Close this search box.

Ep. 177: Masterminds and Your Side Hustle


In today’s episode I’m taking you behind the scenes of a mastermind weekend I did with 5 other girlbosses. It was absolutely amazing, and I think it’s something any side hustler can benefit from – if it’s done right.

So if you’ve been around the online business space for any amount of time, you’ve probably heard of masterminds, but if you haven’t, a mastermind is basically a support group.

It’s a concept that’s attributed to Napoleon Hill, author of Think and Grow Rich, and the idea is that the collective intelligence of more people can help you reach your goals faster than going it alone.

People in mastermind groups help each other set goals, hold each other accountable to accomplishing them, brainstorm ideas and support each other with honesty and respect.

So in this episode, I want to share with you my top 5 tips to help you make your mastermind a success.

But before we dive into exactly what we did at the mastermind, I gotta say, I’m surprised that I even went.

And here’s why.

I have always been extremely independent.

For whatever reason, I’ve always felt like if there’s something I wanted to accomplish, it was all on me to make it happen.

Like, put your blinders on, put your head down, figure it out and get it done.

Asking for help?

It just doesn’t occur to me.

It’s not like I’m against asking for help, it literally just doesn’t occur to me as an option.

I’m totally working on that part when it comes to figuring out how I can build a team and working less hours.

And I’ve been working with my business coach for the past 3 years which has been a total game-changer when it comes to my mindset and my beliefs and all of that.

And I read books and listen to podcasts all about business, so it’s not like I’m reinventing the wheel.

So in my mind, I’m like, “I’m getting help. I’m offloading some of the day to day stuff. And I have a business coach. And I’m always learning. What more do I need?

Head down, blinders on, hustle it out.

Can you relate to that mentality at all?

So then I interview Bree Pair, the creator of the Thrive Conference for Bloggers in episodes 113 and 114, and after the interview, we’re chatting about how it seems like she and I are at similar places in our business – working way too much and trying to keep it all together, and looking for support.

Then I get a text from Bree with dates, and then a few days later a link to the most perfect little AirBNB in San Marcos, Texas.

I sent her my part of the rental and grocery money via PayPal, booked my ticket with my Southwest Points, and then when I told my husband about the trip he’s like, cool, who are you going with?

And I’m like, “Um… Bree… and 4 other girls that I have never met and have no idea who they are.”

And he just looks at me kinda like, Seriously? “So you’re going away for a weekend with 5 people you’ve never met.”

“Well, I’ve met Bree…”

Like I didn’t even question who these 4 other girls were, or what they did. I just said yes without thinking.

And then I start to get a little anxiety… Like, what if she’s friends with a bunch of serial killers? Yes, I watch too many Netflix documentaries…

And then I start thinking like, I’ve been part of masterminds before and they have fizzled out. Some had no real structure, some met too often, some weren’t the right mix of people, and some ending up actually being a marketing tactic for a bigger program, is this really going to be a good use of my time?

But as I’ve learned, I get anxiety when a new opportunity creeps up that’s going to help me grow…

And then I’m like, “NOPE, not today, Bully!” which is what I say to myself when I can feel the bully in my head trying to keep me from doing things that are uncomfortable for me. It’s straight outta Vicki Fitch’s book, Evict the Bully in Your Head ( which you can get a link to in the show notes.

So I think, let’s reframe this. What’s the worst that could happen?

The worst thing that happens is that I take a 3-day vacation, meet some new people and get no work done. The best thing that could happen is that I take a 3-day vacation, meet some new people and get super clear on the future of my biz.

Um, pretty much either outcome is awesome, and I really needed a vacation.

So then I get a text from Bree asking my availability for two meetings prior to the mastermind weekend so that all 6 of us could meet each other, and then she also mentioned that I could expect an email with all of the details for the trip.

Which leads me to my first tip for a successful mastermind group:

#1 Have a planner in the group.

I am NOT a planner when it comes to creating awesome experiences for other people.

Yes, I’m very structured, I like to have a plan and know what I’m doing and when, but when it comes to planning for other people, that is not my forte.

I tend to attract friends that are amazing planners.

Like, “You want to go where for vacation? Oh, you’ve already got the place picked out? You already know who is sleeping in what bedroom and have all the food figured out? Awesome, just give me the dates and tell me how much my part is and I’ll book it.”

Like, I love it.

But the person who is the planner has to WANT to be the planner.

When you have a situation where one person is doing all the planning because no one else will pitch in, that’s when resentment can start to build up. I’ve been in a couple of groups where that’s happened.

But someone does have to take the lead, at least at the very beginning, until the group starts to gel, and then if it makes sense for the dynamics of your group, the responsibility for planning any mastermind events can be rotated throughout the group.

So Bree was super awesome at taking the lead, picking the dates, the location, working with another girl to create a menu and a shopping list, and to bring us together to meet before the actual mastermind weekend.

Which leads me to tip number 2:

#2 Get to know each other before you start masterminding.

Before we went away for three days to mastermind together, the six of us met online twice.

The first time, we each had 10 minutes to introduce ourselves, share our business journey thus far, and then share our WHY and what our dream life would be.

And then we also set up a group text… Now normally, I’m not a fan of group texts because my phone just blows up all day, but this one? These girls are hilarious! Now I actually look forward to picking up my phone when it vibrates because I know I’m going to crack up!

But our second meeting was really unique, and I think it was the key to pulling together such a great group of people.

Prior to that meeting, we each took the Enneagram personality test.

I’d never heard of the Enneagram. I’d done the DISC, I’ve done Strengthfinders, but this is one I hadn’t done before.

So we each take the test, and then we come to the second meeting and we share the results of our personality test.

And I really felt like that helped shave off some of the time that it takes to really get to know a person, and what drives them and motivates them, why they might react certain ways and all that.

And I don’t know about you, but I love stuff like that.

If you’re into the Enneagram, I’m equally a 3, 6 and 9. Which typically I guess you’re only one number, but in every personality test I take I always get a blended result like that which makes me always feel a little weird, like, am I fake? But anyway, that’s a topic for another episode…

Because what I noticed about our mastermind group, and I don’t know if this was done on purpose by Bree when she invited us, or if it was just coincidental, but we each have a strength that can really help the others – not only in our personality, but also in where we’re at in our businesses.

So after those two meetings, by the time we showed up for our weekend retreat, I felt like I knew these girls on a deeper level than what I would have had we just talked about our businesses on that first call.

Because if you know me, I’m really, really slow to make deep friendships. I’m a great listener, but it takes me awhile to open up about myself.

Except this podcast… I just blurt it all out on this podcast – but you guys are my friends, right??

But it was easier for me to share my biggest fears and struggles and my big dreams with these 5 girls because I really felt connected to them, that it wasn’t just one sided where I learned everything I could learn about them to avoid talking about myself – we all equally shared and listened.

So that leads me to tip #3:

#3 – Meet in person at least once a year

I absolutely love that we started off our mastermind group with a 3 day retreat, for a few reasons.

One – we had to make an investment to do it. Not an investment as in we paid someone to be in the mastermind, group, but an investment in actually doing it.

This is different than paying someone to be in their mastermind, because there’s a certain expectation that the person you paid is responsible for helping you get results.

This is investing collectively in a mastermind where we’re all responsible for showing up for each other and putting the work in to get our own results.

Some of the girls had to arrange childcare for those 3 days. Some of them had to take time away from their businesses that are open on the weekends. Some of us had to get on a plane and fly to the destination.

We each chipped in for the AirBNB and for food and paid for our own travel to get there. I mean, it wasn’t a huge amount of money or anything but it was significant and we were invested. In ourselves and each other.

It’s a very different experience than I had in groups where we hopped on a Google Hangout once a month.

Two – we really, really got to know each other. Chats about our families over coffee in the morning. Sharing rooms and a bathroom. Cooking together, cleaning up together.

Okay, there was one girl who cooked most of our meals, and she’s absolutely amazing. I’m like, I will do dishes all day every day just to eat your food!!

Sitting together on the big couch with blankets, wine and snacks sharing our dreams and squashing each others fears…

And finally, it pulled us away from our everyday lives so we could really focus on our businesses and planning for the future. Which leads me to tip number 4:

#4 – Have a structure for the weekend.

Here’s what really made our weekend special. Bree created an agenda for us for the whole weekend.

On Friday night we put together a gorgeous spread of appetizers, broke open the wine and socialized for awhile and then we sat down with dessert and went around the room sharing our biggest dream, and our biggest fear – and we all supported and encouraged each other as we shared.

Saturday morning after breakfast we did a hot seat. So we each had 30 minutes to share problems or roadblocks we were encountering in reaching our goals and listen to everyone’s ideas, advice and encouragement on how to overcome them.

Saturday afternoon, we did planning. We each got a few giant post-it notes and markers, stuck them to the wall and brain-dumped. All of our goals and what it would take to make it happen. The best part of this session was that after we had time to get our thoughts on paper, we went around to each other and held each other accountable.

Like, “Shannon, you told us that you’re working too much, but you just added a bunch of new work to your list of goals. Is that really in service of what you’re trying to accomplish? Will doing that really help you get to where you told us you wanted to be? When will you do that? Q1,2,3 or 4? You’ve already packed too much in to Q1, do you really need to do that in Q1?”

I found those conversations to be extremely valuable. Because I can rationalize every decision I make to be in service of reaching my goals… But when really challenged on it, I can see that it’s just adding more work to stay busy so that there’s no time for the fear to creep in.

Then we made dinner and ate together, and in the evening we just sat around talking about life, and business and continuing to get to know each other.

Sunday was systems day. This day was awesome. We went around the room and shared what systems we use, how we use them, and what things we’re doing where we needed better systems. We even did little demos for each other on how use Trello, or Tailwind, or multiple inboxes in GSuite.

Then we had the rest of the day to work on creating processes and systems and plans for the goals we had outlined the day before.

We had some work time, and some down time, and that evening we played a game, we put on facemasks slumber-party style, and stayed up late talking.

And Monday morning, we lazed around, and then we cleaned up and checked out.

So the weekend was just structured enough that we accomplished a lot, but not so structured that we all left feeling exhausted.

I left feeling totally energized and like I had 5 new best friends who completely understand my business and my goals, and the parts of my personality that help me reach them, and the parts of my personality that hold me back.

#5 – Create a space for conversation between meetings.

As I mentioned earlier, we created a group text to chat, and share our wins, things that happen that bum us out so we can lift each other up, and just have fun.

We also scheduled a monthly meeting on Zoom to update each other on our goals and hold each other accountable and encourage each other.

And my favorite thing that we’ve done is set up a group Marco Polo. It’s something I’ve never heard of before, but it’s basically like video messaging. You just record yourself talking, and then the group gets notified, and you can watch in and respond with a video.

So we’ve created a few different ways to stay in touch, encourage each other and just make each other laugh!!

So to recap:

#1 – Have a Planner so that you maintain momentum.

#2 – Get to know each other on a deeper level so that you can develop trust within the group.

#3 – Meet in person first. Not only will putting skin in the game help you contribute on a deeper level, it gives you the space and time to really craft your plan and help others understand how to hold you accountable.

#4 – Have a plan for the weekend so that it’s structured enough that you actually accomplish something, but not so structured that you leave feeling drained.

#5 – Create a space for continued conversation so that you get used to asking for help and feedback before you find yourself in a desperate situation.

I think being a part of this awesome group of girls is going to be a total game changer for me.

Not because I’ll be held accountable, and not because I’ll have a go-to group of people who I can ask for feedback or help, but because I finally feel like I have friends who get it!

Like, my husband and all my friends in real life, they are proud of me. They are super supportive. But they’re not going to sit down with me for three days, unpack all my crap and hold me accountable to it. That’s not their role in my life – and I can’t do the reverse for them because they don’t own businesses.

It’s like, instead of working by myself, I have work friends again. And I forgot how much I missed that.

So if you’re feeling a little lonely, like no one really gets you or like it’s all on your shoulders, consider starting a mastermind. Find like-minded people, locally or online and take the lead. Be the planner and pull it together. Or find a planner.

And if the first group doesn’t work out, keep trying. You will find your people!

Today’s pep talk is brought to you by Bluehost. Go to and get 36 months of web hosting for just $2.95 a month. That’s less than one trip to Starbucks a month – and if you’re anything like me, you’re at Starbucks more than that!

Then you can sign up for my Free 5 Day Website Challenge at and I’ll show you step by step how to get started building your new website for your side hustle.