Being a painter may seem mundane, and that may be true for commercial painters; however, I was really intrigued when I spent time with a high-end entrepreneurial house painter named Massimo. Massimo has a general business degree and grew up with seven painters in his family. He started off doing commercial painting because that is the easiest way to do an apprenticeship, and then started his own business. Massimo puts his heart and soul into the quality of his painting during the day and is very attentive to the smallest details. He takes pride in his painting and does an unbelievable job.

Massimo goes up and down ladders using upper body muscles all day. His work is physically exhausting and he says that he notices it at night when his body “shuts down.” Unfortunately for him, being self-employed also means doing the scheduling, price estimates, and administrative work himself so he isn’t done after a physically demanding day of painting. He does get to listen to sports and talk radio all day, though—that’s pretty sweet. 

The good part of starting his own painting business is the relationships that Massimo builds with his clients and their families. He has the trust of his clients and really enjoys working for them. Also, being self-employed means setting his own hours, which Massimo says is great for his lifestyle. 

Cool Fact: Massimo painted the outside of the Royal Trust Tower in his twenties while being suspended tens of stories off the ground (it still frightens him).  

A Typical Day

A painter has similar days throughout the week. The painter I shadowed does 1-2 jobs per day. A typical job includes preparing the walls, priming the walls, and painting the walls.

Top 3 Perks

1) Can be self-employed 

2) Being active and outside sometimes 

3) Building relationships with clients  

Job Culture

Indoors and outdoors, physically demanding, moving objects, operating equipment, using formulas to mix products, face-to-face discussions, job autonomy.


1) 2500 hours as an apprentice (3-4 years) 

2) Write an exam to become certified 


- Take chemistry in high school to understand the chemical properties when mixing paints, for safety. 

- Receive a Red Seal certification to work in other provinces.  

Skills Needed

Artistic, precision, care, athletic, customer service, administrative, steadiness, near vision, cooperation with other trades.

The Field

- Paint companies keep on reinventing their products so it is hard to keep up with the new formulas and paints. 

- The paints these days are harder to work with because companies are producing cheaper products. 

- Commercial painters have been struggling because of the economy but high-end house painters have steady referral business.