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  • caedynwheeler

How to FAIL & WIN the Job Hunt

Updated: Sep 8

I’m a 2019 high school graduate that has no plans for college. Almost everybody gave me the side-eye. In January of 2020, I was the lowest position at a dry-cleaners. By July I got a job I really wanted as a Sales Support Specialist for a Healthcare Consulting startup, that traditionally I would be underqualified for. Written down it seems like a quick leap, but my timeline was meant to be much more condensed. My plan was to start working at a startup in March, by quickly learning how to succeed in the job-hunting process. Well, no such luck. I did learn this, but over the course of several months.


In this post, I want to help you understand initially, what took me months to figure out. You’ll find that nothing in here is particularly exclusive advice, but rather simple things that will seem obvious, yet almost nobody does. So here it is, the months of lessons I learned the hard way so you don’t have to:


For five months I failed in every way. Here's how to fail the hunt, from my personal experience


Spend minimal time on the process as a whole

Save time by just creating a minimal resume and cover letter that you can use for every job and mass apply. This is a way to keep your options open and give you the illusion you're doing more in applying than you really are.


Spend way too long on each application

Alternatively, you can spend hours going over it for the possibility of the hiring manager doing an in-depth evaluation of your cookie-cutter application.


Apply to jobs you don't really care about

You'll seem super bored, which is perfect for getting passed over immediately.


Make the applications impersonal

Showing your unique skills is a waste of time when trying to fail immediately. To show how much you shouldn't have the job, write the application as if it could apply to literally anyone. Think cold-reading. You want it to be painful for the hiring manager to read.


Don't follow-up on anything

Following-up indicates you're interested in that role and are serious. You don't want that. Apply once and leave it up to fate. If you have an interview, don't thank them for their time, they might think you care.


Follow the traditional process. Never go outside the box

The traditional application process is what everyone does, and almost everyone will get rejected. It's the perfect way to stay in that category.


Don't apply if you don't meet all the qualifications

Get discouraged immediately and move on if you don't meet the qualifications.


Only check your email once every couple days

Show you're not professional and miss potential interviews.


Don't research the company or role

When the interviewer asks why you want to work there, you'll be caught off guard and stumble around grasping at straws. This is another great way to demonstrate you shouldn't have the job.


How to win the hunt


Spend an appropriate amount of time on each application

This means doing enough research to solidly understand what the company does and what your role would be, but not so much research you know the founder's sister's name.


Apply to jobs you actually want

If you don't like the job, you'll feel like you're wasting time while applying. And if you actually get the offer you won't want to take it. It doesn't have to be your dream job, but you should at least be excited about some aspects of it.


It takes more time to find these jobs, but in the long-run you're saving time. You're not making yourself go through a whole process, that at the end of, you'll end up rejecting anyway.


Approach the application in the best way for that role, not the traditional way

Whenever possible, do something to show more of your value in a different way. It's hard to stand out when you're not doing anything to stand out.


Send a video of yourself instead of a cover letter, do a project for the company. For many of my applications, I would use a video pitch for what a cover letter is meant to do, demonstrate through personal experience how I'm qualified and would be valuable to the company.


Remember the entire purpose of the application is to demonstrate how you can be valuable. The current process isn't set up for you to succeed. So change it to what will serve you best.

Maintain professionalism and enthusiasm even if it's not reciprocated at first

This means FOLLOWING-UP. It's something that I overlooked A LOT.


Three things to remember:

  1. You're not entitled to a response. Plain and simple. You should make them want to give you a response.

  2. No one tells you this, but the professional world is actually super unprofessional. Ghosting is very common, and relationships get neglected. YOU have to be the initiator for most things. Don't wait weeks and weeks. You're most likely not their highest priority, you have to fight to be on their radar, don't wait for an invitation.

  3. They won't care if you don't care. If you're putting in minimal effort and look the exact same as the other candidates, why would you get treated any differently?


Understand and illuminate your transferable skills from previous experience

Unless you have a very specific niche or are far along in your career path, chances are you won't have specialized skills that the job is looking for. This does NOT mean you don't have experience. In almost anything you've done you've gained a transferable skill from if you abstract it.


For example, I used to work as an assembler at a dry-cleaners. I now work for a healthcare company in an ops and sales role. How would I pitch myself for my current company?


At the dry-cleaners, I learned how to use a program called Spot and how to troubleshoot the bagging machine. At my current company, I learn EMRs. Both of these break down to problem-solving and quickly learning new technology. I would illustrate that I can do both of those things by using the experience as an assembler as an example.


Communicate through relevant stories. Exemplify by showing not telling.


Hiring-managers aren't coming up with the qualifications for no reason, but they're not necessarily good reasons.


They want to know that you can do the job and will make up for the cost of hiring you. That's what the qualification lists are for, but if you don't technically meet all of them, how do you make up for it and bring something to the table that other candidates don't?


Almost everything is negotiable.



Learn proper email etiquette

You'll be able to clearly and concisely show what you want while appearing professional and not needy.


Don't feel entitled to a job if you're "over-qualified", and don't feel unworthy if you're "under-qualified"

You chose to apply to this job. With any luck, you took the other advice in applying to one you liked. But regardless, you chose to throw your name in. No one cares about your feelings, positive or negative. They're looking for someone to get the job done. The only time your feelings come into play is if the entitlement or insecurity you're feeling bleed over into your application and interview.



Prepare questions for the interview

Yes, it will demonstrate that you're interested, but the questions are more helpful for two more things.

  1. Whoever asks the questions in a conversation has the control. If you ask questions it makes the interview more conversational, which is usually preferable.

  2. Learning things you're genuinely curious about. Find things you actually want to know about the company. You don't want to work for any company, in any environment, doing any job. Make sure this company is the right fit. The actual answers and HOW they answer will be indicative of that.


Find a process that works for you

This was key for me. You can read and listen to all the advice you could ever consume, but at the end of the day, only you can know what will work best for you.


Everyone is different in what works for them. Reorder the process, add new things, fall on your face a few times. You'll learn. It might hurt, but you'll learn.

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Personal Note of Encouragement


All this being said, I struggled hard through the process. I had to fail in almost every way to learn what worked for me. Some people learn easy, some have to fall on their face 50 times learning how to walk right.


I would have a really good interview that I would eventually get rejected from. It would break me down for about a week. I had to get to a really low place before the rejections got easier. But they did get easier. Once I got into a groove of applying, even if I got rejected, I was proud of the work I put out. I knew I couldn't have done anything more to make it work, but I also knew I did good.


I have an entire notebook full of jobs, how I pitched the jobs, hiring manager's contact information, and projects I did for them. I was rejected from 95%. Some were out of my control, but a lot weren't. I just had to learn every lesson above. I love having that notebook because the entire growth process is documented. From absolute hell to being hired.


I hated this while going through it, but the lessons stick so much more when learned the hard way. If you're struggling looking for a job, I hope this is a helpful resource for you. Or at the very least, moral support.

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