I have attempted two different technology startup ideas in the past six years and my cofounder and I finally called it quits earlier this year. It has been a heart-wrenching ride because we poured our heart and soul into them like many others. Having been mentally exhausted, I decided to take a four month trip to reassess my life as to what I want to do next. It was a much needed rest and I just returned from the trip fully reinvigorated. The problem? I am having a hard time deciding whether to pursue another startup idea or get a job.
Financially, I am not in a super bad place, even though I haven’t earned any income for the past six years. I bootstrapped my own business so my immediate savings is pretty much depleted…not a good thing obviously. However, I can potentially sell my house or take out my retirement savings to keep myself afloat if I have to. The alternative is to get a job. Being a developer, I should be ok in that department. The trouble is, I still haven’t given up my dream of having my own business.
People say you learn the most from your failures and I definitely learn a lot from them. I now know more of what it takes to make my startup a success. I am developing some new ideas but I don’t know whether I should pursue them or not. The choices are: a) Get a job for the next little while to regain my financial footing or b) Work on my new ideas. My friends and family want me to choose the former because it is the sane and safe approach. I, on the other hand, want to give myself a max of 3 months to figure out whether my new ideas would work or not.
I am 39 yrs old and single. Not young by any means, but I still have my energy. I am worried that if give up now I might not have the courage to try again. The reality is relationship and societal expectations always force one to give up their dreams. Should I get back into the workforce? Am I crazy to try entrepreneurship again so soon?