8 Awkward Questions Freelance Web Designers and Other Freelancers Face

We freelancers sometimes get asked the oddest things. Some of the questions are odd, and some are awkward to answer. You have to wonder what people are thinking.

The sad truth is that a lot of people don’t think. So, they blurt out awkward questions and leave us to respond.
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In fact, it seems like I get odd and awkward questions nearly every week. You probably do too.

In this post, I’ll share some of those awkward questions with you. At the end of the post, feel free to share the odd things you’ve been asked, along with your response.

Question #1: What Do You Do All Day Anyway?

Ouch! That stings.

This hurtful question usually comes from those who mean the most to you, but still don’t get what freelancing is all about. Expect to hear this from your friends, random relatives, and neighbors.

The sad thing about this question is that some of these people will never understand. You could spend hours explaining your field to them and they would still think that freelancing is just your way of saying that you are unemployed.

If you get this from someone who should know better, someone who you’ve already talked to about your freelancing, it’s sometimes best to pretend like you didn’t hear the question. An alternative is to start listing every project you’ve worked on in the past three months, providing as much detail as possible.

Question #2: Can You Volunteer for [My Pet Cause]?

Yikes. This questions is even worse than the first one.

Your time is valuable and, in fact, spending your time on client projects is how you earn a living.

The people who ask this have already answered question #1 in their heads. They’ve decided that you aren’t really doing anything and should therefore be available for volunteer work. They may even think they are doing you a favor by getting you out of the house.

When I get this question, I usually don’t give many details. I just say something like:

“I’m sorry. I can’t help you because I have to work.”

If they are persistent and try to insist that I help them on a specific day, I sometimes add:

“I have a client deadline to meet on that day, so there’s really no way I can help.”

Since you’ve used the work lingo with them, that’s often enough to make them back off.

Question #3: Can You Review My Work for Free?


We joke about freelancing not meaning that we work for free, but there must be some people out there who really believe that it does mean that. At least, the inquiries I get about doing free work seem to indicate that.

These folks are often sneaky about their requests too. They often don’t indicate that they want free work in their initial contact, so I wind up treating them like a client. That means getting the details of the project and preparing an estimate (a process that can take several hours).

Usually, it’s only after I’ve quoted a price that they come back and say something like,

“I really don’t have a budget for this.”

Then they go on to give the reason why they think I should work for free:

  • Good exposure
  • To help a fellow freelancer
  • They’ll have work for me in the future
  • Their project is important

And so on, and so on…

Guess what? Every one of those reasons is bogus. What nerve!

This is where you have to stick to your guns about not working for free. (Unless, of course, it’s your mom asking for the free work. In which case, you might want to do the work anyway.)

Question #4: Will You Tell Me The Names of Your Best Clients?

The next sentence usually reads something like,

“I want to work for them too.”

When this first started happening, I couldn’t believe the nerve of some people. I always feel like saying,

“Find your own clients.”

Then I realized that so many freelancers are used to getting gigs from bidding sites and content mills that they think all freelancing work is like that. They don’t realize that most successful freelancers work for private clients who never use bidding sites or content mills.

In contrast to mills and bidding sites, most private clients don’t hire a small army of freelancers. At most, they need a handful. Many only hire a single freelancer.

Once in a great while a client will let me know they need an additional freelancer and they’ll ask me to recommend someone. When that happens (and it doesn’t happen often), I typically give the name of someone I’m very familiar with. I never give them the name of some random freelancer who contacted me out of the blue.

If you’re looking for work rather than ask a freelancer the names of their clients, try reading one of the many posts about finding work:

Question #5: Will You Hire Me?

Somehow, this question always comes from someone who I’ve never heard of.

The truth is that it’s pretty rare for me to hire other freelancers, web designers or otherwise. I’ve done it, but not very often. I’m not an agency, I’m a solo professional and that’s how I work on most of my projects.

When I do partner with another freelancer, I always turn to someone on the short list of freelancers whose work I am familiar with and who I trust.

If you’re serious about working with another freelancer, take the time to build a relationship with that freelancer first.

Question #6: Can I Promote My Stuff on Your Blog?


My first reaction is,

“You’ve got to be kidding, right?”

But they aren’t.

For some reason, people always want to announce their product/book/business on my freelancing blog. And they want me to do it for free. They totally miss the point that my freelancing blog has a purpose already, and that purpose is not to promote them.

There’s another word for promotion. It’s called advertising. If you want a freelancer to promote your product/service/etc. on their blog, the best way to ensure that happens is to buy an advertisement.

Question #7: Will You Review My Software/Book/Etc.?

This question probably should have been #1. I probably get more requests from people and companies wanting me to review things on my freelancing blog than anything else.

To be truthful, I do sometimes review things on my blog. They are mostly things that I am already interested in or things that I think will interest my readers.

There are many reasons why I don’t review things more often, though:

  • Time. It takes a lot of time to review something. If it’s a book, I have to read it. If it’s software, I need to play with it.
  • Popularity. Reviews tend to be unpopular posts. Even though I don’t accept money for them and always disclose any relationships, I think readers assume I’m selling.
  • Vendor demands. I tend to be honest in my reviews, and some vendors don’t like that. What they’re actually asking for is not a review, but an endorsement.

So, as you can see, asking for a review is a big deal. I can’t review everything I’m asked to review.

Question #8: What’s the Quickest Way to Start Earning Money?

Usually, the unspoken part of this question is,

“…without much effort on my part.”

The answer is not one that most of the questioners like to hear. There’s really not an easy shortcut to freelancing. It takes time and a lot of hard work to build a successful freelancing business. At first, you may not even be able to support yourself with your freelance income.

No matter how many times I get this question, the answer is always going to be the same.

Your Turn

What awkward questions do you get about your freelance business? Share your stories in the comments.

Vandelay Design Blog

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