I've been pulling off overemployment for over two years now. I graduated from an Ivy League undergrad and a top-seven business school. My main job is at a big-name management consulting firm, and my second is at a boutique one. Living remotely in Bangkok, I've doubled my income since starting out, all while traveling the world and running side hustles. I've helped tons of people navigate remote work, AI shifts, rising costs, and job insecurity through J2 Confidential.

People often think you need to show up as a rockstar from day one. Maybe you hyped yourself too much during the interview. Or, maybe you wanted to make a splash. But in OE, that mindset can backfire. It leads to more work piled on, less time for your other gigs, and quicker burnout. Setting expectations low changes the game by giving you control. You get more space to manage multiple jobs without anyone noticing. This isn't about being lazy. It's about smart moves that protect your time and let you focus on building real wealth (and I would argue, tasks that actually move the needle for your job, as opposed to ‘busy work’)

In my last article on optics, I talked about being over-communicative to keep things smooth. (Check it out here.) This builds on that idea. Setting expectations means sharing info that helps you out when things get tricky (as they inevitably will in OE).

The core here is making your manager see you as someone who's ramping up slow. This creates buffer in an OE world where every hour counts. Ambiguity can invite more oversight, so you squash it by oversharing. But in this case, you're oversharing details that work for you. Only do this after you've got the job, not in interviews. And remember, it's not a one-time thing. You set expectations at the start and keep doing it as the job goes on.

When you first join a team or start a project, humility can be your best friend. Tell them you're nervous and might need extra time to get up to speed. This softens those early weeks, specially if there are regular meetings or updates. It buys you grace when things are new and chaotic.

If you haven't checked my upward communication guide here, do it now. This tactic shines in setups where you can't control how often you report, like daily stand-ups or group shares. For new grads, point out you're entry-level. For others, mention getting used to the culture, family issues, or not having full context yet. Pick something that feels true. If a second job is coming up, hint at personal stuff that might make you less active for a short time.

This approach might carry you through the first month. But jobs don't stay the same. New tasks pop up, projects shift. That's when you need to refresh those expectations to keep the buffer alive.

A fresh assignment after wrapping one up offers a perfect chance to voice some doubts. Share reservations about the task to guard against not having enough time. In OE, bandwidth is always tight, so this hedge can save you.

Worst case, you seem a bit negative, which is an easy thing to improve on later. Best case, you deliver strong and look impressive. Low risk, high reward. That's why it's a solid play for managing optics in multiple jobs.

Simple Phrases to Set Expectations Without Sounding Weak:

These lines help you come across as thoughtful, not unable. I've used versions of them to carve out time for side work without raising flags.

Burnout hits different when you're juggling jobs across time zones. Let me tell you about a rough patch in my OE journey. I was in Bangkok, working flipped hours for two consulting gigs. J1 had me up at weird times for strategy sessions, J2 needed client updates that clashed with everything. On top of that, I had side hustles brewing—a newsletter like this and some app ideas that could really pay off. I was easily working 80+ hours a week due to the nature of overlapped commitments at the time.

I felt the wall coming. A big personal project was on deck, one with way more upside than my corporate roles. But the OE grind was killing my focus. Dropping a job suddenly felt too risky—I needed the steady cash. So, I started seeding the idea early. In team calls, I'd casually say my health wasn't great and I might need some time off for treatment to come back better. I'd add that I felt bad about it but thought it'd help the team long-term.

Weeks later, when I took the break, it wasn't a shock. Everyone knew it was for health. I stepped away for a few weeks, dove into my project, and got it off the ground. It started bringing in side income right away, enough to ease the pressure. When I came back, people still asked about my well-being, which actually led to easier assignments. No one pushed hard, and I kept both jobs humming while growing my own stuff. This move showed me how setting expectations can turn a tough spot into an opportunity for more freedom and cash.

This example links to "seeding," which I'll dive into later. Setting expectations is more about your short-term image. Seeding preps people for bigger moves down the line. Both are tools for steering things your way in OE.

Some managers make you earn every bit of space. I once dealt with an overbearing Indian boss who checked all the bad boxes—micromanaging, calling late, always on about commitment. My work was good, review said so, but he wanted more hours, more everything. (I hate to say it, but unfortunately he fit all of the stereotypes of the “Indian manager”)

He'd hit me up 9 PM, complaining I wasn't dedicated. With OE, this ate into my other job and side time. After one too many late rants, I drew the line. I told him straight: I commit during work hours, but I have a life outside. Let's set clear expectations so I can do my best.

He threatened to escalate and fire me. I stayed calm, mentioned family stresses adding to things—like a relative's health issue making extra hours tough. (Really, it was OE juggling, but it fit.) I shared the convo with a coworker, and it turned out others felt the same.

Instead of getting canned, he eased up. I even talked my way into a lighter role with more flex. That gave me time to start my J3 search (indeed, I saw the writing on the wall), boosting my income further. The real win? In OE, firing isn't scary—you've got options. This pushback not only saved my setup but fired me up to keep stacking wins, breaking free from that daily grind.

Tools like this one fit into a bigger picture of optics. Just like upward reporting to keep your manager hands-off, setting expectations acts as backup when they do get involved. It plants ideas that protect you, letting you focus on doubling that paycheck.

In OE, it's all about hacks that let you earn more without more stress. Low expectations open up time for travel, side empires, or just living better. Go humble, plant doubts, and watch your options grow.