Should anyone ask, hiring a virtual assistant.

A few weeks ago I was hitting the admin wall: many small tasks that needed doing. Many small tasks that were turning into mountains. Many small tasks that were taking up space in my brain.

I admitted to myself:

  • I’m not good at this. 
  • I don’t need to be good at this. 
  • I don’t aspire to be good at this.
  • This has to be done.
  • I can hire someone to help me who will be excellent at this!

To solve this problem I started looking for a virtual assistant on Upwork.


I needed someone that could also help me while working both in English and in German. I received 5 applications from as far afield as Vancouver and Australia. One Applicant was Elisabeth. From Berlin too!


I dislike personnel administration: time zone differences from working with far off places would mean I’d be also sacrificing my nights to the beast. Vancouver and Australia were out and I hired Elisabeth. Having someone in Berlin with the option to potentially meetup seemed like a good option. I went ahead and arranged an initial Google Hangout call with Elisabeth. 

While I was waiting for the hangout call, I setup a Trello board and started dumping all my admin tasks onto a to-do list. And basked in the warm GTD feeling of getting things out of my head and onto a list.

This week started with my first session with Elisabeth. 9am and a strong coffee and knowing that I had support were powerful motivators for getting into the office! We powered through the tasks together: she doing some of them, me the rest: it was so much easier working this way. Yes, it took two hours, but that was a lot of build-up. I expect the next session to be about 30 minutes.

Without thinking too much about where this fear/hate/loathing of admin tasks comes from, I feel much better for knowing that a bunch of them are done. 

Perhaps not perfectly. But done!

Steps to slaying your own personal admin monster

Wanna do the same? Here’s the “I hate admin” summary plan if you want to setup a system like mine:

  • Create a task: Sign up to Upwork, create a task and estimate about how much time you will need from your assistant. On Upwork you can elect to pay hourly or by task. It seems only fair that for such a variable task to use hourly.
  • Find an applicant: Post your task and wait. I waited about 24 hours to get some applications. I also chatted with the applicants to find a good fit.
  • Hire your applicant: Simply hit the Hire button. This will let the other applicants know that, as nice as they are, you don’t need their services.
  • Setup an initial call: I wanted to get to know Elisabeth before working with her. Before setting up recurring events see if you can work well during one session.
  • Create a Trello Board: You could also use a shared email inbox. You could use an issue track. But both of you need to be able to action tasks: Trello works well for this.
  • Out of the brain-onto Trello: Create a Trello mail-in-email address so that you can forward tasks/bills/scary-emails from your inbox directly to the Trello board (and forget about them until the call).
  • Add the address to your contacts. I have a new contact called “Orga”. New tasks are emailed to Orga and land on my Trello board. 
  • The initial call: During the initial call talk about what you want to achieve.
  • Invite your applicant to the Trello board. We looked through the tasks and started nailing them.
  • Setup a recurring calendar event:  I waited until after the first session to decide on whether the new assistant was someone I felt comfortable committing to. Elisabeth was great and so we setup a call for every two weeks and dropped a reminder into the calendar.
  • Rinse-repeat: Keep dropping tasks onto Trello. Keep forgetting about Admin tasks until once a fortnight when you get a reminder for a call.

Do great things without admin hanging over you!

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