SSS #240: VA_v2



Extremely grateful to receive this compliment from someone I look up to in the #REtwit community.


Livin' La Vida Luna y Luca


WFH life.


Things have been slipping through the cracks in the Shakhawala home.

  • We've been struggling to get the kids to school / bed on time
  • I've missed or almost missed a few appointments
  • We're often getting things done at the last possible moment*

*i.e. Going grocery shopping when there's literally no food in the house or buying presents for a friend's birthday party on our way to the party.

Although it makes for an excellent blanket excuse, I refuse to identify as someone who is "busy".

Meanwhile, I just went under contract on (another) new construction project and Dia is hitting her stride in month 6 of her new job.

Something had to change so I decided to run a 90-day experiment.

Insert: New Virtual Assistant

I contacted my friends at Somewhere (FKA Support Shepherd) and told them I needed a part-time virtual assistant to help me with personal and business tasks.

There wasn't a defined role or job description. I simply aired my grievances during the intake process and Somewhere created the job description for me.

About a dozen people applied for the role. I interviewed 2 based on their resumes and hired someone in Peru.

The person I hired had two things no other candidate had:

  • A phone that could make calls in the US
  • A VPN that allowed her to log into US-based websites

Week 1 ✅

Our assistant started on Wednesday, May 15 and so far it's been great.

We use Monday to track her tasks and Google Sheets to track our preferences. We also use Lastpass to share sensitive information with her (credit cards, passwords, etc.)

Here's a list of a few things she got done this week with very little input from us.


I'll be the first to admit this list looks pretty elementary.

I don't think any of these tasks would take me (or Dia) more than 10 minutes to complete.

But here's where that line of thinking (previously) got us in trouble.

All of these tasks take us away from the highest and best use of our time and when you include the time it takes to get back into a "groove" the opportunity cost is too high.


This is my second go around with a Virtual Assistant. The last one ghosted me after a few months. I think she was overworked and didn't have the heart to tell me.

I'm hoping (for obvious reasons) this time is different. But for that to happen, I'll have to be different.

This will be a good challenge for me as someone who thrives while working in solitude.

I'll report back in ~90 days. That's when I anticipate her transitioning from part-time to full-time if things go well.

In the meantime, if you manage people (specifically remote employees), I would love some advice on optimizing for retention.