Ten years ago, a mentor told me to hire a personal assistant. I was dubious. Today, I can't imagine myself getting the job done without one. Here's why a personal assistant can help you earn more and find more free time.

Before I tell you about my personal assistant, why I have one, and the financial benefits of hiring one, I’m going to give you permission to make fun of me. That’s right: Assume his name is Jeeves or Alfred, that I ask him to wash out my dirty socks and filet my pheasant under glass. And since I can’t live in a palatial estate just yet, you can also assume I’m acting out some self-indulgent fantasy of being rich and important, even though you know, natch, that I’m neither one of those things.

Yup. Go right ahead. Laugh. Because I’m laughing all the way to the bank.

Then again, if you’re willing to learn a little something about time, money, and value from a person who’s validated his hypothesis at least a half dozen times over the last decade, then sit up straight and take some notes. I want you to learn from me, and I want to make you the envy of your friends and family.

If you’re a busy person trying to make headway in your business and financial life, a personal assistant might seem like an expense you can’t afford. But to get rich, you have to think like rich people do, and the first step begins with what I call “abundance mentality.” A person who lacks this looks at the possibility of a personal assistant and says, “Oh no, I can’t afford that.”

But a person with abundance mentality sees the same exact possibility through different lenses: Cost-benefit analysis and return on investment. Let me explain how these financial concepts work, especially as they pertain to the personal assistant I want you to hire.

Cost-benefit analysis is exactly what it sounds like: If it costs you $50 a week to get a personal assistant, what’s the benefit? Let’s say that money buys you five hours of help. You ask the personal assistant to run errands, send mail and attend to tasks that otherwise would prove a time suck on your week. The benefit, in this case, comes in the form of five free hours that you gain from having the personal assistant help out — and you can do anything with that time you like.

Return on investment is the very close cousin of cost-benefit, but in this case, I will apply it in a strictly financial sense, and use my real-life work as an example. My personal assistant, whose name is Eric, does a lot of research, logistics, and planning for me as a journalist. Because he expands my efficiency, I’m free to take on more assignments and make more money. I would estimate that for the $50 investment I make for each week I hire him out, I make twice as much money minimum because of his help. So if I pocket $100 I wouldn’t otherwise make, and pay him $50, the return on investment is $50. Makes sense? (By the way, that’s during a slow week. Sometimes the return on investment is two or three times as much.)

Now that I’ve explained why personal assistants provide great value, I’m going to address the obvious issues that come with finding, hiring, and keeping one.

Starting is as simple as running an ad or using word of mouth

I’ve never had to run an ad on Craigslist, but I would definitely consider it, as it’s a great way to have the applicants come to you. Thus far, I’ve used word of mouth with great results. People you trust will tend to only recommend people they trust, which saves a lot of time vetting candidates for honesty and integrity. That’s super important because just like a housekeeper or a babysitter, a personal assistant will get to know some key things about you (maybe even your digital passwords). You have to make sure they’re 110% trustworthy, and nothing less. It’s certainly possible to find that golden person with an ad, but recommendations from your mentors and posse will streamline the search process.

Define key tasks from the start

You can ask a personal assistant to run your errands, or help you with the most demanding tasks of your job or business. There are no rules, but you don’t want to switch roles without warning once a person starts. Tell them what they’ll do and get their buy-in first. Once you have that, it’s full steam ahead.

Use a probationary period to make sure it’s a great match

When I try out a personal assistant, I give them two weeks of probation no matter how much I may love them in an interview. This gives me a chance to see how reliable they are and how comfortable I feel with them. During this time, I may pay them half the going rate to see how much they want to do the job right and follow through. If you have to let them go, be humble and smart: “I’m not sure it’s a great fit for either of us” is much more tactful than “You suck.”

Remember the Golden Rule

Sure, it’s tempting to send “Alfred” to fetch your slippers and introduce him in public as your hired help. Don’t do it. Eric will tell you that I always introduce him in public as “my right-hand man” or some such. I also use “please” and “thanks” with him, just as I would expect a compassionate boss to do with me if the roles were reversed.

Give clear, simple guidance and instructions

If I ask Eric to perform research, I give him all the tools and instructions he needs to do a great job. Yes, that takes time, but it’s minimal compared to the amount of time he saves me. What’s more, it’s unreasonable to expect someone to “do this” if you don’t at least tell them how you want it done. It’s like sending someone for coffee and not telling them what you want in it. (Note: I’ve never once sent a personal assistant for coffee, though I’ll get coffee for him. It reinforces the humility aspect of things.)

Keep good financial records

Keep in mind that if you pay someone more than $600 per calendar year, the IRS has pretty strict guidelines about making sure you issue a 1099. Of course, that means the assistant has to pay taxes on the earned income, which dents his bottom line. So you can always make the choice to pay an assistant under the table. What you do is up to you, but let me repeat: Always keep in mind what tax laws dictate, and make smart choices based on that.

Incentivize rewards

It’s human nature that most people will do what’s expected—no more or no less—to earn their keep. With my personal assistants, I’ve historically dangled tiers of incentives: X pay for doing the minimum, 2X for providing more value, 3X for a mind-blowing great job.


Ten years ago, I felt dubious when a mentor told me to hire a personal assistant. Now I can’t imagine myself getting the job done without one, and at times, I’ve even used two to handle vastly different tasks. You may think, “Why not hire a college intern for free?” I’ve had those, too, but here’s a friendly warning: Internships should always be conducted in conjunction with a college program that offers credit, and you have to spend time supervising the person on a documented learning journey that takes them from point A to B. So if you’re looking for free help from a college student, and falsely labeling it an “internship,” you could get both yourself and the student in big trouble. Plus, it’s sleazy.

That’s why I like paid personal assistants so much: The exchange is upfront, honest, and simple. In a decade of doing this, I’ve had a few misunderstandings and some botched assignments, but never once a bad overall experience.

The rewards often extend beyond what they earn, or what they’ve helped me to earn; personal assistants often turn into dear friends once they leave my part-time gig behind. Though that’s golden, you can’t put a price on it.

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Author Bio

Total Articles: 33
Based in Chicago, Lou Carlozo is a personal finance contributor for Reuters Money, a columnist with DealNews.com, and a former managing editor at AOL's WalletPop.com. Contact him with story ideas for Money Under 30 at [email protected], or follow him via LinkedIn and Twitter (@LouCarlozo63).