WFH: Tax Policy Edition

Assume working from home is still generally common, at least at some level, two years from now. How would or could employment conditions and tax policy catch up with that?

For example, if a self-employed worker can deduct the cost of her home office (in rent or mortgage by area) from her income, at what point would it make sense for salaried worker to do the same thing — by incorporation if necessary?

Frankly, I don’t know the details on this well enough to begin to attempt the math, but it’s not hard to imagine more salaried positions moving, if possible, toward a B2B or contractor structure.

In the abstract, I would guess that the early adopters won’t be numerous enough to totally unbundle employment, work, salary/income, and insurance at a stroke (in the United States), but I wouldn’t be at all surprised to see gig-like arrangements jump much closer to the mainstream, much faster, and at much higher levels than most people would have predicted six months ago.

Why lose money on a new associate for three years, for example, when you could just contract with the lawyer you really need for the six months you really need her?


As long as we’re indulging flights of fancy beyond my sphere of expertise, let’s take this one step further: if a lot of formerly W-2 jobs get reincarnated as 1099 contracts — because employees see a business case to become businesses, businesses see a business case to pay only for what they need by 1099 at 80–120% of what used to be annual W-2 rates, or both — how will we smooth income, investing, and insurance?

Let’s table income and investing for another day, but imagine that a mass dislocation — especially of white-collar workers — from relatively steady to relatively unsteady employment might drive enormously increase enrollment through ACA marketplaces and/or public options.

And that might turn out to finally put enough pressure on our broken insurance system to drive real reform. When enough people who thought they were safe start to feel the precarity of their situation over the long term, they won’t stay quiet for long.