Love Your Work Creative Habits | Writing | Solopreneur | Productivity | Entrepreneurship | Startup

Five years ago, I wrote about how - after ten years as a self-employed independent creator - I hoped to "make it." I now realize, I never will. Five years ago, I sat at my keyboard to have a serious conversation with myself. It had been ten years since I had woken up to a day with nothing scheduled, and wondered how I was going to fill it with something that both made life worth living, and also paid the bills. In this conversation, I asked myself, How did you end up here? Have you made a big mistake? I had spent a good chunk of my retirement savings, left Silicon Valley in the midst of a boom, and now found myself barely getting by in South America. About a thousand words in, I stopped and cracked into tears, not only because I was scared out of my mind, but because still – despite not seeing a clear path to making this work - I couldn't see myself giving up. I concluded: Take it from me, a ten-year veteran self-employed creator: If you are looking for security or reassurance, I do not recommend this line o