31/M/US. I had somewhat idealistic and hippie-ish values in my 20s that led me to get a useless degree (debt-free, at least) and make less-than-wise decisions regarding work and income. I tried working as a musician and freelance web developer in New York for a short while, but was really poor at negotiating. One of my co-musicians was much more of a mercenary, but he was also much more focused and driven to be a musician than I was.
Then I went to India on a volunteer opportunity. I was working all the time, doing very depressing work at that, for almost no money, and I had very manipulative bosses that ran the organization a bit like a cult (it was a very isolated live-work campus). They wanted to have a kind of "family" feel to the team, but whenever I approached them about personal issues, I was shot down. I should have left after a year, but I ended up staying for almost 4, after being given the opportunity to develop an app that I was told would be very lucrative. (Spoiler alert: I finished the app and it never saw the light of day.)
It was a psychologically trying experience, and after I left, it took me a few months to readjust to the outside world. Then, with under $20K in the bank, no debt, no job, and a desire to get out of the US, I decided to try the "digital nomad" thing. I came to SE Asia with no particular plan. I got lucky and randomly got a decent freelance contract with a translation agency, which has allowed me to sustain my travels. However, the assignments come too irregularly and the total income is too little to live a real lifestyle. I have tried to find more work, but it has been very discouraging. I am not really into this work, so the motivation to be a prolific freelancer (or even a more specialized one) is not there.
Being in Vietnam, where it seems like everyone runs a small business of some sort, has really inspired me to take more control over my work/income (and life in general). However, I don't want to do any sort of hourly-based digital work (translation, design, web dev, English/music lessons via Skype, etc). My interests are pulling me toward import/export, product design, or F&B (non-restaurant). However, I'm introverted and not really a natural salesman. I feel like my diffidence is an obstacle to achieving success as a small business owner, but it is also perhaps one that could be overcome somehow.
Do you think assertiveness training would a good investment to make in oneself, for a person like me, before investing in a business?
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