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A Day in the Life: Jessie Cannizzaro | Family Handyman

January 9, 2024

By Rebecca Wright Brown


A master plumber who owns her own business, Cannizzaro talks to Family Handyman about her journey and career.

Jessie Cannizzaro, 42, is a master plumber who owns Milestone Plumbing, Inc., a residential and small commercial plumbing company in Wauwatosa, Wisconsin. She’s been in the industry for 19 years. As the owner of a small business, Cannizzaro fills many roles and, she says, “wear[s] a lot of hats.”

Cannizzaro didn’t originally plan on becoming a master plumber, like her father. When she was younger, she wanted to be a veterinarian or a surgeon. I always swore I would never follow in my father’s footsteps,” she says. “But here we are, all these years later, and I’m so happy that I did.”

How Did You Get Here?

With a master plumber father and a mother who worked alongside him and handled the books, Cannizzaro was well versed in the industry at an early age. She even went along on jobs during weekends and summers.

The first in her family to go to college, she planned on taking an office job once she graduated. But she found she missed working with her hands and puzzling out solutions, so she leaned into some of the things she loved as a child.

“From a very young age my mom demonstrated that the construction industry was something that women could do,” she says. “[She] was never a licensed plumber, but incredibly knowledgeable about what she assisted my dad with for all of those years.

Cannizzaro started her journey in plumbing by working for her parents’ company while finishing her degree in business administration at the University of Wisconsin-Milwaukee. When her dad had a stroke and her mom went back to nursing school, she stepped in to help. She assisted her mom with the paperwork and went on jobs with her dad.

She worked with her father for a few years before he retired from full-time plumbing, though he still does occasional jobs for his longtime clients. He turned 80 this year and still goes out on a couple of calls a week.

Cannizzaro completed her apprenticeship with another company while pursuing a master’s degree in business, also at UW-Milwaukee, at night.

Eventually, Cannizzaro decided to combine her plumbing experience and background in business by launching her own company As she wrote the business plan, she set a goal to launch prior to her 30th birthday. On June 1, 2011, two weeks before turning 30, she launched Milestone.

Highs and Lows

Cannizzaro’s path has been full of ups and downs. She says she wouldn’t change a thing though it was stressful at times, which really helped her grow.


Cannizarro is especially proud of providing career opportunities and adjusting the public perception of the industry in general. Cannizzaro pushed back against the notion that construction and plumbing are for “the kids that couldn’t cut it.” Rather, these are vital industries that take lots of dedication and hard work to succeed in.

“Many people do not realize that the primary responsibility of a plumber is to protect the public health,” she says. “Without following the codes that have been put in place, the public would become very sick.”

To become a licensed journeyman plumber, Cannizzaro needed five years of schooling and on-the-job training. Achieving master plumber took an additional three years.


One of the biggest challenges Cannizzaro faced was “establishing credibility in a very male dominated industry, especially in the beginning.” Her advice for others facing similar struggles? “Focus on working hard and doing what you say you are going to do,” she says.

Cannizzaro also needed to develop her time management skills. Running her own business involves constantly juggling commitments and responsibilities. She tackled this by taking a few minutes each morning to lay out the plan for the day. This helps her easily keep track of everything on the docket.

Cannizzaro also spoke candidly about how her desire to “have it all” impacted her personal life. She waited to start a family. “[It] provided the most amazing two blessings that I could have ever asked for,” she says, “but also massive heartbreak as we lost three babies through miscarriages in between both of my boys.

“I buried myself in my work so I could be numb to what I was going through. which was not healthy, but was my way to cope with the heartbreak and feelings of failure that each of those losses brought.”

Favorite things

Cannizzaro couldn’t pick one favorite thing because there are several rewarding aspects of her work. She loves the teamwork and variety that comes with working in a small business. “No two days are ever the same, which makes it very exciting!” she says.

She also loves that her work helps people and has a lasting impact. Client reviews are incredibly important. “We actually read reviews and emails during our weekly team meetings to celebrate our wins,” she says.

Cannizzaro also enjoys volunteering in her community with her team. They visit schools to educate kids about the opportunities in the trades; serve time in leadership roles for non-profits in their industry; teach kids basic plumbing skills; and advocate for the trades at the state level.

“I truly enjoy helping people and believe that plumbing is a great opportunity that is often overlooked,” she says. “I get to be an advocate for a great trade while taking care of our clients and helping improve the lives of our team.”

A Day in the Life of a Master Plumber

Because there is such a variety in the jobs Cannizzaro takes, no two days look the same. She loves this about the industry. Each day is a unique mix of jobs and challenges that keep things interesting and engaging.

For those looking to break into the industry, Cannizzaro recommends hands-on experience and a diverse skill set. “Each trade has so many different levels and opportunities,’ she says. “You really need to explore the trade you decide to pursue in depth to find what you are most passionate about.”

Using plumbing as an example, she lists out the major levels — residential, commercial and industrial. Each has further layers — new construction, remodeling, service and repair.

To get that experience, Cannizzaro suggests looking for opportunities to interview companies or shadow someone on a job. “Exploring as many areas as possible will help to ensure you find what you will enjoy most,” she says. “Put the extra effort in on the front end to ensure you are in a field that you will truly enjoy for your career.”

Five Things She Learned

We asked Cannizzaro to tell us five things she’s learned throughout her career:

  1. Do the right thing, no matter what. This has been something that really challenged me as a leader these last few years. It will take more effort, but having a clear conscience and standing up for what you believe in is worth it.
  2. Surround yourself with great people. One person cannot possibly know everything there is to know. Having a great support network can provide an immense amount of support, both professionally and personally.
  3. Never stop dreaming. It’s so easy to get wrapped up in the mundane day-to-day items. Find something that inspires you and make sure it’s part of your plan. This is where I was able to find my passion in our trade.
  4. Always look for ways to help and take care of others. I always look for things that I can do to positively impact on others — sometimes without them knowing. I have found that the more I do this, without expecting anything in return, the more rewarding my life has been.
  5. Figure out what you want your legacy to be and build your career around that. For me, it’s always been that I wanted to leave our industry a little better than I found it. It comes from a story that my dad used to share with me when I was little. He told me that if you borrow your neighbor’s wheelbarrow, you should return it better than it was given to you. I have looked at everything that I have borrowed or been involved with that way ever since.