Life lessons from 7 job searches

In my 10+ yrs of working in tech, I have done 7 job searches. With enough time and practice even the most difficult activities start to feel easy, but not the job search, at least not for the first 6 times.

Job Search #1

2008-2009: My first ever job search after graduating college. Worked at a company for a few months, after which they let me go and didn’t pay all my salary.

2010: Started working freelance jobs creating Wordpress websites.

Job Search #2

2013: The job search initiated after 2+ yrs working freelance, creating websites for small businesses. This search wasn’t so much a search, as it lasted 1-2 months of applying for jobs and taking the first job offer. I wanted to quit the first day, but I stayed on for a year, for “experience on my resume.”

Job Search #3

2014: 6+ months job search where I helped out a local cafe by becoming a regular at the cafe, while I applied for jobs and interviewed. The options seems sparse and rent was coming due. I ended up taking a very underpaid role at an advertising agency. Worked there for 6 months.

Job Search #4

2015: Spent a few months scanning job boards while still working at the agency. Decided to respond to a request from a recruiter for a Project Manager role in the marketing department of a large financial company needing a contract Project Manager, ASAP. Went to the interview, was impressed with the manager. I was offered the job in a few days. Stayed on for 1.5 years.

Job Search #5

2017: Moved to NYC from Boston. 8 months job search from Jan till August of applying, interviewing, explaining why I have an interest in this company, for that role. Landed a role at my first startup, but found out it wasn’t real after all, because founder was investing his own personal fortune into company. Culture at company steadily declined, people were fired, I quit, then stayed on, only to be fired anyways. Worked there for about 1 year.

Job Search #6 (sorta)

2018: Was looking to go freelance, when I met a guy that worked at a health-tech startup that was remote-friendly, recommended I meet his team, was introduced. Ended up working there for a year, Product and UX work. Enjoyed it until I realized they were never going to raise funding and my salary wasn’t going to increase, ever. Left the job after working there for a year.

2019: Travel break from Aug 2019-March 2020

2021: Decided to launch a coaching business. Spent most of the year focused on learning how to coach others and translate my own personal experiences into lessons for others. Started offering coaching on personal development and career navigation, specifically transitioning into a career in tech.

Job Search #7

2021: Spent 3 months applying to jobs through online communities, interviewed and created good professional connections. Found a company that aligned with values and goals. Accepted a Product Manager role at market rate salary at high-growth series B-funded startup, tackling unique market challenges. Still working there!

What did I learn?

Of all the lessons that I learned from the job search experiences, these are the most valuable ones that stuck with me:

  • Never take a job to ‘pay the rent’ or ‘for the resume’, if you can avoid it.
  • Never take a job without understanding how you like to work or who you want to work with.
  • Never take a job that pays below market rate except when it very clearly makes sense for your career trajectory or aligns with your values.
  • Understand WHY you are looking for a job in the first place (ex. financial goals, career interests, personal values, etc.)

All those times when I agreed to a job offer that didn’t make sense for me, I spent very little time considering how the offer met my values and goals. When I started working at a place that didn’t align with my values, it became difficult to do the work and stay motivated. During those times I frequently felt lost and frustrated.

Yet, when I took time away from it all to evaluate what I care about and who are the kinds of people I want to work with, the process of finding a job became effortless.

Throughout the years I learned that if you keep doing things a certain way, you get the same results. When I finally decided I wanted different results in my job search and career, my approach towards the job search and towards everything in my life - changed.