I was at a conference recently where a speaker talked about being “overemployed.” In his case, he was holding two simultaneous full time W-2 jobs. Both were project-based and largely virtual, and his argument was that as long as he delivered what he was contractually obligated to deliver, the rest of his time was his own.

I don’t disagree. To me, the key distinction is output versus presence. If an employer is getting exactly what they paid for, then what someone does outside of that agreement isn’t really their concern. If work is being neglected, that’s a performance issue. But if expectations are being met, it’s harder to argue there’s something unethical happening.

Katie and I have had our own version of overemployment during our FI journey.

I’ve never held two full-time W-2 jobs at once, but I’ve often combined one full-time position with multiple 1099 roles—some of which approached full-time hours. Peak crazy was during COVID. At one point I was teaching a full-time university role (online), adjuncting at two other universities, and consulting with K-12 schools around the country on their transition to virtual learning. Meanwhile, Katie was working her W-2 job, teaching online, and doing the occasional tutoring gig.

Seven different jobs between the two of us.

It sounds intense (and it was) but it worked… for that season.

Why It Helped

Katie and I have always had a household budget based on our regular jobs, but made a deal early in our relationship that whoever brought in extra income could spend half of it however they wanted…with no questions, no recriminations.  For me that meant paying for graduate degrees and investing more.  For Katie it meant a couple of additional luxuries or bonus travel.  In the end, multiple income streams really accelerated our savings rate. There were years we exceeded 50%. That kind of margin dramatically changes the FI timeline.

Maybe even more importantly, it also made the transition to early retirement gradual instead of abrupt.

We didn’t jump from full speed to zero. We pruned.

• The adjunct roles that weren’t leading anywhere..
• The W-2 where you and the new boss didn’t see eye to eye
• The projects that weren’t fulfilling.
• The gigs that weren’t profitable enough to justify the effort.

It’s a lot easier to “retire” when you’re walking away from one of several income streams instead of cutting off your only paycheck (link to “Winding down to FIRE post).

There’s also a psychological shift that happens. When no single employer controls all of your income, you feel freer. You’re less afraid to say no. You’re less likely to tolerate work you don’t enjoy. That optionality is powerful.

Right now, I’m still holding onto one last 1099 gig. It’s flexible. It’s interesting and meaningful. It pays well. Maybe next year I’ll satisfy the Retirement Police and drop even that 🙂

But I don’t feel rushed.

A Word of Caution

This only works if it’s intentional. There’s a difference between strategic overemployment and burnout. We’ve had seasons where the calendar was too full. The key is knowing your “why.”

For us, the goal wasn’t to work more forever. It was to create flexibility. Overemployment wasn’t the destination. It was the bridge.  Sometimes the fastest way to freedom isn’t quitting. It’s stacking wisely… and pruning deliberately.

Have you ever held multiple roles at once? Did it feel empowering?  Or exhausting?