Ups and Downs of a Job Search — Part I

tl;dr — Here

I have just concluded a two-month-long job search. My start date is still a month out. From a cycle time perspective, the point at which I started looking to the point at which I will start a new job, would be exactly three months—the first half of those three months included a lot of sleepless nights. From everything I hear, three months is on the low side. There are people who have been looking for jobs for a while, and those starting their search every day. Hopefully, this post (and Part II) helps you all cope with the ups and downs of your job search.

Context

The last time I looked for a job was in 2021. At that time, it was more like jobs looked for me. Without doing any applying on LinkedIn or other job sites, I got two interviews, one of which turned into a job offer. In fact, I was recruited for that position by a leader I greatly respected, but had not worked with directly before. All of this was within a couple of weeks of letting people know that I was looking for work.

Since then, I went on a self-marketing spree. I have given keynotes, written books, and currently host a pretty successful podcast, as well as consulted for some high-profile clients. My base assumption was — If I need to look for a full-time job, one would appear within a matter of days…Oh, how wrong I was.

LinkedIn Will Wreck You

I entered the first stage of job search — The ‘LinkedIn to rule them all’ stage.

Photo by Souvik Banerjee on Unsplash

I started looking for jobs that matched my profile. Luckily, I was well suited for both Technical Program Management and Engineering Leadership roles. I set my sights on ‘Head of’, VP, and Senior Director roles. Every day, I could find at least 10–15 new postings that seemed to be great fits. Those that I was really interested in, I would tailor my resume and cover letter to. My wife joined in to help as well. She became proficient in using AI to tailor resumes and draft offer letters. We kept (for all of 2 days) a spreadsheet of job applications and updates. It all unraveled pretty quickly, though.

We realized that most applications were going into black holes. Did not matter how much effort you put into the perfect cover letter or resume, or how good a fit you were. The bots were more than likely to reject you. Every new job posting would give you hope, but four rejections from other ‘perfect fits’ at the same time would lead to despair. It felt personal — How is it that I have done so much and achieved so much, and I am not even able to get an interview?

The cycle of hope and despair via LinkedIn is vicious and unrelenting. Here was the first big lesson of the job search — A rejection is almost never personal; there are many factors outside your talent, accomplishments, and control at play.

This is hard, very hard. Especially in these beginning stages, when you are full of hope. The psychological effects of hope turning to despair should not be underplayed. The more seasoned you are, the more hope you have going in, the worse this hurts.

The rejections also lack rhyme or reason when it comes to timing. You might receive an auto-generated rejection overnight or a month later at 3:00 am. AI works in mysterious ways.

Activating The Network

Photo by Shubham Dhage on Unsplash

I realized that I was relying too much on my resume and past accomplishments and not enough on the connections I had built during my 20 years in the industry. The solution was obvious and in front of me — Reach out to people who know you to see if they can help.

I did this in two ways -

1. Put a general call out on LinkedIn to say that I am looking for a full-time job and would love to work with people I have worked with before. This had great success in terms of visibility and also garnered a couple of inquiries from individuals who wanted to speak with me — more on this later.
2. Look at job postings on LinkedIn and see if there was someone I knew who worked for the same employer. Reach out to them individually to ask if they wouldn't mind putting in a good word.

This paid off almost immediately, at least in getting me to speak with a few people. People I had worked with in the past, including my old bosses and colleagues, as well as those I had taught a class to but not worked with, all came to my aid. Many provided references to ensure my resume wasn't simply ignored. I am indebted to these folks who took the time to help me in my journey. In fact, it was one of the references that eventually worked as a ‘foot in the door’ for me to successfully land a job.

Of the nine companies I ended up interviewing with, references played a part in eight of them. Your network is your greatest job-hunting asset. More than your accomplishments, more than your experience. Your ex-colleagues and the relationships you build, the competency you display while working with them, are what gets you a job, not necessarily your resume.

A mistake people often make is that they cool their heels while at a job. The steady paycheck can make you lazy, till it goes away. The best way to be ahead of the game is to bring your best to work. Be the person everyone wants on their team, even after you're no longer working at the same place. The job hunt actually begins when you work with people while you still have a job. Do not wait to be laid off or otherwise forced out to start demonstrating your skills.

A note on the references — regardless of the position, influence, and passion of the person giving you the internal reference, it is still a roll of the dice. Some good friends with a lot of mutual professional respect referred me in, and the application still seemed to end up in the proverbial black hole. This was also true for people who actively reached out to say they want to work with me, even without me reaching out to them.

Summary

Looking for a job in the current market is not for the faint-hearted. You will lose sleep, you will learn lessons. It is the continuous learning of lessons and honing your approach that will get you through.

In Part II, we will get into the interview process. That is a whole different animal.

Highlights from Part I -

1. A rejection is almost never personal; there are many factors outside your talent, accomplishments, and control at play.
2. The psychological effects of hope turning to despair should not be underplayed. The more seasoned you are, the more hope you have going in, the worse this hurts.
3. Your network is your greatest job-hunting asset. More than your accomplishments, more than your experience. Your ex-colleagues and the relationships you build, the competency you display while working with them, are what gets you a job, not necessarily your resume.
4. The job hunt actually begins when you work with people while you still have a job. Do not wait to be laid off or otherwise forced out to start demonstrating your skills.