The struggle to be unemployed: Life after a Redfin layoff

Note: I wrote this as a sort of response to the post How to be unemployed: Glenn Kelman on life after Redfin posted to GeekWire on Friday

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In June of 2022, Redfin laid off 470 people. When the layoff was announced, those of us who remained were given a one-time stock grant to incentivize us not to jump ship, and assured that the cuts had been thoughtful and deep enough to position the company “to become profitable, and then very profitable” and to face “years, not months, of fewer home sales.” Five months later another 862 people, including me this time, had our jobs taken from us in the second of what would eventually be six rounds of layoffs.

Just two weeks earlier, my wife and I learned that she was pregnant. What should have been a joyous and exciting time in our life instead became one of the most stressful, soul-crushing periods I’ve ever had to face. Instead of looking forward to taking advantage of Redfin’s generous paternal leave, I now had to worry about how I’d be paying my mortgage. At the time my wife’s tea and spice shop Chai Cupboard was still costing us money (that’s a whole different story), so our family depended entirely on my income. While I did receive a severance of about three months’ worth of salary, none of the post-first-layoff-stock grant was vested. The reward for those of us who took leadership at its word in June was basically a slap in the face.

After a couple of months of intensive job hunting, I was “lucky” enough to get a job offer. “Lucky” is in quotes here because the pay was below what I had been making before, the medical insurance was paltry, and other benefits—including any time off for the impending birth of my son—were non-existent. Plus, I wasn’t really sure what the company even did. But once I had a job offer in hand, I had to take it or I’d lose my paltry unemployment benefits, putting us in a far worse financial condition.

As it turned out, there was a reason the company was cagey about the nature of their business… it was basically a scam. Or at least highly scam-adjacent. I held out as long as I could, thinking that at least I’d be better off having medical insurance when my son was born, even if I wouldn’t be able to take any time off. Well the joke was on me yet again, because even after insurance we ended up with over $20,000 in debt to the hospital that we couldn’t afford to pay. As you might imagine, my time at this company did not last more than a handful of months before I was back to being unemployed, now with a newborn baby at home.

For whatever reason, the Washington State unemployment office took an unusually long time to begin sending me benefits. After applying, I waited, and waited, and waited. I would regularly call the office—a line which has only a recorded message and zero options to ever speak to an actual person—only to consistently hear that decisions are made in “four to six weeks.” After seven weeks and no response, I went down to the local WorkSource office and discovered the secret phone that connects to an actual person at the unemployment office (yes, this is a real thing, see the picture). Not that it helped. All they would tell me was that they hadn’t even assigned someone to my case yet, and they couldn’t even say when they would. Finally, eight weeks after losing the scammy job, the unemployment checks started flowing again. Which, by the way, were capped at about a third of what I had previously been earning.

Over the next 14 months, I applied to over 600 jobs, customized my resume more times than I can count, wrote hundreds of thoughtful cover letters (on my own—without using AI), and networked with every past colleague I could think of. 98 percent of these applications received either a form letter rejection or no response at all.

By December of 2023, my savings ran out. The following March I swallowed my pride and started a GoFundMe to beg friends and family to help us out. In May, I decided to finally call it: my career in the tech industry was over. It was time to look elsewhere to support my family. In June, I hit the 26-week cap on unemployment benefits, taking my income all the way to zero.

For me, unemployment was not a time for navel-gazing and waxing philosophical about the nature of work, it was survival mode. I spent most of my time desperately trying to find a new job. I was too broke to take a road trip I had been planning with extended family for years to see the total eclipse in April 2024. I couldn’t afford to be picky about what I wanted to do next. I was ready to take any job that fit my skills and would pay the bills. I even interviewed for a position at a company whose sole mission is to aid coffee farmers, and I hate coffee.

In the conclusion of my May post calling it quits on tech, I wrote that only a “deus ex machina resolution” would keep me in the industry. Wikipedia describes “deus ex machina” as a situation in “which a seemingly unsolvable problem in a story is suddenly or abruptly resolved by an unexpected and unlikely occurrence.” Literally just as my unemployment was running out in June, that unexpected and unlikely occurrence came when a former Redfin coworker (who had left before any of the layoffs started) reached out to connect me with someone with his team. Even though they didn’t have any open roles at the time, he thought it would be good for us to chat.

By the time I had that chat a few weeks later, a role had just opened up, and I immediately began the official interview process. Two months later I finally had a new job at a healthy, growing startup with a solid product, great financials, and a very enthusiastic customer base. The pay was still about 15% less than what I used to make at Redfin, not counting stocks—23% less after accounting for the 10% inflation during my nearly two-year period of career purgatory. But nonetheless I am extremely grateful and happy to be working again.

Today I’m more than two years into my new job, and it feels good to be employed, but our savings account still sits near zero, and the hospital debt is unpaid. My story is just one of the 2,114 unemployment experiences brought on by Redfin’s layoffs, which themselves are a drop in the bucket of the hundreds of thousands of layoffs brought on by AI and the end of the ZIRP era of free money. And I know that my story is not the most difficult—at least it has a happy ending! The company I’m at now is in great shape and the leadership team has been nothing but honest with me, but I frequently catch myself expecting bad news just around the corner. The paychecks came back, but the financial and emotional scars remain.

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P.S.: I didn’t use AI to write this, either—I have always made good use of the em dash, and I’m not going to stop just because some expensive computers have decided it’s trendy now.