Going 1099

  • Negotiation is listening

    There's an episode of The Office where Daryl, an employee of Dunder Mifflin, asks for a raise and Michael, the bumbling regional manager, rese...
  • You need to be your own manager

    What exactly are free agents free from? In sports, a free agent is someone free of allegiances to a particular team. In knight-errantry, a freela...
  • SAM.gov registration update: Don't be a DUNS

    When I wrote the Going 1099 book, I provided instructions on how to register your business with the government at sam.gov. Registering at sam.gov ...
  • Take more UPTO

    Microsoft announced that they are doing away with their traditional PTO system and giving everyone "unlimited" PTO.​ So my advice to you is to get...
  • Should you go 1099 in a recession?

    The economy is in a weird state right now. Inflation is pretty high, the stock market is a bit sluggish, and yet there is still robust demand for ...
  • Tactical, strategic, or existential problem

    You have a tactical problem when you don't know how to do something. You have a strategic problem when you don't know what general approach to tak...
  • The psychological benefit of an LLC and an e-mail

    ​In my book, my general philosophy towards administrative stuff is to do as little as possible and only after you've taken care of the important s...
  • You are the prime's insurance policy

    Every month my wife and I pay about $100 each for term life insurance. If either of us kick the bucket in the next 25 years, our beneficiaries wil...
  • How to have uncomfortable conversations

    It's uncomfortable for most people to get into a negotiation. It's uncomfortable because we rarely get the chance to do it and we're worried about...
  • No deal is better than a bad deal

    When you get excited about an idea, it's easy to ignore any potential red flags coming your way. If you have a possible 1099 opportunity coming yo...
  • What's different when you hire employees?

    My company now has four employees, which makes six people if you include me and my business partner. Here are a few differences I've observed betw...
  • W2 employment is weird

    I read an article in the Wall Street Journal titled Your Coworkers Are Less Ambitious; Bosses Adjust to the New Order. The gist is that employees ...