The Art and Science of the Side Hustle: How to Pursue Your Passions and Get Paid

Written by guest blogger: Ben Eubanks, upstartHR

I couldn’t sleep. It was 4:17am and I had stared at the clock for half an hour. Might as well get up and get started. I rolled out of bed with a big smile. It was my first day as the new owner of Lighthouse Research, and I felt like it was what I had always been preparing for all throughout my career.

This scene played out a few months ago when I officially took over an HR technology research and advisory services firm, but I’ve been an entrepreneur for quite some time now. I started the journey back in 2009, and I have continued my various “side hustles” over the years. Looking back, it has been an incredible joy. I’ve taught myself many new skills, had the opportunity to work with and meet some very interesting people, and grown by leaps and bounds professionally.

I completed some research in October 2016, and the number one thing that my audience was curious about was how to get into contracting/freelancing either as a part time or a full time opportunity, so I know this is top of mind for many people. Maybe you’re one of those people as well? If so, I’ll give you some helpful advice and insights that I have picked up along the way.

Handling a Second Job/Gig/Activity

As I mentioned, I’ve been doing something outside my “day job” ever since 2009. For most of that time, it has been the blog. However, I’ve also done speaking/training, HR certification study instruction for one test prep company, freelance writing, HR consulting, etc. Today I’m working part time as an HR consultant to help stay plugged into the HR community, because I left my practitioner position back in 2014 to become a technology analyst/researcher.

Handling that second position is not always easy, but it’s doable. I have three kids (and another that will be born shortly). I go to church. I volunteer. I have other responsibilities, and I make sure they all get taken care of. Here are a few things to consider if you want to start your own side hustle:

• Does your day job take up more than 60 hours of your week? If so, you probably can’t fit in additional work. It’s time to back that down, find another job, or put your side hustle dream on hold. Be willing to talk with your boss or explore other opportunities if it means you get to pursue the dream you’ve been holding back on.
• Do you enjoy working on projects, connecting with new people, and wearing the “business” hat? I know that accounting, billing, etc. is one of the least favorite activities for many independent workers, but it is a part of life. Today there are many tools to help make this easier, from apps for tracking business mileage to online banking for keeping your business expenses/revenues separate from your personal funds.
• Are you self-motivated? This is touched on below in the “passions” discussion, but it’s important that you can make something happen when it’s time to get to work. Some people don’t have the discipline to focus when nobody is standing behind them, and if that’s you, then you will have trouble making the transition to self-employment.

How to Monetize Your Passions

The first part is obviously to know your passions, right? Yet I see so many people that start off with the thought, “How can I make some money? What’s hot right now?” That’s a torturous path, because you can only work so hard at something that you don’t truly care about.

In my case, I started with something that was top of mind for me, but it also tied to an activity I love. Back in 2009 I earned my HR certification. During my preparation, I started writing my thoughts and study schedule online as a way to hold myself accountable. One week, I got off schedule due to a personal issue, and I received several emails from people asking where that week’s blog was! It was then that I realized that this was bigger than a project to keep myself on track—others were interested as well.

After I received my certification, I took my study notes, added some lessons learned, and started selling it from my website as a $19 eBook. I’ve sold hundreds of those since 2009, and I actually took it down a few years ago when I started selling a higher priced course that expanded upon the eBook content. The fun part is that I don’t have any hands-on work involved in these purchases. I created them once, and now when someone hits my site or joins my email list, they learn about the courses and can purchase them without me having to do anything. The course is delivered automatically, and everyone walks away happy.