Oh hello 2023: New year, new career

by Jan 16, 2023

 In my 20s, I thought something was wrong with me because I switched careers many times. At one point, a friend told me, “Meda, I think that what you’re looking for does not exist.” For weeks I sat with this comment because I was worried she was right.

Turns out, we were both a little right. I was looking for a career I’d love ALL  the time, not realistic. At the same time, as I explored a little more I learned to identify the key characteristics that I needed in order to enjoy my work life. I ultimately did find what I was looking for. 

In my family and group of friends, I’m often the point of reference when someone is contemplating a career change. I find that I often repeat the same piece of advice and the product manager in me thinks in frameworks and lists. I like to be fancy like that (says the same woman who thinks that dyno nuggets count as dinner). If you’re considering switching careers, take a look, if you think it’s BS let me know too! 

Careers I’ve had: wealth manager, dog walking business owner, engineer, startup founder, and now product manager. 

 Acknowleding my privilege

One thing — I’m privileged. I was raised by loving parents who sacrificed their youth to create opportunities for me. I had the privilege of attending an excellent high school which led to an Ivy league degree, and for this reason I’ve always had ample options. I was also raised in an immigrant household where money was often a worry, where the most stressful part about college was navigating financial aid, and figuring out how to fit into white spaces where I felt like an alien. I mention this because as a BIPOC professional, I’ve learned to check myself when it comes to doling out my advice based on circumstances. I realize the cute advice below is not often an option for many others including my mother.


  1. Why do you want to make the switch? 
  2. What is the most beautiful career you can imagine for yourself? 
  3. Do you want to eat the shit sandwiches? 
  4. Do I want baby steps or a radical approach? 


Step 1: Why do you want to make the switch? 

It’s inevitable that there are the occasional hard days at work, that is normal. However, there are sometimes deeper, more systemic frustrations that you can’t ignore. 

Normal frustration: Every quarter-end we’re rushing to ship new features, that one week is so stressful.  

Systemic frustration: Nooo, Monday again. There’s so little, if any work,  I look forward to doing this week. 


A couple of questions to think about: 

  1. What in particular is making you unhappy? Is it specific to this company and would the same role elsewhere be different? 
  2. Is there a particular personality conflict 
  3. Do you just have a shitty manager? 
  4. Are you running away from challenges? An opportunity to grow. 

The first time I made a shift was when I went from working in finance (wealth management) to starting a dog walking business. There was a fundamental reasons why I needed this change. 

Personality conflict: The fundamental parts of this role were not a fit. I’m an introvert, I like to take my time to ponder and think through what I need to say. In this role, I had to be ‘on’ throughout most of the day. I would often arrive home, only ready to eat cereal and pass out because my energy was absolutely drained from the never-ending interaction with people 


Step 2: What is the most beautiful career you can imagine for yourself? 


So you’ve checked yourself and know that there’s a fundamental reason why you must leave your role. But what do you do next? Ah, why are all of these questions so hard. When things get hard, I often turn to Untamed to find an essay that speaks to me. The quote below runs through my head rent-free all the time: 

“[Whenever we wonder] ‘What should I do’, instead of asking ourselves what’s right or wrong, we must ask ourselves: What is the truest, most beautiful story about [this situation in] your life you can imagine?”


A year ago, when I was unwinding my start I was trying to figure out what to do next. I thought of going back to engineering. I interviewed and landed a job offer. Except something did not feel right. Something felt off. The more time I had to think about the role, the more I realized what I truly wanted was to be a product manager at a tech company.

Don’t troll me, I must sound like a tech bro, okay I am a little bit a tech-bro who drinks mud-water (look it up). Deep down, the reason why I tried my hand at a startup is because I love to build, make, create and that is primarily what a product manager does. Once I was clear on where I needed to go, I made a list of the shit sandwiches. 

Step 3: Do you want to eat those shit sandwiches? 

Every role you take makes you eat shit sandwiches. I learned about this concept from Mark Mason BTW.  For example, a writer often becomes a writer because they enjoy the solitude and the creative process. However, once a book is released, that same introverted writer has to do a press tour, book readings, etc. I bet that writer also received a ton of rejections before getting a book published. The part of a role that is not so your jam, that is the shit sandwich. 

The fundamental question is: What do I enjoy doing so much that eating all the sandwiches still make it worth it? 


I compiled my list of shit sandwiches that I’d have to endure as a product manager: 

  • Attending lots of meetings (yes, the introvert in me was worried) 
  • Reporting to executives and often telling them no 
  • Long work hours: I knew this, PMs often struggle with work-life balance bc everyone needs us to field their requests 

In the past, for a different role, the shit sandwiches would have caused me to run away. But I was willing to pay the price in order to learn the art of building digital products. So far, it feels like the right call. So much so that I received a promotion after 7 months! 

If the shit sandwiches associated with the new role you want don’t phase you, you’re on to something! 

Step 4: Baby steps or radical change?  

I’d like to end with action items. This too is very PM-ie of me. We’re like that. We go to meetings and often define the next steps or action items. 

  • Baby steps: Start conducting your informational interviews with people on LinkedIn + read blog posts from people in those roles. Immerse yourself in it to figure out how to get your foot in the door. 
  • Radical change: Find you a career coach! I will write an entire essay on my experience but this is the route I took. I worked with Stephanie Ciccone and she changed my life. We targeted PM roles that valued my experience as a former engineer and she helped me land my dream role. 

Switching careers is tough. Often you start over, as I did, in an entry-level role but remember this. Eye-roll, I know , but I LOVE The Alchemist

“And, when you want something, all the universe conspires in helping you to achieve it.”


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