Automating and Outsourcing

for normal people (or “How this can calm you life down”)

Danny Smith
Feb 20, 2016 · 10 min read

Of all the non-fiction books I’ve read, I can safely say that there have only been two which led me to think:

  1. That’s amazing. I need to do this.
  2. This does’t apply to me and my life. I can’t do this.

Those books are Getting Things Done (GTD) by David Allen and The 4-Hour Workweek (4HWW) by Tim Ferriss.

I read David’s book back in 2004. It was the first book I’d read on process optimisation and, moreover, it was about optimising the process of one’s own life, rather than those of a business. On the surface it’s a slightly dated manual that prescribes an immutable and inflexible method for managing the day-to-day — but reading between the lines, it offers a fascinating insight into how and why people feel overwhelmed, and why certain methods can help address that.

Fortunatley for me I wasn’t particularly busy in 2004, and the world of 90's- leather-bound folios, dyno machines and buff folders described seemed both dated and unnecessary. It did not apply to my life.

I first read Tim’s book in 2007. It promised freedom from the rat-race — a life of luxury far away from cubicles and grey suits. I had similar feelings to those I’d experienced reading GTD: the ideas in this book were a big deal. They could help shape my life in the right way.

Fortunately for me I wasn’t in the rat-race in 2007. The idea that I might make my fortune by productising some knowledge or skill didn’t seem relevant. I was playing guitar and building websites at the time — both charged at an hourly rate. I was selling my time. Tim’s advice didn’t apply to my life.

Of course, my hunch that both these books would be personally important has been proven right over the last few years. The lessons from Tim’s book have helped me eliminate, automate or outsource a lot of the niff-naff, and David’s book has helped me keep on top of what’s left over, and handle the busiest periods of my life without dropping the ball. Both have also affected the way I make decisions about work and career.

The 4-Hour Workweek and Getting Things Done

What can normal people take from these books?

Over the years, I’ve often recommended these books to friends. Except for the self-help/productivity geeks (who’ve already read them), almost everyone has looked at me as though I’m mad and, having read them, thought what I did ten years ago: “That’s great. But it’s not applicable to my life”.

I don’t agree. It is applicable. Though perhaps not all of it.

For me, the most easily accessible concepts are those of Ubiquitous Capture (from GTD) and Eliminate, Automate, Delegate (from 4HWW). I’ll cover the former in another article on GTD, so for the rest of this one I’ll look at some ways we might outsource and automate bits of our lives — and in particular, how I do that.


Automation and Outsourcing (or delegation) are all well and good, so long as the thing is worth doing in the first place. Here’s Tim Ferriss in 4HWW:

Never automate something that can be eliminated, and never delegate something that can be automated or streamlined. Otherwise, you waste someone else’s time instead of your own, which now wastes your hard-earned cash. How’s that for incentive to be effective and efficient?

I’ve eliminated a whole bunch of stuff from my life over the last five years. Much of it was stuff I did because I felt obligated, yet when I stopped — nobody noticed. (At one point I got rid of 90% of my possessions and lived out a bag).

So before you automate or outsource something, consider if it really needs doing at all.

I’m a normal person — what can I outsource?

In The 4HWW, Tim Ferriss discusses outsourcing in great detail. He outsourced everything to a team of Virtual Assistants — from managing his calendar to sending his mum a birthday card. This makes a huge amount of sense to me, but good VAs are both expensive and hard to train and manage. If I’m ever busy enough that handling my calendar is a major source of pain then I’ll hire a VA (or use Clara). For now though, I don’t really need one. Of course, that’s not to say there aren’t boring or painful tasks I can farm out to someone else.

Here are some of the services and products I use to handle the stuff I don’t like doing:

  • I’ve hate food shopping and deciding what to cook, but I love cooking itself. I have a box of amazing healthy food delivered by HelloFresh every week. The fact they come with recipes means I don’t need to think about what to cook — I can just enjoy the act of cooking.
  • Even with these deliveries, I don’t always have the time to cook — and I certainly don’t want to cook twice a day. If I haven’t got any leftovers from yesterday or I’m not at home, I use Deliveroo. For the times when I just want to fuel my body, I keep a stock of Joylent at home and at work. All this reduces the effort required to maintain a balanced and healthy diet.
  • I don’t like cleaning, so I have a cleaner from Handy come and do the house. This isn’t quite perfect, since the quality is variable and I still have to let them into the house.
  • I don’t want the headache of owning a car, so I get about by public transport. For the times when I need a car, I use Uber (for cabs) or ZipCar (for self-drive). Both allow me to book a car and be sat inside it within ten minutes.
  • I don’t like ironing, so I take my shirts and trousers to a dry cleaners near work and have them wash and iron them for me. I’d love to use a service that picks up and delivers, but I’ve yet to find one cheap enough.
  • I don’t like worrying about data backups. Nearly all my “stuff” is digital. I used to back up my laptop to an external hard drive on a weekly basis, but hated doing it. I now keep most of my thoughts in Evernote, all my documents live in Dropbox and my code is on GitHub. If I lost my laptop tomorrow I’d still have access to the stuff I need. Just to be on the safe side, I have my whole hard drive backed up to Backblaze. All this happens automatically.
  • I’m a software engineer, so I have a bunch of websites and apps that I need to maintain. I used to run my own servers but have long-since deployed everything via GtHub, Codeship and Heroku. I let those guys worry about keeping it all working.

None of this stuff is particularly radical and many would’t consider the services and tools above to be “outsourcing” at all.

Whenever I find myself doing something that feels wrong or laborious, I ask myself this:

Am I the right person to be doing this? If I don’t enjoy it or learn something useful from it, then I’m not.

That question is the reason I ended up with the services and tools above. If I’m not the right person for the job, I’ll try to find someone who is.

Of course, in some cases its hard to find the right someone. I hate handling the bills for the shared house I live in — I neither enjoy it nor learn from it. While I could easily outsource the task to a VA, when I balance the cost with the time/energy it’d save it’s not economical. If my life gets busier, and the mental freedom of not thinking about bills outweighs the cost, I’ll get a VA.

As a final note on outsourcing, I’ve used PeoplePerHour to hire designers, developers and marketing people before. This was actually quite difficult for me since I can do all of those things to a decent standard myself — and I enjoy doing them!

What can I automate, then?

As a software engineer who’s also obsessed with process, I’m obviously pretty keen on Automating All the Things™. I spend quite a lot of my time at work looking for ways to remove the human element from processes that don’t need it (I’ve another article in the pipeline about business tooling and process automation).

At a very basic level, here are some personal things I automate:

  • Recurring Payments. It’s obvious to most people, but paying your rent/mortgage and bills automatically is very easy, and takes it off your mind. I live in a shared house and have the other tenants transfer a set amount to an account by standing order. I also pay into it by SO. Our rent and fixed bills go out automatically and the dates are set up to ensure it always works. We still have to pay a few variable bills manually — I haven’t yet found a way to automatically split them.
  • Finances and Banking. The automation of my personal finances is something I’ve always thought could be improved. Standing Orders can only go so far, since they’re very rigid. New banks like Mondo make it possible to hook personal banking into other online services. I’ve yet to receive an invite to their beta programme, but am looking forward to it. Their blog showcases some of the cool stuff that will be possible once developers get access to financial data.
  • Ordering Coffee. I drink a lot of coffee. Instead of buying it when I run low, the guys at Pact send me a new packet every couple of weeks.
  • Onerous Software Tasks. There are a few things I do regularly on my laptop. Where at all possible, I’ll try to automate them with scripts. Here’s an example:
  • Handling Emails. To reduce the amount of email coming into my inbox, I have a number of mail rules set up. LinkedIn and notifications are tagged and archived while Uber receipts and Handy notifications are sent directly to Evernote. I also send Amazon order confirmations direct to Evernote.
My mail rules

Again, none of the stuff above is rocket science. It’s simply designed to remove the more mundane tasks in life and replace them with automation. In a similar vein, I also use IFTTT to automate a few little tasks:

  • Photos I’m tagged in on Facebook are saved to Google Drive.
  • Stories I recommend on Medium are automatically tweeted.
  • GitHub issues assigned to me create a new task in OmniFocus.
  • Instagram photos are cross-posted to Flickr.

Automating a more complex process

None of the automation I’ve discussed so far is particularly complicated, and most of it is designed to remove the smaller pains in life. There are, however, certain processes that need a more complex automation setup.

As part of my work for the RAF Air Cadets, I have to process course applications from students across the country. In the past, students have applied by sending an application form (a Word document) to me via email. I’ve then manually entered their details into a Sharepoint-based system and used that to manage the on-boarding process. the whole setup was inefficient in the extreme, and prone to human error.

The solution: Zapier.

Zapier is a business automation tool that allows non-developers to connect web apps together.

They’ve recently enabled multi-stage zaps and code steps, both of which open up a huge range of possibilities.

In order to handle student applications, I’ve got a multi-stage zap configured as follows:

A candidate completes our online application form on TypeForm. This triggers the Zap:

TypeForm Application

A Trello card is created containing all the applicants details, along with a checklist of next actions:

A message is sent to Slack, containing a link to the trello card…

A task is automatically created in OmniFocus, since I’m unlikely to act on the slack notification immediately…

An OmniFocus task, created by Zapier

Finally, an entry is made in a spreadsheet on Google Docs. While trello is used to handle the application-related actions, it’s this spreadsheet (and it’s built-in filters) that provides the Nominal Roll for Day 1 of the course.

In addition to the steps outlined above, there’s potential to improve this workflow further. I might add the applicant to a MailChimp mailing list, or send a notification email to their line manager (at an email address provided by the applicant). Thanks to trello’s email features, I could even have any responses from line managers appended to their card.

In summary

Tim Ferriss’ belief that we should strive to eliminate, automate or outsource any work we can is a great idea. It frees us up to spend time on the things we love (or with the people we love) — I’ve only been able to write this article because I’m not processing course applications or cleaning my bathroom.

If any of this has got you thinking, or you’ve got some awesome personal automation set up yourself, let me know on twitter or via a response on here.

If you’re interested in seeing how this sort of thinking can help your business, keep an eye out for the article I’ll be publishing soon.

If you enjoyed this article, please recommend it on medium 👍.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store