2026 Trends: Polyworking – Double the Paychecks, Double the Risk

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Anne: Have you ever wondered about the real impact of juggling more than one job in today's fast-changing workplace? According to SHRM's 2026 Trends and Predictions report, poly working is on the rise, not just to make ends meet, but rather to create flexibility, fulfillment, and sometimes pure survival.

But what happens when your side hustle bumps up against company policy or even your well-being? Today we're joined by Jonathan Segal, an attorney at Duane Morris, to unpack both the legal and personal sides of poly working, weighing the risks and rewards for employees and what HR professionals need to know about this growing trend. Welcome to All Things Work, Jonathan.

Jonathan: My pleasure to be with you and thank you for including me today and the audience for being here as well.

Anne: Yeah, it's really great. We're really looking forward to diving into this conversation. There's a lot to get through. So let's go right into it and explore some of those key legal considerations employees really should be aware of when it comes to poly working.

For those who are thinking of taking on that second job, what should they consider to avoid getting into legal trouble with their current employer?

Jonathan: Sure. So Anne, so I don't get into legal trouble, you get a lawyer, you get a disclaimer. This isn't legal advice for specific factual situations, giving some general suggestions only.

I think the most important issue if you're an employee is transparency. Where I've seen things go wrong from the employee side and the employer side is when the employee is hiding the ball, not talking about another job, perhaps not being honest about the other job. And we'll talk about the flip side where the employer doesn't set forth its expectations or restrictions, but to me the most important issue is be open about it.

And if you think your employer may have a problem with it, wouldn't you rather know before than later when you may lose the job and your reputation that can go with it? So honesty and transparency.

Anne: And on that note of transparency, it kind of answers this next question I had. For those who maybe already have the two jobs, they're already working it, maybe they started the new job, they got hired on, but they had this side hustle. Should they really disclose this information to their employer? Should they disclose it upfront? And if so, what's the most appropriate way to approach this conversation?

Jonathan: These are all great questions. First of all, if you have a side hustle, and it can be employment, it can be as an independent contractor, being an entrepreneur on the side, the first question you really need to ask yourself is: is it competitive? If it's competitive, you got a potential problem you should disclose.

Anne: Mm-hmm.

Jonathan: If it's not competitive in terms of the work you're doing, is it competing for your time?

Anne: Mm-hmm.

Jonathan: If you can't give your all, then you probably should have a conversation about what the expectations of your employer are and can you meet them.

Anne: Mm-hmm.

Jonathan: If there's not, then you should check your policies. Check yourself first, think of your business second, and then look at your policies. And that's not meant to be necessarily in that particular order, but does the employer have a policy? If the employer says you need to disclose, then comply with the letter as well as the spirit of the policy.

I recently saw a policy that said if you have outside employment, you need to disclose. Well, as you know, a lot of the outside work, some of the side hustles, they're not employment opportunities. They're entrepreneurial, independent contractors.

Anne: Mm-hmm.

Jonathan: Technically, you might not have to disclose under the policy, but I think you would score points with your employer if you did. And I think when you go in, I wouldn't go in and say, "I want to make sure I'm not doing anything wrong." And I wouldn't go in and say, "I know I'm doing everything right."

Look, I didn't see anything in our policies that prohibit this, but I want to make sure you're aware of this so you hear it from me. If there's nothing in the policies that prohibit it, if you don't have an employment agreement that prohibits it, you probably don't have to disclose. But if you think your employer would want to know or you might feel better telling them.

One of the things that I find, Anne, is that sometimes people are afraid if their employer finds out, how will the employer respond?

Anne: Yeah.

Jonathan: My question is, would you rather them find out from you or from a third party? I would rather people hear it from me and say, "Look, I value working for company ABC. This is my primary source of income. This is where I can, this is my employer. I just want you to know, I do have consulting on the side. I want you to know I bartend on the side. I just want to let you know what I'm doing so if you have any questions, we can work them through together."

Treat it as a collaborative dialogue where the goal is to be able to keep that side hustle, so long as it doesn't conflict with the nature of the job and your job responsibilities, but in a way where your employer feels comfortable too.

Anne: Yeah, I like that. Making the employer understand this is my priority. I just have this side hustle, or just this little extra income to bring in for my family or for me. I think that's super important to let your employer know, "Here's my priority: my full-time position and the company and the company's goals." I think that's when their shoulders tend to lower and they tend to listen a little better.

Jonathan: I think that's right. And you can use the words that you just used. "You come first. You're my priority." I just want to make sure if there's any questions, we talk about them together.

Anne: Yes. Yes. I love that. And so something that didn't really pop into my head right away when we were approaching this subject, legal considerations aside, poly working can significantly affect an employee's taxes and benefits. This is something that I thought was really interesting. What would you advise employees to be aware of regarding the tax implications of holding multiple jobs?

Jonathan: So this is great because I get to give the answer I would give if I were giving legal advice, and I'm not: you need to talk with a tax lawyer.

Anne: Disclaimer.

Jonathan: You need to talk with your accountant.

Anne: Exactly.

Jonathan: I'm an employment lawyer. Take tax advice from me and no good will come from it. I rely on my tax lawyer. I rely on my accountant. If you don't have an accountant or a tax consultant you can speak with, then at least for this discrete matter, engage someone, because having multiple gigs, a primary and other jobs, can have tax consequences.

It's going to vary on the nature of those relationships, how much you're earning, what state you're in. There's not going to be a one-size-fits-all, but get professional advice on that discrete issue.

Anne: Mm-hmm. Love it. All right, so let's be honest, one job in itself can be very stressful. If you're a full-time attorney or you got a high-pressure environment, add another job on top of that, your personal well-being is at risk. I definitely feel stressed on a daily basis. I can imagine working two jobs, but some people feel the need to do that because they need extra income. They just need it, especially in today's economy.

What are some of those early warning signs of burnout employees should really watch out for when they're managing multiple jobs?

Jonathan: Sure. And if you don't mind, can I throw one thing in first? For some people that have one job, they may say, "I feel like I'm poly working. I got three jobs I'm trying to handle." It really depends in part on how many hours you work for your primary job and how much emotional commitment there is, because it's not just what you're doing, it's what you bring to the table.

I think when you have this second gig or this side hustle, does it energize you or does it drain or weaken you? And the only person who's going to know is you yourself. I have my own tells for myself, and this is where we know with emotional intelligence, self-awareness is so important.

If you're getting angry at both, if you're getting angry at everyone around you, you're overextended. If you begin to resent your primary employer because you can't get to your side hustle...

Anne: Yeah.

Jonathan: You're feeling that resentment, that's really a warning sign that trouble lies ahead, or you resent your side hustle because it's interfering with your primary job. The feelings will often come before the conflict. Pay attention to the feelings. If you feel like everything's too much, then you have to check your feelings.

But if you get to the point where you say, "I don't know if I can handle this anymore," step back and ask yourself what can give. It can't be "I'm going to pull back on my primary job." You have to be prepared to pull back on the side hustle because if you give less to your primary job because the side hustle is taking too much out of you, then I think there's a problem.

So all the signs that you would have if you had only one job of burnout: fatigue, anger, anxiousness, all those kinds of things. And in your head, if you're thinking about them relative to the jobs, pay attention to them. You may think you're doing a quality job of dissembling and not sharing how much it's getting to you. People that love us will tell us when it's getting to us. Don't wait for a loved one to tell you. You'll know. You'll feel it.

Anne: You'll feel it. Self-awareness is big. And our president and CEO, Johnny C. Taylor Jr., actually went on the Today Show earlier this year on this exact topic. I remember sitting down with him and he even said the biggest thing he wanted to address in this discussion was the well-being of employees, because when you're juggling all this and you got the stresses of "I just need more income to support my life" or whatever situation you're in.

Sometimes the side hustle isn't just a passion, it's a necessity for some people. He really emphasized the need to be aware of those early burnout signs because it can, at the end of the day, impact your primary job, and that's not something you want to lose.

Jonathan: No, no, and I saw that piece on the Today Show. I was so happy to see the human approach as opposed to just the legal matters too. That same issue can apply to volunteering for overtime.

Anne: Mm-hmm.

Jonathan: We all have different limits, and that's why I went back to, you may need that side hustle for money, and then you may have to push a little harder. If you're not doing it for money, but you're doing it for a passion, the question I always ask is: is it giving me more energy or is it taking the energy away?

If it's taking my energy away, if that's what I'm waking up at night worrying about, then maybe the side hustle is more of a drag than a plus, but each person needs to decide that for themselves.

Anne: That's a good question to write in a journal. And if you go back and you try to answer it again, your brain, your mind, your body will tell you what the answer is. So I love that you brought up that simple question that can really provide a more in-depth answer for you.

Let's say you were the people manager in this situation. You're having that discussion with the employee who's trying to approach you about handling multiple jobs. What advice would you give your employee on how to approach the situation? We kind of touched on this a little bit, but let's dive a little deeper from the people manager side.

Jonathan: Well, first of all, as a people manager, you may think you're one of the people, but don't forget, you're a manager and I think the first thing you want to do is remember, transparency is good. So is some courage.

Anne: Mm-hmm.

Jonathan: It takes some courage to walk into your boss, to the people manager and say this. If you're the people manager, thank the person. "Really appreciate your letting me know." You don't need to say "that's respectful," but it should feel like respect. If you're the people manager, I think it would feel like respect.

Thank the person first. And then don't judge, don't run to conclusions. Say "I really appreciate your letting me know. I'd love to learn more. Can you tell me a little more about what you're doing, where you do it, how many hours you think it takes?"

If you have a policy, remind the employee of the policy. If you don't have a policy, then just talk about your expectations. Generally think first, listen second, advise third. That listen part sometimes gets lost.

I know for myself that sometimes when I hear someone talk about something that may pull them away, inside I think, "What about me? How is this going to affect me?" I know enough not to say that. And so yeah, you may have concerns about you and how you're going to manage your department. Don't go into that. Don't start firing "What if we have overtime required? What if we have a customer expectation that is all of a sudden more than we had anticipated?"

Don't throw out all the scenarios of what could make this difficult to manage. Again, thank them. Listen, and then if you have a concern, then say something like, "Again, I appreciate you're sharing this with me. Our lives here aren't always predictable and I appreciate you said we come first. What happens if we need sixty hours in a week? How are you going to manage both?"

Ask the question, don't make the statement "You can't manage both."

Anne: Yeah. Yeah, that's a good way because it also allows the person to speak about what maybe strategy they already had come up with to ensure that the priority is the priority no matter what. So I like that you brought up asking the questions, following those three steps to start off the conversation. It's really empathetic. I like that approach.

Jonathan: You said it's empathetic. As we know, empathy is so important.

Anne: Mm-hmm.

Jonathan: See it through the employee's window. There may be multiple reasons the employee's doing this. They may need the money.

Anne: Yeah.

Jonathan: They may need this for satisfaction. We provide employees on the second point. What makes me feel fulfilled? It may be family, it may be in particular children, but just because someone is older and doesn't have children they're raising or younger and doesn't have children doesn't mean they shouldn't have a life outside of work.

So I don't like when, I don't want to judge the outside interest. I want to think, "Okay, you have something that could be an issue with work. Some outside interest, some outside pull. Let's see how it fits in within work." Because I wouldn't want the message to be, "We're flexible for work/life if it's family, but not flexible with work/life in terms of passion." And I mean flexible, not in terms of hours and expectations, but allowing something to occur.

Anne: Exactly. Yeah, I like that point you made. Thank you for that. So let's move on to some rapid questions here. We're going to call it our next segment "On the Record Rapid Fire." We're going to get your hot take on a few situations and scenarios.

This is one I really am so curious about. What's the wildest poly working scenario you've either encountered in your practice or even heard about without naming obviously a specific person or company?

Jonathan: Oh, this one comes to mind right away. The employee, I'll just keep it very general, that was working in two professional services firms at the same time while being remote. And within reason remote works, sometimes it can be full-time, but neither company was checking in on him.

And for nine months was earning income from both companies. And I remember when I got the phone call, someone says, "We want to fire him." And I ask the question, "Who's the him?" The employer, his manager. It could have been a her. This case more likely to go awry if there's no supervision, there's no discussion.

Got to be really clear that when you're doing remote work, and this is where the conversation often can be, that doesn't mean "All right, I'll start at nine with my primary job, and then between one and four I'll do my side hustle." I want to be really clear on your expectations on working hours.

So this person made a lot of money for nine months working for two jobs. I know he lost the job with my client. I'm not sure what happened with the other employer, but it went on a long time and that to me, lack of supervision.

Anne: Yeah. And that speaks volumes to how remote work has really impacted people's ability to do multiple positions. And also, AI coming into play. You can either use an AI tool to complete a job task very quickly, so it gives you time to do side hustle here and there, or vice versa. The side hustle can be done pretty quickly using AI or you're literally helping AI development for another startup or something. So there are just so many layers to it. But I won't go too deep because we got a lot more to break down.

Jonathan: I'll just add, Johnny C. Taylor, Jr., SHRM-SCP, President & CEO (Taylor) speaks often about the importance of culture. It should be remote work, not removed work. And if this is more likely to happen with your remote work, then it's a symptom of the problem, not the problem in and of itself. We have to make sure our culture works where people feel comfortable doing this, and we have sufficient oversight if something's going awry, to catch it before it becomes really serious.

Anne: So smart. Smart. And so I've worked with noncompete clauses before. I've had them in a couple of jobs. So would you say, is there ever a good reason to break a noncompete clause in this situation?

Jonathan: Well when I think of noncompete, I think of two timeframes: during your employment with us and afterward. I can't say for certainty in all fifty states, but even those states that say you can't compete after employment generally say you can prevent competition during employment.

Anne: Mm-hmm.

Jonathan: Now, what was that disclaimer I said at the beginning to employees? Got to say again to employers. You got to look at the law of the states in which you operate, but I think it's very reasonable to say, as an employer, and I do recommend that employers have a policy, so there can be no question on this: "While you are employed by us, you're not to engage in competitive activity" and describe what that is. Because if you don't tell someone, it's a little harder to find fault for what they do.

If you're an employee and you want to break a noncompete during employment, you're putting both jobs at risk. After employment, you want to talk, obviously you want to get your own lawyer on something like this, but SHRM has done such a wonderful job covering the evolution of non-competes and the changes that are going on with them. There is more hostility among the courts to non-competes. There are state prohibitions and restrictions, but generally speaking, those are after employment terminates.

So don't Google or ask AI "Is a noncompete lawful in X State?" The answer you may get is no. But they're talking about after employment, not during employment, and this whole issue with side hustles during employment.

So bottom line: reasonable to expect employees not to compete with you while they're working for you. And number two, if you have a noncompete, honor it.

Anne: Exactly. Yeah, those are definitely tough. Is there a particular industry where poly working is especially risky or even problematic? You gave us an example of a situation that happened, but what type of industries could be worse?

Jonathan: I think any industry where trade secrets are critical to the organization's survival. If you get a robust trade secret agreement, you really need to ask yourself the question: in my side hustle, is there any possibility I could be using or disclosing confidential information? If the answer is "I could be," you got to think twice. Even if you don't get a confidentiality or nondisclosure agreement, but particularly if you have that.

I think you have to look at whether trade secrets, confidential and proprietary information critical to your organization may be a factor in a side hustle, and the fear of disclosure would be an issue. Another area may be, do you have a public-facing role? And I think about that a lot because let's assume that you are the director of marketing for an organization and your side hustle is a little funky. How is that going to affect your brand?

I had a case where someone worked for a drug and alcohol treatment center and then someone's side hustle arguably was competitive in theory. So you kind of have to ask yourself the question, but again, this is going to depend a lot on the employer and its values.

I remember interviewing someone, if you don't mind, and they worked in their job and then they bartended at night. That was their side hustle when I interviewed them. That was a real plus for me. I loved the fact that someone wasn't in an ivory tower and they were doing good hard work, applying for a white-collar job and talking about it. Someone else might see that differently in the context of their employment.

Anne: Right.

Jonathan: I don't know if Duane Morris would be happy to see me slinging hash or serving alcohol in a bar, even if it's noncompetitive. So I think we kind of need to think a little bit about proprietary information being one issue, security clearance another issue, are you public-facing another issue where someone might question the impact.

That, by the way, connects to the whole issue of off-duty conduct, what we do in social media, those same kinds of issues. How does what you do off duty potentially impact your employer's reputation and your involvement with them?

Anne: There's a whole web of things to it. Thank you so much and thank you for these wonderful insights today. We really enjoyed it. Now there's so much more to this conversation going beyond just the employee experience from an HR and policy side to discuss.

Each week we ask All Things Work newsletter subscribers to submit questions for an upcoming episode, and we got so many great questions around poly working that we even created a special legal Q&A bonus content exclusively for our Assure members called "Ask a Lawyer." I really love this. So just follow the link in our description or click the link above if you're watching this on YouTube to get insights on all your pressing questions on this topic as a continuation of this episode.

For everyone else tuning in, thanks for joining us. And Jonathan, thank you so much for sharing your insights today.

Jonathan: Thank you Anne, and thank the audience for being with us today, and thank you, SHRM, of course.

Anne: All right, we'll get you next time.