4 Brutal Lessons From 356 Days of Unemployment (From Someone Who Should Know Better)
Time is a flat circle and, apparently, so is my job search.
Hey there, it's me again; your friendly neighborhood unemployment expert — and by “expert,” I mean I've been jobless for 356 days. Yeah, I'm counting. Ha ha haaa.
In that time, I've submitted roughly 80 job applications — a number that would be higher if I hadn't spent an entire night crafting the perfect Federal resume, only to wake up and find the posting closed — participated in interviews while pretending my mom wasn't asking me how many peeled tangerines I wanted in the next room, and learned the hard way that teaching other people how to get jobs for years doesn't make you immune to unemployment yourself. The universe has a sense of humor, and it's laughing directly at my LinkedIn profile.
Look, I could write another “10 TIPS TO OPTIMIZE YOUR LINKEDIN!!!” post — trust me, I've read them all questioning every career decision I've ever made — but instead, let's talk about the messy, real lessons from someone who should theoretically know better. Here are four things I wish I'd known 357 days ago, starting with the biggest lie in tech: your professional network.
Lesson 1: Your Professional Network Isn't What You Think It Is (And LinkedIn Is a Liar)
I have approximately 1,990 LinkedIn connections — which, as it turns out, isn’t worth squawk at the end of the day. (Note: unless we are connected on LinkedIn! In which case, I totally don’t mean you; you’re cool. I mean that other person I’m connected to; they suck.)
See, I thought I had this networking thing figured out. I've been blogging since 2000 — back when we called them "web logs" and fought about RSS readers — worked at major tech companies — shoutout to my Yahoo! Photos crew, all three of you who are still speaking to me — and taught hundreds of students how to code. I'm basically a connection collecting machine, right?
Wrong. So very, very wrong.
Here's what actually happens when you're unemployed: You start reaching out to those connections, and suddenly everyone's profile picture starts looking like the "I don't know her" Mariah Carey gif. I mass-messaged some people in my network when this all started — carefully crafted messages, mind you, not just "hey hope ur hiring lol" — and the response rate was… lackluster. I may as well have created a new Gmail filter just to hide the tumbleweeds rolling through my inbox.
But then something interesting happened. A contact at Code for America — who I'd actually, you know, kept in touch with — tipped me off about a federal position. Former students started reaching out with leads because we'd built real relationships in the classroom, not just "networking opportunities." Even if those classrooms were conducted over Zoom in the midst of COVID.
The takeaway I was learning really quickly: Those LinkedIn connections from 2003 aren't going to magically turn into job referrals just because you both survived the first dot-com crash together. Your "network" isn't about that impressive number under your profile — it's about the people who actually remember what your voice sounds like.
Speaking of voices — let's talk about our new robot overlords and how they're supposedly going to help you land that dream job.
Lesson 2: AI Tools Won't Save Your Job Search (But They Might Save Your Sanity)
Let's talk about AI, because apparently that's all anyone wants to talk about anyway. This isn't another “AI will take all our jobs” piece — though at this point, I'd welcome the competition. At least the robots answer their emails.
I've spent an embarrassing amount of time with ChatGPT and Claude, to the point where I'm pretty sure they know more about my career than I do. My workflow involves creating what I call a "brag document" — because “list of things I did that sound impressive but somehow haven't translated into employment” was too long — and feeding it to various AI assistants.
Here's the thing though — AI is like that friend who's trying to help you date but embellishes your stories a bit too much. Without explicit instructions not to hallucinate, AI will straight up lie about your achievements. “Oh, you taught web development? Surely you must have single-handedly built 25 full-stack applications while teaching 40 hours a week and curing cancer on the weekends!”
Narrator: He did not cure cancer.
I've learned to be very specific with my AI friends. Imagine this, for example, as if I were audibly talking to my LLM, face buried in my hands:
“Claude, Please don't make up achievements, even if they sound plausible.”
“No Claude, I did not 'revolutionize the paradigm of educational technology'“
“CLAUDE. Stop trying to make 'synergy' happen. It's not going to happen.”
A couple of days ago, I started taking a different strategy to address this: the “master resume,” a massive document meant explicitly for chatbots like Claude or ChatGPT to reference when it comes time to build individual bespoke resumes. It not only has every job I’ve EVER had, but every project I’ve done, and an extended brag list thing with references to skills for any role I would ever apply for.
(Let me re-emphasize this: I’m not actually submitting this master resume anywhere; it’s being used as context for AI queries only. NO SUBMITTED RESUME SHOULD EVER BE 2,200 WORDS LONG, Former Student of Mine Who Is Probably Already Hired.)
The real value of AI isn't in crafting the perfect resume — it's in helping you maintain your sanity while you're submitting your 80th job application at 2 AM, wondering if you should just start a YouTube channel about 9-member K-Pop girl group Twice. (Quick answer: according to these 3.5 million search results, the answer is no.)
But even with all the AI assistance in the world, there's one thing no algorithm can control: time. And boy, does time feel different on this side of unemployment.
Lesson 3: The Timeline Is Not In Your Control (And Time Is More Relative Than Einstein Thought)
Remember when I said it's been 356 days? Fun fact: that number hits differently when your mom starts every phone call with “Have you bought it yet?” and you have to keep asking "Bought what?" until you realize she's talking about the dryer that broke down three conversations ago. Time becomes... elastic.
The biggest joke? I literally taught people how to get jobs — like, that was my actual job. Teaching others how to land tech roles. “How long could it possibly take?” I thought, with the confidence of someone who had clearly angered several ancient gods in a past life.
Here's a timeline of how I thought this would go:
Month 1-2: Strategic job search, picking only the perfect roles
Month 3: Multiple offers, tough negotiations
Month 4: Start new job, write LinkedIn post about "my journey"
Here's what actually happened:
Months 1-2: Strategic job search — okay, this part was accurate
Month 3: Panic
Month 4: More panic, but with spreadsheets
Month 10: Watch a perfect federal job posting hit its application limit overnight before I could even submit my carefully crafted resume that took 6 hours to write — not that I'm bitter or anything ha ha ha
Month 12: Start measuring success in how many times you can use the word “resilient” in a cover letter without sounding unhinged
I’ve had promising interviews lead nowhere. I’ve watched former students — people I HAVE TAUGHT — land roles faster than me. I've started measuring time not in days or weeks, but in how many times I've had to update my “current status” on LinkedIn to increasingly creative variations of “Open to Work.” Current favorite: “Professional Resume Distributor and Part-Time Existential Crisis Manager.”
And while we're being honest about uncomfortable truths — there's something else we need to talk about. Something that makes tech hiring even more complicated for folks like me.
Lesson 4: Non-Standard Tech Careers Come With Non-Standard Challenges (And No One Wants to Talk About It)
Look, I don't like being a pessimist online — it makes me sound like an old grump. But this grump is wearing a pink elephant costume because seriously, is no one else is going to address the elephant in the room? No?
Guess I will, then.
Here's the thing about having a non-standard tech background: the cards are stacked against you in ways no one wants to acknowledge. Most folks follow a neat little trajectory: start in engineering, continue in engineering, become senior or staff engineers or engineering managers.
My path was... um, different. It involved moving to Florida for a relationship — as one does — getting into civic technology, starting a couple of community groups and non-profits, and then — because life has a sense of humor — moving back to the Bay Area two years ago hoping to put my name back in the ring.
Want to know how that's going? Two weeks ago, I made it through the first round of a FAANG company interview, only to have my pass rescinded a couple days later. "You were being interviewed as a mid-level, not as a senior engineer," they said.
“But I don't want to be interviewed as a senior engineer,” I answered.
“Doesn't matter when you have the experience.”
After protesting, the recruiter said there was “nothing they could do.” And that terrifies me, because if that's the attitude of one FAANG company, well, that's going to be the attitude for all of them. They don't want to hear my special snowflake story when they're hiring at scale and they can get surefire bets of people with continuous experience. The quiet internal terror settled in when I realized that no modern tech company does.
Already completely defeated, I interviewed a second time at that FAANG company. My stock rejection email arrived last week.
That rejection… that one was brutal. But I'm brushing it off and trying to figure out my next steps because I have no other choice.
Okay then. Let's recap what we've covered — because lists make everything feel more manageable, right?
Real networks require real relationships — not just LinkedIn connections from 2003
AI is a tool for enhancement — but won't write your life story better than you
The timeline isn't yours to control — as my Federal resume can attest
Non-standard careers come with non-standard challenges — and sometimes a pink elephant costume
Final thought: Maybe the real job search was the existential crises we had along the way.
Too dark? Yeah, probably too dark. But hey, we're being honest here. And if you're also counting the days — whether it's 356 or 3 or 1,000 — just know that somewhere out there, I'm probably updating my LinkedIn status to something even more unhinged. Current contender: “Time is a flat circle and so is my job search.”
Ha ha ha ha... ha.
I think the observation @Ernie Hsiung made about "no one wants to hear my special snowflake story when they can hire a sure-thing" is absolutely spot on, and I think there are a bunch of different truisms like that about the job market that people should consider as a sign of a storm.
I just interviewed someone who was a tech team leader, then spent a couple of years as an engineering manager. My questions were geared toward whether or not this person was too "senior" to be useful.
When you're hiring people to write code, the more leader-of-people you are the less in-the-weeds you've been (often), and what company ABC wants right now is drop-in in-the-weeds velocity-driving talent - not thought leadership.
It also doesn't do to hire from the spill of FAANG (MAANG?) lay offs, because when you work for a big company - well, the breadth of your experience is really quite narrow, so you're not a great fit for an upscaling startup that requires the wearing of many hats (and a lack of luxury).
Suddenly, the criteria you're looking for is hard to find. Optionally, you can train people up: but because you don't want to sink current velocity by coaching-up entry- or mid-level engineers, you pass on them, too.
What’s more, a job description is _content_ on a content-glutted internet, and it's really quite hard to target the job description to the cohort of applicants you want, so you tailor your hiring process to weed the onslaught of applications, and you can't help but favor first-come first-serve. You also rely hard on recruiters.
One recruiter told me that the best thing you can do is make friends with recruiters. That "once you are responding to job postings, you're already probably at the back of the line."
The thing that scares me is that I can barely market a podcast with an advertising budget - how am I suppose to market myself?
Thanks for your honesty, Ernie. You are not the only person with substantial experience in the tech industry who finds themself with very few opportunities due to some "unconventional choices" along the way.
The application, interviewing and testing hoops seem perfectly designed to break most applicants, and there's always a "there's lots of jobs if you have the right skills" jerk waiting to lecture you in the wings. There is no room allocated for independent thinkers.
The tech industry is a heartless game of survivor island, and once you're voted off there's often no way back on. Every mass layoff increases supply and reduces demand. We've seen the masks coming off in recent months as to exactly how toxic the industry is, and now tech/AI is eating many of the most viable fallback plans (writing, etc.) so these are difficult times for many people, even if most keep quiet about their struggles.