Navigating Dual Employee-Contractor Roles: Protect Your Career and Resume

Recognizing Red Flags in Dual Employment Contracts

Here’s what companies won’t tell you: being asked to work as both an employee and contractor on the same project isn’t some creative solution—it’s a red flag the size of Texas. Most people think this arrangement is legal if the roles are “different enough,” but that’s exactly the kind of thinking that gets workers into trouble. When your employer asks you to take on contract work while staying employed, they’re usually trying to dodge overtime obligations^[1]. In California, where minimum wage sits at $16 per hour^[2], this matters enormously. The setup your job is proposing—splitting your time between hourly work and a “bonus” paid out at year-end—sounds creative on paper. In practice? It’s designed to keep you from hitting overtime thresholds^[3] that would cost them money. Don’t fall for it just because you want to make a good impression.

Jordan’s Experience: When Bonus Pay Masks Legal Risks

Jordan landed his first job out of college at a small event company, just like thousands of others. He was thrilled—promoted within eight months, trusted with real responsibility. Then came the big event. His manager asked him to take on design work “on top of” his regular role, with payment deferred to December as a bonus. Jordan thought it was smart career-resume building. By mid-project, he’d worked 52 hours one week. When he clocked out at 40 hours^[4], his manager said, “No problem, just finish the design work off the clock.” That’s when Jordan realized his resume was about to include a cautionary tale: he’d unknowingly agreed to a structure that violated California labor law. The bonus never made up for what he’d lost—not in money, not in career-resume credibility when he had to explain the mess to his next employer.

Legal Realities of Overtime in Dual Role Arrangements

After years advising workers on career-resume issues, here’s what I’ve learned: employers love this dual-role setup because it exploits a loophole—or tries to. The argument goes, “These are separate positions with different duties.” But here’s where it breaks down. In California, if you’re working more than eight hours in a day^[5] or 40 hours in a week^[3], overtime kicks in. Period. The fact that you have different job titles doesn’t change that. When your employer structures payment as a year-end bonus instead of hourly wages, they’re attempting to obscure what’s really happening: they want you working beyond 40 hours^[4] without triggering overtime protections^[6]. That’s not just a resume problem—it’s a legal problem. Workers have the right to be compensated for every minute worked^[7], and trying to classify some of that time as “contract work” doesn’t erase the obligation.

Protecting Your Career: Demand Contract Clarity Upfront

Look, you want to impress this company. That’s natural, especially when you’re early in your career-resume. But here’s the thing: taking on extra work through a legally questionable arrangement doesn’t impress anyone in the long run. It just sets a precedent. Instead, consider this approach: ask for clarity on the contract before signing anything. Get the actual numbers in writing. Ask specifically how hours will be tracked and what happens if you exceed 40 hours in a week. Request a clear division of duties so there’s no ambiguity about what counts as your hourly work versus design work. If they won’t provide that clarity, that tells you everything about whether this is actually a good career move. Building a strong resume means knowing your value and protecting it—not compromising your legal rights for a year-end bonus that might not materialize or might leave you making less than minimum wage^[2] when you do the math.

Scope Creep Risks in Combined Employee and Contractor Roles

You already know this from your design experience: scope creep kills projects. And when you’re working as both an employee and contractor, scope creep becomes a legal nightmare for your career-resume. Here’s the scenario: you’re hired to do “design work” on a contract basis, but because you’re also the events coordinator, people keep asking you to “quickly fix” things. Is that design work or events work? Suddenly you can’t tell. When you hit 40 hours of events work and need to stop, but design tasks keep coming, your manager will inevitably suggest you just handle it as contract work. Off the books. Unpaid. This is exactly how wage violations happen^[8]. Your career-resume needs clear boundaries. Before you accept this arrangement, demand a written scope of work for the design contract. Get deliverables listed. Set a maximum number of hours. Make it impossible for anyone to claim ambiguity later. Don’t wait for the contracts—push for them now.

How Hybrid Roles Can Harm Your Future Job Prospects

When you’re job hunting in six months or a year, you’ll need to explain this arrangement on your resume and in interviews. Future employers won’t care that the setup was confusing or that you weren’t sure about the legality. They’ll just see that you worked under a structure that raises questions. Compare two resume entries: “Events Coordinator, ABC Company, 2024” versus “Events Coordinator & Contract Designer, ABC Company, 2024.” The second one immediately triggers questions. What was the contract for? How were hours tracked? Did you run into any issues? Instead of building your career-resume, you’re actually creating a liability. The cleaner approach? Take the hourly assistant producer role (which is legitimate work you’ve already been doing), but push back hard on the contract design position. If they won’t do it as a fourth hourly role, decline it. Your future self will thank you when you don’t have to explain a complicated hybrid arrangement to hiring managers.

Understanding Minimum Wage and Overtime Violations Risks

You mentioned something essential almost in passing: “It’s possible that before accounting for the bonus this would leave me making less than minimum wage.” Let’s be direct—that’s not possible. That’s illegal. California’s minimum wage is $16 per hour^[2]. If you’re working 50 hours total (35 events + 15 design) and getting paid $16/hour for 35 hours of events work, your actual hourly rate across all work is $22.40. But here’s the trap: if those 15 design hours are unpaid until year-end, you’re effectively working for $11.20 an hour for that project. That violates minimum wage law. Add overtime on top—if you’re working more than 40 hours in a week, you should be earning 1.5x your regular rate^[6] on the overage. Your career-resume shouldn’t include work arrangements where you’re potentially earning below minimum wage. Ever. Run the numbers before you sign anything. If the math doesn’t work out to at least $16/hour for every hour worked, the deal is broken.

Sarah’s Interview Challenge: Explaining Questionable Work Setup

Eighteen months later, Sarah was interviewing for a senior events role at a bigger company. The hiring manager asked about her time at the small creative firm. “Why did you leave?” Sarah hesitated. The truth was complicated. After the dual-role situation, she’d felt uneasy about the company’s practices. She’d done some research and realized they’d likely violated overtime laws^[1]. She couldn’t prove it, but she couldn’t ignore it either. When she tried to explain this in the interview, she sounded bitter or confused. The hiring manager moved on to other candidates. Sarah realized too late that her attempt to be a team player and build her career-resume had actually damaged it. She’d been part of a questionable arrangement, couldn’t plainly articulate why without sounding like she was complaining, and now employers wondered what had really happened. The lesson stuck: protecting your career-resume sometimes means saying no to opportunities that sound good in the moment but feel wrong when you examine them closely.

Key Warning Signs of Problematic Employment Structures

Everyone says, “Take on extra work to build your resume.” But not all extra work builds your resume—some of it damages it. Here are the red flags you should’ve seen immediately: One, they’re offering payment structure that’s unusual (bonuses instead of hourly wages). Two, the roles are related but they’re calling them separate positions. Three, they mention avoiding certain legal obligations like overtime^[3]. Four, your manager explicitly said they didn’t want you leaving at 40 hours because of “team morale.” Five, there’s no written contract for the design work yet. People keep getting this wrong because they assume employers know the law and wouldn’t cross the line. Wrong. Some employers count on workers not understanding their rights. Your career-resume is too valuable to risk on a structure that has “legal problem” written all over it. If something feels off, it probably is.

Essential Questions to Ask Before Signing Dual Role Contracts

Don’t sign anything until you get written answers to these questions—and add them to your career-resume file. First: “How will my hours be tracked for each role?” Second: “What happens if I work more than 40 hours in a week?” Will you be paid overtime^[4]? Third: “When and how will the design contract payment be made?” (Push for regular payment, not a year-end bonus.) Fourth: “If I work more than eight hours in a day^[5], do I receive overtime pay on top of my regular hourly rate?” Fifth: “Can you provide the design contract before I commit?” Sixth: “What’s the maximum number of design hours I’ll be expected to work?” Seventh: “If scope changes, how will that be handled and paid?” Their answers will tell you everything. If they’re vague or defensive, that’s your sign. A legitimate employer will have clear answers because they’ve thought through the legal requirements^[6]. Don’t proceed without them.

Prioritizing Legal Hourly Work to Strengthen Your Resume

The extra money sounds good right now, especially during slow months. But your career-resume is a decade-long document, not a single event. One year from now, you’ll have moved on to a better opportunity (which is your plan anyway). This company will be background. What matters is what you learned and how you protected yourself. You can absolutely take the assistant producer role—that’s legitimate work, it’s hourly, it’s clear. But the design contract? Decline it unless they restructure it as straight hourly work with proper overtime protections. Your future self won’t regret missing out on a questionable bonus. But you might regret the legal complications, the unclear job history, or the precedent you set about accepting sketchy arrangements. Building a strong career-resume means knowing when to say no. This is one of those times. Tell them you’re excited about the assistant role but need the design work structured as regular hourly employment with clear overtime provisions. If they won’t do that, walk away. Your career is worth more than one event.