Nick Loper | Following Your Side Hustle Dreams

Forget your parents’ advice: Nick Loper wants you to quit your day job. The founder of Side Hustle Nation and host of podcast The Side Hustle Show has made a career out of helping other people follow their non-9-to-5 dreams.

Nick will be the first to tell you that doesn’t mean climbing on a desk at the next staff meeting and shouting your resignation. As someone who traded corporate life for self-employment, he knows it takes planning, structure, and emotional support.

In this episode, Nick defines the difference between a side hustle versus a second job, explains how to know when it’s time to switch to a new career and lays out what you need to do before taking that full-time step.
 

Forget your parents’ advice: Nick Loper wants you to quit your day job. The founder of Side Hustle Nation and host of podcast The Side Hustle Show has made a career out of helping other people follow their non-9-to-5 dreams.

Nick will be the first to tell you that doesn’t mean climbing on a desk at the next staff meeting and announcing your resignation. As someone who traded corporate life for self-employment, he knows it takes planning, structure, and emotional support.

Speaking of parents, Nick credits his mom and dad with inspiring his first entrepreneurial efforts.

“You get to the age where you want to start buying stuff, and they're like, ‘Do you have any money? Go earn it,’” he says.

Nick’s first job was mowing grass, but he progressed through various money-making schemes, including babysitting and, “trying to sell baseball cards to my equally broke friends.”

After college, Nick ended up in the corporate world, and that’s when his side hustles took off in earnest. Dabbling in online advertising turned into a price comparison site for shoes. Three years in, he was finally able to quit his day job in 2008.

But Nick wasn’t satisfied with being his own boss. He wanted to talk about side hustles with other people riding that rollercoaster. And he wanted to make those conversations public, in case more like-minded people were interested.

In 2013, he started Side Hustle Nation and The Side Hustle Show podcast. He interviews people who have found success with businesses that started out as projects they pursued on nights and weekends.

As you’d imagine, Nick has accumulated a mental encyclopedia of advice.

“The biggest thing is to look at it as an experiment. If you are in the position of having a day job that is paying your bills, you can afford to take your time to do something right for you. You can afford to fail and try something else next month,” he says.

👨‍🦲 Name: Nick Loper

⚙️ What he does: Entrepreneur, author, host of podcast The Side Hustle Show and Chief Side Hustler at Side Hustle Nation, a media company helping people take their side gigs full time.

💼 Company: Side Hustle Nation

💎 Words of wisdom: “For me, to know when it’s time to go full time into something, I like to see a track record of revenue going back six to 12 months. I don't want you to have to dip into savings to get your thing off the ground.”

🔍 Where to find him: YouTube | LinkedIn | Twitter | Instagram | Podcast

💡 Side hustle, noun: Nick defines a side hustle as something you do to make money in addition to your day job, with the intention of one day taking it full time.

💡 To hustle or halt: Figuring out if your side hustle is worth the time and effort you’re putting in is a judgment call you have to make — and it helps if your family is on board.

💡 Testing, testing: If you can, Nick recommends treating your side hustle as an experiment, rather than betting everything on it working out. This frees you up to try different things.

💡 Pushed to succeed: Being under pressure — financial or from a deadline — forces you to be more resourceful and get creative.

💡 Have a fun journey: Instead of focusing only on achieving a goal, appreciate the experience of growing your business. You can control the process more easily than the outcome.

💡 Perpetual motion: The hardest part of starting a business is just that: getting started. Nick says once you’ve found that initial motivation, it’s easier to keep going.

💡 Work richer, not harder: Track your time, see what’s making you the most money — and do more of that.

💡 When to quit: If you find yourself dreading work every day, it’s time to change jobs. But Nick recommends having at least six months of revenue before taking your side hustle full time.

Nick Loper:

“Side hustle is anything you're doing to make money outside your day job. That could be your small business, or driving for DoorDash. But more than just moonlighting, more than just a second job, it carries this entrepreneurial connotation where this could be something that replaces your day job income.”

“So many people want to get to this end goal of personal and financial freedom, but there's this sprint in the near term where you have less time with family and less money. And it might not pay off. And that becomes the question: was it worth it? Some people spend years in that space and it can become infuriating.”

“At one point, I'd been thinking, ‘Man, I'm going to have to dust off the old resume and swallow my pride and go get a real job again.’ And my wife was like, ‘Don't do that. You will figure it out.’”

“Destination is important, but when you get there, the inevitable question is now what? I’ve still got to figure out some way to spend my days. Sure you can drink margaritas on the beach for a while, but I imagine that gets old.”

“The hardest thing isn't necessarily finding the right idea or raising money or even finding customers: it's that initial push just to get started, that motivation.”