Working a Second Job - Part I

Guidance on Working Two Remote Jobs, or Progressing Your Side Project While 'Working'

Part 1 of ?

Below are several principles that may assist if while working a 'white collar' remote job, you choose to work a second 'white collar' remote job or spend time progressing your income generating side project.

Summary

• Working two jobs can be more difficult than initially expected

• Create blocks of time for focused productivity

• Do not context switch

• Create a specific processes to transition between jobs and close out blocks of time

• Preserve your mental real estate - pin down stray thoughts

• Do not multi-task

Introduction

Below are several principles that may assist if while working a 'white collar' remote job, you choose to work a second 'white collar' remote job or spend time progressing your income generating side project.

This note focuses on working two white collar remote jobs. For now, we will consider a side project the same as a job, however there are important differences (not least increasing financial independence!) that we may expand on at a later time.

We realise that many may already be forced to work multiple jobs, and multiple service / 'blue collar' jobs at that. Unfortunately we have limited experience here and are less able to assist.

These principles are our opinions derived from our experiences and will be, by no means, exhaustive or even guaranteed 'good practice'.

We have not had an original thought in years: many concepts and models of cognition are drawn from, outright plagiarised, or cannibalised from other scholarly and less scholarly works - see below for resources. Rather than (badly) summarising these concepts we have focused on suggestions for specific behaviours and taking action. You are also reading the poorly edited missive of an semi-aquatic dwelling land mammal. 

To begin -

One Plus One is...

One job plus another job will generally equally between 2.3 to 2.7 jobs (in our opinion). Even allowing for the fact that the majority of modern white collar jobs include significant portions of dead time and low value activities, a second job will require increased time, effort and resources on your part to manage and coordinate.

General Principles

To successfully produce while working two jobs, you will need to create blocks of time for creation, avoid context switching and avoid multi-tasking.

Studying, creating content, writing or designing something requires continued persistent efforts. Each day you have a finite amount of concentration and focus, generally 2 - 4 hours, that is best spent in an uninterrupted block progressing your side project or the job that you value.

Context switching and multi-tasking will quickly drain your concentration and focus, leaving you less capable of the complex and creative work that will actually progress your projects.

Au. Note: Create the conditions to allow yourself to focus. Alternatively, if you're struggling with a different set of challenges or disorders it may be wiser to ignore this advice completely.

Context Switching

Context switching is one of the biggest challenges working two jobs and likely a bigger risk to your productivity than multi-tasking.

Part of the reason large blocks of uninterrupted time produces results is that all the context i.e. the psychological / cognitive 'materials' that you need, remain close at hand. You can hold and access them in working memory and see, make, and strengthen connections and patterns. Switching between different contexts, such as between two different jobs in different industries where you do different roles in different structures and networks, drags in a host of cognitive materials that will start to clutter up your mental workbench.

Think of a bucket of molasses. When you start working you dip your hand in and start pawing around. When you begin switching between contexts, you withdraw your hand from the bucket and all 'molasses', the cognitive materials that you have been drawing on takes time to neurologically drain off. Plunging immediately into a different bucket or different activity makes it less likely that you'll have time to clear the residue that sticks around and re-focus to progress complex work, resulting in your efficiency and productivity degrading.

Au. Note: this effect seems particularly pronounced for some.

When working one job remote (perhaps another topic to be expanded upon) you will already be at risk of this with constant switching of personal / professional / meetings / calls / focused work contexts (also referred to a 'role bleed' sometimes).

Working two jobs remotely will further increase this risk.

A number of principles in this note are aimed at reducing switching, and mitigating the side effects of switching wherever possible. Again, if possible structure your day around large blocks of uninterrupted time and see also the sections on Calendar Management and ‘A Husband and a Boyfriend’ (Part III and Part II of this note).

Realistically when working two jobs,  switching between them will be unavoidable. You will therefore need to effectively switch and preserve your limited mental real estate. The following practices may assist.

Preserve Your Mental Real Estate

Create specific rituals to mentally close down blocks of context.

If you don't tell your mind on some level that a period or piece of work is finished for the day, it will treat it as still live, and assign part of your mental real estate to ruminating on it.

A short review of the events of the block of work, a recap, updating of your to-do list with next action items and setting your reminders and bring ups will significantly assist your mind to close down the block and consider it completed for today. Even if you are working on protracted multi-part projects, listing the next action item or the update that you are waiting will help temporarily close the mental ticket.

This practice is crucial for preventing a flurry of later stray thoughts i.e.  'you need to / don't forget to / make sure you' - without an effective process in place your mind will maintain an open loop of thoughts and continually resurface them in it's attempt to help you. By setting reminders and writing down next actions, you pin the thought in place , and over time your mind will learn that it does not need to spend mental real estate constantly reminding you: your processes will do that for you.

(On a side note we additionally recommend this for your meetings and calls - especially if running 'back to back'. Immediately after a meetings take a few minutes to do your notes, identify key action items, set reminders and bring ups block your calendar(s) if required. Not difficult at all, but so rarely done. We will likely expand on how to structure your work days in a later note. For now we recommend not booking calls back to back without time for review and notes (one solution is to cap calls at 25 minutes, 50 minutes allowing 5 / 10 minutes of 'padding')).

This will also have the added benefit of when you return to the block of work the next time (often tired, cold, hungry and disheartened) there is a clear starting point and clear next action for you to take. You will not waste valuable time and focus trying to work out where you were up to and where you need to go next.

When switching jobs, interstitial journaling may also assist you - simply write a short stream of consciousness for several minutes on scrap paper to take thoughts from your head and pin them down. In addition to quieting your mind and helping it feel 'heard' you may find that your mind surfaces 'to-do' items that you had forgotten or overlooked.

Following your review and closure processes, allow time for yourself to transition into a different context. Ideally this is supported by a change of physical state, such as push ups, sit ups / v-ups, or a change in physical surrounds: go for a short 10 - 15 minute walk in nature or green space.

If feasible, have a different working space for your different jobs and projects or invest in some way to differentiate them mentally, such as a different room, chair, background soundtrack or an external location.

With two jobs you will experience more than twice the amount of disruption from stray thoughts, reminders and messages. Remember - "your head is for having ideas, not holding them" - (not our quote). This is especially prevalent at the start as you begin to introduce the closure practices outlined above.

At worst these thoughts can jar you out of the context that you're currently trying to work in and add to the residue that you'll need to later slough off. The more cognitive interruptions you permit, the harder you will find it to productively focus on your creative work.

Any thoughts not related to the task / context at hand should be immediately taken from your head and 'pinned' by being written down (OneNote, Evernote, post it on the night stand). Try to avoid dipping yourself back into the molasses bucket they belong to, instead put them in a temporary holding space, such as a book or pad called 'work notes' or 'when next online' which you then regularly review.

Finally, assist your mind with its natural filing process (sleep / REM sleep) by cultivating good sleeping practices (again, perhaps another topic to be expanded upon, and definitely go and see BowTiedOx)

Your Guide to Optimal Sleep

Multi-Tasking

Avoid. Avoid wherever possible. The research unequivocally does not support it. At best, you're depriving yourself of effective singular focus required to progress your work, at worst you're inviting in context switching (see above)

Multi-tasking will degrade your performance and will not facilitate periods of production. There will be also increased temptation to dispatch small unimportant tasks with great efficiency and alacrity to create a sense of achievement.

Basic time management principles of checking emails / messages / notifications at set intervals can support you here. Some jobs will have expectations regarding response times - please see below for additional strategies to help manage this.

Less applicable for a sales role as your value is partly in your speed of response and maintenance of your network.

A complete refusal to multi-task may be unrealistic for some people and situations. In this case, take great care not to context switch if possible, and limit yourself to dispatching bottlenecks or small surface level tasks.