When to invest in your solo business

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.

But not all daunting solopreneurship decisions are the same. While taking creative risks and pitching big names continue to cause some minor fingernail-chewing even after all these years, investing...