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Joey Pinz Digest: September 2026 Second Edition

October 15, 2026 | Joey Pinz Discipline Conversations

Can you believe it? We’re already halfway through October.

Fall is here. The seasons are changing, the holidays are approaching, and somehow we’re already 15 days into the fourth quarter of 2026.

I don’t know about you, but this year seems to have flown by.

Remember January? Remember all those goals, resolutions, and promises we made to ourselves? Maybe you wanted to get healthier, start a business, change careers, improve a relationship, or simply become more disciplined.

How’s that going?

I’m not asking to make anyone feel bad. I’m asking because I think this is an important time of year to reflect.

And here’s something I’ve learned through nearly 1,000 conversations on the Joey Pinz Discipline Conversations Podcast:

Discipline isn’t about how you start. It’s about what you continue doing when the excitement of starting has disappeared.

We still have time. The year isn’t over.

So let’s talk about what we keep, what we change, and how we finish.

1. Fifteen Days Into Q4: Are You Finishing Strong or Just Finishing?

There’s a big difference between finishing the year and finishing the year with purpose.

Think about it.

When January rolls around, everyone seems motivated. We join gyms, buy planners, create lists, and set ambitious goals.

But then life happens.

We get busy. Something unexpected comes up. Our priorities shift. And suddenly it’s October.

I’ve learned that the people who make lasting progress aren’t necessarily the ones who start with the most enthusiasm. They’re the ones who keep going when things become difficult, inconvenient, or downright boring.

That’s discipline.

I often think about my own journey of losing 130 pounds. That didn’t happen because I woke up one morning with some incredible burst of motivation. It happened through countless decisions, made over and over again, even on days when I didn’t feel like making them.

And I’m still making those decisions today.

The same principle applies whether you’re building a company, raising a family, improving your health, or trying to become a better version of yourself.

You don’t need to accomplish everything you wrote down in January.

But you should ask yourself whether you’re moving in the right direction.

Here’s my challenge: Pick one goal that still matters to you. Not five. Not ten. Just one.

What can you do between now and December 31 to make meaningful progress?

Don’t worry about making up for the first nine months. Focus on what you can control today.

Because finishing strong doesn’t mean finishing perfectly.

It means finishing intentionally.

2. Fall Is Here: What Are You Ready to Let Go Of?

Living in Florida, I don’t experience fall quite the same way I did when I lived in the Northeast.

I certainly don’t miss every part of those cold mornings!

But I do appreciate what fall represents.

Change.

The leaves change colors. The days get shorter. Nature begins preparing for another season.

And I’ve been thinking about how that applies to our lives.

We spend so much time talking about what we need to add.

More productivity. More exercise. More customers. More responsibilities. More accomplishments.

But how often do we talk about what we need to remove?

Maybe it’s a habit that’s holding you back.

Maybe it’s the need to say yes to everything.

Maybe it’s spending too much time worrying about things you can’t control.

Or maybe it’s simply comparing your life to someone else’s highlight reel on social media.

Here’s something worth considering:

Discipline isn’t always about doing more. Sometimes it’s about having the courage to do less.

I’ve had to learn that lesson myself.

As an entrepreneur, podcast host, and someone who genuinely enjoys being involved in different projects, I know how easy it is to keep adding things to the calendar.

But being committed to something doesn’t mean every commitment deserves to last forever.

Sometimes we need to make room for the next chapter.

And that requires letting go.

So as we move deeper into fall, here’s a question I’d encourage you to think about:

What is one thing you’re carrying into Q4 that you don’t need to carry into 2027?

You might be surprised how much progress starts with that simple question.

3. AI Is Changing Everything. Are We Changing With It?

I’ve spent a significant amount of time recently traveling, attending events, and having conversations about artificial intelligence.

At MSP Summit in Orlando and Thread AI Service Unleashed in Seattle, I had the opportunity to sit down with some fascinating people who are helping shape how businesses think about AI and automation.

And while many of those discussions centered on managed service providers and technology companies, I believe the lessons are much bigger than one industry.

Because AI isn’t just a technology conversation anymore.

It’s a human conversation.

Think about how much has changed during our lifetimes.

Personal computers. The internet. Smartphones. Social media. Cloud computing.

Every one of those developments changed how we communicate, work, learn, and interact with the world.

Now we’re watching another transformation unfold.

And I keep coming back to the same question:

Are we actually using these tools to improve our lives, or are we simply adding more technology because everyone else is?

There’s a difference.

AI can help us become more productive, make better-informed decisions, and eliminate repetitive work.

But it doesn’t automatically make us better leaders, better listeners, better parents, or better human beings.

That part is still up to us.

One of the things I’ve always enjoyed about podcasting is learning from people who see the world differently than I do.

After nearly 1,000 episodes, I’m still curious.

I still ask questions.

I still learn things that challenge my assumptions.

And I think curiosity is one of the most important qualities we can carry into this new era.

The discipline connection?

Learning requires effort.

Adapting requires humility.

And remaining curious requires us to recognize that we don’t have all the answers.

We shouldn’t fear every technological change. But we shouldn’t blindly embrace every new tool either.

We need to ask better questions.

Not just, “What can this technology do?”

But, “What problem are we actually trying to solve?”

That’s a lesson for business, and it’s a lesson for life.

New on Joey Pinz Discipline Conversations: October 21 and October 28

We’ve got six new conversations coming your way during the second half of October.

Several were recorded during my recent travels to MSP Summit in Orlando and Thread AI Service Unleashed in Seattle.

While the guests come from the technology and business worlds, these conversations touch on themes that go far beyond any one industry: leadership, change, innovation, entrepreneurship, and the importance of delivering real value.

Wednesday, October 21, 2026

Episode #959 — Chance Weaver, Pax8

AI Adoption Means Nothing Without Business Results

There’s plenty of excitement surrounding AI, but excitement doesn’t automatically translate into value. Chance and I explore why adopting new technology is only part of the equation and why organizations need to focus on meaningful outcomes. It’s a conversation about results, accountability, and making sure innovation actually improves something.

Episode #960 — Mike Casey, Flowmind

MSP AI: Are You Getting Answers or More Work?

AI promises to make life easier, but is it always delivering? Mike and I examine the difference between tools that genuinely reduce complexity and those that simply add another layer of work. Whether you’re running a technology business or just trying to make your day more productive, it’s an important question.

Episode #961 — Ahmed Mahmood, Ocean Solutions

From $2,000 to Building a Thriving MSP

Every successful business has a beginning, and sometimes those beginnings are remarkably modest. Ahmed shares his entrepreneurial journey from starting with $2,000 to building a thriving company. This conversation explores determination, taking risks, and the importance of continuing forward even when the path isn’t clear.

Wednesday, October 28, 2026

Episode #962 — Mark Alayev, Thread

Why MSPs Must Rethink Their Business for AI

Change can be uncomfortable, particularly when it challenges the way we’ve always done things. Mark and I discuss how AI is forcing businesses to reconsider their strategies, services, and future direction. It’s also a broader reminder that the willingness to evolve is often just as important as the experience we’ve accumulated.

Episode #963 — Sienna Quirk, Thread

Why Selling Features Makes You Replaceable

It’s easy to talk about what a product does. It’s much harder, and much more valuable, to explain why someone should care. Sienna and I explore the importance of understanding people’s real problems and focusing on outcomes instead of features. It’s a lesson that applies to sales, leadership, communication, and building lasting relationships.

Episode #964 — Matt Tomlinson, Fixify

AI vs. Automation: What MSPs Need to Get Right

We hear the terms artificial intelligence and automation used almost interchangeably, but they’re not the same thing. Matt and I discuss why understanding that distinction matters and how organizations can make smarter decisions about technology. Before jumping into the next big innovation, we need to understand what we’re actually trying to accomplish.

All six conversations will be available through Joey Pinz Discipline Conversations.

Subscribe on YouTube and follow along so you don’t miss an episode.

Looking Ahead: The Next 77 Days

As I write this on October 15, we have 77 days remaining in 2026 after today.

Seventy-seven days.

That’s more than enough time to make a difference.

Maybe not enough time to accomplish every goal you imagined back in January.

But enough time to start building a new habit.

Enough time to improve a relationship.

Enough time to take a meaningful step toward something you’ve been putting off.

And certainly enough time to make a decision that could change what 2027 looks like.

I’ll be continuing my travels and conversations this month, including time in Copenhagen for Pax8 Beyond EMEA and Barcelona for MSP Global. I’m looking forward to meeting new people, reconnecting with old friends, and bringing more conversations to the podcast.

But as we move toward the end of the year, I want to leave you with three questions.

What are you going to keep doing because it’s working?

What are you going to change because it isn’t?

And what are you going to do differently to finish the year with purpose?

You don’t need to wait until January 1 to make a change.

You don’t need a new calendar, a new resolution, or a new year.

You just need to decide that the next step matters.

Because discipline isn’t something we practice only when we’re motivated.

It’s something we practice when life gets busy, when circumstances change, and when nobody is watching.

It’s how we turn intentions into actions.

And actions into progress.

The way you finish 2026 can become the foundation for how you begin 2027.

So let’s make these final 77 days count.

Until next time, stay curious, keep having meaningful conversations, and remember:

Discipline isn’t seasonal. But every season gives us another opportunity to practice it.