When your business achieves a certain level of success, people will start telling you that you need other people.

One of the most common recommendations will be a virtual assistant, someone to handle all the minute day-to-day details. The emails, the phone calls, the invoicing. Someone who can get all the little stuff off your plate so you can handle the big stuff. Someone who can make your day a little less stressful.

The problem, so far as I can see, is that a virtual assistant can’t make running a business any less terrifying. Creating a business is an act of faith, and every business owner lives in constant crisis of faith. Getting rid of the email does not resolve the problem of doubting oneself. It solves the problem of email.

Which, so far as I can tell, is essentially a way to give me more hours in which to doubt myself.

I spend approximately 20 hours every week practicing my trade, which is writing. I spend perhaps another 10 hours in administrative tasks like email and invoicing.

I spend probably 30 hours staring at a wall thinking how nice it would be if I weren’t in charge of holding up this little world I created. That maybe it would be easier, better, more lucrative to let someone else hold up the world while I took care of some little sub-continent for a decent salary. That I’m going to drop this world any moment now. Any moment.

People keep talking to me as if the 10 hours of email were the problem. They’re not. It’s the endless hours of doubt that I need help with. Which is where a right-hand man comes in.

Assistant Vs. Right-Hand Man

The virtue of seeking an assistant is that you can put out an advertisement for one. It is far more difficult to find a right-hand man, especially since the job description tends to be tailored to the person who needs one.

I found mine entirely by accident. Actually, he found me.

I’ve known this man for over a decade. We have been friends a very long time and we know each other extremely well – so well, in fact, that he told me what birthday present I had gotten him two hours before he opened it. We’re each other’s confidantes when life throws us a curveball, and he had noticed the that the curveballs I was dodging lately seemed to be entirely from my business.

He got interested in my business. He started asking what it was all about. I told him about wanting to be better than other businesses, about wanting to care more and feel what I was producing had true worth. I told him about writing, how it’s one of the few talents I have that both challenges me and feels secure, as if it belonged to me. I told him about what I want to do over the next year, the next five years, the next ten.

He went away and thought about what I’d said. He had some long conversations with his wife. He thought some more, wrote some things down.

And then he asked me how he could help.

He wanted to be a part of what I was creating. How didn’t matter. How was a question of what he was good at. He was willing to learn what he didn’t know and he was willing to do certain things he didn’t particularly enjoy so that he could be involved in this project.

And I thought, of all the things I need in my life right now, this kind of faith is invaluable.

An assistant comes with certain skills and tries to make those skills fit your business model. A right-hand man sees your vision and is willing to do whatever it takes to help make it a reality. If that means answering the email, it does, but the right-hand man knows why he’s answering the email. He knows every word he types is for a larger purpose.

I’d rather have that guy speaking for me than the most well-spoken, meticulous, deadline-driven assistant known to business.

Why a Friend and Not a Stranger

Everyone will tell you it’s dangerous to hire your friends.

I think that’s true. I also think it’s far more dangerous not to.

The reason people will tell you it’s dangerous to hire your friends is that emotions get into it. With employees, you’re primarily concerned with whether they can do the tasks you’ve hired them to perform. With friends, you also have to care about them, and that means occasionally you have to let the tasks go hang because your friend needs a hand.

The upshot is that your friends also care about you.

Unloading onto your employees when you doubt the business is never a good idea. It makes them doubt whether they’ve signed on to the right venture. It makes them worry about stability. It makes them worry, period.

My right-hand man signed on knowing not just the hopes I have for this business, but also the fears. He knew what I worried about and why I doubted myself. He knew what I believed I could do and why I thought I was the one to do it. And weighing all that, he believes that my virtues will outshine my vices.

It’s dangerous, because I can’t hide anything from him. But then again, I don’t have to hide anything from him. He signed on when everything was new and raw, and he’s not going to bolt because some corner somewhere works loose again. He was there when all the corners were loose. He knows.

When you’re feeling like you can’t let your guard down, you can’t let anyone see that you’re vulnerable, it helps to have someone who knows what a wreck you can be and is standing there anyway believing you can get back out there.

Working with your friends means you can do that. You just have to pick a friend who has faith in you.

And then you have to be worthy of that kind of faith.

The Problem of Titles

To call this man an assistant discredits what he brings to the table. I need him to fulfill many of the same duties as an assistant, but I need him to be more than that. I need him to know how I talk to clients and what kind of presence I want to be in their lives. I need him to know what I’m working toward and to check me if I stray. I need him to hold me accountable to myself and to tell me if I’m failing.

It’s easy to fail yourself. It is very difficult to fail someone who believes in what you can do.

An assistant, first and foremost, performs the task. The right-hand man knows that the task is less important than the purpose behind it. I need someone who can tell when a phone call would be a better way to reach out to a client even if I told him to email her. I need someone who knows the difference between the letter and the spirit of the laws of this little world I’m holding up.

I’m calling him my Seneschal. He’s the one who takes things off my plate not because that’s his job description, but because it would make my life a little better. Because he knows I worry about this little world of mine, and he can help me worry a little less.

He’s also the one I call in the dark hours when I doubt everything. He’s the one who tells me I can do this, that he’d bet years of his life on it. That he has, in fact, bet years of his life on it, and he knows he’s not going to lose because neither am I.

Ask an assistant to do that.


  1. Hey Taylor,

    You gave me a light bulb moment with this post. I continuously doubt my business acumen so having a right-hand man who’s got my back sounds like the perfect solution.

    They should have an official designation for that.

    I’m glad you found your right-hand man! :)
    Samar recently posted..Writing Exercises for Freelancers That Work Every TimeMy ComLuv Profile

  2. What a great web log. I spend hours on the net reading blogs, about tons of various subjects. I have to first of all give praise to whoever created your theme and second of all to you for writing what i can only describe as an fabulous article. I honestly believe there is a skill to writing articles that only very few posses and honestly you got it. The combining of demonstrative and upper-class content is by all odds super rare with the astronomic amount of blogs on the cyberspace.

  3. Finding the right-hand man is quiet difficult. You have to look for the one who has good attitude and not only for what he can offer. I’ve found mine three years ago, well not the right-hand man but my right-hand woman. She’s my wife now with two cute little kids.
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