Automating your life: 101

I love the idea of simplifying my day to day life through automation. How do I outsource or eliminate any tasks that don’t bring me joy so that I’m only left with things that I love doing? This is something I love thinking about.

The idea of being able to spontaneously take month long trips adventuring around the world only to return to find that everything is running better than I left it, excites me endlessly. For me, it adds a new dimension to the world “Freedom”.

I think when most people think about freedom the first thing that comes to mind is money. A subset of people understand that beyond a certain amount, money actually has very little to do with freedom; the more important metric is time. Being able to spend time with the people you care about, doing what you want to be doing is actually the dream.

Yet on a practical level you can have all the money and time and yet not be free. A practical example is waking up in the morning having an empty calendar but having a feeling in the back of your mind that you need to do something. In my experience that feeling does not go away on its own.

There’s actually a third element to freedom and in my opinion it is the most important. It’s directly correlated to the state of your nervous system. I like to call it “Ease”.

Let me explain — You know that feeling that some people might be lucky to have a few times a year, likely when they are on vacation? That feeling that you have nowhere to be, nothing to do, that anything is possible.

That’s what I’m after. It’s such a thrilling feeling. That to me is the definition of freedom. This is something I’ve actively been working on for over a year now. Part of it is leveraging virtual assistants to outsource any tasks that don’t bring me joy. The other part of it is doing regular life audits and restructuring my habits in a way that I can break down complex tasks into automatable chunks. This allows me to build systems around tasks and the beauty of systems is that you can build on top of them.

Using VA’s is such a great way to off load your responsibilities, systemize them and hand them over to someone else. I think everyone who is looking to up level their productively and decrease cognitive workload can benefit from having a VA.

From my experience there are 3 reasons why people struggle with VA’s

  1. Assigning the wrong type of tasks — I find that most people do not know how to work with VA’s. People often think of VA’s helping with tasks like booking flight tickets, or researching things to do in a city. Both of those have high elements of personal preference and are non ideal tasks for VA’s. As a general rule if you cannot break the tasks down into a repeatable playbook, they are the wrong tasks. Flight tickets are so personal and depend on so many factors. How are your finances? Is this the right time to fly business? What about layovers? Could be fun to stop on the way to visit a friend. How you build a playbook for this? You Can’t! What to do in a new city? No one else knows what you are interested apart from you. Maybe do your own research, come up with a few things you are interested in and then ask the VA to gather more details, get reservations etc.
  2. Not having the patience to get through the onboarding process — It takes time to develop the right rappo with your VA. Initially it’s likely going to be slower than doing things by yourself. You’re taking tasks you do subconsciously and are now breaking them into smaller parts and handing them over to someone else. There is going to be noise and confusion. That’s normal. The reason you’re willing to make this investment is in the medium term the benefits of automation far exceed the initial work you need to put in.
  3. Trying to hand off everything in 1 go — If you don’t have clear expectations of what you expect you are setting yourself both of you up for failure.When working with anyone new I like the idea of working Phases. This allows you make incremental changes heading in the right direction instead of trying to implement everything all at once. More so by breaking it down the next phase gets properly defined while the final goal can still be vague. I love the idea of 1% improvements over a long period of time.

For example here was my process of training a private chef to cook lunch for me during the weekdays.

Phase 1 — Giving them certain guidelines (No carbs, no oils, list of meats, vegetables etc) and having them come up with a menu.

Phase 2 — Feedback from phase 1. Pre planning the menu at the beginning of the week, optimizing buying of supplies & sending recites directly with my accountant.

Phase 3 — Starting to source high quality organic and grass-fed ingredients, being able to send them recipes from online.

Phase 4 — Lunch parties with multiple guests, working with my calendar. Trust & understanding.

There is one last piece to the puzzle and that is around regular life audits. Unfortunately is no playbook for this piece. Over here intuition and self awareness are your guides. Setting out some time once a quarter and being honest with yourself and where you want to go next is a good starting point.

Some questions which you might want to think through over here:

  1. How are things going with the VA? Is this the right person? Are we on the right track or we need to course correct?
  2. What are my goals for next quarter? It’s okay if you these are all moving targets, whats more important is you know which direction you are heading in.
  3. What do I need to restructure in my life to take things to the next level? How much work will that take? Am I ready to make that commitment?

I’ve been helping a few of my friends implement systems like this in their own life and It gives me a lot of pleasure to see them thrive.

We have now hired over 10 VA’s in the Philippines for my company and for friends and are now quite experienced in finding the right talent and helping people get started. We can also guide you on how to structure your time and your engagement with your VA.

Reach out to me at if you vibe with having more freedom in your life and let’s see what we can do for you. 🙏



Passionate about digitalizing tech enabled companies. Founder @5x Previously @WeWork @Salesforce

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Tarush Aggarwal

Passionate about digitalizing tech enabled companies. Founder @5x Previously @WeWork @Salesforce