Episode 8

full
Published on:

21st Jul 2026

The 4 Levels of Business Thinking Every Contractor Must Master

The principal focus of this podcast episode centers on the notion that true liberation in business arises not from mere hard work, but from the evolution of one's leadership and thought processes. I contend that many contractors find themselves ensnared in a cycle of reactive problem-solving, which I liken to firefighting, thereby preventing meaningful growth and development. We delve into the four distinct levels of business thinking—firefighting, tactical, strategic, and visionary—each representing a critical shift in mindset necessary for transcending limitations. As I share my personal experiences, I emphasize the imperative of transitioning from a state of constant urgency to one of proactive strategy, ultimately fostering an environment conducive to innovation and growth. By engaging with these concepts, we aspire to equip our listeners with the tools to construct a business that not only serves their professional ambitions but also enriches their personal lives. The discussion encapsulates the journey of a contractor who has transitioned from a reactive, firefighting approach to a more strategic and visionary mindset in managing a business. The speaker elucidates the notion that many contractors find themselves ensnared in a cycle of constant problem-solving, where the urgency of daily operations often eclipses the necessity for long-term growth and development. By illustrating the pitfalls of being mired in reactive management, the speaker emphasizes the importance of elevating one's thinking beyond mere survival and execution to encompass strategic foresight. The episode articulates the four distinct levels of business thinking, providing invaluable insights into how leaders can shift their perspectives and ultimately liberate themselves from the constraints of their own operations. Through personal anecdotes, the speaker reveals how he transformed his own business by implementing systems that foster accountability and efficiency, thereby allowing him to focus on more critical strategic decisions that drive growth. Notably, the episode underscores the imperative for business owners to cultivate a mindset that prioritizes long-term vision over short-term fixes, advocating for a proactive approach to leadership that encourages growth and innovation.

Takeaways:

  • The essence of true freedom in business is derived from self-mastery and effective leadership.
  • Contractors often become trapped in firefighting mode, which creates an illusion of productivity without progress.
  • To escape the cycle of repetitive problems, one must identify and address their root causes systematically.
  • Strategic leadership involves making deliberate choices about the future direction of the business rather than merely improving existing operations.

Links referenced in this episode:

Companies mentioned in this episode:

  • Contractor Freedom
  • Phillips Home Improvements
  • Phillips Painting
Transcript
Speaker A:

Welcome to the Contractor Freedom Podcast.

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I'm Jason Phillips.

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If you're tired of feeling trapped by the business you worked so hard to build, you're in the right place.

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As a multi million dollar contractor and founder of Contractor Freedom, I've learned that freedom comes from mastering yourself, leading others, and building systems.

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Each week, I'll help you build a business that serves your life.

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Because the goal isn't to build a bigger prison.

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To build a business that creates freedom.

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Welcome to Contractor Freedom.

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Let's go.

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Here's a hard truth.

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You will never work your way out of the trap you're in.

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I know that sounds backwards.

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Working harder is the only tool that most contractors have ever been handed.

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But your business cannot grow beyond the thinking of the person leading it.

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So if you feel stuck, stop asking, how do I do more?

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And start asking, what level am I thinking on?

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There's four levels, and most contractors never make it past the first one.

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Today, the four levels of business thinking and the exact moment each shift showed up.

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In my own company, most every contractor starts at the same place, right in the fire.

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Firefighting is reactive.

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Your day gets decided by whatever problem is screaming at you the loudest.

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The phone rings, the customer's upset, somebody no shows, equipment breaks down, cash is tight, or somebody quits at the last moment.

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Every day feels urgent.

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You're solving problems, but you're almost never preventing them.

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And the real danger is that firefighting creates the illusion of productivity.

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You're busy all day and the business does not move.

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And every problem that you solve just gets replaced with another problem.

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And here's the part that nobody tells you.

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You also get pulled back into the fire when the root cause never gets fixed.

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So you end up fighting the same fires over and over again.

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And sometimes that's on you, and sometimes it's on a manager that won't own the result.

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I had a production manager long time ago, paid him really good money.

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But fires kept popping up in the field, like the standards weren't being held, the jobs weren't being done.

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The Phillips way, maybe.

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I guess they were cutting corners on the Phillips way, you know, and that caused customer dissatisfaction.

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And then we had to go fix it.

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So that's rework.

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And it pushed other projects back on the schedule, which led to further customer dissatisfaction.

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It just began to be a snowball of fires in the field.

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And on top of it, project managers weren't being held accountable to delivering the Phillips experience.

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And that is supposed to be remarkable.

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And on top of it all, collections started falling behind.

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It's just this nasty snowball that keeps growing.

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And it kept pulling me back in to the field more and more until I finally realized I had to do something about it.

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Here is what I actually had a manager who was serving his team, not leading his team.

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No influence.

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He wouldn't hold anybody accountable, so I had to let him go.

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Look, getting stuck in the fire is not always your fault, but staying there always becomes your responsibility.

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And the moment you get tired of fighting the same fire twice is when you start building.

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Man, that's what happened to me.

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I hate fighting the same fire multiple times.

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And tactical leaders, what they do is they replace chaos with systems.

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So instead of just fixing the problem, they ask, hey, why does this keep happening?

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And you get to the root of it.

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So the goal is consistency, repeatable processes, scorecards, training for your people, accountability and standards.

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Now there's two traps hiding at this tactical level.

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And I walked straight into both of them.

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When I first built systems to make things repeatable, I built what I now call fragile systems.

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Why were they fragile?

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Well, they made me a personal powerhouse productivity machine.

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But I couldn't hand them off to someone.

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They were too complex, not simple enough to learn and prone to breaking.

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And every time I delegated one, somebody would adopt it and then there would.

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Something would glitch and it would stop working and they couldn't fix it.

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Now they're stuck waiting on me.

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Like picture someone who uses a calculator for every math problem and one day the calculator dies.

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And but they never learned how to do the math by hand.

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So here's a real example.

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So I built, many years ago, I built a follow up system that helped automate dialing the phone numbers.

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To follow up on our sales opportunities that we didn't close.

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We'll just call it a dialer for now.

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Well, that dialer, it was prone to breaking from little software updates.

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Every time Windows or whatever would update it, would somehow break it and it went down.

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It's like half the team acted like they didn't know how to pick up the phone and punch the numbers in themselves.

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And so all of a sudden follow up calls weren't being made.

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And it was, it was ridiculous, but it was, it was true.

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It was a fragile system.

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I could fix it, I made it, it served.

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It did not serve my team well.

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I had those systems all across the company.

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Great for me, not transferable.

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So I had to think differently.

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Every system that I design now, it has to be built with the handoff in mind.

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And I call These able systems, A, B L E, because they are repeatable, measurable, trainable, scalable, transferable and lovable when they empower the right person.

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So later sales and project management were being run by other people in the company and the office staff handled most of everything else.

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So I started making systems, systems and more systems.

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I was constantly on the computer making this, making that, spreadsheets, programming a CRM back in the day before cloud computing, automating the CRM, building reports, making things delivered to email automatically, building integrations, everything you could think of.

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And I realized, man, I could just keep building this thing forever.

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There's an endless amount of system creation and polishing that's available to you.

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And what I had become was just a full time system builder.

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I was in system builder prison I guess, at the time, right.

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And it was, it was making the today better, but it was, it was not really advancing the business.

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And so tactical thinking.

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What it does is it makes you exceptionally efficient sometimes at doing things that you shouldn't be doing at all anymore.

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And it improves the business you have, but it does not build the business that you're becoming, the one that you need to become for that better future.

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And at some point better stops being the question.

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The question becomes what?

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That's where strategy comes in.

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Strategy is about choices, not about the same things better, not about doing the same things better, but choosing what business you are becoming.

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Strategic leaders spend less time on how and more time on what.

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Which opportunities do we pursue, which ones do we ignore, what do we add, what do we eliminate?

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What capabilities will we need to have on the team three years from now?

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You know when, when Philips home improvements started back in the day, it was just Phillips painting and we did interior and exterior painting and we kept hitting this same wall.

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I would go out to a quote on an exterior paint job and the, the client had these old galvanized gutters and they were rusted through and they needed replacement.

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And because the gutters had been rusting, now the fascia boards, the wooden fascia boards behind them were rotten also.

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So the client would say, well Jason, let me, let me call the gutter, let me find a gutter company and then a carpenter and I'll call you back when all that's done and we'll get the painting done.

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And this, this happened so many times and sometimes I would never hear from those people and they would just put it off forever because it's more hoops for them to jump through as homeowners and it frustrated them and it certainly Delayed us getting the sale.

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And I finally got sick of it and said, you know what?

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We're going to figure out how to do this ourselves.

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We're going to figure out how to do gutters.

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So what I did was simple.

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I just.

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I called around all the different gutter suppliers Asking questions.

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And I ended up with getting a location manager on the phone.

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And he had deep gutter experience in the field, not just, you know, not just running the supply house.

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And he said that if.

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If we would buy our gutter machine from him and set up an account and start buying materials, if I would agree to that, that he would.

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He would come over and personally show us how to do gutters the right way.

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And that's exactly what happened.

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I hired a manager, a champion for the new division, plus some laborers, Set up an account, bought the machine, bought a truck, installed it all.

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And this guy, this manager, he came over and he taught us how to install gutters the right way.

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He had decades of knowledge and wisdom.

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He taught us every.

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Every tip, every trick, the right way and the wrong way.

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And we practiced and we learned right on my house.

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And so, you know, right there, we designed the beginnings of what would become, and still is today, the Phillips signature lifetime gutter system.

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So what happened is we started running into all these projects and getting these combo jobs where it was painting, carpentry, and gutters all together.

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And at the time, none of the.

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None of the other painting companies in town Were offering this.

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So we started getting all of these combo jobs.

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And.

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And.

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And these are still a staple For Phillips home improvements today.

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And we're known in our marketpl solving this type of problem.

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That was.

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That was a str.

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That was a strategic move.

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That wasn't just about painting better.

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It was about becoming a better business and solving a greater solution and becoming more valuable to our ideal clients.

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And so, you know, at some point, you know, one day, the business just runs.

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And then a bigger question comes.

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Comes looking for you.

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And that is about visionary thinking.

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Visionary thinking is.

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It's bigger than the business itself.

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It answers the question behind every other question.

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Why does this business exist?

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Who are we becoming, and what will we leave behind?

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At some point when things are going well and you have a solid team and the business runs, you know, you look in the mirror and you ask, man, why am I building this?

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What am I trying to build?

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What does this mean to my life?

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What do I want to do with it when I'm ready to retire?

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You know, for me, I've known since I was a teenager, that my purpose was to raise up leaders and leaders of leaders.

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I didn't know the full scope.

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I had never done it before, but it's always been since I was a teenager, part of who I am, part of my calling in life.

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And for years, Rochelle and I, you know, we had our family, we had our company, and we also served as children's pastors at our church.

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And about a year before, you know, I stopped the children's ministry, I started feeling disconnected from the vision and the passion of it and where we were going.

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And I shared that with my pastor, and we talked through it from time to time, and I prayed about it constantly.

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And I stayed patient.

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I stayed faithful.

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And then one Sunday night, I literally had a dream.

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And I'm not going to go into all the details right now, but that dream showed me that I was to redirect my energy, that a new season of life was coming, and that I was to redirect my energy from the children's church to pouring into my team at Phillips Home Improvements, and that my impact was moving into the business world.

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And at that time, I had no idea what this was going to happen, snowball into.

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But I just knew that I had immediate relief when I had that dream, and I knew what I needed to do.

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So the very next morning, called my pastor.

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I'm like, hey, we've got to meet.

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So I met with him.

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The first thing I told him, told him what was going on, and, you know, and then he and I worked together to find the right guy to take my place.

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And thankfully, we had the right guy ready to step in in the church.

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And he took over within.

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Within just a few weeks, we had handed it off.

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And then I was able to redirect all my energy into building, into building Phillips Home Improvements.

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You know, and before that, I had viewed Phillips Home Improvements as simply a financial vehicle.

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It was providing for us financially while I poured into the kids at church.

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That was the whole thing that the business existed so that it could finance what I was doing in ministry.

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But this was a totally new thing.

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Now I was.

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I was actually fulfilling my calling through my company, raising up leaders at work, and it continues to this day.

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So much so that now I have a leadership team that runs the company.

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And I spend my time helping contractors become better leaders all across the nation, developing them as leaders so that they can build better businesses, better homes, better futures, live with greater freedom, purpose and impact, be better husbands and wives and fathers and mothers and make a greater impact in this world.

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And it all started literally with that dream.

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And it influences everything we do at both companies.

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Home Improvements is just what we do.

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It's our vehicle.

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But our purpose is developing leaders, is changing lives.

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And that's the visionary level.

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Friends, the business stops being the point, and it starts being the vehicle.

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Notice this whole climb is the same climb out of contractor prison.

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When you're trapped, almost all of your energy goes into firefighting.

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And as you grow your leadership, you build stronger people and you hand them scalable systems, and you buy capacity to think tactically and then strategically and eventually the business doesn't depend on you for its daily operation.

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And that is when you get something most owners never experience.

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The freedom to become a visionary, to stop managing today's business and start creating tomorrows.

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So here's the four levels, and the one question that moves you up at each one.

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Level one is firefighting.

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And the question is, how do I survive today?

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And level two, it's tactical.

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The question is, how do we execute better?

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Level three is strategic.

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Where are we going?

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What's our direction?

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And level four is visionary.

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Why are we building this at all?

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And here's the line that I want you to write down.

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Your business will rarely outgrow your leadership, and your leadership will rarely outgrow your thinking.

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So if you want a better business, if you want a bigger business, don't just start by working more hours.

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Start raising your level of thinking from firefighting to tactical to strategic to visionary.

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And, friends, that is where freedom actually begins.

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If today's episode helped you, don't do this journey alone.

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Join thousands of other contractors inside the Contractor freedom community@contractorfreedomlive.com and start building the business, the team, and the life you really want.

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We'll see you next time.

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About the Podcast

Contractor Freedom Podcast
Escape Contractor Prison and Live With Greater Freedom and Purpose
Contractor Freedom is the podcast for growth-minded contractors who are tired of chaos, overwhelm, and feeling trapped by the very business they built.

Hosted by Jason Phillips, owner of the multimillion-dollar Phillips Home Improvements and founder of Contractor Freedom, this show helps contractors break free from “Contractor Prison” through leadership, people, systems, and personal growth.

Each episode delivers real-world insights on building winning teams, creating scalable systems, increasing profitability, improving leadership, strengthening culture, and designing a business that serves your life instead of stealing it.

Whether you’re trying to grow your company, reclaim your time, develop leaders, or simply rediscover your purpose, Contractor Freedom will equip and challenge you to lead at a higher level and live with greater freedom and purpose.

About your host

Profile picture for Jason Phillips

Jason Phillips

Meet Jason Phillips, a visionary entrepreneur who transformed his one-man show into a thriving empire. His journey from struggle to success with a move into roofing and gutters, his company skyrocketed, earning a spot on the Inc 5000 list five years in a row. Overcoming roadblocks, he reinvented the business, achieving astonishing results. Now, he's dedicated to helping other small business owners to break free by helping them foster a team built on trust, faith, teamwork, and excellence. Join him to create "ABLE-Systems" for scalable, repeatable success and customer satisfaction. Don't let mistakes drain you; let Jason guide you to new heights!