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My Top 5 Calendar Hacks to Regain Control of Your Week

  • Writer: Dan Cholewa
    Dan Cholewa
  • Jul 22
  • 4 min read

Updated: Jul 29

Flat lay of smartphone with digital calendar open — example of effective calendar hacks

Let’s be honest. Most people don’t have a time management problem. They have a priority management problem.


I see it all the time in coaching conversations. Great leaders, smart entrepreneurs, seasoned sales professionals & real estate agents… all of them running fast, but not always in the right direction. Their calendars are filled, but not fulfilled. They’re in meetings, taking calls, crossing off tasks, but still feeling like they’re behind.


Sound familiar?


If you’ve ever looked at your calendar and thought, “How is it only Tuesday?” or worse, “What did I even do today?” then this is for you.


I’m going to walk you through five practical calendar hacks I use myself and teach my coaching clients. These aren’t fluffy time management tips. They’re battle-tested tools to help you run your week with more clarity, focus, and energy. When you use them, you stop playing defense and start executing like the leader your business needs you to be.

 

Calendar Hack # 1: Lock in Weekly CEO Time


If you’re not carving out time to work on your business, you’re stuck working in it.

You need one dedicated block each week, ideally 90+ minutes, where you are not in meetings, not answering messages, and not reacting to other people’s problems. This is your CEO Time. Your job during this time is to zoom out, assess, and make clear decisions that move the business forward.


Ask yourself questions like:


Some of my clients guard this time like a board meeting. That’s because it is one. It’s a meeting with the most important person in your company - you.

Avoid filling this block with admin work or to-do list items. Don’t skip it because someone else has a “quick ask.” When you protect this time, you give your business a structure to grow on.

 

Calendar Hack # 2: Give Every Day a Job


You can’t scale chaos.


When every day is a mix of client calls, internal meetings, lead generation, content creation, and admin, your brain ends up overloaded. You’re constantly switching gears, and that kills productivity.


One of the most effective ways to fix this is to theme your days. The simpler, the better.


Here’s a sample structure I often recommend:

  • Mondays are for internal team communication and leadership

  • Tuesday through Thursday are reserved for client-facing work, sales, and delivery

  • Fridays are dedicated to admin, systems, marketing, and creative work


When your week follows a rhythm, a few things happen. You begin to prepare mentally for what kind of energy and focus each day requires. Your team and clients learn what to expect. Everyone starts operating more efficiently because the uncertainty is gone.

This system builds boundaries without forcing you to say no. It creates focus without becoming rigid.


Calendar Hack # 3: Time Block with Breathing Room


Time blocking works, but only if you do it right.

Most people treat their calendar like a game of Tetris. Back-to-back meetings. Zero margin. And no room for context switching or overflow. That’s a recipe for stress and decision fatigue.

You are not a machine. You need space.


Here’s how to block time effectively:

  • Group tasks into categories such as deep work, calls, admin, and content

  • Identify your non-negotiables and anchor them first — for example, daily prospecting or workouts

  • Leave at least 15 minutes between major blocks to reset

  • Build in one hour of open time every day to handle surprises or unfinished tasks

Time blocking is not about stuffing more into your day. It’s about being more intentional with what goes where. If your calendar gives you room to breathe, your execution improves.


Calendar Hack # 4: End Your Day Like a Pro


It’s easy to talk about morning routines. Everyone loves to start the day strong. But most people never think about how they end their workday… those few precious moments to reflect… and that’s a big mistake.


A simple shutdown routine can change how you show up tomorrow.


Before you close your laptop, take 10 minutes to do the following:

  1. Review what you accomplished

  2. Identify what didn’t get done and make a plan for it

  3. Set your top three priorities for the next day

  4. Log off and shut it down: mentally and physically


This is not about being perfect. It’s about creating a clean ending so that your brain isn’t carrying the clutter of unfinished business into the evening. When your day ends with clarity, you sleep better and start tomorrow stronger.


Your team deserves a clear-headed leader. Your family deserves a fully present version of you. A solid shutdown helps with both.


Calendar Hack # 5:

Stop Letting Everyone Else Control Your Calendar


If your calendar is full of other people’s priorities, then your goals don’t stand a chance.

Every “quick meeting,” last-minute request, or non-essential catch-up adds friction to your focus. You lose time, energy, and momentum without even realizing it.


Your calendar is not a democracy. It is a reflection of your leadership and it shouldn’t be a negotiation.


Here’s how to take back control without burning bridges:

  • If someone wants to meet, check if it aligns with your theme days. If it doesn’t, propose another time that does.

  • If a conversation can happen asynchronously, suggest a Loom video or email exchange

  • Use phrases like “I’m fully booked this week, but let’s reconnect next Tuesday” or “Can you send me more context so I can review it first?”


You don’t need to be harsh. You need to be clear. When people see that you’re intentional with your time, they’ll start being more intentional with how they use yours. 


A Final Thought


Your calendar tells the truth about what matters to you. If it doesn’t align with your values or your goals, then the problem is not the number of hours in the day. It’s how those hours are being spent.


You’re not behind because you’re lazy. You’re behind because you haven’t set the structure to support the pace you’re trying to run at.


Try just one of these calendar shifts this week. Don’t aim for perfection. Aim for progress. And if you’re already doing most of this but still feel scattered, then maybe it’s time to reevaluate your priorities — or how you’re protecting them.


Remember, your calendar should serve you. Not the other way around.

 
 
 

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