Patient Cheetah asked

answered 2h ago

What do you think about OE (over-employment)? I.e. remote contracting for multiple companies at the same time. I'm not talking about the Soham Parekh case, but rather about genuinely doing your best to deliver value for multiple companies by leveraging AI and context-switching efficiently.

I see arguments on both sides:

  • In favor:

    • Obviously increasing your income

    • Learning a very wide range of technologies quickly

    • Getting a broader exposure to the industry

    • Learning context-switching

    • Diversifying your job (less pressure than working in one more prestigious company in case of RIF or toxic company/team culture)

  • Against:

    • Spending less time and energy to execute on truly difficult deep-work tasks

    • Being a bit sketchy for the employer, CV, or future applications to top-tier companies if you want to pivot away from it

    • Might scale worse than climbing a corporate ladder to a very high level

    • Time and effort overhead to manage meetings

Philip's answer

The right path likely depends on each person, but here's what I think matters:

  • There's a qualitative question of whether you'd enjoy splitting your attention. This, for instance, is why I could never get into "multi-tabling" in poker. Yes, you win more money, but I find the experience far less enjoyable. It's like asking for the opposite of Flow.

  • Depending on where you are in your career growth, it might actually pay off better to focus all your attention on one job, working much more time at it, than to split across two. The closer you are to your career asymptote (i.e. top of your game), the better it might be to instead spread your services across two jobs. There's a reason why poker pros tend to play one game at a time; sometimes your yield is actually higher by focusing. Whereas if you're in a dead-end job with little growth, and doing the job is easy for you, working two such jobs will probably get you more income.

  • Nearly all major companies explicitly prohibit this in their employment contracts, which makes this decision easy.

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