How To Make Your Productivity System Easy To Run (with Jake Desyllas)

So you’ve followed the advice my previous talk with Jake Desyllas and set up your own basic productivity system. You know that a system like that is not a pedantic badge of honour, but is in fact the best way to add actions to your ideals – to LIVE your values.

You also know the three components of any successful productivity system:

  1. Capture: Get things out of your head
  2. Review: Check everything regularly

Organize: Put things in their right place

You probably are in a happy place – so allow me to flame some dissatisfaction.

At this phase, your system can be quite clumsy. That means more effort. More effort is more fragility – will you be able to keep things going when you a hit a lower motivation cycle?

Continue reading “How To Make Your Productivity System Easy To Run (with Jake Desyllas)”

0043 – Productivity and Goal Setting: First Steps (audio version)

This is an audio recording of the article Go From Zero to a Fully Functional Productivity System, Today (with Jake Desyllas).

In it, you will find encouragement and practical steps towards quickly and easily starting your first productivity/task management and goal management systems.

Books mentioned:

Goals! by Brian Tracy

Eat that Frog! by Brian Tracy

Becoming an Entrepreneur by Jake Desyllas

Job Free by Jake Desyllas

Getting Things Done by David Allen

The Power of Less by Leo Babuta

Go From Zero to a Fully Functional Productivity System, Today (with Jake Desyllas)

Click here for the podcast version

(This is an audio-enriched article. Throughout it you will find short clips from my interview with Jake Desyllas, which this guide is based upon.)

One of the most valuable time I have ever spent were the hours when, in my tiny (and expensive) London single room, waking up at 4AM before work, I started to build my own productivity and goal setting systems – inspired by Brian Tracy’s Goals! and Eat that Frog!.

It’s funny to read back the goals I’ve set only 12 months ago – I clearly couldn’t predict my growing interests in frugality, minimalism and alternative lifestyle (not BDSM, not yet) at the time, which have made most of them feel quite obsolete. My actual day-to-day personal productivity system has changed a lot in a year too, and has had its ups and downs along the road.

What I most couldn’t predict, however, is that the skill that I was building at the time (and still am) would lead to the most creative period of my life to date.

“I was making five, I believe, quality episodes per week plus having a job”


Such as this month.

Everybody has some form of productivity system and some kind of goals.

The most basic one is keeping it all in your head – which does work to some extent, but at great expense. Wouldn’t you love not to have those “sorry, it slipped my mind” conversations? Or thinking back to your last New Year’s resolution in November and realizing you’ve made no progress?

“you can never really be present in the moment”

A more advanced level is the all-too-common combination of memory, post-it notes, reminders, a paper calendar, starred emails etc. – a “system” that paradoxically is even worse at times.

I’ve unloaded my memory, sure, but where did I put that note again? Heck, I wish I had just tried to memorize everything!

So, are you fed up with these little spikes of dissatisfaction and embarrassment? Have you had enough of being just a little afraid of what you may be missing, all the time?

I thought you would be! I even thought you might want to build some time management, personal productivity, goal management and overall self-leadership skills today. I’ve experienced the benefits of having a predictable system that I can trust, and I want to help you have it too – and that’s why I contacted early retiree, author and podcaster Jake Desyllas.

“get on with being creative, and with thinking about the things that truly matter to you”

Learn From the Best

I consider Jake to be one of the most serious and passionate scholars of a conscious life out there. It’s proven by the quality of the content at The Voluntary Life Podcast (which is one of the best resources on the subject out there) and it’s also proven by his resume.

After leaving university, he built and sold a company in about a decade, and at a price that enabled him to retire fast enough to easily be considered an early retiree. Then he launched his podcast (at episode 268 at the time of writing this article), wrote a book about becoming an entrepreneur based on his experiences and then one where he systematized all the ways in which people retire early.

In short, he’s a guy who has a track record of taking productivity seriously, both in theory and in practice.



We’ve talked about entrepreneurship previously, so this time I contacted him to talk about the entry level of productivity and goal setting systems. This article is based on that episode, with quotes and audio clips taken from it.

The Value of Systems


You might be thinking:

Dude, I already have trouble getting anything going, what makes you think setting up this monumental system is really the best first step?


My plate is full enough already, why take all this effort to think about doing this ? instead of actually doing them ?

I’ll talk about how monumental getting started really is in the next chapter, but first let’s look at why Jake has devoted so much time and effort over the years to building, maintaining and upgrading his system.

“this is how I organize my thinking towards my own purpose – it’s THAT important to me”

I was moved while listening to that quote, real-time, during our interview: I’ve struck gold!

Having a system is more than a pedantic exercise in paper-pushing. It might start looking that way – but it takes very little time for the true purpose to be revealed: living a conscious life, organizing one’s mind and thinking into a tool of empowerment, a tool for revealing and then living the highest values that one believes in.

Productivity and goal-setting systems paradoxically clear your mind of the trivial by focusing on it, briefly. 

Only as long as it takes to get stuff out of your head, and then to review it – freeing your mind to think of your deepest passions without having a constant, annoying background voice reminding you not to forget the milk, paying those bills or making that call.

This point often gets lost in all the technicalities of which book to read, software to use, podcast to follow, technique to implement.

It is, however, the true purpose of productivity systems.

And when it comes to actually getting things done (spoiler) the difference is enormous too. When asked, Jake put it as the difference between running a modern business with or without computers.

I agree, except I think it’s an understatement. There were companies that ran, a lot less efficiently, sure, but still ran on a paper system. These systems, however, have been in my life the difference between getting nothing or very little done, to getting a lot done, more than I ever thought possible.

Sustainability is an area of growth for me, for sure (see the gap in podcast release dates), but having tasted the nectar sure gives a massive boost of motivation for working on it.

If you have experienced something similar, I invite you to the comments section. 😉

(I talk about the importance of respecting and embracing cyclicality, the seasons of productivity in episode 35 and it’s also a part of episode 4 on procrastination )

To do: Set a Simple Productivity System Up in a Few Minutes

OK, but really, isn’t it a lot of work setting up a system, requiring boatloads of willpower? I have a friend who’s got a label on every office item…

We’ll get to that obsessive friend in the next section, but first… Nope, it really isn’t that much work if you follow Jake’s advice. Just listen to it.

“get everything out of your head”

So you can set up a low maintenance paper system (a.k.a a notebook) by simply writing a list of what you need to do, checking it every morning, removing the obsolete and adding new things in. It’s as simple as that.

Sure, it’s not as cool Jake’s system pictured above, or the latest-greatest Ultra Productivity Software 2.0, but simplicity may in fact be its core strength.

“all-singing, all-dancing project management system”

The number one characteristic that you are looking for in your system is the ability to trust it. And you do that by having something that you fully understand, that is fully you.

DIY is gold.

Remember when you first attempted to screw something in? Would you have been happier being given a manual screwdriver or a power drill?

(I still wake up in the middle of the night, bathed in cold sweat, haunted by the first time someone put that beast of a machine in my hands.)

Alternatively, you can use something like Google Drive Docs or Evernote if you prefer carrying your phone around rather than a notebook and pencil. Whichever comes more naturally to you is fine, you’ll be able to mix and match them later (I chose Drive first, then added Evernote to my toolbox).

A word of warning though: there are advantages to paper that you wouldn’t think of at first. People are flattered if you pull up a notebook and write down notes as you speak to them. People are less flattered if you pull up your phone, even if they know you aren’t checking Facebook.

The Three Components of Any Successful Productivity System

Jake identifies three steps to get a functional system going. Let’s look at them in turn.

“get it out of your head, review it, organize it”

1. Keep On Getting It Out Of Your Head
My brain on an average day.
My brain when I don’t write things down for a few days.

After the previous section, your mind should be quite clear. You wrote down everything that you need to do right now. But here come I, with unclean intentions, and tell you that you should check out The Voluntary Life Podcast as it will be a great source of inspiration and encouragement in this journey.

Now I messed it up, since that little bit of information is rattling around in your head again! Sure, you can banish it by writing it down next to everything else.

What if, however, you were away from your piece of paper or your digital file when I said it? Say you remember on your way to work that you need to buy milk tomorrow or  you should be booking a dental checkup six months from now – do you want to juggle that around in your head for the next six months? Or even for 8 hours until you get home?

Jake (and I) would advise you not to – and this is why it’s worth having a portable system on you at all times. It can be your phone, it can be a small pad + pen that you “sync” with your larger notebook later. The form is something that’s personal to you. Get something you are already comfortable with.

The real key goal here, however, is getting into the habit of emptying your mind as soon as possible – preferably in a limited number of “containers” (notepads, files etc.) so you can stay on top of it.

“I’m gonna start doing that… some time”

You might notice that things can get messy – “get milk” being mixed up with “goal: world domination by 2020” or with “cool book: job free”.

That’s not ideal, for sure, and you might want to start splitting these into things like:

  • a list of next actions,
  • a calendar for tasks tied to a certain time,
  • a waiting for list for the things you’ve passed on to others and need a reply,
  • longer term projects,
  • someday/maybe lists of about dreams and ideas,
  • a list of goals and a list of references, information you can not act on now but might need in the future.

That, however, is a next level step, and you don’t have to take it now if you don’t feel like doing it.

In the interview I share a story where one of my first bosses nudged me into unknowingly building my own productivity system.

He was the owner of the company and quite a micro-manager, and thus quite busy. As the marketing guy, I was directly under him, and he mostly shaped my task list, but he didn’t have the time to constantly check up on me, so we’d talk for 15-20 minutes every second or third day.

The first time he called me in, I valiantly showed up empty handed in his office, and started listening to his long list of ideas and projects that I would have to bring to fruition. After nodding and saying “sure, I’ll do that” for about 15 minutes, his dissatisfaction piled up and he put an agenda into my hand, telling me to write things down.

I was naturally quite offended, but I quickly recognized his wisdom after I forgot 80% of what he said in a few days and had to, with great resignation, rely on my notes. Our minds are great at recognizing patterns, but aren’t that great at storing little pieces of information accurately.

Anyway, my notes were a mixture of all sorts of actions, projects, goals and references. I dealt with it, at the time, by marking important tasks with star and a deadline.

It wasn’t ideal, sure, but it worked.

And sometimes getting a simple and less efficient habit going is more valuable than getting some grandiose system not going.

So you can find your own approach to marking what is important to you, and then evolving as you go. But before we get there…

2. Review It Regularly

The tranquility of an unburdened mind can quickly turn into horror if you don’t review your system regularly. You’ve set out on this journey to not forget things by storing and recalling them at the right time, not to write things down and then forget them forever.

The syndrome of finding ancient post-it notes and scraps of paper with great tasks and ideas forgotten along the way is overcome by

a.) having a centralized system, which you’ve already done, and

b.) building the habit of regular review.

A very natural way of doing this is slotting it into your morning routine for day-to-day stuff (or building a new one, you’ve got your first habit already!), and a weekly or monthly check-up for projects, ideas, and other longer term goals.

(Here’s an episode and a free book if you are new to the world of, or needs some pointers around habit-building.)

I’ve personally had the habit of

  • devoting the last day of the month reviewing this month’s goals and setting the next one’s (based on core needs)
  • adding target deadlines
  • printing it out on an A4 and looking at it every morning as part of my routine and
  • reviewing smaller tasks and goals written during the day the next day before I start my work.

A combination of these four practices alone did wonders for my productivity without taking that much time.

3. Organize It

In our interview, Jake stressed the fact that you must build a system that you can trust. A system that gets the information out of your head, and then back into it, at the right time. If you are putting all this effort into it, but you are still missing things, what’s the point, correct?

Since we didn’t go into detail on this point during the interview, what follows is my interpretation of what Jake meant by “organize”.

Many tasks will be covered by your review, but if in some cases it can be either overkill or not enough.

For instance, while looking at your life goal every day can be argued for (I recommend it) but what if you have a doctor’s appointment in 2 weeks? There’s absolutely no point in checking that 14 times. Or what if you’ve got three appointments today, one in the morning, one in the afternoon and one in the evening? Seeing it first thing in the morning is good for planning your day, but you still have to keep a reminder ticking in your head, which defeats the point of having the system.

Calendars and reminders are old news for people in sales, doctors, lawyers or really most client-facing office jobs – or anywhere where they have dreaded meetings. They use it because they have to, but it’s also a great tool for people with a less loaded schedule. I myself only got into the habit of fully using them recently, and wish I did earlier.

You can use the time-tested, paper based system here but this is where digital really shines. Most calendar systems (iCalendar, Google Calendar etc.) have a built-in reminder and syncing system that you can really only recreate on paper if you have a secretary or if you check your agenda constantly. The choice is yours.

This is one example of organizing your system, but on a more fundamental level the idea is

  • splitting information into different categories (as in the previous example),
  • finding the right type container for the job,
  • finding the way of keeping the whole system in sync

And this gets us to…

Evolving Your System

GTD, a potential direction of growth
GTD, a potential direction of growth

How much and in what way you make your system better will depend very much on your needs and personality.

“make it more efficient”

The greatest gain is going from no system to having a system. After that, every improvement faces diminishing returns: great gains early on, cool tweaks later on.

Some people have ran large companies for decades with simple, paper-based systems and see no reason to change. Others will take pleasure in making something as smooth and well-oiled as possible, going from convenience and saving time to works of art (remember that diagram at the top of this article?).

Some approaches, such as David Allen’s Getting Things Done (GTD) work better from some people, while others, such as the Power of Less are preferred by people with different needs.

“overworked information workers”

Growth is a beautiful thing, and I take pleasure looking at the various strategies people choose. The only risk here is being overwhelmed by a leap that’s too great compared to our existing systems. I experienced this with GTD, which I’m very happy to have read, but wish to have read later.

I’ve seen it happen with others too – there’s so much the book asks for that it easily goes into “I’ll do it someday” territory.

(I’ve tried to make the transition a little smoother by smuggling some ideas from it into this article)

Shield yourself by seeing advanced techniques for what they are – an optional improvement for the right people, at the right time. Embrace them if you wish, when it makes sense – there is no “right” way.

“steal some ideas from David Allen”

Bonus: A Dash of Goal Management

I think that all areas of personal development are interconnected, and it’s at least natural, if not necessary to learn and grow in many parallel fields roughly at the same time – hence the wide range of subjects tackled in Valiant Growth.

This is especially true of time and goal management – a beautiful marriage of how and why. So I would’ve been remiss if I didn’t include this question in our discussion.

We all have goals, dreams and plans. But like everything else, bringing consciousness to the field through having a system is the real game changer. Here are some actionable first steps:

Separate Your Areas of Responsibility


Mindmaps can be a powerful tool for defining areas of responsibility
Mindmaps can be a powerful tool for defining areas of responsibility

“I’m talking about all aspects”

In the E-Myth Revisited, Michael Gerber advises small business owners to draw up an organization chart of the company with all the key roles (CEO, Director of Operations, Director of Sales, Director of Finances), and fill in their own names in each box if necessary.

This is to ensure that no key responsibilities are overlooked, that diverse goals can be set up and that when there’s time to outsource, the role and responsibilities will already be defined.

In a very similar way, we are in charge of our own life, a one man company with a singular focus of fulfilling our own needs (which also involve others).

And it’s too easy to miss areas – almost all crisis moments in life arise when a neglected aspect comes to the forefront (physical fitness, finances, family, mental health), and can be ignored no more.

That is why a great way of looking at goals is to start by splitting up areas of responsibility and setting goals within each separate field. Where do I want my income to be in one year? Where do I want to take my relationships? How fit and healthy do I want to be? etc.

( Anarcho-yakitalist Nick Hazelton has made an episode teaching you to mindmap using the exact example of areas of responsibility.

I outline a slightly different, complementary approach of starting from core needs in episode 6 of Valiant Growth, Developing Purpose and Goals)

Three Core Goals – Breakthrough vs. Maintenance

“the most significant ones”

More is not always better, and that’s true with goals as well. The previous exercise can easily lead to a list of 15+ goals, if you were comprehensive – and yet Jake talks of focusing on three core goals, three big wins. That makes a lot sense, given that the human mind is not particularly capable at splitting focus and attention in too many directions. So how do we square this circle?

An idea that I find useful is separating goals into breakthrough and maintenance goals. When habits are formed, it’s not too difficult to do many dissimilar things in a sequence, as long as they are familiar to the point of not requiring a lot of willpower or attention. Think brushing your teeth, taking the dog out to a walk, washing the dishes etc.

It’s not too difficult to pile on simple goals, where you’re doing things you’ve already figured out in the past. I call these maintenance goals – they only require habituation and the maintenance of your routines.

For example, I’m not too worried of tacking the goal of having a lean food budget on to my other goals. It’s a way of thinking that I’ve put effort into previously, and that doesn’t require a lot willpower to maintain, as long as I don’t want to make further strides and improvements.

(In fact, I have a hard time not immediately calculating calories/GBP in a store!)

I’m comfortable having numerous maintenance goals, and thus making sure that no area of responsibility is neglected. I may wish to upgrade my systems at some point, but right now I’m happy to maintain what I already have.

“the most epic way”

On the other hand, managing my own time and exercising self-leadership in my life is a breakthrough goal that I have. I find it very challenging to stay productive, shape my own goals and be a friend and a mentor to myself on a level of consistency that satisfies me – and to also be acceptive of the cycles of life.

This is an area that’s very important to me, where I want to up my game. I’m not comfortable having too many breakthrough goals at the same time, because that very rarely works.

For an entrepreneur with decades of experience, on the other hand, self-leadership and consistency might be a walk-in-the-park maintenance goal.

“permission to go for it”

Milestones vs. Feeding Your Unconscious

A common step, advised in many books is to then take these big goals and break them down into more frequent milestones, objective achieved/not achieved questions that you can check yourself against. I found that to be a very helpful and actionable methodology in my own life.

An interesting complementary (maybe even alternative?) approach came up during our conversation with Jake. Being clear on your goals is feeding your unconscious, and you automagically will get new angles/ ideas/ subgoals during the month (mainly in the shower).

You can then update your milestones, and/or you can simply let these new ideas flow organically into the smaller daily tasks that you set for yourself anyways.

Introducing a habit of checking your monthly goals regularly (say daily) and your larger goals/vision (say weekly, even daily) into your morning routine can go a long way in harnessing the full power of your mind (you might lose witty FB status updates).

So Just Do It!

Some fruits are low hanging. But then there are fruits that are so low they might as well be underground.

It's... peanuts! Got lucky with this one.
One example being… peanuts! Now that’s peanuts! What a great coincidence.

That is what I got from this interview: getting started with productivity is not as complicated as many people think, and it is extremely rewarding.

All you need is a pen and a paper and some alone time. In fact, you can build an entry-level system by simply following the steps outlined in this article.

So maybe turn off your Wifi and start right now!

Help and Inspiration

You may, however, want a more detailed guide. In that case, check out the previously mentioned Goals! + Eat That Frog! combo – that was actually my first step, and you can’t really go wrong with it.

If you’re confident that you can pull through a larger project, and want something more systematic, you can also start with GTD. Be aware, however, that starting there is risky – you wouldn’t be the first person to be overwhelmed by it.

If you would like support and coaching in this process, send me an e-mail.

And when it comes to evolving your system, The Voluntary Life podcast is the best resource that I know of out there.

Good luck! And bring this challenge to your friends as well!

This post contains Amazon affiliate links.

0042 – Live Your Values by Building Your Own Productivity System Today – with Jake Desyllas of The Voluntary Life Podcast

Starting and maintaining a productivity system is one of the most fulfilling and rewarding investments you can ever make. It can, however seem like a very daunting task.

Jake Desyllas strips the complexity away and teaches you how to start a basic but powerful productivity system that you can build upon and evolve. Perhaps more importantly, we talk of the incredible power that this will give you to live your values and to lead a conscious live, encouraging you to get started today.

Jake Desyllas' Project Management Flowchart
Jake Desyllas’ Project Management Flowchart

Books mentioned:

Getting Things Done by David Allen and The Power of Less by Leo Babauta as a balance to it.


Jake Desyllas on Valiant Growth:

0034 – How Do You ACTUALLY Become an Entrepreneur? And Is It Worth Pursuing for Personal Development? – Interview with Jake Desyllas of The Voluntary Life Podcast

0011 – Book Review: Job Free: Four Ways to Quit the Rat Race by Jake Desyllas

Check out The Voluntary Life Podcast for a lot more great productivity content!

This post contains Amazon affiliate links.

028 – Earn Self Esteem, Build Amazing Relationships and Achieve Freedom through Radical Personal Development

Join the discussion! | iTunes | Android | YouTube

In what can be considered a second introductory to the podcast, I discuss the new motto, and the three levels of personal development.