I dreaded Monday mornings for years until I restructured my work life around these 4 principles.

For most of my early career, Monday mornings felt like a looming dark cloud. On Sunday nights, the thought of waking up to a long list of tasks would spike my stress level, and I’d find myself restless in bed. As a serial entrepreneur who’s started and managed multiple small businesses, I’d always heard that running your own show was supposed to give you more freedom—but in the early years, it didn’t feel that way at all. I’d stumble into Monday with a pile of responsibilities, a never-ending inbox, and the pressure to keep everything afloat. It took me a long while (and a few big mistakes) to realize the problem wasn’t Monday itself; it was the way I’d structured my work.

I eventually made a big shift. I decided it was time to really figure out how to run my work life so that Monday could feel like any other day, not a weekly disaster. After a lot of trial and error, I settled on four main principles that completely changed the way I view the start of the week. Now, I don’t dread Mondays anymore—I actually get excited for them, because they mark the beginning of a carefully planned and productive routine.

Below, I’ll break down each principle, explain why it matters, and share some tips on how you can apply it to your own work. My hope is that you’ll find Monday morning can actually become something you look forward to, once you’ve set yourself up for success in the right way.

1. Plan (Way) Ahead and Prioritize

Before I started practicing this principle, I’d show up on Monday morning without a clear plan. I’d open my email and jump from one urgent thing to another, never stopping to figure out if I was actually focusing on the right tasks. This scattershot approach left me feeling overwhelmed and unproductive.

The key shift was learning to plan out my week before it begins. Now, I dedicate time on Friday afternoons to review the projects I need to tackle in the coming days. I jot down the top priorities—the tasks that will move the needle the most—and I schedule them into blocks of time on my calendar. Setting these priorities also helps me figure out what can wait and what might be delegated to someone else.

I always found it helpful to use a simple question when deciding which tasks go to the top of the list: “If I only accomplish this one thing today (or this week), will I feel like I’ve made real progress?” If the answer is yes, it’s a priority. This planning ritual helps me close out the weekend with a sense of calm, instead of dread, because I know exactly what needs to get done come Monday. It also means I can start Monday morning with clarity, not confusion.

2. Set Boundaries and Schedule Breaks

As an entrepreneur, I used to think that working 24/7 was the only way to succeed. Early on, I let my work bleed into my weekends and evenings, believing I had to be always on, always available. This approach might feel heroic at first, but it’s a short ride to burnout. And yes, that intense, always-on schedule also fed right into my Monday morning dread, because it felt like there was no end in sight.

Eventually, I realized that for the sake of my own sanity (and ultimately, my productivity), I needed boundaries. Now, I set specific times for checking email or managing social media for my businesses. I also schedule breaks throughout the day—even a quick 10-minute walk can do wonders for clearing my head. On Sundays, I try to unplug as much as possible so that I can recharge.

One trick I learned is to treat breaks as a vital part of the schedule, not as an optional reward. When you literally block off lunch breaks and mini-breaks on your calendar, you’re giving yourself permission to step away without guilt. This helps keep your energy levels consistent and prevents Monday from feeling like you’re jumping back into a marathon with no training.

3. Delegate and Trust Your Team

If you’re the type of person who feels you need to do everything yourself, I get it—I used to be that way, too. In my first few business ventures, I was the one wearing all the hats: marketing, customer service, product creation, even picking up the phone in the middle of the night for random issues. But one of the reasons I hated Mondays was that I’d jump into a mountain of responsibilities that could have easily been shared among the capable people around me.

The principle of delegation changed everything. I started by identifying tasks that didn’t necessarily require my expertise, like basic bookkeeping or routine customer service inquiries, and I assigned them to team members who were great at those tasks. If you’re worried about training others or giving up control, know that it’s a learning curve—but once you start trusting your team, you free up time for the bigger, more strategic tasks that only you can do.

Delegation isn’t just about handing off busywork. It’s about recognizing the strengths of the people around you and letting them shine. That might mean hiring a virtual assistant or partnering with someone who loves spreadsheets if you hate them. The result is less stress on Monday (and every day), and a healthier, more collaborative company culture.

4. Make Personal Growth Part of Your Routine

Here’s something most people don’t associate with Monday mornings: personal growth. However, building time for learning and self-development into my work schedule was the final piece that truly helped me love Mondays again. Instead of seeing the start of the week as just “back to the grind,” I began to view it as an opportunity to invest in myself.

For example, I schedule a short 30-minute session every Monday afternoon to dive into something that will help me grow—this could be reading a chapter of a business book, listening to a podcast from an entrepreneur I admire, or watching a short video on a skill I want to refine. Making personal growth a consistent part of my routine keeps me inspired and reminds me that my career is a journey, not a race. It also means I’m less likely to burn out, because I’m fueling my own development while keeping up with the demands of my businesses.

Another way I encourage personal growth is by reflecting on the previous week. What went well? What could have gone better? Recognizing both the wins and the areas for improvement helps me start Monday with a plan to keep growing and adjusting. It turns Monday into more of a fresh start than a grind session.

Putting It All Together

Restructuring my work life wasn’t about making Monday less busy (though I did cut down on the chaos by delegating better). It was about having a system that made me feel in control, rather than overwhelmed. Planning ahead and knowing my priorities means I start each week with direction. Setting boundaries and scheduling breaks helps me manage stress. Delegating tasks frees me up to do what I do best, and making personal growth part of the routine keeps me motivated.

If you’re someone who’s been dreading Mondays for as long as you can remember, I suggest taking a step back to see which of these principles might be missing in your life. Do you have a plan for the week when you close out on Friday? Are you consciously creating boundaries between work and rest? Are you leveraging the talents of the people around you, or trying to do it all yourself? And finally, are you making time to invest in yourself, or are you so caught up in the day-to-day hustle that you’re forgetting to learn and grow?

For me, these four principles acted like anchors, preventing me from drifting into that old cycle of dread and exhaustion. It’s remarkable how much more positive your entire week can feel when you handle Monday on your own terms. Instead of the stressful kickoff it once was, Monday has become my launchpad for success and improvement.

Wherever you are in your career—whether you’re running your own small business, heading a team, or working on personal projects—you have more control than you might think. By applying these four principles, you can reshape your work life, boost your productivity, and maybe, just maybe, learn to enjoy Mondays. It won’t happen overnight, but with a bit of patience and persistence, you’ll see the dread slowly lift, replaced by a sense of purpose and excitement for the week ahead. Good luck, and here’s to turning Mondays into a day you actually look forward to!