Pull up a seat at the Mastermind
Working for yourself shouldn’t mean figuring it all out alone. The Sidekick Mastermind is a weekly, live hour with up to 10 self-employed people committed to each other’s success.
Self-employment
gets lonely fast.
You make every call yourself. There’s no one down the hall to bounce around ideas with, no one to tell you you’re overthinking it, and no one to help you when you’re stuck on something.
You don’t need more information. You’ve watched the videos and read the books. You might have every thing mapped out. What’s missing is a room of people who will help you get clarity on the best next step, and then check in on you next week to make sure you’re on track.
That’s the Sidekick Mastermind: a seat at a table with people who get it and who have your best interest at heart.
Why a mastermind works
A mastermind is an old idea: a small group that meets regularly to think out loud together. It works because it gives you three things that are hard to find on your own.
Other eyes on your business
You’re too close to your own work to see it clearly. (We all are.) A table of people who aren’t will spot the blind spot, the easier route, or the thing you’ve been putting off.
Someone expecting an update
Saying a goal out loud to people who’ll ask about it next week makes it a lot harder to let it slide. It isn’t pressure. It’s company.
A spark when you need one
Some weeks you’ll be on fire, and some weeks you’ll be burnt out. Watching someone else work through a problem can kindle new ideas and reignite your motivation.
What a session looks like
Wins and updates
A quick warm up. Everyone briefly shares what’s moving and what isn’t.
The hot seat
One or two members take a turn. Bring a problem you’re facing, an idea you want feedback on, a question, or an outcome you want help building momentum toward.
The group weighs in
We dig in. I facilitate. Members ask clarifying questions and share their feedback and insights.
You leave with next steps
Hot-seat members walk away with clarity and action steps.
Everyone commits to the success of everyone else in the group.
Get ready for change for a change.
Sometimes a hot seat leads to a real breakthrough. Sometimes it’s a gentle nudge to stay the course. We won’t solve everything in an hour, but you’ll leave every call with something useful, even if it’s not your week to be in the hot seat.
- Second-guessing every decisionMaking the call & moving forward
- A to-do list that keeps growingOne clear next step each week
- “I’ll get to it someday”“I said I would, so I did”
- Wondering if you’re doing it wrongKnowing other people are figuring it out too
- Figuring it all out aloneA room of people rooting for you
Who is this for?
The Sidekick Mastermind is for people who are self-employed or actively working to become full-time self-employed. It is for people building something of their own who are tired of building it alone. Maybe you’ve caught yourself thinking:
- I know what I should do. I just keep not doing it.
- I need someone to tell me if this idea is any good.
- I feel like I’m flying blind and making decisions in a vacuum.
- I’d get so much more done if I had a little more accountability.
You’ll fit right in if…
- You’re ready to learn from the room, and to give back to it.
- You’re as curious about other people’s businesses as you are about your own.
- You’d rather get real feedback than cheerleading.
- You’ll make the time to show up, whether or not you're in the hot seat.
You don’t need a big business, a perfect plan, or a full-time schedule. Side-gigs are welcome. You just need to show up and be honest about where you are.
Why I run it
I started Self-Employment Sidekick in 2020 to make the less-than-fun parts of working for yourself a little easier. The videos and podcast episodes help, but they only go one direction. The Sidekick Mastermind is where it finally goes both ways: you get to talk back, and connect with people on a similar road.
I’ve experienced first-hand how incredibly valuable a group like this can be, and I owe much of my business growth to the to the support I’ve received as a member of other mastermind groups and coaching programs.
I often say “self-employment isn’t by-yourself employment.” This is the absolute best way I can think of to put that into practice.
Dave
What it costs
a month
Start with a free, zero-pressure conversation. If you want to move forward, I’ll send you a link to take care of your payment (securely via Stripe).
There’s no charge to click the “Start a conversation” button.
How to start
- Say hello
Send me a short note: what caught your eye, what you’re building, or why this feels like a fit.
- We’ll talk
I’ll reply by email, and if it sounds like a fit, we’ll set up a free call.
- Take your seat
Attend a complimentary session, and if we both want to go ahead, I’ll send you a payment page to continue your membership.
Questions about the Mastermind
When does the group meet?
Right now we meet Thursdays at 11 a.m. Eastern, live, for one hour. The time can shift to fit the schedules of the people in the group.
Where do we meet?
Mastermind calls are hosted via Google Meet.
Do I need to be self-employed full time?
No. Side-hustlers and full-timers are both welcome. What matters is that you’re actively building something and you’re committed to showing up – for yourself and for the others in the group.
How big is the group?
The group is capped at 10 members.
What if I miss a week?
That’s okay. Life happens. Still, make a real effort to be there, not for the group’s sake but for your own. This is your time, and we’re in it together.
If you can’t make it, let us know as early as you can, especially if you’re on deck for the hot seat. There’s prep that goes into it, and nobody should be left waiting to see who’s coming. Missed weeks aren’t refunded.
What if you have to cancel a session?
If I ever need to cancel or reschedule, you won’t lose out. We’ll schedule a makeup session, credit the time to you, or work out another way to make it right.
Is this coaching?
I facilitate, but the value comes from the whole table. If you want one-on-one help, ask me about coaching.
Can I end my membership?
Yes. New members start with a 3-month commitment (just to make sure there’s enough time to rotate you into the hot seat a few times and give you a chance to experience meaningful momentum). After that, you can continue month to month and cancel anytime. Just send an email to [email protected].
Ready to pull up a seat?
Send me a short note. There’s no long application, and no payment until after we’ve talked.
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