Self Employed? Why You Should Join a Mastermind Group Now

Mastermind group core values

I love working for myself. Flexible hours, a variety projects and the freedom to work anywhere in the world. However, the trade-off is that I often feel silo’d and alone when I need support the most. Although my tech consultancy was going well and I could travel when I wanted, I couldn’t kick this nagging feeling that something was missing. Then I heard about Mastermind Groups, and can’t believe how I’ve done without them until now.

What is a Mastermind Group?

A Mastermind is a small group of people with similar interests who get together regularly to support each other in a safe environment and keep each other accountable. The term was coined in Napoleon Hill’s classic bestseller, “Think and Grow Rich“, where it’s defined as “The coordination of knowledge and effort of two or more people, who work toward a definite purpose, in the spirit of harmony.”

Being in tech, I’m on my laptop the majority of the time. When working in a foreign country, some days my only human interaction is with the sweet old lady at the market that stocks the best mangoes. And though online forums are a great resource, a major benefit of Mastermind Groups is having a safe, judgement free environment where real relationships can blossom. And I’m sure you’ve heard it before, but despite all the methods of communication today, face-to-face interactions are irreplaceable (albeit often accomplished through video conference for us nomadic and work at home types). Knowing that your group will be there for you and that you’ll see their smiling faces on a regular basis has so many benefits that I will describe later.

If you’re lucky enough, you have access to a shared workspace, which are popping up everywhere (though I’m still waiting, Ecuador…). However, more often than not when on the road, you are by yourself solving problems alone with no one to bounce ideas off. Sure, you might have a few friends you can email, but you don’t always want to bother them by creating an obligation to reply, and besides, it may take a while for your message to bubble to the top of their busy inbox anyways. So how did I even know what to look for if I’d never even heard of a Mastermind before?

The Catalyst – WDS

This past summer I attended my first World Domination Summit (WDS), an inspirational annual gathering in Portland, Oregon for creatives, writers, entrepreneurs and seekers. It’s unlike any conference – WDS is 100% volunteer run, with no sponsors and a curated line-up of the most inspirational speakers accompanied by engaging workshops. The brain child of Chris Guillebeau, author of “The $100 Startup“, it’s at this conference where I first overheard a conversation about Mastermind Groups and also where I met four of the amazing people that would become part of this.

I knew nothing about Masterminds, so in typical over-analytical and procrastinating style, I Googled it. I read blog posts and even downloaded Scott Dinsmore’s “How to Create the Ultimate Mastermind” PDF, but balked at its 51 pages. (I love Scott’s work with LYL by the way, and will read this PDF soon). Throughout my overanalysis, I kept hearing a loud voice echoing in my head – take “imperfect action”.

Imperfect Action

Think of this as the opposite of inaction – how many times have you had a great idea, brandstormed, bought the domain, brain dumped to Evernote, and then went to bed super excited and even proud of yourself that you even thought of it? Now how many of these ideas have you actually seen through and given a real try?

I’ve done this countless times, and am now squatting on a dozen domains to show for it. I’d go through the cycle of idea, excitement, research, (over)analysis, struggle and self-doubt until a paid gig would come along and push all that to the side, adding another great idea to the ever-growing list of “things I’ll finish someday”.

The key to imperfect action is to take action. Do something, anything, that moves you towards that goal. Then learn from it. It might not be perfect, in fact it probably won’t be, but it’s better to do something than doing nothing. In this case, thanks to those two words resonating in my head, I was able to recognize this pattern, stop it before it got to that point, and decided then to make the first steps towards start a Mastermind Group.

Fear of Rejection

The first step was to craft an email to the people I thought would be a perfect fit for this Mastermind. I’d met two of them on the very last day of the WDS and talked less than half an hour. Here’s the actual email I sent out (PDF), feel free to copy parts of it to start your own:

Screenshot of Initial Email to Mastermind Group - click for PDF

Once I hit send, my heart jumped. Shit was getting real. We all had similar interests in location independence and the tech / marketing space and I had a good feeling from meeting all of them, but I was not sure what to expect. Half of them haven’t even met each other. What would people think? What if they all rejected it?

Within 24 hours, I got four of the most enthusiastic replies ever! My heart was full and I knew then that I’d chosen the right people for this group. I decided on a set of core values and since everyone was on Facebook, threw up this quick header image for our newly created Facebook group a day later:
Mastermind Group Core Values

So Much to Love

We’re now on our 4th bi-monthly meeting, and I look forward to every single one! And it’s important to note that this is not my group, it’s our group. I love seeing everyone’sĀ faces on Google Hangouts and hearing about what they’ve learned, their successes and their failures. I love how we can post questions and ideas in our Facebook group and get responses the same day. I love how we keep each other accountable and push each other to improve not just in our work lives, but as human beings. I love how we come from varied backgrounds and all contribute something different to the group (our current locations when this article was written: Ubud, Sydney, Colorado, Nashville & Vancouver, BC).

And after several inspiring, bonding, fun and productive meetings, I’ve also come to learn a few things that have made our group successful. In my next article, I’ll give tips on starting your own Mastermind, recommend tools to make the meetings go smoothly (and on time!), and share my learnings on keeping the momentum going to make your group a success.

It’s easier than it sounds. Take imperfect action. You won’t regret it.

I’d like to thank Jeff, Helena, Kristen and Dan for their help with writing this article, for taking a chance with this, and for the continued support with our Mastermind group.

And a thank you to Jadah Sellner for her inspiring talk at WDS. “Build trust, be consistent and take imperfect action.”

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