Why I'd never apply for a job online again

Applying for jobs online is no different than online dating: it's either enshittified, fake or impossible to win, along with guaranteed demoralization

Gob Bluth throws a letter into the ocean, which couldn’t possibly be a better metaphor for cold applying for a job online.

Over the pandemic, for the first time in my career, I elected to take time off work. I actually liked my employer, but structural changes beyond my remit gave me a natural exit, and I took it. At this point I had been working since I was a teenager, and so after more than two decades of uninterrupted employment I wanted to see what a break felt like.

It was a welcome reset and very helpful for me. If you have the means, taking time off can be invaluable. The HR midwits who insist you must always be employed don’t understand humanity, personal development, pick a topic. The notion that someone might be responsible enough to save sufficient funds to create optionality in life to have time for side projects and passions, have multiple income streams or build personal autonomy breaks their brains. Laugh at anyone who tells you not to do this. Always live life on your own terms.

When I was ready to contribute to a company again, I decided to try something new: applying for a job online. I’d never done this before so was genuinely curious what might happen. Seemed like a fun adventure, where might this lead? The answer was simple: nowhere. Further, it was a wholly demoralizing experience, to the point I’d never do it again, in fact, I’d rather be tortured Jack Bauer style than repeat that process. It’s so bad I don’t think anyone should do this, save for specific contractual work where there’s actual demand on the supply side that will be fulfilled. Otherwise it just doesn’t work.

At first glance, it seems great, simple even. Platforms like LinkedIn offer ‘1-click apply’ features, and hundreds if not thousands of listings look legitimately relevant and interesting at any given time. On paper this makes sense, they have your resume and experience so in theory it should scale. In reality, you’ll be ignored or auto-rejected the majority of the time, around 99% in my experience. And the few opportunities you do get to talk to people, they’re wholly unserious. It’s really no different than what online dating apps have become: mostly scams, spam, or illusions. Your response rate will be essentially zero, while the process is made to feel efficient but simply doesn’t work. Like many other areas of modernity, we’ve built systems of busywork that feel like you’re doing something productive but go nowhere. Perhaps some things: finding a company to work at in a senior role, a life partner, a creative collaborator are just too complex to fit neatly into form fields.

I’d never applied for a job before because I’d always been recruited or referred into new positions with better compensation and greater responsibility. The next step was always there. I had a sense applying online was going to be annoying, but a several month experiment (I gave it the old college try) only confirmed that it’s beyond frustrating, it just doesn’t work. Nothing you do here matters. Of note I not only applied for roles I’d be a great fit for, I even took the time to apply to companies I consulted for in the past and had prior case studies of success with, some roles slightly below my level, even ones I’m personal friends with people at the company including the CEO just to see if anyone would reply. Alas, none of this mattered. When cold applying, it’s truly irrelevant what you’ve done or how much revenue you could return for a company. It’s a bad route that leads nowhere.

So after near 1,000 applications I gave up and made a single post to my network sharing I was open to work. That post immediately led to several real interviews with serious teams, and I ultimately chose a startup I’m still working at over two years later. My team and the company are doing great, so everything worked out well here.

I was thinking about this topic again as I’m helping a friend determine what’s next professionally. And honestly, tapping your network is clearly the superior method people should use for job searching in the modern age, at least for knowledge economy work. With enough time into your career, everyone has a network and a reputation. Tools like X/Twitter and personal blogs allow you to flip the funnel and attract inbound interest instead of cold applying. You’ll talk to people who are already familiar with your skills and style of work: so all warm leads, not cold. The conversations will be high quality and you’ll spend interview spent effectively. Or, if you are interested in a specific company, just make a direct connection with someone there, preferably a decision-maker, and make your pitch. That will always outperform cold applications to posted listings, which go nowhere and to no one.

The truth is online applications are designed to filter people out, not bring anyone in. Companies are overwhelmed with resumes, so they rely on rigid keyword filtering and automation. No reason to take any of this personally, a human likely never even saw your application. Worse, many job listings are performative and either already earmarked for an internal hire or simply signaling to the market a company is growing and relevant.

At best, cold applying online is a waste of time. At worst, it makes you feel invisible. If you want real opportunities build relationships, create value publicly (publish ideas, case studies, etc) and put yourself in a position where companies and decision-makers seek you out. That’s the better way to find work in the modern world. Some of you may have had better luck here or feel different, but I’m personally radicalized against ever doing this again.