Set A Date

I'm watching through The Bear right now, and I'm currently on Season 2 (just finished episode 7... and I think it might be my favorite so far).

Each episode includes a countdown - "12 weeks to open," "11 weeks to open" - and follows the cast as they scramble to transform their hole-in-the-wall sandwich shop into a fine dining restaurant. They've given themselves an impossibly tight deadline, and tensions boil as days get crossed off the calendar.

Couldn't they have just pushed their deadline by a couple months? Not really. They're broke. They only have so much money to keep them afloat (and a growing pile of debt to pay back) while the restaurant is closed.

It's incredibly stressful, relatable, and entertaining. And it's by no means an example of the best way to start a new business. But it's a real one. And I think it provides a great lesson of the power of deadlines.

The Danger of Being Your Own Boss

When you're self-employed, you're in control of your own schedule. Which is great.

It's also incredibly dangerous.

Sometimes you do have a hard deadline baked in. Maybe you're in a position where you're rushing to lay down track, trying to secure your next client before your checking account hits zero. But sometimes we're in a fairly comfortable position. Sure, it would be nice to open that fine dining restaurant of your dreams - or otherwise introduce a new offer - but you're getting by well enough selling beef sandwiches.

Why subject yourself to the stress of building something new that might not work when you're already getting by with the current system?

A half-ounce of perfectionism or doubt can cause us to keep pushing deadlines; or never setting them in the first place.

But when you have something set in stone and something at stake? You get to work.

This is called creating a voluntary force function (something I'm reading about in Pat Flynn's new book Lean Learning). By intentionally putting ourselves in a situation where we have a tight deadline or other constraints to contend with, we motivate ourselves to action and growth.

My Year-Long Delay

I've been dreaming of launching a mastermind for over a year now. I always loved the idea of creating a space where small business owners can connect to equip and encourage each other.

But part of me never thought I'd actually do it.

Because I didn't need to do it. It’s a cool idea and it would make me come to life, but I'm busy enough and staying alive with other work. I'm bringing in enough income. And this mastermind thing? It's new and... scary.

Why risk the embarrassment and disappointment of it possibly not working out?

But through some coaching and a lot of encouragement (thanks Cliff and Suzy), I finally got the nerve to share my idea and invite a few clients and connections to check out the new Sidekick Mastermind.

I could have gone back and forth forever:

• Trying to pick the "perfect" day and time that works for everyone

• Waiting for a more convenient time (maybe after I get back from vacation next week... or maybe after the OTHER guy gets back from vacation the week after that...)

• Figuring out a better platform for call recordings and transcripts

• Updating my website with a proper landing page

• Or maybe I should wait, and wait, and wait... because....

Years ago, I would have done exactly that. Heck, ONE year ago I did exactly that and didn't launch!

And I'm kicking myself for waiting so long, because I realize the biggest thing holding me back was myself. I never set a date and fully committed to launching.

But Then I Did

I set a date. I let other people know when we'd go live.

And you know what happened? People showed up! And it was amazing.

The conversations were rich, the group quickly developed really great chemistry, and our hot seat participants walked away with a ton of clarity and fresh perspective.

All that time I spent overthinking and second-guessing? Wasted. The thing I was afraid might not work? It worked beautifully, even in its imperfect, first-run form.

The Power of Public Commitment

Here's what I learned: When you tell other people about your deadline or invite them to take part in your new offer, something magical happens. It stops being just an idea floating around in your head and becomes a real commitment.

Suddenly, you're not just accountable to yourself (who is pretty easy to negotiate with). You're accountable to other people who are expecting you to deliver.

That's the force function in action.

What Are You Waiting For?

So here's my question for you: What's the thing you've been "planning to launch" for months (or years) but keep finding reasons to delay?

Maybe it's:

• A new service offering you've been perfecting in your head

• A course you want to create

• A podcast you've been "getting ready" to start

• A networking group in your area

• That book you keep saying you'll write "someday"

Whatever it is, it doesn’t need to be perfect to be valuable.

And I'm willing to bet the biggest thing holding you back isn't lack of knowledge, skills, or resources.

It's the lack of a real deadline.

If you've been putting off something important in your business, consider this your friendly nudge. Set a date. Tell someone about it. Then get to work. Your future self will thank you.

I'm Setting Another Date

Speaking of deadlines, I'm doing it again. I'm setting a date for the next Sidekick Mastermind session: 📅 Thursday, July 31 at 1pm EST.

This will be a free session where fellow self-employed folks can:

• Get honest feedback on current business challenges

• Share wins and work through roadblocks

• Connect with other entrepreneurs who get it

• Leave with practical next steps and renewed motivation

If you're interested in joining us, shoot me a message and I'll share more details.