What are your biggest regrets?

I had a conversation with my co-worker a couple of weeks ago about "fireside" chats that tech companies like to put on, and she share how annoyed she always felt when moderators would ask their interviewee "what was your biggest regret?"  The issue wasn't really with the question itself, but more with the answer that it always got.  The answer would always be "I don't have any regrets--it all worked out!"  Or something along those lines. 

She proceeded to explain that, well, of course you don't have regrets right now--it's easy to say that when they're in the position they're in (read: successful and enough so to be interviewed at this "fireside chat"), and everything has worked out in your favor. In other words, it's privileged to be able to say that you don't have any regrets. It's easy to look back and remember how you had regrets, but taken in the context of how it "all worked out", they were just things that needed to happen.  But that's just giving the same thing a new name, isn't it?

It got me thinking about how I would answer that question, taking into consideration all the doubt I've had in my career the past few years of my life and how to acknowledge how the doubt itself has been crucial to my career development. To be honest, I feel relatively stagnant in my career at the moment, but maybe talking about these "regrets" might clarify all of it.  

So, here are my three biggest regrets:

1. Not being more confident in my opinions of myself
Cheesy, yes, but is it still true?  Yes, I still have a problem with being fully confident in myself; impostor syndrome is a real thing.  I realized that I used to sell myself short and assuming all my failures were caused by a fault of my own shortcomings and that at the end of the day, I just wasn't qualified enough to be listened to.  I also wouldn't speak up in meetings when I had an input, especially in technical situations, and it was more because I was scared about being wrong than anything.  These days, I have a much different mindset.  It's better to speak up and participate regardless, and if I'm wrong, being able to learn from it. 

2. Not being more confident in my opinions of others
I also used to really struggle with feeling confident about my opinions about others, especially if they were negative opinions, or just bad vibes in general.  I've learned since that gut feelings hold weight and after a certain degree of self awareness, you need to trust them.  Especially if this is in regards to a bad manager, or a toxic environment--bottom line, you need to recognize those things and protect yourself. 


3. Not embracing my differences
I realized very early on that maybe I didn't necessarily fit in to the stereotypical engineer role.  I started off in a very male dominated industry where the ratio was so off, it was the first time in my life I saw a men's bathroom have a line and none at the women's.  Aside from being a woman, I apparently was too talkative (I was called "too social" in a past job, and when I prodded more about if there was an issue in the quality of my work or anything, I was basically told, no, but please stop talking so much to people).  When I was struggling through working with a co-worker as an intern, who kept micromanaging me and trusted nothing I did even though I had done my whole master's degree on the topic, I had a fellow intern tell me that maybe I deserved it because I cared too much about spending time with friends and wasn't focused enough on work.  

And outside of work, I enjoyed art and music and live events, but in my first workplace, those interests weren't valued.  Luckily I work somewhere where there's a much more diverse set of people and interests, and my weird is more accepted, but I definitely wish I leaned in more to being myself.  I spent so much time trying to figure out why I was different and trying to fit in, when really I wish I spent the time figuring out where I could put these perceived differences to use in my career. 


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In reflection, all of these are really just things I wish I could have figured out earlier if anything.  And I think I've accepted that in the midst of the struggle, you're always going to be regretting something, since you're always going to be wondering what could have prevented you from being in this rut.  Part of it honestly might just boil down to my personality and my definition of a regret.  There's definitely a lot of growth for me still to go.  Maybe I'll get to a point where I reread this and question how these were even regrets.  I can only hope I get to the level of those who can confidently say to a crowd, "I don't have any regrets, everything that happened was meant to be, because it got me here today".  But I hope when I get there, I can also share these moments of reality.