Newsletter Thursday, November 21
  • I hired a virtual assistant and work with her five hours a week.
  • It was hard to ask for help, but since she started three years ago, my productivity has improved.
  • During that time, I’ve finished my book and started a business.

I burned a pot of black beans the day I hired my virtual assistant. I was on break from my day job, writing my book proposal, preparing beans for dinner, and trying to stay relatively sane during the pandemic. I toggled back and forth from the kitchen to my desk, stirring beans between writing paragraphs.

My attention was divided yet again as I watched the timer alerting me to clock back into my remote corporate hell. I was juggling a lot and finally dropped the proverbial ball; the ball, in this case, was a mass of black beans burned to a crisp at the bottom of a new pot. I needed help.

Months earlier, I learned virtual assistants were a thing. A friend and fellow journalist mentioned that bringing on a virtual assistant for five hours a week saved time, reduced stress, allowed her to focus on what she really wanted to do (write!), and provided a glimmer of the oh-so-coveted work-life balance.

Her experience inverted my naive assumption that all assistants work full-time. She planted a seed that day; I just needed to burn some legumes before tending to it.

I started by figuring out how a virtual assistant could be useful to me

While I was definitely curious about how a virtual assistant could fit into my life, I still couldn’t imagine trusting a stranger with passwords, invoices, or the myriad documents we contract workers juggle. I also knew my relationship with work wasn’t sustainable. I asked her to tell me more about this whole virtual assistant thing, and it sounded like just what I needed.

My friend put me in touch with someone who works with virtual assistants, who had me assess what you were looking for help with. Within 24 hours, I had personalized emails from three virtual assistants who fit my requested description.

One of them — Sarah — stood out because she studied psychology and appreciated my work in the sober space. On any given day, my inbox is flooded with pitches discussing anything from trauma to addiction recovery to queerness to lube recommendations. It was important for me to hire someone comfortable with my work in mental health and sexual wellness. After a quick virtual call, Sarah became my VA. We just celebrated three years of continuous work together.

Asking for help was hard but necessary

I didn’t expect considering outsourcing tasks to bring up so many confronting emotions. Evaluating the opportunity costs of white-knuckling countless tasks helped me decide what my time and energy are worth. I compared the average rate for a virtual assistant ($26.34 per hour nationally, ranging from $30-$40 in NYC, where I live) to what I charge hourly for my services.

I also listed worst-case scenarios (stolen identity, confidentiality breach, needing to change passwords again). Then I listed best-case scenarios (less stress, more focus, working smarter not harder). This valuable exercise changed my approach to self-employment and outsourcing.

But asking for help is freaking hard — especially in our hyper-individualistic bootstrap American culture. Admitting I needed help made me feel weak. “I should be able to juggle all of this on my own. Real entrepreneurs don’t need help,” I frequently told myself, perhaps another example of how self-destruction still lives in my bones after almost a decade of recovery. Thankfully, humility is a big part of any mental health journey. That same humility permitted me to ask for help outsourcing tasks from an assistant.

When hiring someone, there’s a learning curve for both parties. We all work uniquely, developing idiosyncrasies that only make sense to us. Working together requires piercing that veil, revealing the method to our madness to a complete stranger. And, if we dare, let that stranger give us feedback or provide a new way of doing things we never considered.

There’s also the risk of going through the arduous onboarding process only to discover that you two just aren’t a good fit. Hiring a VA is just like dating: if it doesn’t work out, you break up, recover, and put yourself back out there again, knowing more about yourself and the process. Thankfully, I found the right person on the first try.

Hiring her changed my life — and my business

Sarah started at three hours a week (a standard minimum for VAs) at $32 per hour, then quickly moved up to five hours a week, where we’ve stayed. Her first tasks were helping organize my messy inbox, managing social media DMs, and sending invoices. She also organized my book research and created spreadsheets to track literary agents when I was querying my book.

We have an annual evaluation, during which we each provide feedback to each other, identify what worked and what didn’t, and create plans for the upcoming year. I also give her an annual raise for inflation (and because she’s amazing!).

There’s no way I could have written my book or co-founded my business without Sarah. She perfectly handled the tedious minutiae while I focused on building my career. That focus even allowed me to quit my day job and, perhaps more importantly, perfect my bean recipe.



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