How to plan a DIY mastermind retreat + a recap of mine

How to plan a DIY mastermind retreat + a recap of mine – Paper + Oats

I’ll be honest, 2016 has gotten off to a rough start. I try to be transparent in my corner of the Internet, not to glamorize anything I do (because trust me, it is rarely glamorous), but to be totally honest about what the life of a single mompreneur actually looks like. And so far this year it’s looked like a strong-willed toddler, an unexpected breakup, and one very worn out mama. Post-divorce dating is a whole blog in itself, #amiright?! Someday. As much as I’ve tried to be prepared for this new year, I’ve had a lot of other things on my mind and frankly haven’t had the energy to poor into elaborate business goals and strategies to reach them. One thing I have been doing: reading. And lots of it. Reading blogs, reading articles, reading books, reading old journal entries, reading Scripture. In all this reading, I’ve learned a few simple things that I’m trying to remind myself of daily:

  • Change is usually good; it means you’re growing and truly living.

  • Most people are just doing their best with what they have.

  • You don’t have to rush; that timeline you feel restricted by probably isn’t really there.

  • Most of the time we can’t control our circumstances, as frustrating as that is. But we can always learn things from them, as cheesy as that is.

  • Sometimes you just have to sit in whatever you’re feeling (grief, sadness, overwhelm, envy, frustration, fatigue, anxiety, etc.), even if it’s ugly and not the best company.

  • And for some promises that are forever steadfast: Psalm 27:14, Psalm 145:13-19, Psalm 37:4, Proverbs 3:5-6, Isaiah 43:19, and Matthew 6:33.

Ok. Bleh. This is a heavy start, no?

Can we move on to something a bit lighter? One thing I kicked off my 2016 with, before the rough patches came, was a trip. A much needed mastermind retreat with two of my favorite ladies in business – Jamie Starcevich and Phyllis Sa. The three of us organically formed our unofficial mastermind group last spring (which, P.S., we hate the word mastermind – got any better descriptions for that?!) after we were all in an online course together and had already interacted on social media for awhile. We originally were wanting to meet up at a conference together, but eventually decided it would be more beneficial (and cost-effective) to have ourselves a little work-cation. So we picked an interesting city that was new to all of us — Portland!  We booked flights, found an adorable Airbnb, and started dumping our ideas into Evernote.

A lot of people asked about our retreat on social media, so I thought I’d share a bit about how we structured our weekend to make the most of our time – and had a little fun exploring Portland, too! We were in PDX from a Friday afternoon through a Monday morning, and we managed to cram in a ton of business talk, brainstorming, planning and note-taking — not to mention the amazing food, that adorable Airbnb, honest conversations about life + family, a wide array of Uber drivers, a few episodes of Friends, and did I mention food? Here’s how our weekend went:

Friday night  |  Reflecting on 2015

After hitting the grocery store for some weekend staples + snacks, we headed out to dinner at this suuuuper cool place near our Airbnb – Pok Pok Noi. Amazingly delicious Thai street food and very weird (but good) cocktails. Throughout dinner (and ice cream at Salt & Straw!) and back at the house, we each chatted about what worked well and what didn’t work so well for each of our businesses in the last year. We shared struggles and wins, the parts we loved and the parts we hated, the pretty as well as the ugly of solo entrepreneurship. This helped us get a good overview of where each of us was at so we could go into the next day with a clear mind, ready to strategize.


Saturday  |  Hot Seat Sessions

Again, with the funny business lingo, but that’s what we’ll call them. This was the bulk of our weekend, and for good reason. We each got our own 2-3 hours of dedicated time to focus on, well, whatever the heck we wanted. We each came into the day with an agenda of things we wanted feedback on, big ideas we needed help planning out, strategies to brainstorm, fresh eyes on projects in the works, and anything else in our business we needed to revamp. We had laptops out, talking through ideas and sharing resources + inspiration. This was so so helpful to each of us to get this highly-focused time for some really detailed feedback. Even when it was another person’s turn and we were providing feedback on their questions, we could each learn something for our own processes and take it back to apply to our own businesses. Win-win all around. Plus, after months of only talking via Skype or Slack, it was great to get some in-person time to dig into these projects we’ve all been dreaming about for so long. Big things ahead for these ladies, and I’m so grateful to be in their corners!

Sunday morning  |  Individual Work Time

We spent our Sunday morning and early afternoon grabbing breakfast at Petite Provence (an adorable French breakfast spot) then headed to a coffee shop to work individually. We set up at Extracto Coffee Roasters and spent a few hours buried in our laptops and notes from the day before. For a group of introverts, this was a great mid-weekend refresher.

Sunday afternoon  |  Unsolicited Advice Exercise

Ok, guys, this was the doozie of the weekend. This was the one out-of-the-box thing we had planned, and we based it off these posts by Nathan Barry and Sean Wes. Here’s how it works, I’ll use myself as an example:

  • We set a timer for 10 minutes.

  • The rest of the group talks about me and Paper + Oats as if I wasn't sitting there for the full 10 minutes (we usually went a little over once we got going).

  • I was not allowed to talk, I could only take notes. (i.e. no defending myself or offering explanation)

  • We had 3 main questions we tried to answer when talking about each person: How do others view her + her business? What things is she doing well? What things could she be doing better?

After each of us had our turn, we were allowed to go back around again and get clarity and talk through the “unsolicited advice” we had received. This is where the magic happened, and here’s why. It’s one thing to come into a hot seat session like we did on Saturday with a list full of specific topics we wanted to address. It’s another thing to hear what someone else thinks your business could be working on, without your prompting. For me personally, Jamie + Phyllis threw out ideas I had never even considered for parts of my business that I had no intention of making any changes to this year. But guess what? Their ideas were kind of genius, and made total sense. Even if you can’t fly to a fun city and huddle around bags of Milano cookies, try out this exercise via email or Slack with some close pals in business. Make sure they know you and your business pretty well, but ask them what areas they think you could be doing better in. You might be surprised by their answers, and no doubt it’ll make your business stronger if you heed their advice. It's important, too, to be sure everyone already has a foundation of respect for each other's businesses so nothing is taken personally – it's all constructive and meant to be beneficial.

Sunday night  |  Farewell Dinner + Next Steps

On our last night together, we went out to a nice dinner at Pono Farm followed by some Netflix, all the while talking about our next steps and what we’re taking away from the weekend. It was a great chance to decompress, get any final feedback we needed, and celebrate a successful work-cation. Cheers to that.

One last piece of random advice if you’re planning something similar with your mastermind group, especially if you’re a bunch of introverts like we are – draw names. For everything. Within our first few minutes at the house as we’re trying to choose bedrooms, we quickly realized we’re all too laid back to make any affirmative decisions, so we wrote our names on scraps of paper, and drew out of a hat who got what room. We kept our little papers and drew names for the order of the hot seat sessions and the unsolicited advice exercise, too. For Uber trips, we just started a rotation of paying for rides and it all evened out. We were all making big decisions for our businesses that weekend, so deciding little things like bedrooms and the who-goes-first-debate wasn’t really something we wanted to put effort into, so alas we reverted back to our elementary days. And we loved it.

How to plan a DIY mastermind retreat + a recap of mine – Paper + Oats


Here’s what Jamie + Phyllis had to say about our little work-cation...

Phyllis Sa Design

Last year I made a huge decision to pivot my business to focusing on branding and web design for small businesses and creative entrepreneurs, a move that was risky and scary in the face of everything I'd done before. I knew I would need the right kind of business support to keep me accountable and moving forward on my goals. Luckily for me, it was around that same time I struck up a relationship with Kelsey via social media, which quickly transitioned to novel length emails covering anything and everything biz related, and the first seeds of a mastermind group were born. Another chance connection with Jamie of Spruce Rd rounded out our mastermind trio and it's been almost a solid year of consistent support, advice-giving, and accountability that's helped propel our businesses forward in such amazing ways. We wanted to take this masterminding to the next level for 2016 and made plans to meet in person for a weekend retreat this past January, dedicated solely to brainstorming and goal planning for this upcoming year. Because we'd already formed such a trusting and giving relationship through online chats and Skype calls, there was already an amazing level of comfort when we were able to all come face to face for the first time. I came away from our retreat brimming full of ideas, focus, and clarity for my year, something I don't think I could have done on my own at home.  — Phyllis


Jamie Starcevich, Spruce Rd.

Since starting my business last year, it has been a whirlwind to say the least. Prior to our mastermind group, it felt like a solo adventure with the exception of running business decisions ran through the support of my husband :) Thankfully, just a few short months in I stumbled into Kelsey & Phyllis who seemed at a similar spot in their business. To say I'm grateful for their guidance, friendship and support is an understatement! They are the unofficial members of Spruce Rd., encouraging me through all avenues of my business, and helping me navigate uncharted waters. When we finally met in person after a year of becoming online besties, there was such a comfort + ease to our time together. My favorite part of the retreat was the dedicated time to each person's business. We reserved 2–3 hours per person, as they walked us through their business plans. To see their immediate reaction on my business quandaries was SO beneficial. Their outside perspective to something so intimate to me — my business — is something that every business owner should strive for. They see potential income streams you don't. They anticipate what your audience needs, that you might have missed. Down to what areas you are lacking in your business. I can't wait for our next retreat, more wine, cute air bnb's and coffee shop dates with these lovely (now IRL) friends!  Jamie


So what takeaways did I have for the future of Paper + Oats? Well I can’t spoil everything, but there will definitely be some improvements coming to things like my design services (or lack thereof), The Oat Bar, my latest online course and my existing one, and even my shop.

So nice try, 2016. You may have started out a little rough, but you’re gonna end strong. Stay tuned.


Download my free travel planner for your retreat

Need some help planning your own getaway with some business besties? Download the free one-page travel planner below to hash out the details. 

Your turn

What plans have you made to make 2016 the best year yet for your business? Do you have a group of "business besties” you can turn to for feedback and support? How do you get a toddler to eat green beans? She loved them yesterday, I swear. 


Kelsey Baldwin

Graphic designer + blogger providing design resources to help creative entrepreneurs navigate the world of design + branding for digital products so they can share what they know.

Follow my blog with Bloglovin