Side hustlin' got me fired—heed the warning

Spring has a lot of good business memories for me—participating in a top sports accelerator, our first big jump in ecommerce revenue, surges in app growth. 

But one of my favorites is getting fired. 

Thursday marked 11 years ago that I was fired from an ad agency. The company figured out that I had a side hustle. I hadn’t disclosed it, for fear they’d can me. 

Last week I wrote about how to think through making the leap. Consider this the prequel to that—how to be smart about your side hustle. 

My first side hustle

I was a freelancer, contractor, gig worker or whatever you want to call it for my first two years after college. I worked mostly as a photographer, although I did have a run trying to start a music news website. I started a wedding photo agency when I moved to Louisville, but eventually hung up my camera to move into advertising.

I joined a small agency as a social media coordinator, or basically, I wrote Tweets and Facebook content for a living. My clients weren’t anything super exciting—a few chain restaurants and a wine company. 

After nearly a year of working for the agency, I had still never been in a single client meeting (in fact, after two years, I was only in one total client meeting). But I did notice a trend—my clients were putting together expensive marketing campaigns and taking big bets on products, all on a whim. Decisions weren’t grounded in data, it was “Hey, ‘skinny’ products are getting popular, let’s launch a ‘skinny’ margarita and burrito” without asking themselves if their clientele aligned with that trend.

I chatted with Zack, a data guy in the media department. He said he felt the same. Over lunch one day, we talked about creating a product that would help brands with this kind of problem. After a few discussions, we had a good feel for what we could build, and we started working on it. 

We did bring the idea forward to someone in the company, once, but the conversation got really weird when the person we talked to didn’t want us to be involved in the project. We went quiet, and that person forgot about it, I guess. Zack and I kept meeting for lunch, and the lunches turned into meetings at my house and a brewery. 

Soon we brought in a third cofounder. We met three times together. For our first meeting together, Zack took a few screenshots of his reports and data visualizations he did at work. This was purely illustrative of his skill set. He saved the screenshots in his personal Dropbox. 

A few weeks later, Zack was laid off with a few other employees. He tried to remove his Dropbox sync, but was assured they’re wiping the machine anyways, so it didn’t matter. 

Spoiler alert—they did not wipe the machine.

Instead, the company went through his personal Dropbox and found our operating agreement, and the screenshots. 

I was fired a few weeks later “with cause” for apparently using company resources to build my own company. It wasn’t true. We weren’t using any company resources, but it didn’t matter. The deed was done. Years later I’d find out the company was struggling, and I had been on the chopping block in the first round of layoffs, and just skirted by. I was effectively laid off for cause, ha. 

Zack and I would try to rekindle it, but our marketing analytics company never got off the ground. He ended up in grad school, we both had new jobs, and I eventually had a kid. 

We did circle back up years later to form GoWild, though. 

How to do better than I did

When I landed my next gig a few weeks later, I told my boss, “Look, I plan to start another company. I don’t know when—maybe this year, maybe in five—but I want to know now where you stand.” My boss said, “I don’t care what yo do on your own time.”

This is the attitude you need in order to succeed with your side hustle. It’s going to be hard to keep it quiet, and you really roll the dice if you try to (if you don’t understand why, please re-read the section above). 

There are a few things to consider before diving into your side hustle:

1) Does your employment contract allow it?

Some contracts strictly prohibit freelancing or side work. You need to read your contract agreement and understand your restrictions. It doesn’t necessarily mean you don’t still do it, but you will have an understanding of your risk, if and when your employer finds out.

2) Do you have the resources?

It is, without a doubt, a bad idea to try and use company resources to build your side hustle without permission. Before you dive in, think through what you need, and secure it outside of your day gig. Even though I wasn’t using company resources, I was still fired for the perception of it. You could find yourself thrown out of your full time job sooner than you’re ready for if you don’t heed this warning. Like my side hustle, yours may take an early blow and meet an early death. 

3) Is this a potential company or just a side project?

This is a critical distinction. Side hustles can become companies. In fact, many companies and most startups start off as a side hustle. Side hustles can appear as a threat to your company. I’m not saying it’s right, but many employers will see it as competitive to your attention, time and passion. 

Side projects, though, are often for fun (such as hosting a podcast about your hobby, playing in a band, photographing weddings on the weekend—you could even argue this newsletter is a little side project of mine). Sure, those things can all become full-time jobs, but if you’re just doing it for fun as a side project, it’s likely an easy thing to disclose to your employer. They won’t care, and may even be happy you have something you’re passionate about. When I was a Creative Director, I loved hearing about my teams side projects as photographers, singers, bass players, woodworkers, calligraphers, etc. 

You need to decide which one you’re working on.

4) What happens if your side hustle works?

If you’re successful, a side hustle is going to eventually grow. How much time are you willing to put in? If you’re doing the right thing, you’re not going to cut into your employer’s time—so that’s going to put you working early and late during the week, as well as weekends. Is that what you want? Are you ready for that? Are you prepared to evaluate the leap if your side hustle gets traction?

Most people thinking about side hustles do not think through this aspect well enough. There will be a period of your side hustle where you’re crippled—hampered by the lack of time you can put in, but also exhausted by the amount of time you’re spending. The only—and I mean the only—thing that will pull you through this is your enthusiasm for the project. 

So, how bad do you want it?

Content idea for this week

I would love to hear about your side project or side hustle. Assuming your employer is aware, post on LinkedIn or Twitter and share about it. Tell the story of how you decided to start it. Give me a tag so I can see your progress! 

Who I’m listening to: Sierra Ferrell

What I’m reading: “The Things They Carried” by Tim O’Brien

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