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Freedom is what you want, freedom is what you need, freedom to do whatever the heck you please. We all have a picture in our head of how we envision freedom- being able to wake up whenever we want, go on vacation when we want without any guilt, travel around the world just because. But does this really happen for people who own their own businesses? Is it true for you, or do you find that freedom rather elusive… just over the next hill?

If this is you, then you may be in what I call “Contractor Prison”. Let’s take a closer look:

Signs that you are in Contractor Prison

  1. You are wearing a lot of hats. You’re the best or only salesman you have. You are the Chief Problem-Solver…the smartest person in virtually every area of your company.
  2. You have a hard time delegating because “no one can do it as well as me.”
  3. You spend a lot of time working on the parts of the business that you don’t like or are not good at.
  4. Worse yet, you procrastinate on doing some vital tasks because you find them noxious.
  5. You’re putting in more hours and working way harder than your employees, and you tell yourself that it’s ok because you have to “lead by example.”
  6. Your family relationships are stressed, and they’ve nearly given up on having a normal family because you are always working.
  7. You spend very little time doing any real planning for anything beyond a few days or weeks ahead.
  8. You’re making good money, but you still lack a sense of freedom.
  9. You are always the backup. When everything is running smoothly, a small business is wonderful. However, it is just not realistic to expect everything to go right one hundred percent of the time. One of the problems with a small lifestyle business is that anytime something happens, something goes wrong, or someone does not show up, it creates a hardship for the owner.

If you can relate to more than a couple of these, then you’re likely in Contractor Prison. If that’s you, definitely read on!

Take Responsibility for Your Current Situation

This is a cold, hard truth. The results you are getting are the results you deserve. The system, the way you run your business, is of your own design. For good or for bad, you built it. Accept that. Take responsibility, and know that with some help, you can fix it and be free.

Drop the Guilt

Don’t feel guilty, because just about every small business person ends up in the same boat, especially the hardest-working ones. There is really no school that teaches people how to start and grow a thriving home improvement or repair company and break free of the self-imposed chains of Contractor Prison.

Most small business owners, and especially those in the home improvement business, get their degrees from Hard Knocks University. And even HKU doesn’t fully equip you to own a home improvement business. Heck, HKU even makes the problem worse by teaching you that no one can do it better than you and that you should trust no one.

If you’re feeling guilty for being locked up in Contractor Prison, give yourself a break and know that just about everyone else does the same. Although most never make it out, buying into the lies and accepting crushed dreams as the only future options available, you can get out of it. I’m going to tell you how.

How to Get Out of Contractor Prison

Reevaluate Your Relationship with Your Business

Too many small business owners get too emotionally tied to their businesses. I get it. There’s a lot riding on the success of your business. Your house payment, your grocery bill, and even your pride. It’s your baby.

All of this may be true, but it’s time to extract yourself from that reality and switch your mindset just a bit. Your business exists to serve you. <– I wish I could make that period much larger, but I can’t, so I’ll just say it... Your business exists to serve you, PERIOD. You don’t exist to serve your business. I know, I know… you’ve got employees you’re responsible for and you really care about them and their families. Yep, but guess what…

If you closed down today, every single one of them would have a new job by month’s end. What about your wife and kids? They can’t get a new husband and father that easily, or at all. You must “right” the relationship you have with your business.

Your business exists or should exist, to provide you with the money you need to live your life, raise your family, and pursue your purpose and dreams. And it takes more than money, it takes time too! Your business exists to provide you with the time and money you need for your life.

This does not mean that you don’t care about your employees or customers. Your business should be providing great value to your customers and a thriving workplace with opportunities for your employees as well. Wins for your customers, wins for your employees, wins for you. Win-win-win. Too many times, it’s win-win-lose for the business owner and his family.

Build a Team

OK, so with the right mindset regarding your company now, you have to realize that you need people to run your company and to run it well. It’s been said that no one ever did anything truly great on their own. If you want to have a business that supports your life with the money and time you want, then you need to build a team.

There’s not enough room in this post to dive deep into team building, but if you want to build a great team, you need to become a great leader. You’ll have to realize that the bravado attitude of “I can do anything” that helped you get started is now a limitation. You’ll have to drop that and admit that you need help to build and run a great organization.

Become a Leader

If you want to succeed at building and retaining a great team, then I am going to suggest you become a lifelong student of leadership. I am with John C. Maxwell on this. Everything rises and falls with leadership.

Practically speaking, begin to read books on leadership, watch videos on leadership, attend seminars on leadership, and find a leadership mentor.

Also, you’re going to need to know what positions you need to fill. A great place to start is to simply write out an organizational chart with you at the top. Add boxes for all the functions that are needed to run your company, from marketing to sales to operations to accounting to human resources to fleet and beyond.

Write the names of the people performing those duties in the boxes. You’ll likely see your name on several or most of them. All the boxes with your name in them represent people you need to hire.

Now don’t just run out and hire just anyone. You need the right people who share your values and can and will do the job you need to be done. We’ll talk more about people in another post.

Implement Systems

You can hire great people, but if they show up with no real expectations of what success looks like, no training, no clear methods, and no sound system, they’ll end up freelancing. This happens when someone has to “just figure it out” on their own. They do thebest they  can or choose the path of least resistance to get a task done, which more often than not is not in the best interest of the company.

Freelancing by even the best-intentioned employee is problematic because he or she likely does not understand the business on both a micro and macro level. When employees make these well-intentioned decisions, they typically cost the company in either money or productivity.

You need “simple systems” that produce reliable results and are easy to train and manage. This is another topic I’ll be writing about soon, so stay on the lookout for that.

Delegate, Give People an Opportunity to Grow

When you have the right people with good systems in place, it’s time to delegate. Even when you delegate carefully, it takes trust. You have to create room for others to take over, step in, and take ownership. This is risky, and it takes trust. Remember, Hard Knocks University teaches us not to trust others.

I recently heard it said that you can either have growth or have control. You cannot have both. Which do you want? If you want to get out of Contractor Prison, you’re going to have to take some risk, trust, and delegate.

In Conclusion

If you are stuck in Contractor Prison, it’s time to get out! It may not be easy, but following these simple steps will help. Start by taking responsibility for your current situation and dropping the guilt of being a victim of circumstance. Then change your relationship with your business from one that is all about working harder to one that is truly about working smarter. I’ll share more on working smarter later, so be on the lookout for that.

Work smarter by expecting more from your business. Build a team around you so that there is always someone on call who can take over when needed and so that they will have opportunities to grow as leaders too. Finally, systemize your business processes so everything runs smoothly without any need for micromanagement, while trusting those around you enough to delegate tasks as necessary. You deserve an amazing life! No one else is going to do it for you. Get out of that prison!


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