Solopreneurs: How to Know When it’s Time to Hire

Amanda Luzzader

So, is it time to hire an employee? Or two?

You’re a solopreneur. You own and operate a small business. Doesn’t matter if it’s a food truck or a social media consulting business or a legal practice or an online pottery shop on Etsy. You started the biz all on your own, you manage everything by yourself, and you alone reap the profits. 

And it’s going well! For a year or maybe even several years, you’ve been figuring out your market, bringing in money, and developing new offerings for your customers. However, lately you’re feeling worn-out, overworked, and inefficient. You see potential to take on more clients, increase production, or bid for more projects, but you just don’t have the capacity. Or maybe you wish sometimes you could step away, take some time off, and enjoy the rewards of your success.

So, is it time to hire an employee? Or two?

The question is terrifying. Small, one-person businesses often operate within very narrow margins of error. Profits are skinny, production is tight, and a small mistake today can transmute into disaster just a few weeks down the road. 

And hiring people is expensive! According to an article published online in 2019 by hiring firm Glassdoor, the average cost of hiring one new employee is $4,000 and 24 days. This takes into consideration the costs in money and time to recruit, interview, background-check, on-board, and train the employee, along with direct costs such as equipment and tools for the employee (computers, uniforms, tools, etc.). Four thousand dollars may not be much to a corporation with dozens or hundreds of employees and ample cash-flow, but for a solopreneur, $4,000 is probably  make-or-break money. If the employee doesn’t work out, all that time and money is lost.

Interestingly, the question of whether and when to hire must be a common one, because according to reporting by the U.S. Chamber of Commerce, there were 31.7 million small businesses in the United States in 2021, comprising 99.9 percent of all U.S. businesses. And according to articles published by small-business mentoring firm and the news section of, 2022’s economic climate is favorable for anyone interested in starting a new small business. So, you’re not alone—millions of solopreneurs are wondering about this question, too.

So when should you hire an employee?

While every business is different, there are some easy-to-see signs and signals that it’s time to hire.

A 2015 online article by lists two key signals that it’s time to hire. First, hire someone when the tasks the employee will perform will result in more money. The article points out that with small businesses, there’s usually not a lot of money, so there’s less justification for hiring unless the new employee will bring in revenue. Second, Entrepreneur says, “Hire when the tasks to be completed fall under a particular skill set.” In other words, if you can precisely specify all the skills your new employee needs, and if you know those skills will earn money for the business, then it’s time to find that specific employee and put them to work.  

In the same article, Entrepreneur offers two pro tips for solopreneurs. First, hire a “co-founder.” This needn’t be an actual co-founder or someone who helped you launch your solo venture. But try to find someone who could have been your co-founder, someone with the same interests, passions, and skills. The result is hopefully something like a doubling of personnel—so that you now have “two yous.” Second, Entrepreneur suggests that you “kick the tires” by hiring someone on a contract basis. The costs for engaging an “employee” on a contract-basis are lower, and deleterious effects of “firing” a contractor are fewer. 

An article published in 2019 by Forbes has three more signs that it’s time for you to hire someone. First, are your clients are being neglected? If you’ve got customers who are lining up to wait for you, complaining that their orders are unfulfilled, or not receiving the service they’ve ordered, you are losing money and it may be time to add a team member. “If you’re consistently missing deadlines or receiving complaints about your customer support (or lack thereof), it might be time to let someone else shoulder that load,” states the Forbes article. “Or at least the parts of that load that don’t require your particular skill set.”

The second sign Forbes points out is that you’ve got enough work to hand off. Forbes advises solopreneurs to ask themselves the following three questions: (1) Do the tasks logically fit into one skill set? (2) Are the tasks directly related to generating or retaining revenue? (3) Will the work continue for the foreseeable future? 

And finally, Forbes argues that you must have the time (and patience) to recruit and hire the employee. This seems intuitive—of course, you must have the time to do something new. But it’s also tricky—if you’re in a state where you need a new employee, you’re not likely to have a lot of spare time. “Whatever you do,” advises Forbes, “do not rush into this. There are few things worse for your business than a bad hire. Except maybe two bad hires.” 

Both Forbes and Entrepreneur agree in their overall approaches. Solopreneurs must (1) think very carefully about the new position; (2) don’t act out of desperation or with haste; (3) describe the new job and its skillset to a tee; (4) have a sustainable, revenue-generating workload to hand off to the new hire; and then (5) choose the employee with great care.

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