While recent research predicts an imminent shortage of talent and prospective partners in CPA firms due to retiring baby boomers, it seems another important population of aging professionals in the accounting industry has been largely ignored: bookkeepers.  The United States Department of Labor Bureau of Labor Statistics currently reports that bookkeepers and accounting clerks will experience a decline in employment from 2014-2024 compared to an increase in employment for accountants and auditors during the same time frame.  In many companies, technology, software, and outsourcing have driven the projected decline in bookkeeping and accounting staff.  On the surface, this negative growth indicates that the need for new bookkeepers will decrease substantially in the near term.  Upon looking deeper into the BLS and SBA data, professional journal articles, and media articles, we find that the trend toward lower employment and automation replacing bookkeepers may not be wholly accurate.   The combination of an aging population of bookkeepers currently in the workforce and fewer new entrants into the field may not be sufficient to meet the needs of companies, especially small businesses.  We conducted a convenience sample of small businesses to test our basic assumptions and to assess the need for a larger study.  Our hope is to develop a guide for small businesses on best practices for securing employees with the skills sets they desire, and for adopting technology or other strategies to automate their bookkeeping and accounting functions.