Lessons from getting a house painted

Over the last week, I received an object lesson in how important trust and honesty are when you are a freelancer. I contracted a local fellow to paint my home and the experience has been less than satisfactory. But it’s been a great reminder and learning opportunity.

The job I needed done was painting of all my home’s living areas and the master bedroom. I was going to hire a family friend (an experienced painter) but decided to use a local guy in order to support my local community.

What were the problems?

  1. He under-estimated the complexity of the job and how long it would take?
  2. He over promised initially
  3. He under-quoted the price
  4. He kept making promises of when he’d be here
  5. He pulled out of the job before it was done, leaving me to clean up the mess


All of these are challenges I’ve seen before from inexperienced freelancers and contractors in many different fields.

In our keenness to take on more work and generate more revenue, it’s tempting to say “Yes” to every job, thinking we can hit any deadline at a high quality. And we can often overestimate our own ability when taking on a task that’s more complex than we’re ready for.

One of the key skills all freelancers need to develop is sound estimation skills. It’s something I’m constantly honing but being able to accurately assess how complex a job is and how long it will take is key. Without that skill, it’s difficult to ensure you can generate your desired revenue.

Sound project planning is also important when taking on large jobs. I’ve already shared how I plan my week. But the weekly plan is based on knowing what work I have ahead of me. In project management parlance, what I’m talking about is a work breakdown structure. It looks like this.

You start with the big black of work and then break it into smaller chunks until you end up with individual tasks. Then you can estimate the total time and therefore what to charge.

Of course, the task could be broken up in different ways. In this case, it might have been easier to do all the ceilings in one go and then come back and do the walls room-by-room. Either way, the aim is to under stand what needs to be done and how long each piece will take.

There are other ways to estimate how long a job will take and these vary depending on the type of job and what system you prefer. But, by being able to properly estimate how long a job will take, you can save you and your clients lots of pain.

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