By nature, contractors are independent. We have to be, or we’d never have the urge to fire our boss and start our own businesses.

By nature, we’re confident. We have to be, or we’d never be able to risk almost everything to gain the opportunity to have freedom, a bigger income, and more fulfillment in our work.

By nature, we’re proud of the skills we have that allow us to do the work of the trade, our ability to accept and excel at the challenges life throws at us, and our companies.

By nature, we’re tough. We have to be, or we’d just give up. Issues with employees who lose their driver’s licenses because of late child support payments, the IRS suddenly deciding you owe an extra $5,000 for penalties, insurance companies jacking rates 25 percent for no apparent reason, and customers who couldn’t be satisfied even if you did their work for free and tied it all up with a huge red bow would overwhelm us.

By nature, we’re stubborn. We have to be, or we’d just give in when customers call us at 2 a.m. to relay the news of their latest emergencies that have to be taken care of right away. In that moment, money’s no object. Though, afterwards, the customer decides the emergency wasn’t that big of a deal after all and proclaims we way overcharged them.

By nature, we’re forward thinking. We have to be, or we’d get so stressed about the issues right in front of us.


We need to be constantly learning. We’ll never know everything, and we’ll never have the perfect business.

We need to be focused on the right things. Our decisions will never be the right ones if we don’t have the right information to base them on.

We need to be flexible and able to change. We have to be able to change how we do things as we learn new and better methods. When our customers want changes, if we can’t give them what they want, they’ll find someone who will. Technology changes; if we’re not careful, we’ll be playing eight-track tapes in an MP3 world. If you don’t understand that sentence, ask your dad or grandpa.

We need to be able to rely on our employees to take part of our workload. Contrary to popular belief, we can’t do everything.

We need to be able to know when to, and have the desire to, ask for help when we are out of our depth. No one knows everything. There are answers to everything we need to know if we just look for them.

We need to be knowledgeable enough about the numbers in our businesses to know which way to jump when issues come up. Your P&L and balance sheets aren’t black magic, kryptonite, or deep arcane knowledge. They aren’t actually all that complicated and can give you tons of helpful information.


Are you seeing the conflict here? Almost all the strengths we have that allow us to survive as small contracting business owners are also our greatest weaknesses.

Our independence conflicts with almost every one of the items listed above. We don’t need others’ help. We can do it by ourselves.

Our confidence allows us to make decisions and stick with them. We move forward, knowing we have what it takes. Even if — as is usually the case — it’s based on our gut feeling, which is frequently not the right thing to base decisions on.

Our pride, as small contracting business owners, makes it really hard to admit we don’t know everything. It’s hard to humble ourselves and reach out for help. What if someone learned we have actual weaknesses in certain areas?

It may be difficult to endure the fallout from our bad decisions, but, as tough as we are, we can deal with it. We can fight our way through issues with employees, vendors, cash flow, and the IRS. Of course, if we were a little less tough, we could figure out what the issues were before they became big and solve them then.

Our stubbornness tells us we don’t need help. We don’t need to change, they can just change to suit us. We have a hard time going back on bad decisions we’ve made. If we make what turns out to be a bad decision, get questioned about it, and go ahead with it anyhow, we’ll stick with it no matter what — even after it’s obvious to everyone but us that it’s a disaster.

Our forward thinking allows us to think about the future and all its awesomeness. We can see it out there shiny and bright. Unfortunately, we have to deal with the present. We often don’t do this well. It’s much easier to ignore the day-to-day stuff and go back to work — until the little things become big things, and we can’t ignore them anymore.


As proud and independent as contractors are, we don’t need help figuring out what we should base our decisions on. We’re so tough that we can make it through the resulting aftermath time after time. We’re stubborn enough that we can’t admit there might be a better way.


Boiling it down to its most basic, success in a small contracting business requires a mindset change: Understand that doing the work of your trade is only a part of what needs to be done. Business success is a long-term investment. You’re not going to get rich overnight. Business requires that you take every part of it seriously, because every part of it, if not taken care of, can bring the rest of the business down. Reach out for help. There are lots of resources out there that can help you avoid burnout and eventual failure, which is the end for lots of contractors who don’t break the cycle.

Let me know how I can help.  

Publication date: 8/28/2017

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