Why You Should DIY A Creative Mastermind Retreat + A FREE step-by-step plan for how to do it!

Have you ever wanted to go on a professional retreat? Or take part in a mastermind group - but they're really expensive? You can DIY it! I DIYed my own creative mastermind retreat with 4 friends with February and is was CAREER CHANGING. Click through for a full step-by-step plan on how to coordinate your own retreat >> yesandyes.orgHere’s a fun fact about me: I hate networking events and I (almost) never go to professional conferences.

I love meeting new people and devoting big chunks of time to deep-n-meaningful conversations about life/work/money/creativity.  But I don’t want to have those conversations in hotel conference rooms and I don’t want to drop $1,200 on a ‘Mastermind Group’ full of people I don’t know.

In February, I coordinated my very own retreat with Kathleen, Sarah, Kyla, and Katie. If you’d like a step-by-step plan for how to do that yourself, I wrote you this free guide.

If you need a bit more convincing, here are 6 reasons why you should DIY a creative mastermind retreat:

You can’t beat meeting people face-to-face

Yes, you can totally develop real, meaningful friendships over social media. Supportive, important conversations can be had through Facebook comments and perfectly chosen gifs. But those can’t compare to the magic that happens when you’re on the same sunny patio, sharing a bottle of wine, comparing notes on your favorite Instagram animals. (raccoon_house 4eva)

When you hang out in person, conversations get deeper and more vulnerable. You can ask follow up questions or seek clarification. You can say “How did it make you feel when that happened?” Or “Was it worth it?” You can beyond conversion rates and analytics, past the ‘hows’ and into the ‘whys.’ You can chew on something your friend said and then come back to it at breakfast the next morning.

You can’t really do that in Facebook comments. 😉

You’ll strengthen your relationships

If we’ve shared a condo in Mexico, we’re pretty much blood brothers now. You’ve seen me politely complain to the front desk 17 times? We’ve discussed the merits of buying Retin-A for $10 at a Mexican pharmacy? Obviously, I’m happy to look over your sales page. OF COURSE you can write a guest post. Yes, I’d love to jump on the phone for a two-hour, co-brain picking session.

IRL hangout time nudges Online Friendships into Real Friendships. These friendships are no longer just about retweeting each other’s stuff, now they’re about workout routines, which liquid eyeliner is best, and Netflix recs. (Kathleen, you were right about Stila Stay All Day liquid eyeliner. I immediately threw away my other stuff.)

Most mastermind groups are car-razy expensive

Why not join a professionally-organized, already-formed mastermind group? Well, you certainly can, if you want to drop $500 – $2,000. But if the group uses its collective knowledge and resources to help each other, why are you paying for the honor of helping other people? Presumably, you’re bringing a lot to the table, so why should you pay for access to other, equally skilled people?

You don’t have any say in who’s in a pre-formed group

It’s rare that mastermind groups make their member list public; they might publicize who their group targets, but they probably won’t get into specifics. It’s not unusual to see mastermind groups for online marketers, writers, or bloggers but do you know the people in the group? Will you connect with them? Are they at a similar place in their career?

It’d be a pity to spend $700 on a mastermind group only to discover all the other online marketers are 20-something tech guys from Silicon Valley and they don’t have much time for your ecourse on body-positive fashion.

You get to choose where it is!

You don’t have to go to New York or L.A. or Chicago if you don’t want to! You don’t have to paste on a name tag and sit in a windowless Radisson conference room! You can use this mastermind retreat as your excuse to finally visit Santa Fe or Vermont or Iceland. You can look through Airbnb’s best-of’s. You can go somewhere with a good exchange rate or amazing food.

When you’re organizing a retreat, you get to make it exactly as awesome as you want.

P.S. If you’ve never used Airbnb before, here’s $40 credit towards your first booking!

It’s tax deductible!

It’s a fact. If you’re talking about business with professional peers, you’re working and what you’re doing is tax deductible. Even if you’re doing it while drinking margaritas next to the pool. And if you’re deducting your trip, don’t forget about per diem deductions for meals and incidentals and deductions for personal vehicle use!

Have I convinced you? If you’re curious how to do this yourself, I broke down eeeeeeverything I did here – including the emails I sent, how to choose who to invite, how to share information, all of it! Download and share away!

Photo by Alexis Brown on Unsplash



I am going to download this when I get home, but I am curious, what if you don’t know many or any other professionals that are in the same field, in similar situations to yourself? and maybe this question will be answered once I download the book…

Sarah Von Bargen

Great question, Jenn!

Three possibilities:

1. You can set about befriending people (here’s how I’ve done that in the past)
2. You can dip your toe in with people in your city with a day retreat … and not worry so much if they’re in the same place with their business
3. You can invite people who are at similar places in their business (self-supporting, maybe have a part-time VA … or whatever) and not worry too much if you’re in the same field. I think you’d be surprised by the overlap! We ALL deal with clients, invoices, project management, marketing, even if we work in different fields.

Hope that helps!


It does! Thank you. I will read up and try to start up my own ‘network’ so to speak. Would be nice to have a group of people to reach out to,


I don’t have a business so will probably not be planning a mastermind anytime soon… but I love your emails in the guide so much that I think I will use them as templates for proposing activities with my friends. 🙂

Sarah Von Bargen

Yes! And really, this could be a retreat for anything – it doesn’t have to be business-related! It could be a crafting retreat, a yoga retreat, anything!


Brilliant, as always, Sarah! I need to make this happen in my life. I still think about your hotel room writing retreat ALL the time, by the way. So smart.


Super excited about this. Sarah Morgan just sent me the link to the post because I mentioned that I’m planning my own retreat in March. Thanks so much for putting a guide together, Sarah!


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