How to Plan an Entire Year
How I Plan My Entire Year as a Busy Entrepreneur
Home, Work, Health, Family & One Big Project
If there’s one question I get asked over and over—by clients, team members, and friends—it’s this:
“How do you plan your entire year without burning out?”
The short answer? I plan intentionally, not perfectly.
The long answer is what this blog is all about.
Every year, I carve out time to zoom way out and look at my life as a whole: my home, my business, my health, my family, and one meaningful project that deserves focused energy. I don’t believe in cramming everything into one season of life. I do believe in creating a plan that supports the season you’re actually in.
Here’s exactly how I plan my year—step by step—and how you can adapt this process for your own life.
photo by Sheila Mraz Photography
Why Annual Planning Matters
When your life includes a business, a household, a team, and a growing family, planning isn’t about control—it’s about clarity. Annual planning allows you to zoom out, reduce decision fatigue, and make sure your time aligns with what actually matters.
This approach is especially helpful if you’re managing:
A household with kids
A growing or established business
Seasonal responsibilities (like gardening or travel-heavy work)
Annual planning gives you a framework so weekly decisions feel easier.
Step One: Start With a Paper Calendar (Yes, Really)
At the core of both home organizing and business organizing is visibility. When you can see your time, priorities, and commitments laid out in front of you, decision-making becomes significantly easier.
The same principles we use when organizing a home—clear categories, realistic capacity, and systems that match real life—apply directly to planning your year. A paper calendar gives me a bird’s-eye view of how my personal life and professional responsibilities intersect, overlap, and sometimes compete.
This is why I always recommend starting with one central planning tool. Just like having too many organizing bins can create clutter, having too many calendars creates mental noise. One place to capture everything is foundational to sustainable organization.
Before any digital tools come out, I start with a paper planner. There’s something grounding about writing things down—it slows me down just enough to think clearly.
I am in love with Colibri Paper Horizontal Weekly Planner, and it truly checks every box for my brain and my lifestyle.
Here’s why I love it:
A year-at-a-glance snapshot (essential for long-term planning)
Monthly goals from January through December
Weekly habit trackers
Space for birthdays and important dates
Monthly financial goals and actuals
A built-in meal planner and grocery list every week
And my personal favorite: a daily hydration tracker
One of my biggest goals this year is drinking 100 ounces of water per day, and having that visual reminder every single day makes a difference. This planner supports my whole life—not just work—and that’s critical.
Step Two: Set Goals Before You Schedule Anything
Before I touch dates, deadlines, or logistics, I set high-level goals. This is where most people skip ahead—and where overwhelm usually starts.
I don’t share every goal publicly (there are a lot), but I always identify clear priorities in these areas:
Home
Health
Family & community
Business
One big project for the year
The key is not making these goals huge and vague—but realistic and season-aware.
Home Goals: Planning for the Life We’re Actually Living
When it comes to organizing your home, long-term success comes from planning for how you actually live—not how you wish you lived. Annual planning allows me to anticipate transitions, growth, and seasonal changes so our home systems can evolve alongside our family. If you want to read more on systems that support families with young kids, we’ve shared more on organizing with kids, routines, and flexible systems because your home needs to evolve as your family does.
Our home goals shifted dramatically once we had our daughter. This year, a big focus is simply making thoughtful personal decisions as parents—from routines to spaces to how we spend our time.
One major home goal for 2026 is fully developing our garden and homestead. We originally built it out in 2020. Then we started a business in 2021, life got busy, and the garden took a back seat. Now, we’re ready to return to it—intentionally.
Rather than saying “we’ll build a garden,” I map out:
What needs to happen each month
Prep tasks leading up to planting season in May
Our active garden season, which runs from March through November
Breaking a big goal into monthly actions is what makes it sustainable.
Health Goals: Simple, Consistent, and Non-Negotiable
My personal health goals this year are straightforward—but they require consistency:
Work out four days per week
Drink 100 ounces of water daily
Walk three miles per day
These goals directly influence how I plan my weeks. If my calendar doesn’t support them, the goals won’t happen—and that’s information, not failure.
My Big Personal Goal for the Year: Building Community
This is also where planning intersects with values—something we talk about often when helping clients create homes and schedules that actually support connection.
During the winter solstice, I sat down and wrote out several personal intentions. As winter passed and life naturally filtered out what wasn’t essential, only one goal remained:
Community.
Specifically, deeper connection among:
Moms
Entrepreneurs
Friends already in my orbit
Out of that clarity came one actionable goal: Weekly Walks With Friends
In 2026, I’m starting a community walking group—dogs, babies, strollers, real life and all. We’ll meet twice a month, and the focus is simple: connection, movement, and consistency.
Plan Time Off First (Not Last)
This is the part that changes everything. Before scheduling work goals, I block off:
Family time
Recharge time
Garden time
Seasonal life events (like leaf season)
Major transitions (potty training, moving our daughter into a bigger bed)
Potential vacation time
Time is a finite resource. If it’s not accounted for, it will be overspent.
Anchor Dates Come Second
Before filling in tasks, I block out non-negotiable dates, including:
Monthly team meetings
Bi-monthly leadership meetings
Quarterly one-on-ones with assistants
Tax deadlines and payments
Birthdays and anniversaries (team and family)
Key client milestones
These anchor points determine what’s realistically possible.
Work Goals: Start Where You Are
Business organizing isn’t just about tidy desks or clean digital files—it’s about creating structure so your business can operate without constant friction. When we help clients organize their businesses, we start by identifying functional areas, decision-makers, and recurring responsibilities.
The same approach applies to annual work planning. Instead of listing endless to-dos, I organize business goals by category, ownership, and impact. This clarity allows our team to operate more independently and keeps leadership focused on strategy rather than constant problem-solving.
If you’re a business owner feeling behind or scattered, this is your reminder: planning should match your current capacity, not someone else’s growth stage.
Work planning looks different depending on the stage of your business. Right now, my focus areas include:
Operations
Team development & training
Partnerships & business development
Marketing (broken into blogging, newsletters, and social media)
Warehouse maintenance and systems
Special projects
Instead of treating all goals equally, I group them by function, then prioritize based on impact.
Work Backwards From the Output
Once I define what I want to happen each month, I work backwards.
For every output, I ask:
What needs to be created first?
Who needs to be involved?
What systems or resources are missing?
This is especially important in business, where progress often depends on preparation.
I then:
Break goals down monthly and quarterly
Schedule mid-quarter check-ins (usually around week three)
Reassess capacity and adjust as needed
Planning is not about rigidity—it’s about responsiveness.
Annual Planning Is a Shared Conversation
Every October or November, my husband and I—co-owners of our business—sit down together to plan the next year.
We reflect on:
What worked
What didn’t
What we want to improve as business partners
What we want to prioritize as a household
Where we want to invest our time and money
This alignment makes everything else easier.
Planning Should Support Your Life
Whether you’re focused on home organizing, business organizing, or simply trying to feel less overwhelmed, planning is one of the most powerful organizing tools available. When your goals, time, and systems are aligned, organization stops feeling like something you have to constantly maintain—and starts feeling like something that supports you.
A Gentle Reminder
Your plan is allowed to change. Your goals are allowed to evolve. And rest, connection, and margin are just as important as productivity.
A successful planning session—whether annual or quarterly—isn’t about doing more.
It’s about:
Honoring your capacity
Designing your time intentionally
Creating systems that support the season you’re in
Your plan should feel like a support system, not a source of pressure.
If you’re curious about adapting this process for your own home or business, or want help creating systems that actually stick, that’s exactly what we help with.
And if you want to walk and talk life this year—literally—don’t forget to comment below.
Ready to Plan More Intentionally?
If planning your year feels overwhelming—or if your systems no longer support your life—we help clients design homes, schedules, and routines that actually work.
Interested in support? Reach out to learn more about our organizing and planning services.
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Curious about the community walking group? Leave a comment below and let’s connect.
Updated by Jess Reed 1/29/2026