Business Owner Retreat: What It Is, What It Costs and How to Choose One
By Byron Dempsey · 4 min read · Updated October 2026A business owner retreat is time away from running your business so you can work on it instead. A few days to a week to rest, look at the business from the outside, plan the year ahead, and spend time with other owners who carry the same weight.
The three kinds of business owner retreat
Most retreats aimed at owners fall into one of three camps. Each has its strengths.
Wellness retreats. Rest, healthy food, yoga and recovery. Good for your energy, but the business stays exactly where you left it.
Business retreats. Strategy days and masterminds. Useful, but often you're on your laptop the whole time, which isn't much different to being at the office.
Holiday-style retreats. Golf, quad biking and big nights with other owners. Fun, but essentially a holiday with people.
In my experience the real value comes when a retreat does all three: it looks after your health, works on the business, and works on you as the person running it.
What makes one worth the time away
Time out of the business is expensive for an owner, so it has to count. It comes down to three things.
The other owners in the room. People who understand payroll, staff and cash flow will help you more than any workshop.
The facilitator or host. Someone experienced at running groups, who can get owners talking honestly about what is and isn't working.
What you actually do. Sessions and activities that create real conversations, not just things to fill the day.
Is a business owner retreat right for you?
You're probably not ready yet if:
You've only just started. Early on, your time is better spent building the business itself.
You're flying and don't want to stop. If you've got lots of energy and you're crushing it, a week off will feel like it's in the way.
You just want a break. A good owner retreat means working on the business and on yourself. If you just want to relax, a wellness retreat or a holiday will do it, for less.
What a business owner retreat costs
Anything from a free local day to several thousand dollars for a week overseas. The price comes from the length, location, venue, group size and what's included.
When you compare, check what's actually in the price: flights, rooms, meals, sessions and activities. Then weigh it against what a clear plan for the next year is worth to your business.
Questions to ask before you book
The venue matters, but the people and the host matter most.
Who runs it, and what is their experience? How many retreats have they run, and for how long?
Who else will be there? Owners at a similar stage, screened before they join?
Who have they worked with? Can you see past attendees and what they say?
What do the photos show? Real photos from past retreats say a lot about the venue and the group.
Do they fill their retreats consistently? Regular, full retreats mean a track record. A one-off is a gamble.
Is the venue somewhere you can switch off? You'll be there all week, so it should feel that way.
How we run ours at Driven Young
Our retreat is built for owners and does all three. Seven days in a private villa in Canggu with 20 business owners in their 20s and 30s. Phones go away on day one. You map every system in your business, learn how owners are using AI right now, and leave with a clear 12-month plan. Between sessions there's yoga, breathwork, ice baths, the sauna, a sunrise volcano hike and a private chef.
What past founders say
"Exactly what I didn’t know I needed. A reset, a push, and a room full of people who just get it"
"What you think your going to get out of this, multiply it by ten and you will come close to what this retreat will do for you."
"Life's too short, so you should be going for the Driven Young retreat so you can reclaim that lost time. It truly opened my eyes to the possibilities."
Frequently asked questions
What is a business owner retreat?
A business owner retreat is time away from running your business, usually a few days to a week, to rest, plan and connect with other owners. The best ones combine wellness, business and personal development.
How much does a business owner retreat cost?
It ranges from free local events to several thousand dollars for a week overseas, depending on length, location, venue, group size and what's included. Ours starts at $4,999 + GST with everything included except flights.
Can my business run without me for a week?
Most owners set up cover before they go. Phones are off at our retreat, so plan ahead with your team.
Who is a business owner retreat for?
Owners with an established business who have been heads down for a while and are ready to step back and work on the business and themselves.
How do I choose one?
Look at the host's experience and track record, the other attendees, photos from past retreats, whether they consistently fill their retreats, and the venue.
How do I join the Driven Young retreat?
It is application only for owners doing $100K+ in revenue. Fill in the two-minute application, then we have a short call to make sure it suits you and the group.