We're in that weird space between Halloween and the holiday chaos. You know what that means? In about eight weeks, everyone's going to be talking about New Year's resolutions and fresh starts.
But before you even think about January planning, we need to talk about why your plans keep falling apart. Because I promise you, it's not because you're undisciplined or can't follow through. Your annual planning is failing because you're walking straight into traps that make success mathematically impossible. Let me show you the three biggest ones so you can finally break the cycle.
Step 1: Stop planning in a vacuum.
Before you map out a single goal, layer in your actual life first. I'm talking about the two weeks the kids are home in January, the fact that February is basically a sick-fest, spring break, that massive work event every April, and your 25% summer capacity. When you can see what's already spoken for, you can create a plan with time that actually exists. Grab a calendar and mark everything you already know is happening: school breaks, work events, family commitments. That's your real time budget.
Step 2: Embrace the draft mentality.
Your annual plan gets to be a roadmap, not a contract written in stone. I do all my planning in pencil or with erasable pens because here's what I know: life happens. When you spend weeks trying to create the "perfect plan," you're either never finishing it or setting yourself up to abandon it entirely when reality doesn't cooperate. Instead, create your best intention based on what you know today, with the understanding that you can (and will) adjust it. The magic isn't in getting it perfect. It's in knowing how to shift it when needed.
Step 3: Build in the review system from day one.
This is where most planning completely falls apart. You create this beautiful plan, close the notebook, put it on a shelf, and never look at it again until you stumble across it months later feeling awful. Your plan needs to be a living document you actually use. Create simple tools (I use two one-pagers) that sit where you'll see them regularly: first pages of your planner, pinned to your digital workspace, wherever works for you. Then set up a cadence: What do you review quarterly? Monthly? Weekly? Without this system, your planning is honestly just a waste of time.
Once you understand these traps, you can build a realistic roadmap that actually works with your real life. And more importantly, you'll have the system to adjust it as you go. We all deserve to end our year feeling like we made real progress on what matters most, instead of wondering where the time went.
- The Capacity Confidence Method Starts in Two Days - Are You In?
In just two days, I'm kicking off a free 3-part training series for small business owners who are done feeling constantly behind. The Capacity Confidence Method will show you how to stop randomly picking deadlines and start planning based on actual capacity instead of hope and wishful thinking.
Over three 30-minute sessions (November 4-6 from 11:00-11:30 AM EST), you'll discover your team's true available time, learn to break down any project the right way, and find 10+ hours without hiring anyone. This is for you if you're tired of missing deadlines you thought were realistic, constantly firefighting instead of strategically planning, or feeling guilty for overcommitting and scrambling to deliver. Replays will be available if you can't join live.
Trello vs ClickUp: 5 Clear Signs It's Time to Level Up Your Project Management System
You love Trello for managing your business, until suddenly you're spending more time hunting for information across multiple boards than actually getting work done. If you're constantly playing hide and seek with your own tasks or feeling like your project management system is working against you instead of for you, it might be time for something more robust.
In this video, I'm sharing the 5 clear signs that your business has outgrown Trello (and why it's not a failure on your part), why hobby-phase businesses thrive in Trello but growing businesses hit a wall, and the specific features that make ClickUp ideal for scaling operations without adding team members. You'll also learn how to know the right time to make the switch before you hit crisis mode.
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How to Track Backup Plans Without Your Calendar Looking Like Chaos
One of the trickiest calendar challenges is wanting to track events you've said no to (because of existing commitments) without making your calendar look completely overwhelming. Maybe there's an awesome event happening the same weekend you're scheduled to be out of town, and you want to remember it exists in case your plans change. The problem is that overlapping events make your calendar cluttered and confusing to read at a glance.
In this week's Weekly Buzz, I'm sharing my strategies for both paper and digital planners, including the exact color coding approach that keeps backup plans visible but muted, and why having multiple email addresses for your digital calendar might be the game-changing solution you didn't know you needed.
Remember, this video is updated every Wednesday, so don’t miss it! Head to The Pink Bee app to watch now.
Friend, don’t forget—just 15 minutes of planning today can set the tone for your entire week. You’ve got the tools, you’ve got the tips, and now it’s time to take action. Let’s crush this week together!
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