How to Plan a Founder Retreat: Your Solo CEO Retreat Plan
Nov 09, 2026When was the last time you thought about your business for more than 20 minutes without someone needing you?
No Slack ping. No "Mom, where are my shoes?" No client email you just have to answer real quick.
If you can't remember, you need a founder retreat.
I spent 22 years in Fortune 500 strategy, and a big part of that job was planning off-sites. Leadership teams would leave the building for two days and come back with a plan for the whole year. Then I started my own business and realized nobody was planning the off-site for me. I was the leadership team. And I was running it from the kitchen counter.
Here's how to plan a founder retreat when it's just you: what it is, where to go, what to bring, a sample two-day agenda, and the exact questions I'd answer while you're there. By the end, you'll have everything you need to book it this week.
If you're planning a retreat for a group instead, start with my full guide on how to plan a business retreat. This post is the solo version.
What Is a Founder Retreat?
A founder retreat is a business retreat for one: you, your notebook, your numbers, and one to two days away from the day-to-day. You step out of the role of doing the work and into the role of deciding what the work should be.
You might also hear it called a CEO retreat or a solo business retreat. Same idea. Here's how it compares to the other options.
| CEO Day | Founder Retreat | Group Retreat | |
|---|---|---|---|
| Length | 1 day | 1 to 2 days, often overnight | 2 to 3 days |
| Who | Just you | Just you | You plus a group or mastermind |
| Where | Home office or a coffee shop | A hotel, rental, or somewhere new | A venue or a host's home |
| Best for | Monthly or quarterly check-ins | Big-picture planning and big decisions | Connection, feedback, fresh ideas |
| How often | Monthly or quarterly | 1 to 2 times a year | About once a year |
I use all three. We host one in-person group retreat a year, usually in the fall. A founder retreat is what I do on my own, and a CEO Day is what keeps it all on track in between.
Why a Founder Retreat Works
You can get more done in two focused days than in six months of squeezing strategy into the cracks. I've seen it with clients, and I've felt it myself.
One of the most transformative weekends of my business was a two-day VIP weekend with a coach where we went through my entire business. Two days. That's it. I came home with more clarity than I'd had all year.
Here's why it works:
- You get out of the weeds. At home, the urgent stuff always wins. Away, the important stuff finally gets a turn.
- A new setting changes how you think. Different room, different view, different ideas.
- You make decisions instead of collecting them. That pile of "I should probably..." finally gets a yes or a no.
- You rest. A tired founder makes tired decisions. Sleep in a quiet room counts as strategy.
- You come home with a plan. One page. Three priorities. Dates on the calendar.
If you run your business on part-time hours like I do, this matters even more. When you only have so many working hours, every one of them needs to be pointed at the right thing.
How to Plan a Founder Retreat in 7 Steps
This is the exact process I'd follow if you're planning your first one. It takes about an hour to plan, and you can book it today.
1. Pick one outcome
Decide what you want to walk away with. Just one thing.
- Your 12-month vision
- Your plan for next quarter
- One big decision (a new offer, a price change, a hire, a launch)
- A reset after a hard season
Not all four. If you try to do everything, you'll leave with a long list and no decisions.
2. Choose your length
| Option | What it looks like | Pick this if |
|---|---|---|
| Day trip | Leave early, home by dinner | You're new to this or can't be away overnight |
| Overnight | Arrive midday, leave after lunch the next day | You want deep work plus a full night of rest |
| Two full days | Two nights away | You're planning a full year or making a big pivot |
One overnight is the sweet spot for most women I work with. Long enough to go deep. Short enough to actually happen.
3. Pick a place
Leave your house. Even if your home office is gorgeous (mine is my happy place), it's also where the laundry lives.
- A hotel 30 to 60 minutes from home
- A small rental with a good table and good light
- A friend's lake house or cabin in the off-season
- A bed and breakfast in a small town
Look for three things: a real desk or table, a place to walk outside, and food you don't have to think about.
4. Set your budget
A founder retreat can be simple. Your main costs are:
- Lodging for one or two nights
- Meals (book somewhere with room service or easy takeout)
- Gas or travel
- Optional: a massage, a fancy notebook, a great bottle of wine
Treat it like a business expense, because it is one. Talk to your accountant about how to track it.
5. Gather your numbers before you go
Do this the week before so you don't burn retreat time hunting for reports.
- Revenue by month and by offer
- Email list growth and your best-performing emails
- Where your sales actually came from
- Your expenses and subscriptions
- Last quarter's goals and what actually happened
Decisions are so much easier when the data is sitting right in front of you.
6. Go offline (for real)
- Set an email auto-responder with your return date
- Tell your team or VA exactly what can wait (spoiler: almost everything)
- Delete social apps from your phone for the weekend
- Put your phone on Do Not Disturb with a short list of people who can break through
With twins at home, my first step before leaving is always the family plan. Who's driving where, what's for dinner, who to call. When home is handled, I can actually focus.
7. Build your agenda
Give every block a job, and leave white space on purpose. Here's the agenda I'd start with.
A Sample 2-Day Founder Retreat Agenda
Steal this. Adjust the times to fit your energy.
| When | Day 1: Look Back | Day 2: Plan Ahead |
|---|---|---|
| Morning | Arrive, settle in, take a walk. Write down everything on your mind (the brain dump). | Slow coffee. Re-read your Day 1 notes. Write your 12-month vision. |
| Late morning | Review your numbers. What sold? What didn't? Where did sales come from? | Pick your three big priorities for the next 90 days. |
| Lunch | Off the clock. No laptop. | Off the clock. No laptop. |
| Afternoon | Answer the review questions below. Celebrate your wins. | Break each priority into monthly milestones. Put the first step on your calendar. |
| Evening | Dinner, a bath, a movie, early bedtime. Rest is part of the plan. | Head home with a one-page plan. |
Doing a one-day version? Keep the same flow: morning to look back, afternoon to plan ahead.
Founder Retreat Questions to Answer
These are the questions I'd bring with me. Write your answers by hand if you can.
Looking back
- What am I most proud of from the last 3 to 12 months?
- What brought in the most revenue for the least effort?
- What drained me?
- What did I say yes to that I should have said no to?
- What do my numbers say that I've been ignoring?
Looking ahead
- What do I want my average week to look like a year from now?
- How many hours do I actually want to work?
- Which offer deserves more of my attention?
- What can I stop doing, hand off, or automate?
- What would make the next 90 days a win?
Deciding
- What are my three priorities for the next 90 days?
- What's the very first step for each one?
- When will I check in on this plan?
That last one matters. A plan without a check-in date is just a nice journal entry.
What to Pack for a Solo Business Retreat
- One notebook (I'm a big believer in the one notebook rule)
- Your numbers, printed or saved offline
- A calendar for the next 12 months
- Sticky notes and good pens
- Comfy clothes and walking shoes
- Snacks you love
- Something just for fun: a novel, a face mask, a playlist
Leave the to-do list at home. You're not there to catch up. You're there to decide.
After Your Founder Retreat: Make the Plan Stick
The retreat is the easy part. The magic happens in the 90 days after.
- Put your three priorities somewhere you'll see daily. I use a version of the CAKE method: three big things a day, and everything else is sprinkles.
- Block the first step for each priority on your calendar the week you get home.
- Tell someone. Your partner, your team, your mastermind. Saying it out loud makes it real.
- Schedule a monthly CEO Day to check your progress against the plan.
- Book your next founder retreat before you lose momentum.
If you want a deeper framework for the planning part, here's my process for how to plan your quarter in 6 simple steps.
Solo Founder Retreat or Group Retreat: Which Do You Need?
| If you... | Choose |
|---|---|
| Need to make a big decision and want quiet | Founder retreat |
| Feel stuck and want fresh eyes on your business | Group retreat |
| Are planning your next quarter or year | Founder retreat |
| Feel isolated and want women who get it | Group retreat |
| Have a tight budget or a busy season at home | Founder retreat (or a CEO Day) |
Honestly? Do both. A group retreat once a year gives you connection and perspective. A founder retreat gives you the quiet to turn all of that into a plan. If you're hosting or attending a group retreat, my business retreat planning guide has the full timeline, cost breakdown, and checklist.
Here's How to Get Started
- Pick your one outcome.
- Choose a day trip, an overnight, or two full days.
- Book a place at least 30 minutes from home.
- Pull your numbers the week before.
- Set your auto-responder and your family plan.
- Copy the agenda and the questions above into your notebook.
- Put your 90-day check-in on the calendar before you leave.
Not Sure What to Focus On at Your Retreat?
That's the most common thing I hear. You know you need time away, but you're not sure what the plan should even be about. Is it your offer? Your email list? Your visibility?
Take the 2-minute quiz and I'll point you to your next move. Bring your results with you and you'll walk in already knowing where to start. 💛
Want something to listen to on the drive? The Crush the Rush™ Podcast has 600+ episodes on building a life-first business.
XO, Holly
Frequently Asked Questions
How do you plan a founder retreat?
To plan a founder retreat, pick one outcome, choose a length (a day trip, an overnight, or two days), and book a place away from home. Gather your numbers the week before so you're not hunting for reports on retreat time. Set an email auto-responder, tell your team what can wait, and make a family plan so you can actually focus. Then build a simple agenda: spend the first part looking back at what worked and what didn't, and the second part planning ahead. Leave with three priorities for the next 90 days and the first step for each already on your calendar.
What is a CEO retreat?
A CEO retreat is time a business owner takes away from daily work to think, plan, and make big decisions about the business. For a solo business owner, it's the same as a founder retreat: one to two days, usually somewhere new, focused on reviewing results and setting priorities. Larger companies use the term for leadership off-sites, but for women running their own businesses it's a planning getaway for one. The goal is to step out of doing the work and decide what the work should be.
How long should a founder retreat be?
One overnight is the sweet spot for most founders. Arrive midday, spend the afternoon looking back, sleep, then spend the next morning planning ahead and head home after lunch. A day trip works if you're new to this or can't be away overnight. Two full days make sense when you're planning an entire year or considering a big pivot. Longer isn't always better. The point is focused time with one clear outcome.
What should I do on a solo business retreat?
On a solo business retreat, review your numbers, answer a set of reflection questions, and leave with a 90-day plan. Start with a brain dump to clear your head. Look at revenue by offer, email list growth, and where your sales came from. Ask what drained you, what worked best for the least effort, and what you want your average week to look like a year from now. Then pick three priorities, break them into monthly milestones, and schedule the first step for each. Build in rest, walks, and real meals too.
How often should entrepreneurs take a founder retreat?
Once or twice a year works well for most entrepreneurs, with a one-day CEO Day each month or quarter in between. A founder retreat is for the big picture: your vision, your offers, and your priorities for the next season. A CEO Day is the shorter check-in that keeps that plan on track. Many founders like to do one before the new year and one mid-year. Pair it with a group retreat once a year if you want connection and outside perspective too.
