I am kind of an odd position where I am looking for supplemental income, it isn't that I am not being paid enough, but rather I am trying to better prepare for the future, and prepare for a debt free life. Basically I am looking at starting contracting work in my off hours. To be clear I have a full time salaried position, but we generally do not work over 45 hours, and I am looking to supplement my off hours for this work.

The odd part of this being that, like many other companies we are short staffed, and it is common knowledge that they are actively looking for additional resources. It could be mutually beneficial for me to work additional hours as a contractor, I already have the business knowledge, and I could be productive right away, as compared to someone else that is not familiar with the business aspect. I envision starting a conversation with my manager (who is very understanding), and inform him of my situation along with my motivation (to payoff debt). At that point I would advise that I am looking for this supplemental income, and ask if there could be a mutual benefit to have me perform contracting work for the company that has me hired as an exempt(salaried employee).

Honestly, I do not think this is feasible. The purpose of exempt employee is not paying them overtime, essentially this becomes overtime. Is it a bad idea to even start this conversation with my manager? I would appreciate any advice you could give.

  • 1
    Isn't it possible to just do overtime and be paid for that ?
    – MlleMei
    Commented Jul 5, 2019 at 11:58

2 Answers 2


It doesn't hurt to ask, but consider options other than contracting with your current employer.

Your current employer likely can't employ you twice. Depending on your locality, it's likely not possible to employ you without overtime compensation for more than full-time work. Regardless, employing you in two different capacities would be new territory for administration, so I doubt it would be allowed.

However, your employer is likely to be supportive of you pursuing other contract work outside of work hours. If you do great work already, your manager isn't likely to be concerned with you taking other work. You should ask to make sure you don't have an exclusive-employment agreement ("while you work for us, you may only work for us"), but these are typical only in professional firms.

Additionally, you should ask your employer about debt-assistance programs. Many companies subscribe to employee benefit programs. Your employer may subscribe to a program that does things like provide free financial planning, help you refinance, or even help you with specific debts (e.g., home mortgages).

  • Thanks, that makes sense. We do not have an exclusive contract, so at least that portion shouldn't be an issue.
    – broot02
    Commented Jul 5, 2019 at 13:04

If the company was to allow you to work extra hours they would be concerned that you are doing the same amount of work, but charging more hours.

I have seen this work in a couple of situations where employees were looking for extra income:

  • One was a receptionist, who was then hired by the company with the cleaning contract for the building. She did the work for the second company after hours. This worked because another company hired her and the two sets of tasks didn't overlap. Both companies were aware of this.
  • One manager also worked as a security guard at the visitor entrance on weekends. Again this was a second company and the tasks didn't overlap. Again both knew.

Sometimes the need for extra hours was a requirement by the company/customer.

  • I was once paid to be my own assistant. I worked for a contracting company to write software. There was a dispute between the customer and another company regarding who was allowed to write software. The second company won the argument but had nobody on staff who could start working on the software. A compromise was worked out where the second company awarded my company a subcontract for me to work halftime on software development for 6 months. So for the next 6 months I did 40 hours a week for company A and 20 hours for company B. For the same project. It was very confusing. I wondered if I could double bill during staff meetings.

Overtime maybe the best option, because even at 1.5x time you will still be cheaper than a new hire. Much of the overhead for you doesn't change just because you work extra hours. This type of arrangement works best when your production is easily measured.

  • The advice is appreciated. I will bring up the overtime solution, my issue is that the company benefits from having me as an exempt employee, and I do not see that changing. To be paid for overtime, I cannot be an exempt employee, correct?
    – broot02
    Commented Jul 5, 2019 at 13:07
  • I have worked for companies as exempt employee. They can still pay overtime. They aren't required to pay overtime, but they can. Some only pay when you exceed 44 hours, some only when tasked with working on a weekend or late at night. This can be negotiated. The company made more money when they can charge customers for all my hours. Commented Jul 5, 2019 at 13:28

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