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5 Reasons You Need (or Don’t Need) an Assistant
Updated: March 11, 2021 |
Taylor Kovar, CFP

5 Reasons to Hire an Assistant (Or Not)

There’s a common thread for anyone building wealth early and often. Whether you’re committed to the FatFIRE mission or you’re just looking to maximize those earnings, there’s a clear connection between financial independence and quality of life. How you make good use of your wealth is a much more complicated issue. You will never exhaust the options for comforts and commodities that will supposedly make your life easier. You can also always find someone telling you to save as much money as possible and spend only on the bare necessities. The point of prosperity isn’t to hoard every penny, nor is it to spend with reckless abandon; we want money to work for us, both now and in the future. Do you need an assistant?

Money Spent Is Not Money Wasted

In the right context, every dollar spent is an investment. A tank of gas is $40 toward getting yourself to and from places you need to be. Mortgage or rent puts money into the security you and your family need to live a comfortable life. If you really want to stretch the definition, the pool you install allows you to save money on future vacations and entertainment costs for the kids. 


I get into a lot of discussions with people about how to spend and save, and it’s never hard to find two people willing to have an argument. The motivation for writing this post is listening to people come down on different sides of the paid assistant debate, with some adamant supporters and some people diametrically opposed. In my mind, this debate shouldn’t exist, because every business and employer is different, as is every assistant. 


When it comes down to whether or not YOU should hire an assistant, your uncle or sister or real estate agent or whoever else might have good advice, but they don’t know the answer. You’ve worked hard to get to the point where a little paid help might be useful, and you have to make the final decision on that. 


I’m not going to tell you what to do, but I will throw out some food for thought that might help you get to a place where you can make your choice with confidence.

1. Buying Time

If I could get another five hours in my day, I feel like I’d have enough time to solve a lot of the world’s problems. Sadly, I’m stuck with 24 hours like everyone else, and every day seems to sneak by a little too fast. 


Within my company, we have so many things going on at any given moment. I keep my clients as priority number one and then use any leftover brain space for all the other hustles and projects. Then I pay a team of people to help get things accomplished and ensure we have the necessary skillsets to keep our standards high. In essence, I’m paying brilliant people and absorbing the hours of their days into my own schedule. 


Perhaps it’s how we’ve historically used the word assistant, but there’s usually a distinction between a personal assistant and an office manager or the head of social media marketing. When employers need assistance with a specific type of work, we put out a job listing for applicants with that background and experience. When we need help with an array of stuff, or just want to try to free up time, we jam it all into the title of assistant and then hope the perfect worker miraculously comes our way.

Instead of thinking just about the title and the tasks, you might be better off thinking about the time you’re trying to buy. Do you find yourself losing hours each day because you can’t keep your passwords sorted out? Do you leave for lunch meetings at 12:30, get back to the office at 2:30, and feel like you have to do busywork until 4:30?


Or do you have bigger aspirations, like starting a blog that will reach more people? Do you want to get your body out of the office so you can work remotely while sending the ideas cooked up in your brain back to someone who can implement that policy? If you’re getting extra time in exchange for some of the money that could otherwise be put toward retirement, what’s happening with those extra hours? 

Putting Your Aspirations Into Action

When you figure out what you want to accomplish with the time saved, you can bring a new hire in on those accomplishments. View the assistant as someone who does more than menial tasks, but rather enables you to get more done. Place that importance on the assignments you dole out, because you’re only hurting yourself by trivializing the work someone does for you.


I’ve known people from all industries who are serial assistant hirers. When business is good and they can afford to bring in an extra set of hands, they do so and free up their schedules. Then an economic slowdown or a regular old return to the mean has them tightening the purse strings and sending assistants off to the unemployment counter. Everyone’s entitled to run their own business as they please, but I’m not the biggest fan of this approach. 


If you’re making good money, there’s a decent chance it’s because you’re pretty busy. If you wish you were less busy, that might not be enough of a reason to start searching for an extra employee. You need to dig deeper into what you need to be done, and why you need someone else to do that work for you. Once you get some clarity on those goals, go find someone who can help you make them happen.

2. Virtual Work

In certain circles, the virtual assistant is all the rave right now. It’s a cost-effective way to have someone take on digital organization and scheduling and other internet-based duties. It’s also a great way to find out if you actually need an assistant who’s physically present.


Businesses of every shape and size have discovered during the pandemic that remote work is a very real thing. For the traditional, controlling CEO, this has been a tough adjustment. The sense of oversight gets drastically reduced when you can’t see everyone sitting at their desk. At the same time, it’s been eye-opening for a lot of business owners who had people commuting to an office to deal with things that could really be handled anywhere.


There are two factors that are typically deal breakers or makers when thinking about a virtual PA:


  1. Part-time employment
  2. Physical labor


If you need someone to prep meals or get the dog to and from the groomers, you’ve probably already stopped reading this section. A virtual assistant can’t handle the nanny duties that a lot of people want to delegate. Do you need someone to run the personal errands that force you to drive across town? Want help with food prep? Need the animals cared for? You need an in-person worker with open availability.


It can be a lot harder to employ someone to be physically present part-time. This might work for a younger person or a college student, but they won’t have time for another career. This limits the talent pool a little bit, meaning you probably won’t get someone with a business degree. 

Virtual Assistants

Meanwhile, a virtual assistant with a higher hourly rate will be able to work more efficiently. Try ten hours a week doing accounting stuff, prioritizing emails, proofreading articles, etc. The PA doesn’t have to spend any time driving to and from your appointments, and can work for you and three other employers. That way, they can earn a full salary and keep everyone happy. 


If you feel like you need help on both fronts, with someone to respond to emails with a professional tone and then hop in the car to go get the kids from soccer practice, you either need a one-in-a-million executive assistant or two separate employees. Honestly, if I found someone who could perform professional and personal tasks with the same competency, I’d feel bad keeping them on as my assistant; that person should be off earning more and becoming the boss of their own company. 


If there’s any uncertainty about virtual vs. in-person, start with an online hire. You can shorten the vetting process by a few steps and see how much time a part-time worker frees up for you. It might be the perfect fit, or you’ll find out quickly that what you really need is a live-in chef.

3. Local Employment

Assuming you do need help with odds and ends in the home and around town, you have the opportunity to do something great: help give a good wage to a member of your community. 


To be perfectly honest, I love hiring people. I find such happiness and fulfillment in giving someone an opportunity to be productive, feel accomplished, and achieve some financial stability. I’ve employed people in all types of positions over the last few years, and it’s almost always been mutually beneficial. The work done frees up time and allows me to generate more income for my business, so I have no complaints about signing that extra check.


Assuming the added payroll doesn’t mess with your retirement goals, providing someone with respectable work is one of the best things you can do with your good fortune. You can start a recent high school grad on the path toward long-term success, or help a new parent slip back into the workforce without going straight to 40-hour workweeks. 


It’s not your job to make charity hires, and that’s the last thing I’m suggesting. However, if you’re 50/50 on hiring someone to help with administrative stuff or other odds and ends, the benefits go beyond checking items off the to-do list. 


Start with the money you have and what you can realistically afford to spend. Then consider what you need to be done and whether hired help makes sense. If you could still go either way, think about what type of opportunity you can provide and the positive effects such a hiring could have. 

4. Too Bossy

We do a lot of things to show status and wealth. From the cars we drive to the clothes we wear, we put plenty of effort into presentation. It’s never the most important issue, but it’s part of how we approach the day and try to make an impression. 


In my opinion, using employees as anything other than valued team members should be off-limits. If you have any thoughts about the thrill of referring to someone as “my assistant,” there’s a good chance you’re considering this hire for the wrong reasons. Ego shouldn’t play a part in when and who you employ, and it’s pretty unfortunate that it often does. 


Try to rule out all the subpar motivations for bringing on an assistant. If you’re jealous of a friend who never grocery shops, that won’t cut it. If you want to lighten your workload but aren’t sure which processes you’re ready to unload, hold off. Or, If you simply like telling people what to do, that’s a personal issue to work through first. 


You want to have a good relationship with anyone who works for you, right? If an assistantship is in the cards, either personally or professionally, you need to be hiring for the right reasons. As opposed to trying to impress workers with all the things you want to get done, try giving someone a chance to prove what they can do.  

5. Burnout

This last reason might be the most frequent bad excuse for hiring a personal assistant. If you get to the point where you don’t enjoy work, that’s not always a sign that you need an assistant. Finding yourself in this position can be more indicative that you need a life change. 


Maybe you’re ready to retire. You might be short of that FatFIRE goal, but burning yourself out for early retirement isn’t a good strategy. Work hard to achieve your goals, but don’t make yourself miserable in the process. And please, please don’t make someone else miserable just so you can share the burden. 

It Doesn’t Have To Be A Drastic Change

It might not be as drastic as changing careers or retiring earlier than you expected. A simple shift in procedure can cure a lot of what ails you. It’s entirely possible that a new approach might merit hiring an assistant, or updating your scheduling software. People with the mentality to join the FIRE movement often think in grandiose terms. This serves them well in many cases. That same impulse can lead you to hire an executive assistant as a means of breaking out of a routine. That might not be the best choice for your bank account, career, or the person getting hired. 


The smaller jobs that get too monotonous can be passed along to virtual assistants to handle the work effectively. There’s nothing wrong with efficiency and delegation. It’s when you convince yourself that someone else should occupy your exhaustion that your motives become a little misguided. 


Financial independence should mean exactly that. You have the freedom to earn and spend as you see fit. One version of financial independence includes a paid assistant who helps you manage your time and make the most of your dollars. Another version has you scaling back on your needs and responsibilities. Try to find the simplicity that makes the money you saved go even further. 


The direction you take is up to you, and both paths deserve consideration. Just make sure to approach any hiring decisions with a clear head. Don’t get caught up in keeping appearances. Stop trying to convince yourself that someone has to pick up your dry cleaning. Stay respectful and responsible, just like you’d want any future assistant to be.


As always,

Taylor Kovar

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