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(Not) Finding the Right Job

Personal Growth
Career Path

5 February, 2021

Glenn Block
Glenn Block

Co-Founder at Stealth Mode Startup

Glenn Block, Principal PM Lead at Microsoft, highlights the importance of intentionality and being careful about making any assumptions when looking for the right job.


At one point in my life, after I had already changed several roles and industries, I found myself in a company that was working on something I was not passionate about. I had joined the company as part of a rebound after a startup that I had helped found shut down. I was eager, perhaps too eager, to find another opportunity without being intentional as I should have been about my next job.

Actions taken

I took several months off after leaving my job to clear my mind. I was not at a place where I wanted to expend a lot of energy looking for a new opportunity. I approached a former boss who was looking to hire a leader and told him I was looking. We had a great relationship in the past having worked together at several companies and so I didn’t hesitate. He seemed really happy at the new company and was excited about his work. I assumed based on our history and that it looked like a great company that things would just work out. I interviewed and got the job.

Very shortly after being hired, I realized I was working in a space that did not align well with my experience or my passion. I had gone in with blinders on and not been as critical as I should have. I assumed it would just work out. It didn’t. After my initial on-boarding, things started to go down-hill. It was clear to me that the role required someone with deeper experience in a space that I was not confident in. I was unable to deliver to the expectations of the role. This ultimately contributed to a poor relationship with one of my peers which evolved into a bad situation. It all intensified the feeling that I was in the wrong place. I even questioned whether or not I should leave the tech industry altogether.

I got interviewed, got a job, and ended up working in a space that I didn’t enjoy a bit. I failed to ask all the critical questions during the interview, and we only discussed what I could bring to the table. I had my assumptions and failed to be intentional at the interview and ask what I would be doing and if that was aligned to what I cared about.

The company itself was great, but I ended up in a role that was just not for me. Because that role wasn’t for me, many other things didn’t work out as well. I got entangled in a very antagonistic relationship with a peer of mine that only intensified the feeling that I was at the wrong place. It became a tense and dilemma-ridden moment in my life that made me even question should I leave technology altogether. Simply, I was not able to deliver at the level that I was used to delivering, and that heavily affected my confidence. I also felt loyalty to my boss, which made it hard for me to leave the company. There were so many things on so many levels, and as it was not getting better, I left.

I took the learning with me and when interviewing for my next role, I was very intentional. I did a lot of soul searching to understand what was important to me, what were my non-negotiables? I reflected on the kind of role that aligned with my passion, the culture, the environment that I needed to be in. I had a series of questions that I took with me on my interviews which helped me to validate whether or not it was the right opportunity. Being intentional paid off and I landed in a role that was a much better fit for me.

Lessons learned

  • Don’t let loyalty cloud your judgment. I accepted an opportunity based on a previous great relationship without being critical enough. We had worked well together before, but this opportunity was very different, I failed to see that.
  • Know yourself! Know what you want and what you are good/not good at. If there is something you are not good at, often there is an opportunity to learn and grow. Be conscious of your needs, not only of what you will bring to the company.
  • The further you get in your career and the higher you are within an organization, the less wiggle room you will have. The expectations will be higher in terms of what you should deliver, and I faced that expectation misalignment first-hand.
  • Recognize when you are not in the right place. If you are in a situation where you really believe you can’t prosper, be honest with yourself and recognize that. There is no shame in acknowledging that you are in the wrong job. It may be better to leave than to stay at a place where you are not happy.
  • Just because you had a great experience working with someone before doesn’t mean that you will have that same experience in a new company. Make sure you ask the critical questions to ensure it is right for you.

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