How to Setup & Run a Freelance Mastermind Group

Along with sharing an office with another freelancer and hiring several coaches, starting a mastermind group has been one of the best decisions I’ve made for my business. The feedback, accountability, and resources I’ve gotten from the group have been invaluable.

So I thought I’d take a few minutes and write a short post on what a mastermind group is, why you need one, and how to get started with building and running your own.

What is a mastermind group?

A mastermind group is just a small group of people who meet regularly to discuss issues and lend support to each other. You could also call it a support group or an accountability group. They’re especially popular with the online entrepreneur crowd, but I think more freelancers and solo consultants should be doing mastermind groups too.

I launched my first mastermind group in 2018 with four other internet entrepreneurs and it’s been a great experience. Prior to that I had a more informal arrangement with several other freelancers and consultants, and I wish I had made the group more explicit and organized.

Why would I need one?

Freelance can be isolating and having a group of people who understand what you’re going through and who can give you advice and accountability is vital.

Yes, you can do this on your own, but why would you? It’s so much easier to have someone with whom you can commiserate, seek advice, be kept accountable, swap contacts and resources, and collaborate. And it’s also more fun.

Take it from me, you need a mastermind group.

Who should be in my group?

There are a bunch of ways to structure these, but I recommend a mix of 3-5 people. I think four is probably ideal, maybe five at the outside. If you only have three and someone can’t make a meeting, it starts to feel less like a group and more like two people just chatting. And with more than five people, it’ll take forever to get through your regular meetings.

In terms of who these people should be, you want people who understand your day-to-day reality and the struggles you’re going through. But you also want some different perspectives on those same topics, so I recommend you find a mix of a few different kinds of freelancers, not just people who do the same kind of work as you. So if you’re a designer, maybe don’t pick 4 other freelance designers, but instead try a writer, a marketer, a developer, etc.

They also don’t necessarily have to be freelancers, but I would recommend that you stick with other entrepreneurs. That’s not because there’s anything wrong with having a job, but the struggles of an employee building a career are just so different from those of a freelancer or founder building a business that I don’t think you’ll get as much value out of the experience.

Finally, I recommend you shoot for people who are roughly at the same level as you, in terms of experience and income. This can obviously be a little tricky, but you want to avoid a situation where you have one person who is pretty advanced / experienced in a mastermind group with people who are just getting started. That experienced person will have great advice for the others, but they won’t necessarily be able to add much value for her.

Where do I find them?

This is definitely the hardest part of putting together a great mastermind. Here’s what I recommend:

The ideal mastermind group is one with full transparency and trust, which means that you need to enforce strict confidentiality.

Beyond that, you want helpful, generous people who are fun to talk to and have good things to say. These people are not easy to find, but you’ll know them when you see them.

I invited four other entrepreneurs to join me in our mastermind because all of them were wonderful people who had previously been very generous with me in terms of advice and connections. This told me that they’re good people and we’d all benefit from helping each other, and we have.

How often should we meet?

Assuming you’ll be meeting online like most groups, I recommend you meet every other week. Every week can start to feel like a burden when you’re really busy and you’ll be tempted to skip.

But once a month is too infrequent; if you need input on a situation it might be a full month before you can run it past the group. Additionally, if you miss a meeting and someone else misses the next one, it could be a full three months before you get to talk to that person again!

I also recommend trying to meet in person once or twice a year. There’s something special about meeting face-to-face that changes the relationship and makes these people feel more like good friends than just people you know online.

Typically conferences are a good place to meet up, although many mastermind groups also just rent a cabin or something to hang out for a long weekend a couple times a year.

What should our meeting format be?

I recommend selecting one person each meeting to be in the “hot seat”, which means they’ll be the focus of the meeting. They can talk through any big issues they’re facing and get focused attention and feedback from the group. Every meeting the hot seat rotates so that everyone gets a turn. You can also switch up the order on an ad-hoc basis in the case where someone has something they’re really struggling with that they need feedback on.

In terms of the amount of time, I’d say 60-90 minutes should be sufficient. Smaller groups might find that an hour is enough, but my group of five meets for 90 minutes and we always use the full time. The non-hot-seat people can kick off the first half of the meeting by giving shorter updates and seeking advice on their situations, and the second half of the meeting is for the hot seat.


That’s it! As you can see, this is really pretty simple, but if you haven’t tried starting a group like this before, I highly recommend that you collect a few other people and give it a shot.

You don’t have to do it on an open-ended basis. Commit to an initial “season” of 3-6 months with the understanding that you’ll all reevaluate at the end and there will be no hard feelings if someone decides it’s not a good fit for them.

Good luck, and drop me a note to let me know how it goes!