Building a Structure to Prevent Overwork (II/III)

I’m happiest and work best when I do short hours of intense work, yet often I find it difficult to resist the urge to work more than this ideal amount, i.e. to overwork.

Overwork is something I’ve struggled with, to varying degrees of success, in study, jobs and running my own business.

To impose structure and discipline on my efforts to avoid overwork, i.e. to help me actually do what I know is best for me, I’ve set out to consolidate and publicly publish I’ve learned.

In this article, I share my work/life calendar, my number one defense against overwork. I share the structure of my current weekly calendar (how I work today), as well as the structure of my future weekly calendar (how I will work in the future, and what I am working for).

In order to learn how to design your own calendar, let’s quickly look at its 3 building blocks: thinking, doing and relaxing.

Technique 1: Balance thinking vs. doing vs. relaxing

One of the most important techniques I’ve learned to avoid overwork and its associated stress is to get the balance right between thinking, doing and relaxing.

This means:

  • Thinking: taking the time to plan exactly what high value activities I need to work on and when I’m going to work on them. A key component to avoid overwork is to work effectively, and this prioritisation and planning is a requirement of effective work
  • Doing: actually sticking to the pre-defined plan and getting that work done. Most often this means not doing things that were not in the plan: if the work was a priority, I would have planned to do it
  • Relaxing: a predefined time to neither do nor plan work

It is worth noting that all these elements depend on the other, hence the need for balance:

  • I can only relax when I know I’ve thought about and will get all my important work done
  • I can only think clearly when I’ve had the time to relax and refresh and have the confidence that I will actually implement the plan I’m crafting
  • I can only put my head down and focus on getting work done when I know that there is nothing more important that I could be doing, and that I will be rewarded with relaxation time to recharge after my intense effort

It took me a long time to realise that relaxation needed to be explicitly added in order to balance the thinking vs. doing equation.

Without specifically setting times to relax (i.e. to neither do nor plan work), I struggled to ever give myself permission to relax at all (aka perpetual overwork).

Technique 2: Design a Work/Life Calendar

One of the results of the thinking phase is a weekly plan i.e. when I will stop and think, when I will do specific types of work, and when I will relax. Personally, I prefer if this plan is:

  1. A regular routine, so that each week has roughly the same shape to it and doesn’t require re-thinking each week
  2. Not overly optimised, but just has some loose structure to it. I especially aim to keep non-work slots interchangeable and open to spontaneity – in fact, having a structure in place actually helps me to be more spontaneous

My weekly plan depends on the type of work activities I need to do and the level of energy required for these different types of activities. As such it is constantly in flux as the months go by and work requirements change.

One of the biggest benefits of setting this plan is that it allows me to catch myself when I begin to overwork.

A primary goal of this plan is to prevent overwork. I know that in order to do my best work, I cannot afford to overwork: I am not prepared to overwork.

Do I deviate from this plan? All the time.

  • Sometimes when I have to – there are fires to fight
  • Sometimes when I want to – I am building my own business
  • But never when I simply feel like I have to – that’s overwork

To identify and differentiate between times when I actually have or want to work, versus when I just feel that I do, that’s why I created this calendar in the first place.

  • To clarify my expectations to myself: knowing when I plan to work means that I know when I am breaking this plan. I can then stop and ask myself “Why am I working outside my planned time? Do I have to work now? No. Do I want to work now? No. Then stop – I am overworking”.
  • To clarify my expectations to others: I share this calendar with my team. I give them the opportunity to discuss this calendar with me, if asked I explain my reasoning, and, if anyone is unhappy with any part of it, we then have an upfront debate around the underlying principles. This way, I don’t have to worry about what people think if I leave work “early” on a given day.

So this calendar helps me avoid overwork in 3 ways. It enables me to:

  1. Catch myself overworking (working outside calendar)
  2. Trust myself to stop working (I trust that the calendar is correct) and
  3. Not worry about what others might think (it’s there for them in black and white).

Knowledge work is notoriously undefined, both in terms of input and output. However, by no means does this mean that the time you spend working need be undefined too – indeed there is no excuse for not structuring your time.

In many ways the work I’m doing lends itself to setting a structure (no boss; no demanding clients; little travel; no constantly varying schedule), but in other ways it is less than ideal (ultimate responsibility for performance; an ever changing mix of managing team members, doing client calls, ongoing admin, payments and IC work). What I’m getting at is that no work environment is perfect. No matter what your setting, I am sure that you can still build an underlying structure to your time that can help you avoid overwork.

Current weekly plan

Here’s my current “ideal week” plan:

Yellow: exercise (7x per week)

  • I aim to exercise once per day
  • Monday, Wednesday, Friday and Saturday morning are fixed “requirements” (e.g. gym, classes)
  • Tuesday, Thursday and Sunday are flexible “bonuses” (e.g. jog, PT)

Green: work (~40 hours per week)

This is set up to balance the demands of my current role, which requires both management and individual contribution (IC)

  • Light (green) work: management work: admin, meetings and calls. I also try to keep a list of quick IC tasks that I can do during this time. I typically work from the office for this type of work. I see this work as a “requirement” to give me the opportunity to work on the more satisfying deep work
  • Deep (green) work: IC work: uninterrupted time to think and work deeply. Tuesday and Thursday morning I keep totally clear for this and aim to work from home alone

Blue & purple: personal

  • (Purple) personal time: this is time I use to make sure that I am meeting all my personal expression needs, be it writing, reading or just quality time for myself. Typically it is in large enough blocks to go “deep”. On Tuesday and Thursday afternoons, I purposefully allow “work” that I am curious about to spill into personal time if I’m working on something interesting
  • (Blue) Chill – alone: this is time I use to do whatever I feel like to relax and unwind. Although enjoyable, I see this time as a requirement
  • (Blue) Chill – friends: again, although enjoyable, I see this time as a requirement
  • Personal – admin: dealing with chores, messages etc.

Empty: to smell the roses and switch gears

Some points worth noting on my weekly plan:

My context: this current plan is of course a function of my current duties and responsibilities, in my case as a co-founder of a VC funded startup. If my role was different, my plan would be too.

My priority: my current priority is to successfully build my business and my week is designed solely to help me to do this as best as possible.

In order to do so, my week is essentially set up to enable me to keep Monday afternoon and Tuesday and Thursday morning slots free for deep work.

  • Even aiming to keep Tuesday and Thursday afternoons free is designed to facilitate this (it’s hard to focus on deep work if you have a pile of unrelated work waiting for you later in the day)
  • I normally prefer deep work in the mornings, but I’m at my freshest on Monday and always motivated to start the week well, so the afternoon works (and allows planning time in the morning)
  • Management tasks like admin work, meetings and calls are essential tasks and equally as important to building my business as deep work. However, they don’t need to be scheduled as carefully as deep work time, and scheduling them is structured in a way that best facilitates and ensures adequate deep work time

This results in me effectively having 3 days of uninterrupted deep work per week!

I work about 40 hours per week: While I consider this as being careful and deliberate with my time and energy, some people might consider this to be not doing a whole lot of work.

I imagine the vast majority of those people are so careless with their time and indolent in their planning that:

  1. They have opted for the mental laziness of overwork ahead of the disciplined exertion of identifying their optimal work patterns (I know from experience that doing more work than this on a regular basis is counter-productive for me), planning their routine accordingly and sticking to that routine
  2. They get far less than 3 days of intense, fully focused deep work per week as a result of this lack of planning and discipline
  3. They need to work more hours as a result of this lack of focused work
  4. The hours they do work are often full of distraction and low quality work, constantly and reactively shifting between various types of work with no clear sense of direction

The above are clear symptoms of overwork and, yes, having worked jobs where overwork was the norm (leaving at 6pm would earn you your colleagues’ condescending wishes to enjoy your half day), I have a large amount of disdain towards those who not only ignorantly overwork, but through their words and behaviours try to inflict overwork on others.

I work best when I have a balanced life: This doesn’t mean that a balanced life is my priority rather than to build my business. They are not and indeed cannot be mutually exclusive. I need to have a balanced life so that I can focus on and bring my best to achieving my goal of building my business.

I am prepared to make some sacrifices for work: this plan reflects my ideal routine given the activities that I need to do to build my business. I have chosen to make this work and my growth in this area my current priority, therefore I have chosen to make sacrifices in some other areas of my life to achieve it. This means that, although maintaining a balanced life in order to be able to work well, this plan is more weighted towards work and facilitating work than it would be if I my priority was my longer term priority of broader personal growth and development (in whatever form that may take – retaining this optionality on the form of future growth requires that my work today earns me time (or money) to pursue this potentially non-work related growth in the future).

It is important to me to regularly check that my current work is still bringing me towards that goal, by comparing my current activities and routines to my ideal ones, and confirming the trajectory / development is on track.

Personal deep work: just as I always need to have a defined goal to work on for work deep time, I need the same for personal deep time, from planning my weekly tasks to defining what a “finished” product looks like. This time is meant to be relaxing and recharging, but that doesn’t mean that it is left unscheduled: I set specific times for new habits or deliberate relaxation e.g. writing to relax

Bonus: using your calendar for motivation

My current plan reflects my current life situation and needs.

If I had no constraints (financial, commitments etc.), I’d choose a different weekly plan, with less time spent working.

Moving to this “ideal” plan is a long term goal of mine, and comparing my current plan to my ideal one both motivates me (as something to look forward to and work towards) and keeps me on track (is this work I’m doing getting me closer to my ideal plan?).

Given my current context (as a co-founder trying to build a startup), I recognise that there is likely an interim step between my current and ideal plans – my interim plan. This is the plan I’m currently working towards.

I haven’t given these future plans as much thought as my current plan, as they are not actionable and cannot be iterated upon, whereas my current plan was designed, tested and refined to reflect the actual reality of my situation.

Ideal weekly plan (in ~2-3 years)

If I had no constraints (financial, commitments etc.), I’d choose a different weekly plan, with less time spent working.

Here is my ideal week plan:

Work: ~20 hours per week

Some mornings, I will do personal deep work instead of work admin/ deep work

The main difference is less time spent on work and more time instead working on more personally meaningful activities such as mastery of physical activities (exercise) or exploring new areas of knowledge, the world etc. (adventure).

A note on working “only” 20 hours per week:

The fact that having a goal to work a minimal amount of hours is seen as something unusual or that needs to be explained is an aspect of modern life that I find entirely baffling. I discuss this obsession with work in more detail here.

Getting from today to my ideal plan:

In order to get from my current plan to my ideal plan I need to:

  • Spend less time doing work calls
  • Spend less time doing work admin (especially dealing with clients) (so can bring Wed meetings into morning)
  • Make 1200 a hard stop, start work an hour earlier (no need for luxury in morning)
  • I enjoy both management and IC work, and this balance feels about right to me

Interim weekly plan (from ~0.5-1 year until ~2-3 years’ time)

Here is what I expect my interim plan to look like

  • Probably an interim stage where most afternoons are full of meetings
  • Do more management first, to create a structure that requires less time to manage
  • Building a team, so less need for IC, more management
  • This changes the week’s energy flow: afternoons of meetings uses a totally different type of energy to admin and deep work
  • Although more hours are work, it is less energy draining work (i.e. less demanding), but also less stimulating / attractive in the long term

Next: Beyond Work (III/III): a call to define your own ambition outside of society’s work-centered ideals

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