I've been juggling multiple remote high-powered consulting roles for over two years now, starting right after grad school from a top Ivy League program. This has let me double my income in Bangkok and traveling freely. (my story here)

For those who are new here, it refers to ‘overemployment,’ to be employed in 2+ jobs gainfully. I’ve maintained since the start of this newsletter that OE isn't a push for laziness or dodging hard work. OE is about doing good work fast and making the most of your time. Today’s post goes into some of the relevant theory.

Employer contracts have gaps because information isn't ‘perfect’ Your pay doesn't match your output since it's hard to measure everything. If there is indeed ‘perfect information’ (a lingo from my econ major days), your salary would be completely linear against the output that you create. In other words, it would be completely commission-based.

I believe that AI has further exacerbated information asymmetry between the employer and employee. Now, it’s not about firms unable to measure manageable (think a hypothetical 10-30%) variations in an employee’s output. One person now can handle 200% or maybe even 1000% the work. Far from being ‘perfect,’ the information that employers have in designing contracts and informing hiring decisions is now in complete ‘chaos.’

When I started OE, it was mostly about squeezing more into my day thanks to no commute, bathroom breaks, or blocking off your outlook calendars. Now and more so than ever, AI helps me crank out results quicker than ever.

Instead of dumping your extra capacity into one job for maybe a small bonus (the part of your compensation that is designed to reflect the ‘availability of information’ in your output, why not spread it across two jobs? Your effort remains the same but the paychecks double. That's the core of OE. And with white-collar jobs not getting fully replaced by AI anytime soon, this edge will stick around for those who are risk-tolerant enough to handle it.

I know a guy from college – let's call him Mike – who was at a big tech firm, putting in solid work but using AI to finish tasks in half the time. One day, out of the blue, his team got hit with layoffs.

Boom, half his income gone. But Mike had quietly started a J2 a few months back, same field, remote setup, having been spooked by layoff news at other firms.

Without it, he'd have been scrambling, dipping into savings, stressing over everything. Now he's back to OE, stronger than before. Moral? Don't wait for the axe to fall; build your safety net early.

OE is like insurance against all sorts of bullshit happening at your J1, from not only interpersonal beef with your colleagues (I will cover in another article that I’m tentatively naming “the OE Monk,”) but also layoffs. If you're relying on one job, you're putting all your eggs in one basket – not smart for you or your family.

Full-time work isn't set up to max your efficiency. It's more about booking your time, even if you're not using every minute productively. Contracts are designed to fit the lowest common denominator of risk tolerance – such that your co-worker, single mother of 2, Betty is able to reliably pay for her rent next month. Or, it’s to enforce a system of fairness in an environment where not all performance outcomes are measured.

You're paid for hours on the clock, not purely for what you deliver. Companies want steady workers without watching your every move. You want predictable pay to plan your life. So, they mix base salary (for time) with bonuses (for results). The base pay keeps you committed, bonuses push for better output. But it's not perfect for you. Why? Because they can't track your true effort perfectly, especially remote. That's the inefficiency OE taps into. You're not cheating; you're using the system's gaps. Firms set these rules, and smart workers optimize within them. It's rational, as the econ models predict.

An anecdote from my recruiting days in college: before my final-round interview in NYC (I don’t work there btw), I got one of those “oh shit” moments. The recruiter sent the calendar invite and accidentally cc’d everyone instead of bcc (blind carbon copy). It was what you’d expect: Stanford.edu, Harvard.edu, Yale.edu… a couple other usual suspects, plus a few HBCUs. About 20 people total. I felt honored for a second but also freaked out that I’m competing with some pretty hardcore folks.

I’m lucky I was raised in a cut-throat environment with creatures like this. High school classmates took uni-level classes and spent more time in extracurriculars than studying. In college, people skipped class to cram for another exam that mattered more or prep for the interview or networking meeting that mattered more. Folks were allergic to low-ROI (return on investment) time.

If you’re in a firm you don’t see as your long-term home, you need to get more ruthless with your calendar. Fuck the BS company events if there’s no networking upside. Stop donating prime morning hours to performative business.

To be honest, it’s already normalized in some “elite” pipelines. Investment banking → PE (private equity) is essentially a “take this job so you can get the next job”-type of job for some. Jamie Dimon (CEO of JP Morgan) has complained about first-year analysts checking out because they’ve basically lined up their next role before the current one even starts. (JPMorgan has had enough of grads accepting future-dated roles elsewhere)

Extra income from OE could mean financial freedom faster, family security, or living bigger. Don't leave money on the table.

This newsletter's grown to over 100 readers since last time, so I'm reiterating these basics for newcomers. J2 Confidential is all hand-written, with real stories to add value. Rate this out of 10 in the poll below or email me at [email protected] with thoughts.

If you want to learn more, I recommend you check out some of my other recent articles here: