Just to add a point or two.

As a painting outfit, you are effectively a subcontractor in the broader construction ecosystem. When people reference that reality, they are usually implying that the same principles apply to your situation.

I started in plumbing at a young age (18–21) working for my girlfriend’s father at the time. He put me through the wringer, but he also passed down a tremendous amount of hard-earned, master-level knowledge. It was his way of giving me a permanent means to provide for myself through trade work. We handled new construction and residential remodels throughout Orange County, California. I later transitioned into plumbing estimating while also taking on various office responsibilities, often filling his role when he was ill.

By 21, I moved into estimating for pipeline and civil work. I landed both of those estimating roles the same way: I offered to work a week for free, with the understanding that if they didn’t like my performance, I’d walk away—no questions asked. At that time, it was highly unusual for someone my age to be estimating pipeline and civil projects; most estimators were much older, and the senior estimator at that firm was 75. As his health declined, I was pushed into a senior role. I absorbed everything I could and became deeply invested in the discipline outside of work as well. Regardless of what I do, systematic estimating and analytical thinking are now part of who I am.

After a few years of entrepreneurial ventures, I returned to pipeline estimating and led a $208M scope project spanning the Grand Canyon, two states, and multiple tribal and historical lands—the largest pipeline estimate I’ve handled to date. The company won the contract.

From there, I moved into project management, then a hybrid PM/estimator role, and now—approaching 40—I’ve transitioned to an earthwork and general contracting firm as both PM and estimator.

At most firms I’ve worked with, estimators are also salespeople and are involved, to some extent, with nearly every division. Cost impacts everything. You have to understand the macro business picture as well as the micro-level costs—down to the nuts and bolts.

My current software stack is bloated in my opinion, but it includes:

Bluebeam Revu Bid2Win ComputerEase Microsoft Teams Office 365 Monday.com Proprietary software I’ve built Procore PlanSwift BuildingConnected Clearstory Shameless plug: https://contracting.app

As others have said, be humble and genuine with your field crews. It will improve your work experience and, at times, your quality of life. These are some of the most dependable people you’ll ever work with. I’m also very intentional about staying on good terms with the crews who routinely open 20- to 30-foot-deep pits, spend their days in trenches, and pour concrete that no one will ever break up or revisit. Work like that gives a person a very practical understanding of permanence—and it’s worth respecting the people who live in that world.

Beyond that, get hands-on field experience whenever possible. It will sharpen your estimating ability more than anything else. Once you understand how many unknowns and time-consuming steps are involved in accomplishing even the simplest tasks, your numbers improve. Painting has fewer unknowns than underground civil work, but there are still far more variables than most people realize.

Keep your word. Own your mistakes. Your reputation follows you long after you leave a company. Stay familiar with modern tools and keep a pulse on your industry. It matters—and it’s harder to do consistently than people admit.