Nothing feels riskier for a solopreneur than investing money in your business when there’s no guarantee of an ROI. Here’s how to decide when to invest and when to save. Though I long resisted the label, I have been a solopreneur ever since I started working as a freelance writer in 2010. As the owner, manager, and only employee, all decisions about my solo freelancing business are up to me—which continues to feel simultaneously invigorating and terrifying.