I’m not normally a big sports guy, but stick with me for a minute.
A few weeks ago the Eagles played the Jaguars in London. Philly was down two with twelve seconds left, scraped together a messy drive, and Jake Elliott hit a 48-yard field goal to go up 17–16. Eight seconds on the clock. Game over, right?
You know where this is going. The Jaguars returned the kickoff way further than they should have, got into range with one second left, and their kicker hit a 57-yarder. Jaguars win, 19–17.
If you’re a Jacksonville fan, that’s a fairy tale. For the rest of us, it’s a reminder: it ain’t over till it’s over.
I bring it up because this month I almost called a game in my own business before it was over. One of my favorite things, a project I’ve been building for over a year, and I was a couple days from shutting it down.
Why solopreneurs get stuck
One of the best things about running your own business is that you get to make up all the rules. You write your own playbook. You pick your offers, your customers, your prices, your hours.
One of the hardest things about running your own business is that you have to make up all the rules. There is no playbook. The freedom cuts both ways.
I’ve been full-time self-employed for over five years, and at some level I still feel like I’m in uncharted territory. Some people thrive in that and chase every shiny new idea before any of them get momentum. Other people want their ideas fully cooked before they tell anyone, which usually turns into overthinking and perfectionism, and again, no momentum. Most of us bounce between the two.
Wherever you land, if you work alone you are especially susceptible to getting stuck. Stuck in your own head, or stuck under a pile of half-finished projects. Or both. (Hi.)
The good news is there’s a cure for stuck. It’s other people.
Other people give you feedback and fresh perspective. They hold you accountable. They point out what you’re doing right when it feels like everything is wrong. They challenge you and catch your blind spots. They connect you to more people and resources. And they remind you that you’re not alone.
That’s why I started a mastermind group.
What a mastermind actually is
A mastermind is a small group of people who meet regularly to help each other clarify and reach their goals. Part accountability, part peer mentoring, part brainstorming and troubleshooting. The key is that everyone in the room is committed to everyone else’s success.
The Sidekick Mastermind, the group I facilitate, is for people who are self-employed or actively working toward it. We meet for one hour every week. We open with a quick check-in where everyone shares a win from the past week. Then one person takes the “hot seat” for the rest of the hour. They bring a question, a problem, or a half-formed idea, and the rest of us ask clarifying questions, share feedback, and offer cautionary tales from our own experience.
It’s been running for over a year, and it is one of my favorite things I get to do each week. Even when you’re not in the hot seat, even though everyone runs a completely different business, everybody leaves with something.
And I almost pulled the plug on it.
The week I almost quit
The group launched in July 2025 with four of us. It stayed small. Two members showed up consistently for almost a year, and every so often someone would pop in to check it out. I never promoted it heavily. It’s not the main thing I do, and I wasn’t disappointed, exactly. But I knew the experience is better with more voices in the room. Six to eight is the sweet spot, and I hadn’t done much to get it there.
Then one member had to step away because of a change in their work situation. That left one.
So I finally got intentional. I invited two people I thought would be a great fit, we’ll call them Lauren and Lin, and they both said yes to a few guest sessions. We had some of the best energy the group has had since it started.
Then it came time to ask them to join as paying members.
Lauren told me she got a ton of value out of it and would love to join, but she just wasn’t in a spot to commit financially right now. We’d keep in touch.
Fair enough. I get it.
But that one “no” got me twisted. I still had Lin to talk to, but I decided I already knew how that would go. I knew a few things about their situation. Probably not a good fit anyway. They were going to say no.
So the math looked like this: I tried to recruit and failed. I was down to one member. One-on-one is a different dynamic, and I wasn’t sure they’d keep getting as much out of it. Maybe it was time to change the frequency, or go on hiatus, promote it properly, and relaunch later.
I was very close to messaging that last member and saying, “Hey, how about we take a break?”
I was about to shut down one of my favorite things because it wasn’t going the way I hoped. And I hadn’t even asked Lin yet.
I didn’t see it in the moment. Somebody else had to point it out.
A quick word on why the group is paid
I’m not trying to get rich off the mastermind. I enjoy it enough that I’d run it for free. But I want members to have some skin in the game.
The numbers back this up. Paid courses see about three times the active engagement of free ones (8.4% vs. 2.55%). Free online courses average a 3–15% completion rate, paid self-paced courses run 40–72%, and high-ticket coaching and cohort programs report 85–96%. Behavioral economists chalk it up to loss aversion: skipping a session you paid for feels like losing something, and skipping a free one doesn’t.
I want my members to practice investing in themselves, and I believe a financial commitment is part of what gets people to show up every week and take it seriously.
I’m not asking anyone to do something I don’t do. I’ve paid for coaching for several years, and the return has been enormous.
My turn in the hot seat
I’m not just the president of a mastermind, I’m also a member. I work one-on-one with a business coach, and I’m in a mastermind he runs. We meet every Tuesday. A video production guy, a solo digital marketing agency owner, a nonprofit consultant, a veteran podcaster, a school administrator moving into coaching, a musician turned mid-life career coach. Totally different businesses, and it’s remarkable how much you see yourself in people who are nothing like you.
Recently it was my turn in the hot seat, and I almost passed. Things were on autopilot. Podcast launching, projects moving. I could have said “everything’s good” and handed the mic to someone with something more pressing.
But this thing was gnawing at me, so I brought it up. Great couple of weeks with a full room. Invited someone to stay, got a no. Pretty sure the other person will say no too.
And before anyone else said a word, I heard myself.
I’m making an assumption. I haven’t asked the other person. I’m calling the game with time still on the clock. I don’t know if the kick is going through, but I have to kick it to find out.
Sometimes talking it out with people who know you know better is enough to make you remember that you know better.
Then my coach sharpened the picture. Sure, I could table it. Then I’d have to work my butt off to promote it and relaunch, and I’d lose every bit of momentum I had. Or I could keep going and work with what I’ve got.
He pushed on something else too. If money isn’t the biggest thing for me, but it’s the biggest obstacle for someone else, I can accommodate that. I can go back with a different offer. And if I’m not assuming everything is falling apart anymore, who else do I know who should be in this room? Don’t just stop leaning away. Lean back in.
Where it stands now
I went back to Lauren with a steeply discounted rate for a set period, so she could join, keep getting value, and we’d reassess later. I sent Lin a similar invitation.
As I write this, both answers are “not right now, but maybe soon,” and I have follow-up conversations on the calendar. The door is open. The mastermind is still running. I’ve invited a few more people, and at least one has already said yes. They’re joining us this week.
I could have let discouragement drive, called it a lost cause, and kneecapped any chance of this working. Instead I asked. I kept my options open. And it’s already having ripple effects.
None of that happens without other people helping me process, redirect, and keep moving.
Three things to take from this
1. It ain’t over till it’s over. Don’t shut down before you take the shot.
I got one “no” and apparently that gave me the supernatural ability to predict the next one. That’s silly. But I bet you can relate. Rejection takes the steam out of you and makes it hard to see a way forward.
Maybe for you it’s a proposal you’re sitting on because you’re worried about how the client will react to the price. Maybe you need to raise your rates to keep up with costs, but you won’t, because you “know” your clients will walk. So you stay underpriced and stay stuck.
You might be right. Sometimes the answer is no. But you will never find out if you keep filling in the blanks for them.
2. Find out.
You are not going to get clarity by sitting there spiraling. If you have a question, ask it. If you’re unsure whether a client will accept your proposal, pitch it. Take enough time to be thoughtful, then take the step. The answers you want rarely come looking for you.
3. Get connected with other people. Regularly.
This is the big one. We were never meant to do all of this alone. There are limits to what we know and what we can see from where we’re standing. You might think nobody understands your business better than you, and that’s true, but sometimes you’re so deep in it that you miss what’s obvious to someone standing outside.
Pat Flynn from Smart Passive Income talks about needing “label readers.” Picture your business as a pickle jar, and you’re standing in the middle of it, knee-deep in vinegar. Every cucumber and peppercorn is exactly where you want it. But what does the jar look like from the outside? What does the label say to someone walking past in the store? You can’t read it from in there.
I got a dose of this when I redesigned my web design business site. I had what I thought was a great idea: open with an ugly, outdated website, and as you scroll it falls apart and a beautiful modern one assembles in its place. I showed a couple friends. They opened the page and said, “Huh. It looks kind of ugly.” They hadn’t scrolled yet. Once I told them to, they got it. But their point stood: the first impression was bad, and plenty of visitors would leave before the payoff. I was too close to my own clever idea. I changed it.
Be picky about your label readers
Not everyone qualifies. Not your mom. Not flatterers. Not the people who mean well but have no clue. “That’s so great, honey, I’m sure it’ll be amazing” doesn’t help you.
You need people who actually get it. People who don’t just cheer you on but challenge you, who’ll call you out before a misstep because they’ve made it themselves. Maybe they’re further down the road, maybe right beside you, maybe a few steps behind. People on a similar path who ask good questions and don’t blow smoke.
And sometimes they don’t need to say anything. Just having someone you can confide in and think out loud with is half the value.
I’ve been working with a coach and sitting in rooms like this for a while now. How I price myself, how I find new business, how I build systems, how I came to believe in what I have to offer. I would not be where I am without those conversations. I could not do this by myself.
Self-employment is not, should not be, cannot be by-yourself employment.
Your homework
First, ask the thing. If you’re stalling on something because you don’t know how someone will respond, go find out. Send the invitation. Send the proposal. Make the follow-up call. Put it on the calendar and do it. Don’t carry that uncertainty around any longer than you have to.
Second, find some label readers. You probably already know someone. Grab coffee with a friend who runs their own business and commit to a regular check-in. Look into your local chamber of commerce or a BNI chapter. Join a mastermind or an online community.
And if you don’t know where to start, shameless plug: come take the Sidekick Mastermind for a spin. We’ve had some incredibly valuable conversations in that room, and I’d love to talk with you about whether it’s a fit. Head to sidekick.show/mastermind and we’ll set up a call.
Whatever it looks like for you, take one step toward regular time with people who get it. Don’t find the corner of the lunchroom and stew over a lackluster sandwich. Plop down with some other kids and start a conversation.
I’ll keep you posted on how the mastermind shakes out.
