The biggest challenge of solopreneurship, consulting and freelancing is that the money often stops when you stop. If you aren't working, then, depending on your strategy, your business isn't working, if not shrinking. Passive income has been the best approach for me and leaders I admire, especially within the creative fields.

In fact, "How do I know I have a potentially successful passive income?" is the most common question I get as a coach and as a  speaker. It often boils to three key questions, as my fellow independent Jeanette Hurt and I talk about in our new book, The Passive Writer: 5 Steps to Earning Money in Your Sleep.

Do people actually want this?

It's a simple question, but it strikes to the heart of the biggest problem: Making products or services in a vacuum. For every successful creator, there are a dozen other ones who are building alone without feedback or concern over actual needs (and those that have gotten support for their ill-fitting idea often do not last long).

The key is to get out, travel and listen to what people want. It is even easier to do when you already have a direct connection to the potential audience, which you want to be building before you come out with a new idea or product.

How hard will this be to pull off?

My first step into an entrepreneurial side hustle, founding the app So Quotable, happened in daily slices, from 3:15 am - 6:15 am, before I took care of my newborn baby through the evening. As I talk about in The Bite-Sized Entrepreneur, you can create something great within the parameters of your current life.

The key here is to be realistic about how much you can accomplish within the timeline you have and ask yourself if you will actually commit. My app took five months of work, whereas someone with less outside responsibilities could have done it in a matter of weeks. It was something I had to accept before beginning. The process of creating and launching the app led to a book with TED, a TED Talk, and co-founding and leading the successful app Cuddlr to acquisition. The timeline stretched, but the impact delivered just the same.

What would be required to get this to the right people?

It may be what people want, and it could be something within your reach, but you need a reliable way to actually get it to the audience. This concern is even higher with passive income because, as Jeanette and I say in the book, passive income that requires more work than it is worth kind of misses the point, and trying to find the audience for your product or service can take an incredible amount of work.

The key is to remove as many barriers as possible between the audience and you. Daymond John puts it succinctly: "Always be one step away from the money."

My newest passive income service is The Ultimate Bite-Sized Entrepreneur boot camp. It has become successful because I literally emailed my email list and asked them what they wanted - and they said an online boot camp based on the book series! It wasn't me asking my social media audience, as that involves a third-party and a vague reply of likes, shares and follows. Instead, it was the people who opted-in to talk with me and already had an interest in what I had to offer.

One of the best ways to create a passive income stream people will support is to simply ask.

Ready to take your ideas to the next level? Join Damon's priority-empowering discussions at and download your exclusive solopreneur guide.

Published on: Jul 30, 2018