CHAPTER 27Tax Strategies for a Sideline Business

Millions of Americans today have a sideline business. According to a 2022 survey from Bank of America (BOA), nearly half (49%) of all small businesses started as a side hustle to generate income as a supplement to their owner's job earnings. Having a sideline business has become easy with the advent of eBay, Etsy, and other online marketplaces. The “gig” economy, with options for part‐time and freelance work through Uber, TaskRabbit, Upwork, Takl, and other platforms, also provides sideline business opportunities (assuming state law does not treat you as an employee of the platform). But sideline businesses, such as dog breeding and gentleman farming, have been around for years.

Starting and running a sideline business can be a savvy move. It can be a way to supplement your current income. It can be a safety net in case of a job dislocation. And as the BOA survey shows, it can be a way to test the waters for a full‐time business in the future, say, on retirement.

For a further discussion of business expenses, see IRS Publication 535, Business ...

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