How I Got Out of the Day-to-Day of Running a Painting Company

The life of an entrepreneur is one of excitement, action, new ideas… and no time to get everything done, let alone have much of a personal life. If you feel this way, you’re not alone. This is one of the most common challenges I find that is prevalent not only for myself but many of the hundreds of trades entrepreneurs I’ve worked with over the years. I’m going to explore some common habits we all have that trap us in the day-to-day, then give you the quickest, no BS way for freeing up more of your time.

My Life as an Entrepreneur

Since I was 18 years old, I've been running my own business. Starting in the house painting industry, I found my hands-on nature and ability to “get’r done” was an asset well suited to being a successful entrepreneur in the trades. In the beginning, working long hours was a sense of pride for me. I would often find myself bragging about my 80 hour work weeks and how you can’t be successful if you don't work hard. I would put everything I had into my business and was by far the hardest working person I knew.

Working that hard came with a ton of material success and respect from those around me. But over the years this obsession with work developed a dark side, one that many of us go through but that very few were willing to talk about. I was losing touch with reality; I lost most of my hobbies, my wife felt distant from me, and with the addition of our kids, I felt I was missing out on being a great Dad. To make matters worse, most of my staff had become used to what they called “Danny Octane." They didn't know how to be self-reliant employees without my motivation and horsepower behind them. This resulted in a noticeable plateau in the business and a general disdain for the awesome company I had put so much work into. Something had to change and quickly.

How to Get 10 Hours Back Each Week

One of the first things I needed to do was simply to get my head above water just enough to take a breath. It’s tough to make changes when your entire day is spent in reaction mode. The first step I took towards fixing this was to delegate the low hanging fruit. I'd cluttered up my week with things like doing crew moves, getting materials, setting up estimates, etc. This was taking me away from more high-level activities like ensuring our jobs were profitable, developing my team's skills, and creating company procedures and checklists. I knew I had to work more ON the business than IN it, but finding time to do so was proving impossible. Then, one day a good friend of mine gave me a simple little exercise that cleared up 10 hours a week. It was quick to implement and cleaned up just enough time that I could breathe a little in the day-to-day of the business.

Here’s that simple time-saving exercise:

  • Make a list of all the things you do in a week.
  • Circle everything that is high time consumption but low skill.
  • Decide if the circled items will be passed to your team or if this is a new FT / PT position in the company.

I found a ton of relief in something as simple as delegating crew moves to my job site managers. They were already on the site and had the ability to do it but somehow I’d never set that expectation with them. After a meeting with the painting crews and adding a few new roof racks, I had freed up 10 hours a week.

It’s funny, we spend so much time doing things a certain way, we never stop to reflect on why that is. As your business grows over time, so should your job description. What I realized after this is that every year, I should be making this list and formally injecting new responsibilities into my team. That way, in the long term I don't get caught doing tasks that are outdated for the level of responsibility my business demands of me.

Invest Your Newfound Time in Growing

With these extra 10 hours a week, I started committing one day a week to working on the business. As someone who suffers from entrepreneur ADD (Another Darn Distraction), I needed a full day of space to produce anything of value. I started watching our company numbers more closely, made a list of all the systems my business needed, and each week would take some time to implement changes. What I started realizing was how important it was to be consistent with my time outside of the day-to-day.

Before, I would spend one week between Christmas and New Year’s to improve my business and then hit the ground running again in the next year. But after making this change, I realized that slow, methodical improvements were 10x more powerful. Month after month, I was slowly getting more proactive in my approach, and my staff was learning to be more independent. After a year of working like this, I had brought my work week down to 45 hours and had grown the painting company by 35%. Looking back, it was obvious: 40 of my 80 hours a week were spent putting out fires and reacting to things. The 80 hour week that I had been so proud of was actually a symptom of my inefficiency as an entrepreneur.

With all this being said, I want to add a dose of reality. After 15 years of being an entrepreneur, no matter how much I understand these principles, I still find times where I go back to my natural state of working harder, not smarter. We’re only human and we'll all make this mistake along the way. Don’t be discouraged by this, though, take it as a chance to learn and be better in the long term. No one is perfect but if we don’t attempt to be better leaders and make time to enjoy our lives, one day we will wake up and it will be too late.

Ready To Implement?

There’s no time like the present. In the time that it took you to read this article, I’m sure you could make quite the list of activities you do in a day and start making some circles around the areas that need to change. And this is just one aspect of running a business. I have found that the keys to success for my company, and for all of our Members here at Breakthrough Academy, lie in 6 pillars.


Danny Kerr

Managing Partner


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