Changing Your Career in 2021

Define the Terms Ahead of Time

Avoiding Burned Bridges: Don’t get caught up in scope creep or late payments — figure it out now!

Illustration: Piya Willwerth

It happened. Your cousin needs that website for their auto shop. “Cool,” you said. “It will be easy,” you said. After all, it’s just a brochure site, with a contact form, an “about” page, and a short description of the kinds of cars they specialize in, right?

One absorbing weekend later, you’re putting the finishing touches on it … when your cousin calls and says that he talked to the boss, and the boss thinks that it would be “really great” if they could also sell some stuff on the site, like motor oil and anti-freeze. “Just simple stuff, right? Thanks. Oh … and could you also set up a scheduling system so that customers can make appointments online?”

I beg your pardon

When I was younger, someone told me that I should say yes to everything, and then figure it out later. That’s still true … ish.

When you should say yes

  • If you can do these things and charge them for it
  • If you can do these things, charge them for it, and you need the work

When you should say no

  • If you don’t know how to do these things
  • If you aren’t getting paid that much
  • If you know they would be surprised or upset to learn that it would cost more
  • If you have other jobs on the horizon and you don’t have time for this
  • If you don’t have other jobs on the horizon, but you were planning on hunting for more work and this would get in the way of that

There are a lot more reasons to say no than there are to say yes, and it’s for your own protection and sanity. And if you were smart about it, you already got half your money up front.


The general rules hold true for smaller OR larger projects.

  1. You should charge per project. Calculate approximately how much time it will take you to do, and apply your hourly rate. (Don’t know what your hourly rate should be? Check out this amazing calculator!) Give them the total number. Don’t forget to include anticipated meetings, phone calls, and revisions. Speaking of revisions …
  2. Revisions should be included in the contract. Decide on a number. One or maybe two should suffice, depending on your line of work.
  3. More revisions will be charged for at your full hourly rate. Make sure this is in the contract.
  4. Make sure there is a written agreement, even if it’s just a deal memo. You want to get this stuff in writing. The good news is that it doesn’t necessarily have to be in legalese to be binding!
  5. The simplest payment scheme is to get half your rate up front, and half upon completion. Some people set milestones and break the payment down into thirds for bigger projects. You should be getting something up front, though. No deposit, no work. Do not do work on spec.

“Yes, and …”

I love “Yes, and.” Most people know it as an improv comedy rule, but it also works for the kind of soft-skill client wrangling that we all have to get good at, if we want anyone to speak to us again. Has your client asked you to basically recreate the Facebook website for them? That’s a “Yes, and” … even though it’s clearly a no.

Let me explain: People don’t really like hearing the word “No,” even if they understand the reasoning behind it. They feel the negative, even if it is 100% correct. So when you’re saying “No,” you could also say something like:

  • I’d love to help you with this, but there are already ways to do what you’re asking. For instance, you could do this on Facebook.
  • I see what you’re saying! Let me refer you to someone I know who can help you with that.

I remember reading somewhere that the words that are used matter, greatly. So if the phrasing is positive and open, you’re more likely to get a good result, even if you’re technically turning this person down. It matters even more if you think that this contact would lead you to more work in the future. It’s the difference between “No” and “I can’t help you with that right now, but I’m open to other stuff in the future!”

Don’t fall for the oft-repeated notion, “The customer is always right.” You need to get that notion out of your head. Otherwise, why are you starting a second career? I thought you wanted to be your own boss? Part of being your own boss is being able to set your own boundaries. Define those, and you’ll be avoiding a lot of time-consuming, confusing situations.

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