person holding compass in forest

What it is like to look for a job

I recently did something that I have never done before. I quit my job, and I did it without a new job lined up.

Here is why I decided to make the jump:

  • I felt stuck in my current roleā€”like I wasn’t increasing my skillset and was doing things that were antithetical to my improvement as a person.
  • There was no opportunity for growth left. It was a small business, and my boss was the CEO.
  • The job market was high demand, low supply.
  • I had enough money saved to where I felt comfortable in having some time off if truly needed.
  • I was encouraged by a number of colleagues who had recently left and got other positions.
  • I felt that, given my push for transparency at my current role, I could be open and honest with my current job about my intentions.

That last one is a big one. I told my boss that I wasn’t happy in September of 2021, and we put together a plan to backfill my role and cover a relatively busy schedule of client work. I would leave in early 2022. This is not always the case, and many workplaces are vindictive to employees considering leaving their jobs.

The experience of finding a job

What I learned, especially once I had officially left my past role, is that finding a job is harder than actually working a job. There is a lot of prep work involved, a lot of time management, and plenty of wasted time and rejection to emotionally overcome.

Much of my time looking for a new job overlapped with my prior job, but I spent nearly four months looking, applying, interviewing, negotiating, and managing in this process. I also had to find extra time to research concepts for the jobs in which I was interviewing, where there were gaps in knowledge.

The biggest gaps to hiring were unrealistic expectations from the hiring team and long, extended hiring processes. In one experience, I interviewed six(!) times for a role and then waited over two weeks to learn that I didn’t get the job, with no feedback as to why I didn’t get the job provided. Hint: it was money, and salary was the first thing discussed, two months prior to the rejection. In another role, I reached for a loftier role than I should have and lowered my salary ask by well below any reasonable expectation to cover for it. Their feedback, after deliberating for over a week, is that I was too expensive. Go figure.

At final count, I applied for over 200 jobs, and was rejected in about 30 interview opportunities, which all included at least one call past screening. When I finally got a job offer, about two weeks after leaving my role, I was so exhausted that I barely reacted to the phone call, which alarmed the person on the other side of the line! I was excited internally, but I felt like I had just ended a battle for my life that had no clear end in sight.

What went well

  1. The support of my current team was amazing. Everyone knew, and everyone was supportive of my decision and my next path. I was able to use them as a reference when needed.
  2. The threat of not finding a job inspired me to pursue some certifications and professional development that I had skipped for a couple of years.
  3. I really liked the spreadsheet and documents I created for tracking my daily work in finding a new role. It allowed me to easily reference past conversations and next steps, while taking multiple interviews a day.
  4. I really liked Indeed for finding work as well as Glassdoor for looking at or leaving reviews about interviewing for jobs and staying away from bad jobs.

What needs to improve

  1. Working with recruiters was awful. Any role found through a recruiter was a profound waste of my time, from role mismatches to getting “feedback” on why I didn’t get a role.
  2. Even with the buffer time and savings, I did not like the experience of having no income and looking for a new job. In retrospect, I would much rather look for work while still employed at a current role, moving forward.
  3. ZipRecruiter was a terrible and spammy service that provided no value whatsoever. I recommend staying away.
  4. Most interview opportunities were focused on meaningless certifications that I had. I was told that I was considered for jobs strictly because I had certifications that took me one weekend to complete, four years ago. I guess they want people who would bother to certifications in the first place, over actual field experience.


  1. Don’t quit your job if you can line up a new one without looking or are very confident in your finances and fit. Even with stability, I wouldn’t do this again.
  2. Follow your gut when looking for work and cut off opportunities as soon as they feel like bad fits. The initial screening call is actually a great indicator of how things are going to go at the company and with your interviews.
  3. Compare salaries for similar positions in Colorado (where they have to post salary) and keep applying for jobs with slightly different salary asks to understand your value. I kept exploring until I found my value, which was $20,000 more than I expected.
  4. Don’t give up! I am a white guy, and it took me a third of a year to find something in a strong employee market. Stick to it, and you will land!
  5. Any team that needs more than three hours of interviews to understand your fit is not a good fit for you.

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