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The art of extending freelance projects

Landing clients can be a challenge, but once you get over the hill know as pre-freelancing and land your first client, you begin to see the light.

You land a client, then land another, followed by another. Your portfolio is starting to expand. More clients are reaching out to you in hopes of bringing you aboard.

Life is good.

Then you begin to realize that jumping from project to project so frequent can be a little exhausting.

At this point, you should start to question the duration of your projects.

Short term is great when starting out. It helps you get your foot in the door of the vast freelance world. It also beefs up your portfolio enough to attract new projects.

Longer terms projects begin to get more and more appealing for some obvious reasons.

  • Manage your availability better
  • Worry less about being between projects
  • Establish long-term working relationships
  • Allows you to “get into a groove” opposed to “get up to speed”
  • Stabilize income for the foreseeable future

Needless to say, long-term projects are needed in order to maintain your sanity (well, what’s left of it) while freelancing.

Let’s get into some ways to extend your projects so you can keep your remaining sanity.

Ask regularly about remaining work

I’ll go ahead an just say it. Projects never end when they are supposed to. Period.

I have yet to be on a project (and I’ve been on MANY) where the initial ask from the client met the what I actually delivered. Same goes for the time frame, on a good project it usually extends a month or so past what was initially requested.

97% of the time, it was at the fault of the client. With that said, I never fault the client, I usually don’t mind projects going past their desired time frame. After 15 years of freelancing, I plan for it.

I accept that it will always be something that prolongs a project. More importantly, it’s critical to be mindful of the actual project end date opposed to the desired.

By asking the client about remaining work, it will bring to their attention that the project is being extended, even unintended.

This is a cheap win as you’re extending the project by allowing the client to see they’re extending the project. The desired end date is now moving closer to the actual end date. Congrats, you extended the project without asking to extend it!

Keep asking for more tasks

Don’t wait until you’re done to ask for work. Ask for more tasks often, seriously, pile those tasks up until the client can no longer think of anything.

You can never have enough tasks. Even if you’re swamped with work, make a habit of asking for more.

Keep in mind, just because you have a few dozen tasks, doesn’t mean they all need to be completed all at one time.

Unpopular opinion: Multi-tasking sucks. It’s a myth that it makes you more productive, just like open floor plan offices. Please don’t do it. Single-tasking allows you to focus and deliver quality work that will keep your client pleased. Don’t deliver sloppy multi-tasking induced work.

The key of piling up tasks is to make sure you are managing them properly, or everything can blow up in your face. Have you ever tried to go outside and catch a squirrel or rabbit? I hope not because you will most likely fail and embarrass yourself. This is the same feeling you’ll get if you fail to manage your tasks.

It’s many ways to manage your tasks. It’s also a plethora of ways to handle them poorly.

Don’t use email. Don’t use a word doc. Don’t use a spreadsheet. Not only are these not made to do what we need to do.

Use something more structured, like Trello (or something similar)

Trello provides a few things we need

  • A high-level view of what you need to do, what’s in progress and what needs to be done
  • Each task has it’s own comment thread (like a Facebook post)
  • Seamless collaboration with you and the client
  • Single location for info related to your tasks

I would argue the most important in that list is the commenting per task. Each task should have a private conversation going. Anytime it’s a question about a task; it should in the comment section for that task. Whatever you do, don’t rely on emails for details on tasks.

Once you have Trello setup, pile those tasks sky high. Your “todo list” should have at all times a minimum of a dozen tasks. Don’t be afraid to triple up. While they list grows, be sure to over-communicate what’s in progress and what you completed.

Pro-tip: The better you plan out the delivery of your tasks, the better you have an idea of the actual end of the project. It may sound bad, but you should have a better idea of the end of the project than the client. Just like your mechanic has a better idea on how long it will take to replace the engine in your car than you do. Don’t forget you’re the expert here.

Ask for more insight

A freelancer can be brought onto a project for many reasons.

In some cases, you come aboard to complete tasks and help out. You’re given tasks, you complete them, you both go your separate ways. Simply put, you’re given instructions.

In other cases, you’re brought onto the project to lead others and/or do some critical problem-solving. In these cases, you’re given direction.

Whichever group you fall into, try to get as close as possible to the decision-making process that led to those instructions and directions.

If tasks are just given to you without any context of where they come from and why you’re doing it, it may be safe to say you’re far from the decision making. We need to change that and get “closer”.

Make a habit of asking how and why more.

  • How did we decide we needed to use XYZ?
  • Why did we take this approach opposed to the XYZ approach?
  • Why are we using XYZ opposed to ABC?

While asking these types of questions, it starts conversations about the decisions made. When these conversations happen, the client will most likely give you an explanation.

Now that you have more context on why decisions were made, it’s time to be proactive and ask to be included next time.

It can be as simple as:

“Thanks for explaining, this helps me have a better idea on how to approach my work, mind including me more often?”

If they say yes, be prepared to get up to speed as quickly as possible to contribute as soon as possible. If the project is nearing an end, you may want to move fast on this.

If they say no (which is uncommon from my experience), they’re now aware you want to be more involved in making sure the project is a success.

From a client’s perspective, it’s usually not much harm to get opinions from their freelancer. Especially if those opinions are from the person doing the actual work (that person is you!).

Fun fact: This is why it’s so important for large companies to survey their employees. It’s valuable insight that shouldn’t be ignored.


It’s fun to read a helpful article, and it’s even more fun to take action! Reach out to your client right now and ask about upcoming work because you’re trying to plan your bandwidth.

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© freelance after five 2019
no gmo's, gluten or themes were used in the making of this!
by @FreelanceAfter5