BLUF: before you freelance on the side, read your employment agreement. Here's how I got my side gig squared away at a defense contractor

BLUF: I now build and maintain a booking site for a local gym on nights and weekends, legally, with my employer's written OK. It took three weeks of paperwork. Here's the checklist, because a lot of you career changers are about to do the same thing and some of you will skip step 1.

1. Read your employment agreement. All of it.

Look for three things: an "outside employment" or "conflict of interest" clause, an IP assignment clause, and anything about company equipment. Mine had all three.

2. The IP clause is the scary one

Many agreements say the company owns inventions you create "during your employment". Read the exact wording. In California, Labor Code section 2870 limits that: an employer generally can't claim something you built entirely on your own time, with your own equipment, that doesn't relate to the employer's business or come out of your work for them. Some other states have similar laws, some don't. A gym booking site has nothing to do with defense software. That matters.

3. Ask in writing

I sent HR a one-page request: who the client is (a local gym, no government work), what I'm building, hours (evenings and weekends, under 10 a week), and confirmation that I use my own laptop, my own accounts, and no company time. Approved in writing after two weeks. Keep that email forever.

4. If you hold a clearance, talk to your security officer

Cleared folks have reporting requirements. I'm not going to list them here, and they depend on your situation, so walk into your security office and ask before you sign a client. Ten minutes of awkward conversation beats a very bad day later.

5. Separate everything

• Own laptop. Never the work laptop, not even "just to check the client's email"
• Own GitHub account, own email, own password manager vault
• Never on work hours. My time log for the gym starts at 6pm or later, and I keep the log

6. The money

$60 an hour, about 8 hours a week. I set up a single-member LLC, mostly to keep the paperwork clean. Set aside around 30% for taxes from day one. Side income has no withholding, and April will remind you.

Twenty years in the Navy taught me that paperwork done early is boring, and paperwork done late is an investigation. Get squared away first, then code.

Never too old.