkedIn Writer for Executives at Membership Orgs, Trade Associations, Non-Profits
I haven’t experienced the Sunday scaries since I’ve worked for myself. Not working a regular Monday-Friday 9- 5, I’m sure helps with that – plus loving the work I do.
Lucy Patterson, Longevity Innovation Strategist
I don’t experience the “Sunday dread” like I did before self-employment; I like what I do. But I still find it really important to treat weekends as sacred. I’m rarely online, I’m not checking email, and I try to do as much fun stuff as I can. That way, when Monday morning hits, I feel refreshed.
Michael Neidert, Copywriter for SMBs and Startups | Brand + Content Strategist
Somewhere over the weekend, I like to make sure all the kid stuff is locked down for the coming week – pick-ups, clubs, playdates etc. That means I understand my capacity. Then I write my “must-dos” and separate them from my “could-dos”. The must-do list gives me enough structure to keep the business moving (without giving me so much structure I feel like I’m in prison), while the could-do list lets me follow my energy and dopamine when I need the freedom and flexibility. I find that balance of structure and flexibility far more effective than trying to plan every hour of my day.
Elinor Perry, Anti hustle coach
They only come for me when I’m working on a project or client that doesn’t align with my values or goals. To me, it’s a sign that I need to re-evaluate the opportunity and whether it’s worth what it costs.
Candice Grobler, Build a Community to Engage and Retain your Audience
If I feel the scaries coming on a Sunday night, I sit down at my desk, set a timer (so I’m not tempted to get up and clean the kitchen) and have an hour of focus. I’ll schedule and send a bunch of emails, chasers and anything I know I’d like to get off my chest by the morning. That way, I can spend a reasonably guilt-free hour at the gym on a Monday morning without racing back to my desk. It’s not for everyone, but it works for me.
Justine McMenemy, Freelance CRM & Retention Marketing Consultant for DTC & Ecommerce brands
Sunday dread used to creep in when my brain started thinking about everything waiting for me the following week. My solution? A Friday afternoon brain dump.
I get every task, idea and “don’t forget…” out of my head and onto my Trello board, then pick my top three for Monday. As a writer, I know the power of getting thoughts out of your head and onto the page. Once they’re written down, my brain knows it can clock off too.
No more Sunday spiralling. Just a clearer Monday morning.
Amanda Akien MA, Freelance Journalist & Copywriter and Founder of Moo Marketing
