You’ve likely heard about the gig economy, but you might be wondering exactly what it entails. It’s easy to assume that driving for Uber or renting your house through Airbnb is the extent of your options but the gig economy offers a much wider slate of opportunities.

In his new book, Gigworker, Brett Helling provides the essential primer on the gig economy, how it evolved to where it is now, and where it’s headed in the future. He’ll show you that it’s possible to replace your full-time income with multiple gigs or balance nine to five work with a five to nine side gig.

You’ll come away with a new zeal for the gig economy, ready to dive into the options at your fingertips and to make money doing what you love.

Drew Appelbaum: Hey Listeners, my name is Drew Applebaum and I’m excited to be here today with Brett Helling, author of Gigworker: Independent Work and the State of Gig Economy. Brett, thank you for joining, welcome to The Author Hour Podcast.

Brett Helling: Yeah, thanks for having me, it’s a pleasure to be here.

Drew Appelbaum: Let’s kick this off. Brett, can you give us a rundown of your professional background?

Brett Helling: Yeah, my professional background is, in college, I started off working some internships and didn’t really like it. When I was in college, I was studying marketing and management and entrepreneurship, and wanted to go the corporate route–that’s what I thought that you should do. I guess I was just conditioned from an early age that that’s what people did, so that was the route I was planning to take.

I worked a couple of internships in the corporate world and didn’t really like them. My dad has an event planning company and there was a position that opened there, ironically enough, the month I graduated college. We talked about it and I went to work for him and continued to build this business on the side, I started some websites–this is very high level–they ended up taking off and I ended up quitting working for my dad and started out in the gig economy and running those websites full-time.

Now, I have a portfolio of 10 websites and I also do consulting work for an ad agency here in town.

Drew Appelbaum: Now, why was now the time to share this story in your book? Was there something inspiring out there, did you have an “aha moment?” or something as simple as you had a little bit more time on your hands because of COVID?

Brett Helling: I started a website about ride-sharing–I was an Uber driver and saw that there was not much information about doing rideshare driving. I started a website for that and it ended up getting a couple of million people to it a month, and so I realized the power of websites.

I was laying–I’m also a scuba diver–in the bottom of the pool doing a training dive and I looked up at the ceiling and saw a bunch of lightbulbs. That rideshare site was focused on one small portion of the gig economy, which was just ride-sharing.

I realized that there’s so much else out there, such as freelancing, cleaning, all sorts of things you can do. I went home and started a website about that, about the gig economy, and as part of that, did a bunch of research and decided to turn it into a book. I’d say the “aha moment” was in the pool when I was diving and then from there, it was just kind of natural evolution.

Pitfalls and Traps

Drew Appelbaum: Now, when you said, “Okay, I’m going to write this book,” you probably had an idea of the book rattling around in your head, maybe even an outline of what it might look like but during the writing process and just by digging deeper into a lot of the subjects, a lot of writers have major breakthroughs and learnings along the process. Did you have any of these major breakthroughs or learnings during your writing journey?

Brett Helling: I did. When I first started the process of the book and outlining what I wanted it to look like, I had the idea that I wanted to make it easy for people to understand the gig economy–so to see what’s out there, to see how you can get involved and then some things to avoid. That was just based on my experience. I found a way to be pretty successful in the gig economy but it wasn’t always like that, there were a bunch of pitfalls and traps I could have fallen into and I did fall into.

Some of the breakthroughs were just drawing on my own experience and sharing that with the audience.

Drew Appelbaum: Now, in your mind, as you’re writing this book, who were you writing it for? Was it for people who are currently employed full-time or is it for people who are looking for something better out there?

Brett Helling: A little bit of everything. The audience I aim to target is I wanted to identify with everybody. That’s why I wrote it at a pretty high level that is more informational than it is super actionable and tactical. No matter what you’re working in, full-time or you’re already in the gig economy, it will talk to that.

Drew Appelbaum: Let’s dive into the book but I’d love for you to set the foundation for us before we start. Can you tell us the state of the gig economy right now?

Brett Helling: The state of the gig economy right now is very dynamic and fluid, so it’s constantly changing. As time goes on, there are more opportunities than ever, that are presenting themselves every day. With COVID-19, that shook the gig economy as a whole, just absolutely to its core.

Things like ride-sharing, people aren’t really doing that right now because there are lots of cities that are locked down, especially the largest ones in California, Chicago, New York. The gig economy as a whole is bouncing back in that regard, but there are lots of new opportunities such as grocery delivery, freelancing.

The gig economy right now is growing and shrinking and growing and shrinking. It’ll be interesting to see coming out of COVID as the lockdowns keep lifting and things get back to some semblance of normal, to see what happens there.

Drew Appelbaum: For those who are actually considering leaving a steady job with good pay and benefits, what do you say to them, and is there hope for them if they go all in as a freelancer or into the gig economy?

Brett Helling: What I would tell people looking to turn gig work into a full-time profession or career is do your research. There’s a lot of people with shiny object syndrome that hop in, they think it’s easy, there are lots of pitfalls associated with it, and if you don’t do your research and prepare ahead of time, the chances of failing are very high.

That goes for a variety of things that span from the work you’re doing, to how you do the work, to your living situation, to your working situations. All of those factors blend together and if you don‘t prepare ahead of time, you’re setting yourself up for failure.

Freedom and Flexibility

Drew Appelbaum: What would you say some of the top benefits are from transitioning from full-time into a freelancer or gig worker?

Brett Helling: Hands down, above all else, freedom and flexibility. You can do what you want and with the gig economy, you can do what you want, you can have the time to do the things you enjoy, and those are really the two things that when you’re working in the constraints of a nine to five job, exist but really kind of doesn’t.

It’s fair to assume that if you’re at a full-time job, your employer will expect you to be there from nine to five or whatever your set hours are. In return, you get a paycheck.

With the gig economy, a lot of times what you’ll find is you do task-based things. The quicker you get them done, the more efficient you are, the more money you’ll make, but also the more time you’ll have and you can do that work when you choose to.

In my life, I travel a ton and my friends know it, so every time they want to take a trip, they just give me a call and it’s great because I have the freedom and flexibility to go do those things. However, that does come with a downside, so if I go take a week off work, I’ll find myself working very long hours, often times 12, 14 hours a day in the week leading up to that trip, just so I can make sure that nothing slips through the cracks.

Drew Appelbaum: Are there other risks that you feel like you need to tell people before they really go all-in into the gig economy?

Brett Helling: A big risk, one I face personally, was getting depressed and I’ve realized that humans are made for interaction with one another. What I did when I first got into the gig economy is I would work long hours, put my head down, focus on my work, try to figure this whole thing out. Going from having co-workers around, kind of a shared camaraderie on a team, to go into my own thing and I’m responsible for my own success, that was very isolating.

It was kind of a burden to bear at first but also, working alone really did a number on my mental health. I found going to coffee shops, kind of being intentional about scheduling lunches, and social activities, and getting into that cadence of work with human interaction built-in was a massive lifesaver for me.

Drew Appelbaum: You mentioned preparation before you get started. Can you talk about what that preparation might look like and how folks can go ahead and get started, maybe where they should be looking?

Brett Helling: Yeah, if you’re looking to get started in the gig economy I’d say do your research. First, see if the gig economy is a fit for you and second, really pick the right opportunity from the start. Determining if the gig economy is a fit is you researching the values of the companies you’re working for, so if you are just in it for the money that will pay the bills but you won’t be happy. You really have to get behind the mission of the company you’re working for or the individual if you’re doing freelancing.

The second thing is to think of who you are as a person and how you handle emotions. If you’re looking for stability in a paycheck, a full-time job is the better option. The gig economy is probably not for you, but if you can manage time well, you can manage income volatility and that doesn’t scare you, then those are some things to consider before jumping in.

Drew Appelbaum: Now, do you have any tips or tricks on how to maximize your success once you decide that this is the route for you?

Brett Helling: Yeah, the biggest thing I would say is to find what works for you and do more of that. In the gig economy, a lot of times people find one thing they’re very good at and they make a business out of it.

Mine is SEO, I drive people to the websites I have through search engine optimization, backlinks, media, things like that. So, I’m an SEO guy. If I do contract work, I usually do it largely for clients looking for SEO, so in doing so I read about SEO, I look at SEO, I do it every day and that helps me further that skillset.

When somebody is looking for somebody in that industry, they can come to me and I produce results, and at the end of the day, that’s really what it’s about.

If you find yourself doing something that you don’t like that you’re not good at, look around at the gig economy and see what opportunities there are to make money in what you’re good at. I think that ties back to being prepared by doing your research before getting into the gig economy because if you do your research, you find something that aligns with your value system, your skillset, and you will be setting yourself up for success instead of failure.

Drew Appelbaum: Can you tell us about other experiences of gig workers who have thrived?

Brett Helling: Yeah, my friend Jillian, she got into the gig economy, and I was there by her side when she was considering the transition from full-time employment to running a business of her own. We had lots of conversations over lunch, dinner, drinks about her concerns, her potential landmines to avoid, and what she wanted to do, and why she wanted to do it. She jumped in with both feet.

She didn’t quit her full-time job to go do gig work, she started doing it on the side. She was moonlighting as a graphic designer, making some wedding invitations, making personalized stationery, and what I admired about her is she tested what she was doing, validated the concept, and then over time gradually backed away from her full-time job until she was full-time. Now she runs a great business. She is doing more sales than she ever has. She took a strategic approach, didn’t caught up in the emotion, and I think that’s what made her successful.

Drew Appelbaum: Are there any pitfalls that you’ve seen come up constantly or obstacles that you continue to face that you really want to make gig workers aware of or people that want to enter into freelancer or the gig economy?

Brett Helling: One thing I see all the time that’s a very big potential landmine and that people getting into the gig economy really don’t see until it happens to them is lifestyle creep. As people make more money, as they find success in the gig economy, the gig economy can be very lucrative, and it can often come very quickly. If you find what you’re good at, you do a lot of that, all of a sudden, you’re getting more work, you’re really maximizing your skillset.

Well, you can in the process make more money doing whatever you’re doing. I’ve had multiple friends who have started making more money than they ever had before, and for example, one of my friends landed a big contract and went and leased a new Range Rover, and when he lost that contract, he had adjusted his standard of living to a certain amount and it was very hard for him to go back.

Drew Appelbaum: What do you see as the next evolution of the gig economy? Clearly, it’s growing by leaps and bounds, do you see anything else new on the horizon?

Brett Helling: I see the gig economy, it’s growing. I see automation displacing the majority of monotonous tasks. I see an opportunity, so while that scares a lot of people, I see the opportunity to get ahead of that automation and be the one in charge of it. If there is a way to be a manager of the automation instead of falling victim to it, I’d say that’s a big one.


Drew Appelbaum: Does anything get lost in this new gig economy? I know you mentioned before that it could be a little lonely, and you just transitioned to business owner but a business owner of one. What else gets lost in being your own boss?

Brett Helling: Discipline gets lost in being your own boss. I think there are a lot of people that hop into the gig economy thinking it’s easy, whether they’re doing part-time gig work or full-time gig work. They see somebody who has the freedom and flexibility to travel, who does what they want, who works on projects that they want. It’s not easy being your own boss.

At a nine-to-five job, you wake up, you go to work, you work on tasks that are typically assigned to you, even if you have a high level of autonomy in that role, somebody is telling you what to do and you’re held accountable to them.

With gig work, you’re oftentimes held accountable to only yourself, so if you succeed it’s on you. If you fail, that’s also on you. It’s walking that fine line between success and failure and it is really all about discipline when it comes down to it at the end of the day, and consistently producing work. Again, back to finding out what works for you and just doing more of that in a way that you get stuff done.

Drew Appelbaum: You mentioned before that you do run a bunch of websites and your specialty is SEO, and one of those sites is Can you tell us what readers and listeners can go and find over at What sort of resources are available there?

Brett Helling: is a comprehensive resource for the gig economy. When I first built the site, I wanted it to be easy to find gigs in the gig economy, easy to find information about those gigs, and then set yourself up for success in the gig economy. At its core, we help you find a gig, we provide information about that and then provide more general information about how to avoid pitfalls, the best software to work with for efficiency, and all sorts of things.

We help you find a gig, we give you information about it to teach you about that gig, and give you all the tools you need to succeed.

Drew Appelbaum: Brett, we just touched on the surface of the book here but I just want to say that writing a book, which you’re really going to help a lot of folks understand how to transition from full-time to freelance and that’s no small feat, so congratulations on having your book published.

Brett Helling: Thank you.

Drew Appelbaum: I do have one question left, it’s the hot seat question. If readers can take away only one thing from the book, what would you want it to be?

Brett Helling: If readers could take one thing from the book, the big one I’d say is don’t be scared and just do it. What sets people apart, true entrepreneurs from what I like to call want-trepreneurs, there are lots of people that want to get into the gig economy–that want to start a business, that want to get involved but they’re scared too, so they don’t. At the end of the day, life is too short to wait and to be complacent.

There’s one thing that I wish people would take away from the book is that the gig economy is not that scary, and the investment into it, whether it’s time, money, it’s worth getting into and people are missing out if they don’t.

Drew Appelbaum: Brett, this has been a pleasure and I’m excited for people to check out the book. Everyone, the book is called Gigworker and you can find it on Amazon. Brett, besides checking out the book, where can people connect with you?

Brett Helling: They can connect with me on LinkedIn, that’s probably the easiest or just send me an email, it’s [email protected].

Drew Appelbaum: Brett, thank you so much for coming on the show today, and best of luck with your new book.

Brett Helling: Yeah, thank you very much.