Investment Risks

I’ve been having regular therapy for a year and a half and I feel like I’m finally getting somewhere. My sessions are now less focused on whatever happened since the last session and more focused on my behavior patterns over time. I’m starting to look at shifts I can make in those patterns in order to build the kind of life I want.
 
For example, today I figured out that I have been seeking income streams that require minimal investment, which I can start SOON. Income streams that would allow me to pursue the pipe dream/waste of time and money of becoming an entrepreneur in the fashion industry. We’re talking things like becoming a virtual assistant, online transcription, reselling trash made in China on Amazon, or doing a vintage notions and findings store on Etsy (from estate sales and whatnot). If I fail at one of these, then I can just say that it was a side gig and it didn’t really mean anything to me. It’s important to remember that minimal risk almost always means minimal reward.
 
What would happen if I tried something that actually took a lot of work? What if I finished my Library Science degree (highly unlikely) or went back to grad school for women’s studies? What if I completed the Paralegal course to actually become certified for the job I’m already doing? Or what if I pursue a career in mental health counseling? {Facebook reminded me today that I’ve been thinking about that since at least 2009, likely much earlier than that}.
 
What if I spend a crapton of money on grad school [again, mind you] and I don’t graduate [also, again] or I graduate and then fail miserably because I’m not cut out for it – because I picked the wrong thing to pour my heart and soul into? What if, in five years or less, I’m back to square one and just as dissatisfied with my life as I am now – only then, with even more crushing student debt, general financial instability and still not living the life I want?
 
And it’s no wonder I’m gunshy about making big investments in my future. I dropped out of grad school six years ago and I’m only just now getting some relief from the uphill battle. I had to leave my community, move to another state, live with my mom for over a year, and try to make a home and find community in a place that still isn’t quite right for me. Yet I am still as much risk-averse as I am comfort-avoidant. I’ve been in one place too long. The progress has been too slow. I am afraid that if it continues slowing down, that one day I’ll stop moving and in another six years I’ll still be here – tired, overly busy, unsatisfied with the way things are and just too exhausted to try and change it.
My current desire to make big changes is a joint effort between my risk-aversion and my comfort-avoidance. So the question is: am I dissatisfied because things are “too good” or too comfortable? Or am I ready to seek something better while pushing through my fear of epic failure and financial disaster? Both, kinda.
 
I’m unsure where to go from here, but this feels like a breakthrough in my understanding about why my life is the way it is right now.
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