There she goes, there she goes again

And we're back. After trying my best to find a way to settle down, I just couldn't do it. Not here, not under these circumstances. I really wanted it to work out though. Do you know how much effort it takes to keep moving? And not just yourself, but your stuff - not just personal baggage stuff - but big things like sofa and mattresses. For the past 5 years, I feel like there's been a consistent train of it. For the first 3 years or so, it was mostly just moving myself and a few clothes/personal items from one place to another, like a city to the next. Often one country to another - sometimes one continent to another. And then the last 2, I really tried to settle down in Chicago. The first year, I was an absolute hermit. I would just stay in my place and I was content. The second year, not so much - I realized that I needed more from the city and my place. Even though I loved my space as I started to make it my own, I learned it wasn't enough after a while. 

And after a while, the home that I was able to create for myself wasn't enough. It was enough at first. Especially around the beginning when I needed a place where I can just stay for a long time, and more so to be able to express myself. But as if it's on brand, it's just a temporary settlement until my next journey. The city never really clicked with me as much as I hoped. Work got harder - people were let go or left until it's been 11 churns in under 6 months. Additionally, several issues came up especially when they've rejected another go-to market strategy and of course a not-so-pleasant trip in Las Vegas made me realize I should just leave. 

So I started the process to update my resume, get references from previous colleagues, and started an online portfolio. I was pretty eager at first. But I couldn't do it. I tried to get a job and talk to the right people. Amazing opportunities and lots of them great people. Body can't do it. I just can't work at the moment. There are these mental blocks that stop me from being ever so productive (& I tried! I was able to get a part-time consulting gig to kickstart a freelancing/consulting business). But I can't do it. And that's absolutely insane to me because I know I'm ambitious and I can work. So if something inside of me is stopping me from being able to just work, then I've learned enough lessons to know that I need to take that as a sign rather than learn from the hard way of pushing through again. 

What makes it more difficult now? Or easier? 

5 years ago, I thought I was going on a sabbatical. I'm pretty sure I've made some people a bit mad when I even said those words. And looking back I agree - it wasn't a sabbatical in the fact that I took rest. But it was a sabbatical in the sense that I took the leap of faith and took the risk. Although, when I left Toronto, my aim was to go out there but never compromised on my career. In the most convoluted and unorthodox way, that did happen. After struggling to get the title and salary in Canada, I got the product manager title in the UK and got the 6-figure job in the US.

Now, what makes this different? Well, I'm 5 years older and rather than having less stability to embark on a journey - meaning no money yet more youth on my side - I now have left a 6-figure job with a Director title, on the way to a pretty good (in theory) equity and industry with enough stability to buy a condo back in Toronto along with continuing to invest in other assets. So embarking on this new (yet familiar) journey is a bit more of a head scratcher especially since it's not really meant for me to guarantee a great career. Although, to be fair, I also didn't know whether my gamble 5 years ago was going to make me succeed either. I just knew I had a very strong urge to do it or else nothing in this world would matter to me anymore. 

I think that is what's making me a bit nervous this time. I don't have that strong urge to leave even though I love the city. Back in Toronto, I remember coming back home with my groceries thinking what if I just ignore this feeling of needing to leave - and that resulted in the most intense drop of my soul in my stomach and it's akin to my world and life being over if I don't choose to leave then. See, I don't have that extent. I'm just feeling not satisfied and I know if I continue down this road, it'll get worse. So when I ask myself at random unprompted times if I'm okay at the moment. I would truly answer no, but I can't see any other better paths for me either. So unless someone drops in a few million dollars for me to live the life I envisioned for my future, this is the best option out of all. 

 So when I ask myself at random unprompted times if I'm okay at the moment. I would truly answer no, but I can't see any other better paths for me either... so this is the best option

So what's the inner turmoil? 

Well because I can't feel the intensity as I did 5 years ago, nor can I say that I've not travelled since that's what I've done - I guess, I'm doubting whether I'm just attached to this lifestyle that I subconsciously sabotage my chances of putting a stable life for myself or that this is the right choice for me and like before, I'll make it worth it because at the end of the day, I'm gambling on me - and I want myself to succeed. Personally, I like to lean on the second reason, but I do want to provide some space over my insecurities and doubt because while they are quite annoying and frustrating, feeling fear is legitimate especially as I sacrifice a lot more to pursue something very unknown or even unpredictable. 

The inner turmoil comes from a variety of fear that lets me reason why taking a sabbatical is a bad idea. These reasons include: 

• I'm bougie af, I don't necessarily care to buy brand names but I do enjoy shopping for artisan items - I actually have a bag in my bucket list where I need to fund another trip to Florence to buy it in real life rather than online because that's part of the experience. With that said, if I don't particularly aim to focus on my career at the end of this, will I be able to fund my lifestyle again? 
• Before committing on the sabbatical idea, my original plan was to start a freelancing business to help nonprofits with their digital solutions. Well, I was lucky and I was able to meet several people who would be willing to let me help them. So I tried nonprofit, and while more of my values align to it, it's like working in a startup again with more than half my original salary and as seen above, I don't want to be poor. Henceforth, my business plan already needs to pivot and if my sabbatical isn't really planned for me to create that business plan, then would I be able to find what I really need for when starting a business? 
• I would say that because I left a lot sooner than I thought since I was originally planning to leave a bit later. My budget is more of a lavish 3-months/balance 6 months rather than a lavish 6 months/balance 12 month kind of a sabbatical style. On one hand, saving more money means throwing away more of my time that I'll be 32 by the time that I can do a year sabbatical which means I'll be 33 when I'm back. And also, lavish vacations mean I don't push myself into situations that would probably expand my horizons because I'll be taking the most expensive hotels and not needing to talk to anyone around me. So while this can be class as an inner turmoil, but it's not really the most pressing issue 
• There were also concerns with projecting my judgements about myself onto others. For the most part, most people close to me already knows I'm unconventional. My antics these past 5 years have really stopped them from expecting me to abide a lot of the conventional checklist such as settling down. On a side tangent, I'm a bit offended in some ways because I impose those checklist on myself that I talked to a therapist for several sessions with how to handle them. Coming back to topic, a way for my insecurities around this to manifest is myself imagining my friends and family, along with haters (that aren't really real but I've made them into that group for this very narrative) would judge me for not having myself altogether. By thinking that other people are criticizing my decisions and not being able to meet the checklist, I feel insecure about going into a sabbatical. At the end of the day, this is more my problem than anything. Most people are actually absolutely supportive and for those who would actually pose a problem to my choices are dropped anyway. 
• Other inner turmoil includes the lack of stability, routine, and I don't want to get fat again. I was at the best shape of my life before I left Toronto and I gained 20 lbs in Edinburgh because I was sad, not because I like the food there. And then it took me another few years and being able to have a stable life in Chicago to finally be back at the similar weight as Toronto (although, the muscles are not as toned as before). I just don't want gain weight again and there's a higher chance of that when I travel. Also, I would miss cleaning and cooking my own food. I'll miss my clips that I put on bags after they're open or my cooking bowls that are just so consistently reliable when cooking. These are actually the small things that make so much difference for me when you have to keep moving. I'm actually frustrated having to deal with not having these things again when I go on a sabbatical. 
• Several discussion boards like Reddit and Blind are quite oppose to these things unless your TC:>500K with NW:2M+. Now I would say that in general these communities are quite toxic in their own way. And that's still quite true, but they do provide valuable resources and information as well if you know what you're looking for. Anyway, I guess discouragement from strangers don't help. I understand that I'm not them and that yet there is a chip on my shoulder on my end, as if I want to prove these strangers that they're wrong so I can't fail or else it'll be embarrassing. Yet, I wouldn't even be friends with these people. Funny how even though I like to think I don't care about how I'm going to be perceived, this issue still has a place as a bullet point under my inner turmoil. It could be part of a lesson I still need to go through, but maybe I like to think that in one way or another - this judgement, akin to Foucault's panopticon, is inherit to the human condition. That no matter how anonymized we are, or disconnected and far removed other people are - there is still a set of societal standards that we've internalized and consciously or subconsciously abide by when it comes to making life choices. And one of the inherent human condition is we always want some sort of external acceptance. 

And yet this is still what I'm about to do 

I'm about to take a sabbatical. At this moment in time, I've already provided my letter of resignation and I still have 2 more weeks before my last official day. Everyday, I'm dreading the efforts it would take to move-out but feeling more free. I do find it absolutely ridiculous since I haven't really been doing much for work for about 2 months now and it's just about removing that anxiety of needing to show up at work and just be present even though it's been such a hollow role since the major decision in April. 

I heard somewhere (probably the Sabbatical project) that it takes 8-12 weeks for someone to fully disconnect from work. And while my situation isn't as straightforward, I'll take that guideline and start it officially once my end date has started. 

Am I scared to do this? Yeah, mainly because I don't have a clue what's going to happen at the end of it and I guess whether it's worth it. The last part is a bit of a misnomer though, mainly because I'll make it so that it's worth it - if it's a failure or a mistake then I just see it as an expensive and fun lesson. Worst case scenario is I can always go back to some stage of my career and work up from there again. But just because I'm scared doesn't mean I'll stop myself from having a sabbatical. 

Maybe later, I'll lean more into the actual excitement of it all. I have tendency to feel all the grievances in the beginning so that I can just feel as much of the negative stuff and I can just focus on the positive ones afterwards. But also, I am in the middle of it all - work hasn't ended and I need to move out of the country - I'm also taking advantage of the private healthcare as much as I can, as well as grieving the loss of my space, soon-lost of my routines, and the furniture/items I've added to make the space more of my authentic expression. So maybe after all of that, I'll be able to feel more. 

But we'll see. I'm using this blog as a way to document what I'm doing. And so that when all of this done, I can look back and understand the sacrifices and dread that I've gone through and hopefully also have the exciting stories and happiness that made me feel like a child again. I also want to use this blog to share with friends and family who may not know where I am or what I'm doing. While I think it's rude to hog the conversation and I make it to the point to listen, this blog can serve as some sort of one-sided conversation I'd like to have with them.

Whole apartment tour