Should You Attend a Retreat or a Mastermind?

Practical tips to help you decide which peer-to-peer gathering is best for your business, and yourself.

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By Ramon Ray

Opinions expressed by Entrepreneur contributors are their own.

Along with a handful of other professionals in my industry, I recently attended a multi-day structured retreat in Tampa, Florida. We rented a big house, cooked together, ate together and, most importantly, spent quality time building up our businesses together. In addition, we explored who we were as people, and many of us cried, including me. A reader who has not attended such an event might be thinking that such a process has a tiny whiff of cult-iness about it, but rest assured, it was a gathering that had enormous professional and personal payoffs for me, and with no indoctrination!

What is a retreat?

A retreat is a multi-day event, held once or twice a year, bringing together people who have a common professional or personal interest. One of the things that worked well in the retreat I went to is that we had to apply for it, so each person wound up being handpicked. I'm guessing the criteria included professional background, similar business maturity and fit within the group dynamics.

Another indicator of a good retreat is the presence of a facilitator. Without one, the process tends to devolve into attendees feeling unsatisfied at best, utterly confused at worst. The facilitator ensures that the overall retreat agenda moves forward, that things are on time and that everyone is heard, all of which are vital.

Related: 5 Tips for an Effective Team Retreat

During our retreat, we had time for group discussion and heard from guest experts. We also had plenty of "surprises" where the facilitator used discussion cards (or other tools) to help us answer questions about ourselves. Some were designed to foster an understanding of others, others devoted to helping us know ourselves. During the evening, we spent yet more personal time learning about ourselves as humans, not just businesspeople.

What is a mastermind?

A more involved peer-to-peer gathering, masterminds usually take place over a longer period of time (perhaps meeting every month for a year) and often are keynoted by an industry expert. While it doesn't have to have a leader, it'll likely help if there is one to keep things moving forward. In my experience, a mastermind starts to get really good over time. During the first meeting, attendees are strangers, of course, but as time goes on, trust builds and relationships develop. Both types of meeting structures, incidentally, usually involve a fee of some sort.

Related: 4 Things to Consider Before Joining a Mastermind Group

Which option to choose?

Selecting either a mastermind or a retreat is a matter of taste and purpose, of course — the important thing is that both mean you have taken time to invest in the longer-term development of a business and yourself. This hours-investment is particularly important for those growing a solo business — it's an enormous help to check in with others who can provide context, camaraderie and creativity. At my retreat, I found that it was an honor to be placed in a position to help others, and a tonic to be helped by them. It's easy to forget that over years of experience as a serial entrepreneur, there's a great deal I can share.

How to prepare

The last thing you want is to spend three days and $4,000 and feel you've wasted your time.To get the most out of your visit to a retreat or mastermind, plan ahead:

  • Who is hosting the event? Is the event hosted by a person or organization who has done the event before? Feel free to reach out to them to get their best insights. In their experience, what has worked for other attendees? What are some things that haven't?
  • Find out how you can be of most help. What happens at the event is important, but it's also important to find out how you can add value before, during and after the event. Remember, if the person hosting the event and those coming to the event are "A-listers" in your industry, then you being of value to the entire experience will endear you to them.
  • Understand who is coming to the event. If you can find out who is coming or at least the type of people coming to the event, you'll be better prepared in two areas. First, you'll better understand what you can get from the attendees, what questions you might have and what problems they can help you solve. Second, you'll have a sense of whom you can serve. What are the experiences you've had or the expertise you have that you can lend to the group?
  • Take good notes. You'll forget most of the things you learn at the event. Take good notes so you can remember all of the important things.
  • Get contact information from attendees — not to spam them, but to follow up and connect with them.

Event logistics

Consider significant event logistics as well:

  • Food is important. Be sure to understand the eating options. Restaurant? Catered eating at the event? If you have any allergies or food restrictions, let the event host know of them in their entirety. Just in case there are some challenges accommodating your needs, scope out grocery stores ahead of time. In fact, bring a few snacks of your own and to share!
  • Don't forget lodging. If the event is held at a hotel, then that's going to be pretty standard sleeping arrangements for a hotel. If it's in a rented home, then like with food, ask questions. Will you have your own room or have to share?
  • Think about entertainment and free time too. Will there be downtime to check emails, make calls? Can you visit a friend or family member in the evening? Part of a successful event is not just the time spent with each other during the event, but also the "down times" to get to know each other even better. Consider this.

Over the years, I've started five companies, sold two of them and authored several books. One of the most powerful keys to being a well-rounded entrepreneur is investing in your own learning. How can you hire the right team, improve your marketing or have the mindset for success if you're not investing in yourself?

Related: 4 Reasons Why You Should Invest in Self-Development

Ramon Ray

Entrepreneur Leadership Network Contributor


Ramon Ray is unapologetically positive and the founder of; 5x serial entrepreneur; and 3 companies. Ramon is an in-demand motivational speaker and small business success influencer and event host. He's written 5 books, including, "Celebrity CEO" (about personal branding).

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