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What I Regret About Starting a Handyman Business

Before I spill the beans on running a handyman business…

This is why I started my own business.

I've never felt satisfied working at a job. I've gone through several positions fixing up and renovating homes, none of which pushed me to use my potential. I followed orders from a tired-looking manager and picked up the slack of other employees. I definitely didn't get paid based on the quality of work I did. Of course, this dissatisfaction didn't end at work…

After a hard day's work I would go home, eat, stare at the TV and go to bed. If I didn't pass out from exhaustion, I'd stay awake wondering if this is what my life would be until retirement. Then I'd wake up to start this routine all over again. I felt as defeated as my former manager sounded.

It was during one of those tossing-and-turning nights that I made a firm decision to end this cycle. I wasn't happy with the way things were going nor was I making the kind of living I wanted.

That's when I decided to go from employee to handyman business owner.

Making The Shift

I've spent most of my life doing home repairs, painting, fixing tiles, replacing doors and windows, and other hands-on work. I had the skills, but didn't have the business acumen. So once I put my two weeks in, I spent so much time researching and learning about how to start a business: getting organized, learning to market, hiring a team, how to price...

There is so much to learn, but it was exciting! The thought of leaving my job and doing my own thing put me in a more ambitious and uplifting mood. It took longer than expected, but it wasn't long until I was up and running: my very own handyman business was ready to go!

Know The Laws

I knew it wasn't going to be easy, but to say that I made a couple mistakes at the start is an understatement. Things you wouldn't expect cost me so much time and money.

One of the first tasks most business owners take is finding cheap advertising spaces. I started off with Craigslist. Pay a small sum to post the services you cover then and leave a method of contact for clients to reach out to you. Sounds simple and innocent, right?

Within the first three after posting, I got my first call! It was a guy who wanted a quote on a small roofing job. So I offered to come by and take a look.

When I arrived, I took a look and realized that the roof was way too big. I wasn't certified to handle an operation this big so I had to decline. That's when the guy thanked me and handed me a small slip of paper. He was actually an investigator from the contractor's board and he was giving me a ticket. I got stung. Why?

I learned that I couldn't advertise services that required a certain trade license. Even though I could perform them, I couldn't actually market them since I didn't have a license. I got scared and wondered if my business days were over. Was I meant to stay at a 9-5 for the rest of my life? It was disheartening but I didn't want to go back. I had to learn from this.

After doing more research, I learned all about the contractor's board and their laws. Turns out there are a lot of things handyman businesses can and can't do. One other key thing I learned is never to use the word 'Contractor' in your ads.

Don't Be Hasty

I knew that the only way I could stay in business was to get clients. I didn't have many and got desperate in trying to get clients fast.

When I started my business, I was so focused on getting on as many clients at a cheap rate as I could. One of the ways I heard about some handymen getting more business was by calling people. So I pulled out a Yellow Pages phone book (remember those?) and started dialing every single number on a page.

When someone picked up, I got to pitching my service until they hung up on me. For those that didn't pick up, I'd leave a voice mail and pray they'd call me back. Most of the time, they didn't. This was a painful experience. I never received so many rejections before.

Later on, I received a cold call from a stranger who was 'selling leads'. He explained that these were people who were looking for a similar service but didn't find them. He told me that I could call them, tell them I could help and get them as clients.

I thought "If they were looking for someone like me and I showed up, then that would have to guarantee clients! It's like a miracle for them!"

With too much optimism, I paid $300 for a list of about 300 names. I sent the money via a wire transfer and thought it would be legit. I waited for days but never received it. When I gave the guy a call back, his number was disconnected.

I was so desperate for work that I didn't even bother to research the guy's name or ask about his company or anything. He sounded so friendly and helpful that I bought into what he said without verifying. That was a $300 lesson I learned the hard way.

Know Your Value

I started off giving free quotes. Everyone was doing it and it seemed like they were getting business. So I did that as well and it started off well. People would inquire about the service they were looking for and I offered to take a look. My phone was buzzing and my inbox was starting to fill up with inquiries. I thought this was going well.

I spent a lot of time and effort looking at people’s homes. Then I would write up a quote for the cost of the project. The first time I wrote a fair price, the woman said that’s too expensive and rejected my service. Every time since then, my knees shook when I had to write down a dollar amount. My mind would race with things like, "What if they say it's too pricey? What if they don't want to work with me? They might find someone else." 


So I decided I would take the cost I wrote down and cut it down a bit. Then I explained to the clients about the work and how much others would charge them (the cut down price.) Then if I felt afraid they’d say no, I took that price, crossed it out and wrote down HALF that number. I also offered to do an extra service so they would like me.

You bet I got business that way. In the long run, I shot myself in the foot by doing extra, unpaid work while undercharging my services. I also got a lot of extra business doing this as former clients referred me to others as I didn't charge a lot. However, they all talked about the 'extra work' I did and expected me to do the same for them.

In total, me undercharging my services set me back $15,000 in revenue while adding another 30 hours of work a month! This was in a 6-month period, by the way.

I had to get over my fear of clients rejecting me and moving on to the next. My work was well done and clients were very happy with it. I had to charge what the projects were worth while not overworking myself.

S#*t Happens!

I remember on one occasion a family moved into a new home. It was a beautiful 2 story home and they wanted the paint job redid in the living room and the kitchen. In the living room, they had a large flat-screen television attached to the wall. It looked expensive and I told myself several times that I had to be very careful with it and stow it somewhere safe.


Before setting up the sheets and the paints, I went to move the TV. When I saw it from afar, I thought it was light and would be an easy move. It wasn't until I unplugged the wires and picked it up did I realize how heavy it was!

I was so focused on not breaking the TV and placing it in a safe corner that I didn't notice the folds in the sheet in front of me. It wasn't even three steps forward before my foot tripped over the sheet. I face planted onto the floor and split some paint all over the television.

Prepare As Much As You Can

I remember scheduling to meet with a client at his home in the afternoon. It was a roof repair and I didn't expect it to take anymore than an hour or so. Mind that this is taking place in the middle of summer. If you know anything about repairing a roof during a summer afternoon, then you know it is hot and dangerous.

1:30 PM on the dot and it's at least 95 degrees Fahrenheit. The roof is blistering with heat and I'm wishing I didn't agree to this at such a time.

Another thing about the summer is that thunderstorms like to come unannounced sometimes. Not even 15 minutes later and the skies grow dark and I haven't finished. I have to get down, pack up the equipment and wait for the storm to pass so I can finish this roof. Once I get down from the ladder, the sky roars with thunder and I need to get into shelter.

The rain is pouring, the wind is howling, and I'm watching my poor equipment take a beating. Everything's getting thrown all over the place and it's wet. 5 minutes later, the storm ends and the sun comes back out. I have to get my equipment together and fix the roof again. When I step onto the lawn, it's all damp and muddy. Then when I look at the roof, the initial damage looks even worse!

We can't always predict the weather or the circumstances around our work. The best we can do is prepare as much as we can for any worst-case scenario. In this case, checking the weather channel and bringing a tarp to cover the vulnerable roof.

Reflecting On My Mistakes

I made a lot of silly accidents over the course of my handyman business. Some of these happened as a newbie and others through my own carelessness. The important lesson is that I learned from every one of my mistakes.

I learned the regulations and rules set by the contractor's board. I never took an offer or did business without researching prior. I understood the value of my service and didn't shy down from asking for a reasonable price. I also strengthened my awareness and learned to prepare for any bad situations.

In a way, my business also helped me become a better person. It forced me to go outside my comfort zone and do things I wouldn't have done.

Every one of those mistakes taught me something important that I needed to know. Not only how to succeed in my business, but how to prepare for the worst, face my own insecurities and see my blind spots.

I never would've come this far if I didn't take the jump to quit my job and pursue what I wanted.

What Do I Regret?

The easy answer is nothing. I don’t regret anything from the start until now. Everything that happened served a purpose and made me a better handyman and a business owner.

Looking back, there are only two things I wish I could change.

One is getting paint all over the nice family's TV. That was pure carelessness and I still feed bad to this day, even though I reimbursed them for the damages.

The second thing is not hearing about these Indestructible Shoes sooner!

I've spent years wearing Timberland boots and crusty old work shoes that were heavy and tore up quick.

These shoes are so much sturdier and are lightweight. Plus, I've dropped tons of things on my toes and if it weren't for the steel toe, my feet would be done for!

I recommend these for handymen or any workers who spend a lot of time on their feet!