Why Housing Is So Expensive — and Why Timing the Market Is a Myth
Scott Galloway's latest Prof G Pod (Oct 26, 34 minutes) takes up the question every buyer and seller is really asking: why is housing so expensive, and what would it actually take to make it affordable?
The short answer: it's a supply problem, not a timing puzzle.
The episode frames affordability as a structural question — what has to change for homes to be within reach — rather than a bet on when prices or rates will cooperate. That's an important shift. If the problem is structural, waiting for a single perfect moment doesn't fix it; it just moves your life plans around a market you can't control.
The myth of timing the market.
Market timing feels smart in hindsight and is nearly impossible in advance. Buyers who wait for the dip and sellers who wait for the peak are making the same bet, and both pay for it in lost time.
What that means for Boston buyers and sellers.
This is an application of the episode's argument, not Galloway's Boston take: in a tight, high-cost market, the decision usually isn't "is this the cheapest month ever?" It's "does this move fit your life, your budget, and a holding period long enough to ride out a cycle?" If you're buying a home to live in for years, a small rate or price move matters less than buying the wrong house — or waiting years for a dip that never arrives. If you're selling, pricing for today's buyer beats holding out for a peak that may already be behind you.