Episode 1: I quit my job. Now what?

Check out Phase 2, my podcast about quitting my job to find more fulfillment in my work life. You can find it on Spotify or Apple Podcasts. Below is a transcript of episode 1.

The feeling starts on Sunday afternoon.  As the evening approaches, the weekend euphoria wanes, replaced with the mild dread of another work week ahead.  You wake up on Monday and find yourself pretending you’re not up as a way to delay the start of the week. You drag yourself out of bed, into the shower.  Opening your laptop seems impossible.  You call into the first Zoom and put on a reasonably enthusiastic face because you’re supposed to bring energy to the team.  But it’s not working.  Something’s got to change.

Hi, I’m Samir Lakhani and that was me, a few months ago in my last week of work in the corporate world.  I couldn’t keep up the facade any longer so I made the decision to quit my comfortable job without a plan for the future.  This is Phase 2: a podcast about my experience trying to leave the corporate world halfway through my career, to figure out what I’m going to do in my next phase of my life.  I’m inviting you on my journey to find a fulfilling work life through self-examination, meeting people who have found what they love and as I try my hand launching a new business.  I’m recording it as I go – so this could all crash and burn. 

First a little about me.  I currently live in Seattle, Washington but grew up in Toronto Canada.  I went to school at the University of Waterloo and I’ve been a product manager most of my career at various tech companies for the past 15 years.  I started at Microsoft, then worked at Upwork, Amazon, Facebook and most recently, Convoy which is a start-up in the trucking space. 

If I died now, my career obituary would probably say “He checked all the boxes”.  Since my parents are from India and East Africa, I basically had 3 options to major in university: doctor, doctor and doctor.  Engineer is a reasonable fourth place and my parents were super excited when I got a job at Microsoft graduating from college.  Sometimes it feels like the immigrant mentality is that you’re always one step away from living on the streets, which, when you’re in India or E. Africa in the 70s was maybe not that far from the truth. 

I’ve worked at big companies and mid-sized startups on many types of products like consumer delivery apps, video engagement and marketplaces.  I’m grateful to have worked with some amazingly talented people, launched some successful products as well as some flops.  I’ve been an individual contributor and managed teams of product managers and designers. 

Why I quit

When I was a kid, I distinctly remember knowing that I was going to change the world.  The feeling has slowly faded over the years as I became comfortable with a modest income working on products I’m moderately enthusiastic about so that I could retire comfortably.  I’ve done OK in my career but nothing world changing.  What happened to that kid who was so certain about his future impact? 

That’s not to say that I’m totally unhappy.  I have a wonderful relationship with my wife and two kids, and supportive friends and family.  But there is definitely something missing in my work life. 

Convoy is a fantastic company with incredible people who are passionate about transforming the trucking space.  But if I’m honest with myself, I was just not that excited about what I was doing, which hurt the quality of my work and overall happiness.  In fact, even if I look farther back to past employers, its difficult to find projects that truly felt meaningful to me. 

So, what am I actually passionate about?  I’m not sure.  So I quit work to try and find that out. 

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Cue the anxiety

Quitting your job in the middle of a global pandemic seems crazy.  It also doesn’t help that American society seems to be unraveling in the lead up to the national election.  Also, my wife stays home with our kids so we have zero income and have mortgage payments to make.  Saying this out loud is giving me heart palpitations.

The mental anxiety around not having a job – for the first time in 15 years – was one of the reasons it took me so long to make this decision.  I agonized over all the possible scenarios: what if we’re in a deep depression and I’ll never get hired again?  What if we have major health issues and can’t afford health insurance?  Will my parents and in-laws think I’m a loser?  What if our kids don’t go back to school in the fall?   Having two young kids raises the stakes.

To combat my financial anxieties, I created a spreadsheet to figure out exactly how much runway we had financially. How much does health insurance cost?  Where could we cut some costs?   Thankfully, we have saved some money during my past 15 years of working that give us a cushion for a little time. 

I  questioned my decision to quit up until the moment of giving notice to my boss.  The relief I felt immediately after telling him was all the confirmation I needed that this was the right decision for me. 

Coaching

So I needed to figure out what to do next.    To help me with this transition, I decided to work with a professional coach.  One thing I know about myself is that I make better decisions when I work with people rather than in isolation.  I can get trapped in analysis paralysis and sometimes miss the simpler path.  I like bouncing ideas off of someone and have them challenge my assumptions. 

I met Ravi Raman 7 years ago through a mutual friend, and we lost touch after that.  I happened to be on LinkedIn and saw that he had transitioned from leading teams at Microsoft into coaching full time.  His similar background in tech and our personal connection made him seem like a good fit. 

I came prepared to our first coaching call with a list of my perceived strengths, weaknesses, types of careers I might find interested and a 10 point plan on how to achieve my goal of “career fulfillment”.  I tried to apply my typical approach from work: bring overwhelming data, logic and frameworks to every decision.

His first piece of advice to me was to chill the fuck out, put away the bullet point plans and let my brain settle for a few weeks.  He thought I needed to clear my head so I could get into a calm mental space which would bring insight into the right next step for me.   He suggested that we take a trip, spend time with family, be outdoors and have fun.  I should avoid thinking about what I’m going to do next in my career, planning out activities and just… live.  He also suggested that I keep a written journal to regularly record my observations and feelings along the way, particularly moments when I feel alive doing whatever activity I’m doing. 

It took a lot of effort to actually followed his advice.  I felt lost at the start without a schedule and list of tasks to accomplish.  I had monkey-mind and found myself making a daily of tasks in my head which I could check-off:  Wakeup, exercise, smoothie, journal, go fishing, find new book, read book, have lunch, research mountain bikes, etc etc.  Over time, I started dropping the agenda and just did what felt right without a particular aim.  If I felt like going for a walk, I did that.  If I felt like reading a book, I did that.  I was without an agenda for the first time in my life and it was incredibly freeing. 

The journal was also pretty helpful.  Ravi insisted I write it in prose rather than bullet points on my laptop because he believed the act of physical writing allowed inner thoughts to flow better than typing.   I was skeptical of this at first.   I found myself repeatedly staring at a blank page with nothing to say and then, after 5-10 minutes, suddenly experience an eruption of insights and observations from yesterday.  I’d write about how I was feeling, observations about the world, my kids, my wife and what I found brought my energy or took away energy. 

At this time we were in Minnesota visiting my wife’s family and had decided to road trip back to Seattle.  This felt like the perfect trip to help clear my head and just live.  So in a few days, we packed up all our stuff and hit the open road with a rough plan to visit national parks and sites across the American west.  In the middle of a global pandemic.  With two kids.  

Tune in next episode to find out how it went. 

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