And that gambling on myself means I want to win

I've been saying that I want to settle down and be stable but my actions seem to contradict that notion so much that I was starting to doubt myself. I was getting insecure and thinking what if this is just a reaction or a way I self-sabotage. That everyone else seems to be able to stay still themselves and while not everyone is actually happy about it, some can at least suppress it enough to almost at least abide by that societal standards of settling in one place. And maybe by not feeling content in one place is just a trauma response. 

See, I'm not dismissing that and there can be truth to it. But at the end of the day, I just wasn't happy and I didn't see myself as content in the city. Chicago is a perfectly wonderful place but I just don't feel like it's my home. And that's okay - I gave it a shot and now I'm moving on. Could it be self-sabotaging? Well I mean what is self-sabotage? As corny as it is, if I just take Psychology Today's definition or whatever Google's AI throw at me then it's 

 self-sabotaging when it creates problems in daily life and interferes with long-standing goals. The most common self-sabotaging behaviors include procrastination, self-medication with drugs or alcohol, comfort eating, and forms of self-injury such as cutting.  - Psychology Today

But I prefer this definition:

Self-sabotaging behaviour refers to intentional action (or inaction) that undermines people's progress and prevents them from accomplishing their goals. Self-sabotage occurs when people hinder their own success. - VeryWell Mind

I think the key phrase there is ...prevents them from accomplishing their goals. Well, my goals are quite murky today than it ever really was. I think it's actually part of the identity problem I'm currently going through. For the very first time since I can remember, I don't have a clear set of goals. I've been able to accomplish a lot of my goals, pretty big ones too especially related to career, but for the ones I've not reached, I feel like it's changed too and that's exactly what's confusing me. Well, that's exactly what's keeping me stuck - without any direction, where do I go from here? 

One of the things that held me back for a long time is the concept of golden handcuffs. Specifically having a 6-figure salary with a 7 week PTO is a rare find and letting go of that for the unknown is nerve wracking and a crazy gamble.  

I found a video that aptly describes what I'm going through. It's like watching a vision that I've worked so hard fade in real-time. Not only did I just leave everything else I've worked hard and established for in years, I just jumped off that cliff without any life vest so I can't even really guarantee any safety. The only saving grace is that I've done this before, or at least something similar 5 years ago. The act itself of jumping head first and going to unpredictable places - I've done too many times and it seemed to have worked out in the end. But the biggest difference right now is the lack of vision.

Like I'm watching my vision that I've worked so hard for fade away in real-time.

Even when I did jump cliffs, I had a solid goal(s) that I know I need to accomplish, hence guiding me even though I've 'strayed' far from the "normal" path. The most prominent example is 2019 when I left my life in Toronto but with the deep conviction that I won't compromise on my career title - hence, I made sure to still aim to get a Product Manager title. And I did. As unorthodox as it was, I won. No matter what life threw at me then, I knew the direction of where I'm heading so even if I was unsure about my life, at least I know where I wanted to go. 

That's the biggest difference with 2019 versus 2024 is that right now, I left everything without a clear vision of what I'm striving for. To say the least, I'm fairly confuse as to what I want right now. I've achieved a lot of what I've been working towards the past few years which I'd say is amazing. The only natural consequences of it is that it provides another perspective for me that I wasn't exactly expecting. Like having the ability to feel able to do what I want/have what I want for the most part with just half my salary a month. What an amazing perspective to have when I'm lonely in a pretty costly city. 

But what does that mean for me? Ever since I can remember, I've been striving to be financially independent to move away from being reliant on family, and therefore the manipulation that comes with money.  And with that, it means all my ambition and choices since I was young was to help me get that goal. And I did. I'm very grateful about that too, especially with all the sacrifices and effort I've done to get here. But now, what does that mean for me? I can always get that, or get it back - but now I can't ignore "Why?" - why do I do this? what is it all for? 

And I tried to feel grateful about everything. In the beginning, I was absolutely happy with the stability. And I was comfortable towards the end. And it's this same comfort that made it difficult for me to actually move on. Originally, I was willing to spend another year in Chicago before I move back to Toronto at 32. That basically means that, for at least 8 months, I'll be living in a liminal city where I know I'll be leaving at the end anyway. I'll continue working as a director and getting enough money and being successful from a societal point of view. But at the expense of me throwing away 8 months of my life living in a mediocre, yet comfortable and safe place. 

Seriously, I want to emphasize this point. When I turned 31 earlier this April, I was thinking wow - I guess I'll just start my life again at 32 because I knew I wasn't really happy in Chicago and I can try as much as I like - I just know my time here is basically up and I'm just extending it because I'm afraid to disturb my comfy and cushion life. Oh no! You must not have tried enough  - my mind likes to contradict me. And while it's true, I could have always put more effort - blah, blah, blah - I just know know myself and I know I tried what I can. There's also no point in forcing something that I know deep down I don't believe in. I've tried that many times over my life and it's always been pretty unsatisfying to achieve something I've wanted for the sake of external validation or something I wanted even though it doesn't feel like the right time. 

All goes to say, I'm taking this time to understand my WHY and VISION as to what would guide me in the future. And this is a pretty big gamble. Worst case scenario is that I'm down $35k USD (+ all the opportunity costs) and I struggle to find a job in an awful job market, and if I do - it'll be less salary than what I used to have and I'll be complaining "oh Toronto [or insert another city] is so expensive". For me, that's the situation if I lose this gamble. And that's the situation I grappled with myself for a long time before I decided to take a sabbatical. 

Now the saving grace is that - I'm me. And that gambling on myself means I want to win. Also, while I mentioned above that There's also no point in forcing something that I know deep down I don't believe in. The inverse is also true, and because I believe in myself means I'll do whatever it takes for me to be happy in the end.  And that's just who I am.