Choosing the Big Questions for Enhanced Freelance’s Videos

What makes a question a ‘frequently asked question’? Is there a certain number of times you have to hear it before you know it’s a standard question in your particular topic area?

Jen Stakes Roberts and I made a series of videos answering common questions as a promotional piece for We knew that we wanted to answer common questions that freelancers regularly face in a way we could easily link back to our site. But picking out the questions to answer was not the simple matter you might think.

We’ve chosen a very targeted audience: freelancers who have been in business for a while but have somewhat stalled in going forward. There are definitely common questions that we hear a lot, but not all really tied in with what we’re working on for the site. For instance, it’s not unusual for someone in the market we’re targeting to have some very important questions about tax laws — but that’s not a big focus for the site. Since we work with an international group of members, a video about taxes would have been hours long to cover anyone and I would live in fear of giving someone the wrong advice for their locale.

We also wanted interesting questions: it’s not always that easy to keep a viewer’s interest for the entire length of a video, at least online where there are so many other options. Interesting, at least in this context, means something that the audience wants to hear about. While sex and drugs seem to work for tabloids, things don’t have to be quite that exciting to still be interesting to a particular audience.

The questions we chose are ones that we’ve gotten in several different contexts. I have a bit of a leg up on this particular situation: I’ve done numerous agony aunt columns for freelancing sites, giving me a very clear picture of not only the types of questions that freelancers have, but what stages of a freelance career bring those questions into focus. If you don’t have a stock pile of questions sitting in a dusty corner, however, there are two starting points that I would suggest: Quora and LinkedIn Answers. Just read through the questions that appear regularly in the category you’re considering writing or talking about. You’ll get a quick snapshot of what people find confusing right away. It would be ideal to do more research, of course, but that isn’t always possible.

For our promotional piece, we chose five questions:

  1. How much time does a freelancer need to spend on social media?
  2. What should you do a client asks you why your rates are so much higher than an automated service or a freelancer based overseas?
  3. What should you do about protecting projects from people who might steal them?
  4. What should you do when you’ve got more work than you can handle?
  5. How can you find ways to keep earning more money as a freelancer?

I’ll admit that at least a couple of these are what I would consider personal soap box issues — I have strong feelings about the answers and data to back them up. That makes it a lot easier to write up a script and film a response that sounds natural. But that’s only a last-step filter for choosing what questions to use when you’ve already got several options. And, hopefully, you’re working on a topic that you’re pretty passionate about in general and have lots of opinions anyway. If you aren’t and you’re trying to establish yourself as at least enough of an expert to answer standard questions, you’re probably going to have some problems.

In Short:

If you want to find the big questions in your niche (for marketing efforts or otherwise), start by eliminating topics that you can’t easily answer in the format you’ve chosen. Look for interesting topics that can hold attention. Look at places that regularly post questions for a starting point.

And enjoy our first video:

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The Next Level of Freelancing: Enhanced Freelance

The Short Version

I’m launching a membership site today for freelancers who want to up your game. This is a soft launch: for $7 a month, you get to be a charter member and guinea pig. You get to see what I’ve already worked up and tell me what else you need to succeed. I’m limiting this soft launch to one hundred freelancers. Once it’s full, you’re going to have to wait a couple of months to get in and pay dramatically more than $7 a month.

You’ve got my personal guarantee that if you put in some hours on what I’ve got for you, you can make significantly more as a freelancer. I’m not going to say how much, because everyone is different, but it will be more than enough to cover the monthly cost of membership.

Go to Enhanced Freelance and sign up now.

The Long Version

Depending on how you found me, you probably know that I’ve written a lot about freelancing for different sites, like and I even write the ‘Ask a Freelancer’ column on All that advice adds up to a few drops in the bucket, though, and there’s a need for a comprehensive resource on building up your freelance career beyond the basics.

You don’t need a coach or teacher to tell you how to write an invoice or actually complete a project — you need clues on the balance between cheap and effective marketing techniques, step by step instructions on creating an newsletter that turns clients into raving fans and the shortcuts to keep your projects manageable. That’s what EnhancedFreelance is. It’s full of advice from my experience and other freelancers I’ve brought in. It’s a community where you can bounce ideas off one another. It’s the resource you need to take your freelance business to the next level.

Why Me?

First of all, EnhancedFreelance is actually a joint effort. I’ve shanghaied Jen Kentmere (freelancer and project manager extraordinaire) into this project. Jen has injected some of her British flair into the site, as well as kept us on schedule.

I didn’t set out to be an expert in freelancing. But after just a few years of freelancing full-time, I can show you an inbox full of questions about the nuts and bolts of working for yourself (and actually making real money in the process) that I’ve answered.

I’ve been utterly devoted to making my freelance business successful since shortly after I graduated from college. I wanted to avoid being that freelancer that lives in her parents’ basement or has to go to the icky clinic — you know the one — for health care. And I’ve succeeded. I do pretty well for myself and the half dozen contractors that work for me at this point. I’ve got health insurance, a nice house and even the monster of a truck that I’ve always wanted.

It’s not because I’m a better writer than most of the freelancers out there. Heck, I can see plenty of holes in every single thing I write. It’s because I think in terms of business and I’m always looking for an edge. I grew up around business owners and I want to make money even more than I want to write regularly. I’m certainly not suggesting that you should be the same way, but you can take advantage of my willingness to try every marketing strategy at least once, along with anything else that can help me with my freelance work.

So snag a seat at Enhanced Freelance if you are ready to up your freelance game.