Lessons from Unemployment, part 2

Yesterday I received my 501st rejection for a job (not including the 236 I have yet to hear back from), 61 days after applying.

I also received my first offer letter.

Just under four years ago, I wrote Lessons in Product Management through unemployment, in which I reflected on the 6 or so months of job hunting I went through, and what I’d learned throughout the process. Reading that back today, the tone feels positively manufactured for LinkedIn, in terms of the positivity and learnings through adversity. You get the impression it was a humbling process for me, and that I was almost grateful to having gone through it.

This time though, this time it’s different. What did I learn?

Let’s start with the data:

• 72 weeks of unemployment

• 738 roles applied to

• 20 iterations of my CV

• 52 companies interviewed at

  • 26 with hiring managers

  • 26 only as far as a screening call

  • 1 I turned down (the salary offered represented.a 30% pay decrease, with a lot of asks in return)

  • 5 ghosted me: I interviewed with them but they never actually rejected me, and did not respond to any follow ups (and for the record: Hogarth, Bentley Systems, Lightricks, Converge, go fuck yourselves)

• 37 responded with feedback, of which 15 was actually valid (and was either that I lacked sufficient enthusiasm for the role or didn’t have enough domain experience for their particular business); the rest was a mix of the scope of the role changing, wanting someone at a lower salary bracket, or just generally misinterpreting my experience (a lot of people fixated on me having spent the past three years working on in-house products, conveniently ignoring the 7 years prior to that, also go fuck yourself if you think that even matters), or willingness (such as asking me if I was comfortable with the role being temporary, then counting that against me despite the role being advertised as such)

• Of the 69% of companies that actually bothered to contact me at all, the average response time was 15 days after me having submitted the application, a few replied the same day, and the longest (again, that even bothered to respond) was 200 days later.

• 203 (28%) asked for desired salary on the application form. Most of these were mandatory questions

• I wrote 367 cover letters (yes, I used a template to try and maintain some sanity)

• Including a cover letter increased the chance of an initial interview by 2%

Anecdotally, I heard that each job advertisement attracted around 1000 applications. That being true, I at least outperformed random chance in terms of just getting an interview (assume about 20 people are selected for a screening call, or about 2% of applicants, where as I managed about 7%).

However, it also means I severely under-performed at hiring manager interviews (assume 5 people make it to that stage, the odds for success would be around 20%, but for me it was 0% across 26 attempts). This is truly awful, and I wish I had figured out what I was doing wrong here. By nature I am extremely anti-social, but I think I can plaster on enough of a fake smile to convince regular people that I am a fully-functioning human being, but the data says otherwise.

On the other side of it, as much as it is nice to look at all these numbers, stroke my chin and hum about how intellectually interesting all of this is, the truth is it was a pretty harrowing experience much of the time:

• I burned through the entirety of the severance money in the first 6 months or so, despite being relatively cautious)

• I burned through myself and my wife’s life savings in the following 10 months, despite being much more cautious

• I borrowed more just to not default on the mortgage

Even basic groceries felt like luxury items towards the end. There were a few days during the past 72 weeks where I felt the complete unending despair, and the only solace was just to pretend to myself everything was going to be ok, despite all evidence to the contrary.

And then while going through all of that:

• Trying to accomplish anything day to day with a constant drumbeat of failure and consequence of that failure playing out in my head,

• Turning up to interviews, forcing myself to feel super-invested in whatever crap the company was telling themselves about how they only hire the best (at the lowest possible price point, apparently),

• Trying my damndest to not say the “wrong thing”, even though I clearly had no idea what that was, in every interview,

• Completing “take home assignments” for no money but often many hours of my time, just for the sheer hope that either it will fulfil whatever mysterious criteria they have, or at the very least that everyone else applying fails at the same,

• Providing free, high-quality consulting work as part of many of those assignments,

• Answering stupid hypotheticals about everything from a medical app for Facebook to teleportation, with a straight face, because the person interviewing me was ostensibly an expert psychologist and would be able to “see how I think”, and then use that intricate knowledge of me to answer the secret questions they had that they didn’t just ask me in the first place,

• Appearing grateful for the feedback (when they could be bothered) when they tell me I suck at the job I’ve definitely been doing for the past decade, because I am a professional person and absolutely am grateful for whatever scraps of feedback they are willing to dole out,

• Not fucking running out into traffic when I do all of that and I still don’t warrant the basic fucking decency of a reply (seriously, Hogarth, go fuck yourself, in case I didn’t make that clear),

• Just generally not just putting up with some of the scummiest people on the planet (recruiters), because they hold the keys to my family’s continued survival and I have no actual self-respect at this point,

• To the point where I actually put an interview (that of course went nowhere) before my health because they didn’t reply to my emails needing to reschedule and I didn’t want to lose the opportunity (which I did anyway)

It is fucked.

I see it on LinkedIn, I see it on Reddit. It is fucked, and it is everywhere, and all I can do is nod my head and hope that everyone somehow makes it through all this crap, at the same time listening to any number of executives and thought leaders going on and on about only hiring the best and then having those people making shitty decisions that show they don’t give a damn about the product or job and just their brag about how much they know about AI, which every other person on the shop floor knows is bullshit, because Google only hires the best but their AI Overview is somehow worse than regular Google search was 20 years ago, because Apple only hires the best but somehow basic spell-checking doesn’t work at all, because Meta only hires the best but the web version of Instagram doesn’t let you upload images half the time.

Because ultimately none of this matters. No-one moves the needle. The “best” are either already doing something else, or are otherwise being held underwater while a committee of middle managers stalls any meaningful progress by rabidly debating tiny details no-one actually gives a shit about, and basically only end up shipping bug fixes that themselves introduce more bugs, occasionally new things that don’t work properly and only get worse from there, and (most commonly) UI that is deliberately designed to create friction, because Product-Led Growth, despite entirely being based on the cynical hypothesis that “if only our most stupid users understood that they need this thing they’d see how valuable it is” is the only actual product work of any value to people paying your salary.

But fortunately, fortunately, it’s not all bad news:

• I’ve regularly gone running 3-4 times per week, which makes me feel good physically and mentally, and regularly now run with my wife as well, which is indescribably wonderful and I’m truly grateful for

• I’ve permanently given up drinking alcohol. It started as a semi-regular thing a few years ago. Then at some point I promised myself I wouldn’t drink until I had a job again, and then at some point a year into that, I just decided I was done for good

• I shed 10% of my body weight

• Overall, I would say I felt happier, despite all the challenges, than I have been in the past 8 years or so

• I started a company (sort of, it’s not incorporated yet) based around a product that I built from scratch.

No, that company is not successful in terms of any metrics you care to look at right now, but there has been one big, big learning from the past 72 weeks: depending on a company for your livelihood is a fool’s errand.

Right or wrong, you can see that the entire structure of capitalism is continuing its slide towards favouring hustlers, hucksters, executives or entrepreneurs (at least in my line of work). Everyone else will likely be cast out at some point without much of a thought (particularly once the AI bubble actually bursts).

It will happen to me again. I have no doubt of that. But hopefully next time I will be prepared.

I tried doing it the way they tell you to do it. CV, cover letter, research the company. Talk about how the company values really resonate with you. The mission is so inspiring. Rehearsed retelling different anecdotes from my career that attempt to prove I know what the fuck I’m doing. Embellish some. Take credit for others.

I asked people I’d worked with for referrals. I asked people I barely knew for referrals. I messaged recruiters on LinkedIn. I cold-messaged CEOs and CTOs directly on LinkedIn. I listened to podcasts about companies, then I applied to those companies directly. I submitted applications where all I did was try to stand out by saying something contrarian or using a different tone. I tried bragging, and I tried raw honesty.

None of it moved the needle. Like, nothing at all. I still see “viral” posts on LinkedIn with people spouting this crap and wondering why on Earth anyone is listening when it irrefutably doesn’t work.

If I was humbled during the last go-around, I don’t even have the right word for it this time. I considered and then just accepted that I’m clearly not as good as my job as I think I am, and that probably most people doing the same job must be much better than I am. I approached everything like I was definitely in the bottom 10% of applicants, and still struck out every single time. If I learned about product management from my previous unemployment experience, this time I only learned that I was the product with 0 product-market fit.

In the end, I was offered a job by a CEO who was vaguely aware of my previous work. There was no CV or cover letter. No recruiter screening. There was no take home exercise. No panel interview. No hypotheticals. Just a couple of conversations between two professionals, who agreed it would be mutually beneficial for them to work together.

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To everyone who has supported me over the past 72 weeks, you mean the absolute world to me. Thank you.