How to Plan a Solo Business Retreat for Entrepreneurs
Every fall, I lock myself in a hotel room for three days with nothing but my laptop, a ridiculous number of post-its, and enough champagne to make the strategic planning feel celebratory instead of suffocating.
There's no team-building exercise, no trust falls, no forced networking over continental breakfast. Just me, my business, and the space to actually think about how I’m going to accomplish my goals instead of just reacting to whatever fires need putting out this week.
This is the most important thing I budget for in my business every year, and if you're a solo entrepreneur who's been running your business from reactive mode—answering emails during dinner, planning your quarter on Sunday nights when you're already exhausted, watching weeks dissolve into scrambling instead of intentional progress—then you need one too.
Not because retreats are indulgent or because you need motivation. Because you need a focused structure that lets you make decisions instead of deferring them until "later" when you mysteriously have more bandwidth (you won't).
Why Solo Entrepreneurs Need Business Retreats
I know what you're thinking. You can't afford to take time off. You'll just plan on Sundays like you've been telling yourself you will. You tried planning before and your week fell apart by Tuesday anyway, so what's the point, right?
When you're running your business from inside the daily chaos—client emails piling up, social media algorithms demanding attention, fires that need putting out before you can even think about long-term strategy—you can't see the bigger picture. You're making decisions about what's urgent while what's actually important gets pushed to "someday" indefinitely.
You're rewriting the same goals quarter after quarter because you never created the conditions to actually execute them. You're carrying around a running list of "I should really" tasks that live rent-free in your brain (those open loops create mental clutter) but never make it onto your calendar because there's always something more immediately pressing.
A business retreat solves this not through inspiration or motivation, but through giving yourself white space. You're creating uninterrupted time to think strategically, distance yourself from daily operations so you can see what's actually working versus what you're doing out of habit, and space to make decisions that have been sitting in your mental backlog for months.
This isn't about coming back "refreshed" or "recharged" (though that's a nice side effect). This is about doing the CEO work that never fits into your regular week—assessing what's working, cutting what's not, planning your revenue strategy, deciding what you're NOT doing next year so you have the room for what actually matters.
You already know you need this. The question is whether you're going to keep telling yourself you'll get to it eventually, or whether you're going to actually block the time and go.
When to Schedule Your Business Retreat
I do mine in October or November every year (and have since 2017). By then, I can see how the year has actually played out (not how I hoped it would play out back in January when I was full of optimistic planning energy), and I have enough time to plan next year before the holidays hit and everything gets chaotic anyway.
The benefit of fall timing is this: I finish my retreat with complete clarity on what I'm doing next year and what I'm NOT doing. That means I can actually rest during the holidays instead of waking up on January 1st with no plan and that familiar pit in my stomach that I'm already behind.
But if you're reading this in January and thinking "well, I missed the window," you didn't. January could be the perfect time for you to do a business retreat (I’m all about making your own rules).
If you're a few weeks into the year, you can already see which of your goals are actually happening and which ones you wrote down because they sounded good but don't fit your actual life. A January retreat gives you permission to course-correct early instead of spending the entire year forcing something that was never going to work.
Mid-year retreats (June or July) are also excellent for businesses that move fast or entrepreneurs who need more frequent check-ins. You assess the first half honestly, adjust strategy for the second half, and avoid that sinking feeling in November when you realize you've been doing the wrong work for six months, or have gone totally off track.
If you want to go deeper, quarterly mini-retreats (one to two days) keep you from drifting off course too. Every three months, you step back and ask: is this still the right direction? Do I need to adjust? What's working that I should double down on?
→ The planning paradox is this: you need to schedule your retreat BEFORE you feel like you have time for it. If you wait until your calendar has "space" or until you're "less busy," you'll never go. The point is to create the space, not to wait for it to magically appear.
How Long Your Retreat Should Be
Two to three full days is ideal. Last year I did 3 nights and 4 days and it was, quite frankly, amazing. I got everything done, with room in my agenda to relax. But 2-3 days will absolutely work too.
Day one you settle in, review your current state, get your head out of the weeds and brain dump on post-its.
Day two is deep strategic work—the CEO decisions you've been deferring because they require actual thinking, not just reacting.
Day three you plan implementation, tie up loose ends, and figure out what you're doing when you get back so this doesn't turn into another notebook full of ideas that never get executed.
But if two to three days feels impossible, one full day works. Eight-plus hours of focused, uninterrupted work (with time for breaks to reset and clear your mind) is infinitely better than zero hours. It's still real CEO work, still actual decisions made, still clarity you didn't have before.
One day is the minimum. Anything less than that and you're just getting into the headspace for deep work when you have to leave.
Let's talk budget because I know this is where people get stuck. You don't need a luxury resort, a mountain cabin, or a beach house in Maui. You need uninterrupted focus. A clean hotel room with a desk, decent wifi, and room service works perfectly. Even a full day at the library if overnight isn't financially feasible right now.
→Think about it this way: one day of strategic thinking can prevent months of doing the wrong work. The cost of the retreat—a hotel room, meals, a few hours of lost billable time—is negligible compared to the cost of continuing in the wrong direction because you never made time to assess whether your current path is actually taking you where you want to go.
Where to Go for Your Retreat
Your location needs to meet these criteria in order of importance:
no interruptions (you can't hear your household calling your name or see the dishes piling up)
different environment (not your usual workspace where your brain defaults to the same patterns)
comfortable workspace (actual desk, decent chair, lighting that doesn't make you want to take a nap)
minimal distractions (not a busy coffee shop where you're overhearing everyone's phone conversations)
Location options:
hotel room with a view and restaurants/room service so you don't have to think about meals
Airbnb in a nearby town where you're far enough away that you can't just "run home real quick"
day spa that has quiet workspace areas
library or coworking space if overnight isn't feasible
I prefer hotels because I'm an introvert who recharges by being completely alone, and having room service means I don't have to make decisions about what to eat or when. I can order dinner at 9pm if I'm still in the middle of strategic work and I don't want to break the flow. The room doesn't have to be fancy—it just needs to have a desk, a comfortable chair, and a view of something other than my own neighborhood.
For work-from-home entrepreneurs specifically, getting OUT of your house matters more than how nice the location is. Your brain needs the environmental signal that this is different work, not just another Tuesday where you're trying to think strategically between loads of laundry and client calls.
What to avoid:
your own home (too many distractions, you'll convince yourself you can "just quickly" do three other things)
anywhere family or friends can easily reach you (they will reach you, and your retreat will turn into regular work with a different backdrop)
anywhere with unreliable wifi if you need to access cloud documents or financial data
The location doesn't have to be Instagrammable. It just has to be conducive to thinking without interruption.
What to Pack for Your Business Retreat
Tech essentials: laptop and all relevant chargers, external mouse if you hate trackpads like I do, earbuds, a portable speaker, and your phone on airplane mode after you've deleted social media apps. If you need your phone for two-factor authentication or accessing documents, fine—but you don't need Instagram, TikTok, or the ability to check email every seven minutes.
Planning tools: post-its in multiple sizes (I'm serious about this—visual organization helps), colored pens and markers for color-coding different areas of your business, notebook or blank paper, year-at-a-glance calendar either digital or printed so you can see the full scope of next year, and your current business plan or revenue data.
I bring a carry-on suitcase just for office supplies because basically, I go full-on “A Beautiful Mind” at my business planning retreat, but you genuinely don't need that much. Post-its, pens, paper. That's it.
→ Shop my favorite office supplies and business planning retreat essentials on Amazon
Personal items: comfortable clothes because you'll be sitting for hours and tight waistbands are the enemy of strategic thinking, snacks and water so you're not making decisions while hungry, a book (business or fiction, whichever sounds better), a journal, and whatever makes you feel cozy and focused. I bring champagne. You might bring fancy coffee or a specific playlist or nothing at all.
What NOT to pack: your entire task list, client files you're "catching up on," anything that will pull you into day-to-day reactive work instead of strategic planning. If you're sitting at your retreat answering client emails or doing admin work, you've missed the entire point.
The goal is strategic thinking, not task completion. You have the other 362 days of the year for tasks.
Setting Boundaries Before You Go
Notify your clients at least two weeks in advance that you'll be unavailable on specific dates. Set your out-of-office email to something like "I'm away for business planning and won't be checking email until [date]. For urgent matters, contact [backup person or plan]." Make it clear you're unavailable unless there's an actual emergency—not an "I have a question" emergency, a real one.
Family boundaries: this is work, not vacation. You need to be as unreachable as you would be if you were in back-to-back meetings all day. Schedule it like you would any other non-negotiable business commitment, communicate it clearly, and don't apologize for needing focused time.
Technology boundaries: turn off Slack notifications, delete social media apps from your phone (you can re-download them later if you're that worried about it), close all unnecessary browser tabs before you even leave home. Use the Gmail “pause inbox” feature so you don’t even see new emails coming in if for some reason you’ve ignored me and your inbox is open on your laptop or phone.
If you don't protect this time, you won't get what you need from it. One distracted day of "planning" while you're still monitoring email and responding to messages is worse than no planning at all because you'll have the illusion of productivity without any actual strategic progress. You'll come back just as unclear as you were before, except now you've also spent money on a hotel room.
→ Either commit to being fully present for the retreat, or don't bother going.
How to Structure Your Retreat Time
Do not plan eight straight hours of deep strategic thinking. Your brain will give out, you'll end up scrolling your phone, and you'll feel guilty about "wasting" retreat time when actually you just tried to force a pace that isn't sustainable for anyone.
Energy management matters. Here’s a structure that actually works, based on my own experiences with more than 8 years of doing solo business retreats:
Wake up time is space to ease into the day—have a fancy coffee, meditate, journal, think about the day ahead. This is how you set your day up to be calm, spacious, and focused.
Morning block (two to three hours) for your highest-level CEO work—the decisions that require the most mental bandwidth. This is when you tackle the big questions about what your business does and doesn't do, your one priority for next quarter, what you're cutting entirely.
Midday break where you do something physical—walk, go to the gym if your hotel has one, sit outside, eat an actual meal. You need to move your body and let your brain process what you've been working on.
Afternoon block (two to three hours) for focused project work. This might be mapping out your content strategy, planning your revenue model, assessing which offers to keep or retire. Still strategic, but more concrete than the morning session.
Late afternoon is for administrative tasks that don't require deep thinking—organizing your notes, updating your calendar with implementation dates, journaling about any insights that have come up. This is your "brain break" work, not your focus.
Evening is light planning, journaling (more) if that's helpful, reading something relevant to your business (or not relevant, if you need the mental break). Don't try to power through another three-hour strategic session. You'll burn out and the work won't be good anyway.
Buffer your deep work blocks with actual breaks. Take a walk between morning and afternoon sessions. Eat lunch away from your computer. Don't try to maximize every single minute—strategic thinking needs space to breathe.
Sample schedule for a 2 night, 3 day retreat:
Day 1:
10am: Arrive, unpack, settle in
11am: Brain dump everything on post-its and sort into retreat time blocks
1pm: Lunch & walk
2pm: Review where you’re at with your business - what’s working & what isn’t
5pm: Break
6pm: Light planning or reading
7pm: Dinner & journaling
Day 2:
8am: Breakfast
9am: Strategic planning (ONE priority for Q1, what I'm NOT doing)
12pm: Lunch & walk
1pm: Offers + pricing decisions
3pm: Spa appointment
4pm: Marketing + content strategy
7pm: Done for the day
Evening: Rest & journal
Day 3:
8am: Breakfast
9am: Implementation planning (first actions, calendar updates)
11am: Admin tasks (organizing notes, updating systems)
1pm: Pack up, review final decisions
2pm: Check out
Adjust this based on your own energy patterns and how much time you have, but the principle stays the same: alternate between deep work and breaks, don't try to force marathon sessions, protect your energy so you're still thinking clearly by day two or three.
What to Actually Work On During Your Retreat
Here’s the critical distinction that most people miss: CEO work is making decisions about what your business does. Admin work is executing those decisions. Retreats are for CEO work. Everything else is a brain break between strategic sessions.
You're not organizing your Google Drive during your retreat (unless you're doing it as a five-minute brain break between big decisions). You're not updating your website copy, cleaning your email list, or batching content. Those are valuable tasks, but they're not strategic, and strategic is what you're on a business planning retreat for.
The core questions you're answering during your retreat:
Business Assessment: What actually worked this year versus what I thought would work? Which offers made money AND didn't completely drain me? What am I doing right now that I actually want to stop doing? What patterns do I see in what's working versus what's falling flat?
Strategic Planning: What's my ONE priority for just the next quarter? Not seven goals, not a complete business transformation—one thing that would genuinely move my business forward. What do I need to do more of? What do I need to do less of? What am I NOT doing next year, period?
✨That last one matters as much as your goals. Your "stop doing" list creates the capacity for everything else.
Financial Review: Revenue by offer—what actually made money this year? Profit margin by service or product (revenue doesn't matter if you're barely breaking even). Where am I undercharging? What's profitable but not scalable, meaning I can't grow it without working more hours?
Offers and Services: What's staying? What's retiring? What needs to be completely redesigned because it made money but made me miserable? What new offer would serve my existing clients best instead of trying to attract a completely new audience?
Marketing and Content: What content actually drove results this year—not what I enjoyed creating, what actually brought in clients or sales? What platforms am I genuinely using versus "should be using"? What's my content strategy for next year that fits my actual bandwidth? What marketing and/or platforms am I stopping entirely?
Operations and Systems: What processes need documentation so I can eventually delegate them? What could I automate right now that I'm doing manually for no good reason? What tech am I paying for but not actually using? What's the bottleneck in my business? (Hint: it's probably you, and you need to figure out how to remove yourself as the limiting factor.)
How to Know If It's CEO Work or Busywork
CEO work looks like: deciding what your business does and doesn't do, choosing your top priority and saying no to everything else for now, determining your pricing strategy, planning your revenue model, making decisions about what to delegate or automate, assessing what's actually working and what you're doing out of habit or obligation.
Admin work looks like: organizing your Google Drive, updating your website copy, cleaning up your email list, batching content, filing receipts, updating your CRM.
Both are necessary. But admin work is not strategic, and if you spend your retreat doing admin work, you've wasted the time you set aside for strategic thinking.
The trap is that admin work feels productive because you can see immediate progress. You organized a folder, you updated a page, you checked something off a list. Strategic work feels murkier because you're making decisions that won't show results for months. But strategic work is what determines whether you spend the next year doing the right work or just doing more work.
Give yourself a time-boxed slot for admin tasks if you have to (although I don’t recommend it for a business retreat)—maybe an hour in the late afternoon when your brain is tired and you need something concrete to do. But that's your brain break, not your focus.
What NOT to Do During Your Business Retreat
Do not try to plan every single week of next year in detail. You will not stick to it, life will happen, your priorities will shift, and you'll end up feeling like you failed when actually you just made a plan that was too rigid for reality.
Do not create seven new offers because you got excited about possibilities. Pick one thing to focus on. Launch it, refine it, make it profitable, THEN consider what's next.
Do not spend your entire retreat perfecting your plan. Done is better than perfect, and a plan you actually implement at 80% is infinitely more valuable than a perfect plan that sits in a notebook because you never finished making it pristine enough to execute.
Do not spend all your time on admin tasks that feel productive but aren't strategic. I know it's tempting to finally clean up that Google Drive or reorganize your project management system, or create a new product or sales pages, but if you do that instead of making actual strategic decisions, you've missed the point entirely.
Do not plan without considering your true capacity. You still need to sleep. You still have a life outside your business. You still have a maximum number of hours per week you can work before you burn out. Build your plan around your real bandwidth, not the capacity of some imaginary version of yourself who never gets tired or needs rest.
The goal isn't a perfect plan. The goal is decisions and clarity. You're choosing direction for your time and energy in your business, not creating a rigid roadmap that accounts for every possible scenario.
How to Actually Implement What You Decided
This is where most retreat planning falls apart. People leave their retreat feeling energized and clear, full of good intentions and strategic decisions, then they return to daily chaos and within two weeks they've forgotten half of what they decided and deferred the rest to "when I have more time."
If you don't have an implementation strategy, your retreat was expensive journaling.
Within 48 hours of returning home: Block one to two hours on your calendar to review all your retreat notes within a week. Choose your ONE top priority for next quarter—the thing everything else supports or gets pushed aside for. Schedule the first action step for that priority. Decide what you're specifically NOT doing anymore so you have more room for what you just decided matters.
First week back: Communicate any changes to clients—new boundaries, updated policies, pricing changes, availability shifts. Update your calendar to reflect your new priorities. Delegate or delete at least one thing from your "not doing anymore" list. If you said you're going to stop offering a service or participating in a networking group or posting on a platform, this is the week you actually stop.
First month back: Check in on your one priority every single week. Is it actually happening or is it getting pushed aside for urgent tasks? Adjust your plan as reality hits, because it will—you'll realize some things take longer than you thought, or a client emergency will eat your week, or you'll discover your timeline was overly optimistic. That's fine. Adjust. Don't abandon the entire plan just because it's not going perfectly. This is why checking in with your progress on your goals matters.
Annual retreat planning only works if you have a weekly planning system to support it. This is where something like Chaos Detox becomes essential—you need a method for building your weekly structure around the priorities you set during your retreat, not a weekly plan template that assumes your life is predictable and nothing ever goes wrong.
You can have perfect strategic clarity from your retreat, but if you don't have a system for executing that strategy week to week when our kid gets sick and your website crashes and all the normal chaos of running a business happens, your strategic plan won't matter. It'll sit in a notebook while you go back to reactive mode.
Strategic planning needs operational planning to support it. The retreat gives you the strategy. Your weekly planning system gives you the operations.
Make Your Next Business Retreat Actually Happen
You don't need weeks or thousands of dollars. You need uninterrupted focus, honest assessment, and strategic decisions. Retreats are for CEO work, not admin tasks or “catching up”. The right questions matter more than the right tools. And implementation through weekly planning matters more than having a beautiful strategic plan that never gets executed.
Start now: block the dates for your business planning retreat on your calendar before you talk yourself out of it or decide you'll do it "later when things are less busy." Choose your location—doesn't have to be fancy, just different from your regular workspace. Notify your clients and family that you'll be unavailable, and mean it. Decide what specific questions you're answering and what decisions you're making. And plan how you'll actually implement what you decide afterward, because strategic clarity without operational execution is just expensive daydreaming.
The difference between entrepreneurs who make consistent progress and entrepreneurs who feel stuck isn't that the first group has more time or fewer obstacles. It's that they create the conditions for deep work and strategic thinking instead of waiting for those conditions to magically appear. They schedule the retreat, protect the time, do the work, and build systems to implement what they decided.
Your turn. 💪
Ready to plan your own business retreat? Get my Business Retreat Planning System—the exact workbook I use every fall, plus planning checklists and post-retreat implementation guide for turning strategic decisions into actual progress. [coming soon]
Join The Productivity Rebellion—your free monthly guide for women who refuse to choose between success and sanity. Strategy, boundaries, and real talk delivered once a month.
Learn how to create a custom weekly plan to support your annual business retreat plan. Chaos Detox teaches you how to build YOUR weekly system around YOUR priorities—not rigid templates that assume your life is predictable.
Related Posts:
Entrepreneurial Mindset: Proactive vs. Reactive
Digital Spring Cleaning - How To Clear The Clutter Like A CEO
How To Create Simplicity as an Entrepreneur
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