Employers: You Should Hire Employees With Side Gigs. Here’s Why

January 18, 2021

In my work building writing teams for startups, I sometimes come across companies that forbid employees from having side gigs or don’t want to bring new folks on board who have revenue-generating passion projects.

Assuming you want to build the best team possible, a world-class team, having a formal or unspoken policy against the side gig is an outdated way of thinking that will work against you.

I get it, it sounds scary to hire someone who has options for money-making outside of the paycheck you provide. You worry:

  • They won’t be dedicated to their day job
  • Their side gig might support a competitor
  • They’ll eventually leave you for the side hustle

These are common employer fears. But applying this old-school mentality will keep you from hiring the best people. 

In this post, I’ll explain some of the benefits of hiring employees with side gigs and share some simple strategies that will help you do it successfully. Then we’ll circle back to these common employer fears — and my hope is you’ll see them in a different light.

While I suspect this could apply to most companies that want to foster innovative thinking, I’ll speak to content teams specifically since that’s my experience.

Why are side hustles attractive to full-time employees?

People who make time to grow a side gig are hustlers. They are learners, go-getters and problem-solvers. They know how to figure things out without hand-holding, because they’ve had practice.

That’s why when I review an applicant’s website or talk with them during an interview and realize they have a side gig, I see it as a positive.

But not all company leaders see side gigs this way. They might cling to how things used to be, when most workers had just one job. 

Sometimes that’s because they don’t understand the mentality of these go-getters. I’ve had leaders within companies ask, but why would an employee want to work more after a workday? They might assume it’s because they, as a leader, have done something wrong, that the employee isn’t getting enough support or are bored in their role. And while that can be true, there are lots of other reasons employees want side gigs that have nothing to do with poor leadership.

Here are a few reasons why a staffer might want to freelance outside of their day job:

1. It’s Fun

To certain types of people, work is enjoyable. They might enjoy writing about a specific topic that’s not part of their day job. Say they write about finance at work and contribute to a few websites about health on the side. Or maybe their side hustle is more creative than their primary role. They truly enjoy the work and the challenge.

2. Variety

Related to the example above, sometimes content creators want to dabble in topics or mediums that are different than what they’re exposed to at work. Experiencing this variety is enjoyable for them.

3. Personal development

Expanding one’s skill set is not only enjoyable for people who value learning, it also helps them grow and become more valuable, no matter where they work. For writers specifically, it can be appealing to get feedback from multiple editors who have a different style or expectations than their day-job editor.

4. Bylines

Writers are always looking to improve and broaden their portfolio, and the best way to do that is through bylines at different publications. For copywriters and ghost-writers who don’t get bylines at work, this is an opportunity to have their name stamped on a piece of work. 

5. Networking

Having a side gig is a smart way to meet new people and grow one’s network, which can expose the freelancer to more opportunities down the line.

6. Money

Especially with the heavy student loan debt young workers tend to carry, many look for ways to bring in a few extra bucks. This might be because they wish they were making more money at their day job, but that’s not necessarily the case. I’ve worked with plenty of well-paid content creators who still enjoy the challenge of earning more on the side.

Freelancing on the side is particularly desirable among content creators, including writers and editors. And while it tends to be more common amongst individual performers than executives, I’ve also known executives who manage consulting work on the side of a demanding role, for many of the reasons described above.

How companies benefit from employees with side gigs

So how does it benefit companies to employ full-time workers who also have side gigs? 

Here’s why I believe it’s worth considering.

1. You will hire better people

This sounds counterintuitive, but you might actually hire better employees if you allow them to work outside of the job they do for you.

Your pool from which to hire will no doubt be bigger. If you have a rule that employees can’t freelance on the side, you eliminate some of the best workers from the get-go. Freelancing is popular amongst content creators, and having the freedom to do so is a non-negotiable for many writers. 

Not allowing it is also a red flag to potential employees that the company might 1) have an old-school culture 2) not fully trust its employees and 3) have other policies that also reflect that approach. This isn’t necessarily true, but the possibility might discourage high-quality, forward-thinking people from applying or staying with you.

Writers in particular are a freedom-loving bunch. Even if they throw themselves into working for a company and appreciate the paycheck, they are often reluctant to let go of complete autonomy.

Can you find employees who will agree not to earn money outside of the paycheck you offer? Absolutely. But limiting yourself to that group means missing out on some of the best candidates.

2. The employee will do their job better

Employees who invest in themselves outside of day job hours will no doubt get better at whatever they’re doing for you.

If they’re pushed in a side gig to write more creatively, some of that creativity might rub off onto the work they do for you. If they learn about how to be a better communicator for their side business, guess what: you get to benefit from that, too.

Even if you offer opportunities for your employees to grow, they will grow faster with additional projects than they will working for you alone.

Whether they’re going deeper with the skills they already have or broadening their skillset to become more well-rounded, you and your business will benefit.

3. They might help your company gain exposure

Your employees will meet new people through their passion business, and sometimes that will result in the employee talking about their role with your company. It will reflect well on you when those connections think, wow, this company has some fabulous employees.

In some cases, your employee might even build a brand through their side gig that becomes well known. Yes, this might make them more likely to leave you. But in the meantime, your company benefits from their brand and free publicity, which might bring new opportunities to your company.

Companies love to benefit from having a famous personality on the roster or writers who have contributed to well-known publications. Ironically, sometimes those same companies don’t realize that their writer could have a byline in the New York Times if they were allowed to pursue that work at the same time as excelling at their day job.

4. You showcase the company’s values

If you say your company is innovative and forward-thinking, employees will notice when your policies don’t align with those values. Do you value ambition and spark? Show it by hiring people who exhibit those qualities both at the office and during their off hours.

At The Penny Hoarder, a media company I helped scale as the third employee, side-gigging was in our blood. The brand helped readers earn more money and figure out how to start side gigs — and the company stood behind that by giving employees the freedom to do the same. And wow, did we have a diversity of side gigs and go-getters! That policy aligned with our values.

5. You’ll keep your people happy and on board

Let’s face it: no matter how great your company is, you will never be everything for your employees. They will have lives outside of work. Even if they love their job, they will see gaps your company or their role simply can’t fill for them and pursue those interests in other ways.

Allowing employees to pursue growth opportunities outside of work keeps them happy, which might help keep them working for you. This might sound counter-intuitive, because we’ve been conditioned to believe that someone who has a side gig will eventually leave to spend more time on that side gig. But it also might help them explore in a way that satisfies them, which could keep that talented person on your roster longer.

Yes, there is a balance to strike here: most companies don’t want to hire people who have strong ambitions to start their own company, because they might not stick around long, and it takes effort to hire and train a new person every time an employee leaves. 

But dreaming of entrepreneurship and freelancing on the side are often two different ball games. Lots of writers want the freedom to pursue variety in their projects, but they’d rather have the security of a full-time job than run their own business.

Tips for creating guidelines around side gigs

Now, I’m not suggesting you open the door for a free-for-all. Instead, put some ground rules in place so it’s a win-win for the employee and the company.

It might even make sense to prohibit certain types of side work, for example, anything that benefits competitors. But here’s the key: rather defaulting to a “no freelancing” policy that allows for certain exceptions, take a “yes and” approach. That “and” outlines your guidelines, which should be part of your employee agreement.

Here are a few expectations I recommend including in your guidelines for full-time employees who want to work on the side.

Disclosure: None of these ideas are legal advice; I’m not a lawyer. Talk to your lawyer about how you can achieve these expectations in your employment agreement.

1. No freelancing for competitors

You don’t need to outline exactly which companies you consider competitors, as that will probably change over time. Instead, foster a culture of trust and make it clear that you expect your employees to use good judgement. If they’re ever not sure whether another outlet is a competitor, they should talk it out with their manager.

2. Side work can’t reflect poorly on the company

You don’t want employees freelancing for companies that are known for shady business practices, nor do you want employees active in industries that could reflect poorly on your company.

This is a judgement call, so hopefully you hired employees with good judgement. If an employee isn’t sure whether their opportunity meets this expectation, they can talk to their manager for help making the decision.

3. The employee must continue to perform at a high level

Clearly define what makes for good performance so it will be easy to identify when the employee doesn’t meet this expectation.

4. Employees should talk with their manager about side gigs

This isn’t a “lay down the law” conversation; it’s an opportunity to deepen the manager’s relationship with the employee. By asking questions about their side gig, that manager can learn what motivates the employee and apply that to their primary role, too. Plus, encouraging conversations like this creates a culture of transparency and honesty.

Some companies require employees to get permission from their manager for every freelance project. While this makes sense in some cases, I’d avoid it if possible, for two reasons:

First, it suggests a lack of trust. If you hire great people and outline the rules, you should expect them to follow those rules, coming to you when they have questions or need clarification. 

If you can’t trust employees to follow your guidelines, ask yourself: Is this because I hired the wrong person? Or because I don’t have a practice of trusting my employees and giving them autonomy to do their best work?

When employees feel trusted, they will work hard for you. And in the off-chance they take advantage of that trust, they no longer belong with your organization.

Second, it makes more work for your managers. You don’t want your managers spending valuable brain power on scheduling, discussing, and thinking through whether an employee can take each freelance project. It’s simply not a good use of their time. It wastes valuable decision-making energy and doesn’t move the needle for the business.

You do, however, want communication lines open. So when you hire someone, discuss the policy, and take time to talk about how the side work they do fits in. Discuss specifics, and let them know if they have questions, they can come to you any time. Then when they feel confident they’re adhering to your policy, they can get on with it.

As a manager, if you know one of your employees works on the side, this can be a touch point during your regular check-ins. A few times each year, ask the employee how those side projects are going. Open the door for a discussion so everyone can stay on the same page. In addition to giving you insight on this employee, showing you care about life outside of work is a chance to gain trust.

Debunking common employer fears about side gigs

To close this out, let’s circle back to the common employer fears we outlined at the beginning of this piece.

Now, you’ll understand why you shouldn’t waste brain space on them.

Fear #1: The employee won’t be dedicated to their day job

This is one of those worries that rarely comes to fruition; remember, employees who have side gigs tend to be hustlers and A-players who take pride in being high performers. 

If the side gig ends up being a distraction or preventing the employee from doing great work, you’re in the right to terminate. Just make sure you’ve clearly defined expectations so you both know they’re not being met.

Fear #2: The employee’s side gig might support a competitor

This shouldn’t be allowed in the employee agreement (see previous section), so it needn’t be a concern. If they violate this rule, you terminate.

Fear #3: The employee will eventually leave you for the side hustle

Whenever you have a go-getter on staff, you take the risk that they’ll leave you to do their own thing. But the truth is, you take this risk with every single employee, for they could leave you to work for someone else at any time. 

Ironically, your best employees are most at risk, because they will always have other opportunities. 

That means it’s your job to pay them well, to challenge them, to help them grow, and to make them feel secure so they don’t want to leave. That’s how you keep them. Not by limiting what they can do, but by helping them flourish.

And even if they eventually outgrow you, those A-players will have done a lot to grow your business. You’ll be glad you hired them.

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