You’re Applying For Tech Jobs Wrong [1-25-2021]

You’re Applying For Tech Jobs Wrong [1-25-2021]

@Dustin McCaffree

Stop Applying For So Many Jobs 🛑

I read your last posts on LinkedIn and Twitter. The numbers were impressive:

“328 applications sent, 91 interviews, 0 offers. Thought 2021 would be different.” - You

Have you ever heard of vanity metrics? Well, it’s basically when you use numbers to tell a story, but those numbers don’t actually matter the way you’re making it seem like they do.

328 applications... 91 interviews... That doesn’t mean you’re working hard! It means you’re bad at applying and interviewing for jobs!

And that’s actually okay. I’m good at it, and I’m self-employed. So I’ll live my career aspirations vicariously through you.


The Time I Hated My Job 😤

In 2015-2016, I had 7 different jobs in just a few months. Yikes. I hadn’t realized I wanted to be in tech yet, and I really wasn’t enjoying my college education.

I got jobs selling insulation door-to-door, doing phone sells for a scammy Google listing “partner”, selling pest control, working for BlueHost as support/sales, teaching Russian to groups of students, and even doing some janitorial work at one point. I didn’t love it.

At some point, I got fed up with it all. I decided I had very little to lose. I went online and found 3 job listings that I was wildly under-qualified for. I sat down and came up with the craziest, most interesting ways I could apply for those jobs.

As an example, I applied first for a job at a small but successful design/development agency. The job listing said something like “UI/UX Designer Needed”.

I had never even thought about UI/UX before that day 😂 Frankly, I had to Google what UX was and how it was different from UI! But I knew I wasn’t at all qualified, to say the least. They were asking for 1-2 years of experience in that role... For an intern... Yeah.

And here’s where things get interesting.


How To Stand Out 👀

I had to get in the mindset of the employer. How could I get their attention, even if there are 100 people with actual experience applying for the job?

I knew I wouldn’t lie or fake like I had experience. But what could I do to make them feel like they should take a chance at least just enough to interview me in-person? That’s the laser focused first step.

I started by doing research on the company. If I knew enough about them, I’d be able to use language in my application and interview that they would jive well with. I’d also be able to throw out phrases like “I know you guys care a ton about seeing from your clients’ perspectives, and I think that’s definitely what makes client relationships last!” Stolen from their Values page, then used by me.


I also Googled a bunch of design phrases, since I didn’t want to sound like a total nobody right out of the gate. I focused on empathy as being something that makes UXers great. But I had no idea what I was really talking about.

After some brainstorming, instead of a typical resume (which I didn’t have), I sent a screen recording of THEIR WEBSITE with my floating head. Like a simple Loom-style video. I walked through their landing page, going through 3-5 things I would change about their website and why. Because I had done research on the company (along with Googling some design terms), I dropped a bunch of buzzwords I thought would resonate specifically with this company.

And then I pressed send.

The Secret To Great Interviews 🤫

This one will be hard for you, and I mean it.

Stop caring so painfully much. Geez, you’re creeping us out.

By now, you should have spent an hour or two really researching the company and applying in an interesting way. And you heard back. They want to interview you! Hurray! 🎉

But the interview scares you. Especially after getting to know so much about their company, you want to work there so badly. You can feel the perfectly room temperature office air on your skin, taste the free Lacroix on your lips...



I know you did a bunch of research and everything, but hold your freaking 🐎 🐴 🤠

You have got to remember that even though this job sounds great, there are 1,000’s of other jobs as good or better out there right at this very second. And just as important as them liking you is you liking them. It has got to be a good fit.

So, going into this interview, have your own questions prepared. Make sure this sounds like a job you’re going to LOVE. Be prepared to ask other employees there how they like it. See how long other people have been working there, as an indicator for their turnover and job satisfaction.

And then (here’s the 🔑) MAKE A NEW FRIEND. That’s right, I said it. Just go into the experience, again remembering that there are plenty of other jobs out there that would be lucky to have you, with the mindset that this will be fun.

You have to believe that. You have to start enjoying interviews and taking the pressure out of the situation. See if you can connect with the interviewer(s). Laugh with them, admit things you don’t know, ask about their life and experience, tell them how awesome you think the company is, find out that you both were in punk bands in high school, ask if they personally saw your video application, quote Friends and see if it lands, ask if you can show them the silly app you built for quizzing your friends on Pokémon trivia...

You get it, right? Just relax. Be yourself, make a friend, and do your best to show that you’re a cool person to work with.


My interview as UI/UX Designer felt like the friend part went 90% well. Then they asked me to draw on a whiteboard my thought process for solving a design problem they gave me. If I hadn’t been relaxed, I would have panicked to be honest. I’d never done a single design in my life 😭 But I did my best and just talked out loud while doing it, explaining how I would think through the problem.

I think I did pretty bad on that part lol. But it didn’t matter because the entire rest of the interview felt great. And if I didn’t get the job, I’d still feel great about the experience, my new friend at this company, and that I even landed an interview for a job I was so under-qualified for!

You Got This 👊

I got that job. And you could too, since you have exactly has much experience as I had as a designer (or more if you actually are one). It’s even the job that convinced me to start a career in tech and eventually to start my own design/development agency!

As an employer now, I look for these same things:

  1. Someone that seems like they want to work for me and my company, not just applying to 100’s of places.
  2. Someone I’d like to work with. Every employer has different specifics that they are looking for, but I care about optimism, passion, self-motivation, desire to learn and grow and be wrong a lot, and general niceness. Notice how I didn’t say a degree or crazy amounts of experience?
  3. Someone that can learn the necessary skills quickly. I hired a developer recently that had 0 job experience and no degree. Not even for a junior or intern role.

Conclusion 💡

I don’t believe in applying in bulk or at random for every little job out there. Do some extra research, find something that seems like a good culture fit, something that will stretch you, apply in an interesting and caring way, and close it by making a new friend at your first relaxed interview of your life.

In my experience, I can get most jobs that are out of my reach. With a few tweaks, so can you. I’m like the most average person I know, so trust me when I say this— I am not special. I’m just not afraid of a rejection letter. I just learned how to enjoy the whole experience.

Now go get a job, you wonderful bum. ❤️

What did you think?

Read Some Other Stuff I Wrote