Working a Second Job - Part IV
Guidance on Working Two Remote Jobs, or Progressing Your Side Project While 'Working'
Part 4 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
Recap
Planning and Prioritisation
Two Jobs
Progressing Your Side Project (Recommended)
A Side Note on Sleep and Workouts
Calendar Management
Block It In
Timezones
Your Personal Life
Introduction
This note is a continuation of an earlier note. 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 elsewhere for resources. Rather than (poorly) summarising these concepts we have focused on suggestions for specific behaviours and taking action. You are also reading the badly edited missive of an semi-aquatic dwelling land mammal.
If you have not read the earlier parts of this note we would recommend that you do so before continuing.
For brief revision, Part I Provided a high level overview of how to work two jobs (or a job and a side project). Part II then focused on factors that you should assess and consider before deciding to work two jobs and Part III discussed factors that you should consider when selecting a second job.
Throughout these notes we considered a second job somewhat interchangeable with a side project, however our recommendation is that where possible and feasible, you should consider starting a your own business rather than finding a second job (the short term significant boost in USTT flow should not be overlooked however).
Part IV and Part V (unreleased as of time of writing) of this note will now discuss specific, concrete strategies to work two jobs.
Planning and Prioritisation
Broadly we would recommend some form of regular planning and prioritisation practice in your life. We will discuss our own recommendations in more detail in a later note.
Two Jobs
For now; if you are working two (or more) jobs for the increased USTT flow then planning your week is *fairly* straightforward
Working backwards from your biggest constraints, your prioritisation should broadly be
Sleep
Workouts
Husband job busy / focus / visible hours
Boyfriend job busy / focus / visible hours
Husband job admin / surface tasks
Boyfriend job admin / surface tasks
Neglected personal life, spouse, partner, children, girlfriend, boyfriend, family etc.
Busy / visible hours refers to the hours that you've already assessed in Part II - when are the periods of time that will be most effective for you to be visible and responsive (never mind how productive you really are at the Husband job).
Remember that you are not aiming to be an exceptional employee, and in most cases you should be aiming at level just above average to keep both your jobs. You will miss things, projects and deadlines will slide.
Overall, we also recommend keeping some "empty" or reserve time (slack) in the system where you may have to stabilise key pieces of work or relationships (hopefully not personal relationships) due to unforeseen circumstances. The focus here is about maintaining a sustainable pace to keep the Husband job and to acceptably manage the Boyfriend job
Progressing Your Side Project (Recommended)
If you are here because you are wishing to progress your own side project while working a Husband job then the focus for planning your week will be slightly different. Again, suggested below
Sleep*
Workouts*
Side project - a block of uninterrupted time
Husband job busy / focus / visible hours
Side project prep and planning
Neglected personal life, spouse, partner, children, girlfriend, boyfriend, family etc.
Husband job admin / surface tasks
Again, begin planning your days and the week around your constraints or the large "must do" pieces. Sleep should be your first piece to plan and block in, followed by your workouts. See the side notes / caveats below on both however. Following this, block in your side project, recalling from Part I of this note you will need to create large blocks of uninterrupted time to facilitate the focused, continued persistent efforts needed to actually progress.
A Side Note on Sleep and Workouts
We will likely return and expand on this in a later note (and note that BowTied Ox has also already covered sleep in the past)
Our current recommendation at this time is to try and keep sleep largely in place (as best you can). A somewhat innocuous statement that may prove controversial. You will ultimately have to make a number of decisions here with different trade offs.
The current evidence base suggests that performance starts decay when working more than 55 to 60 hours per week, however its unlikely that breakthroughs and significant progress will occur working "9 to 5" (recall that you will also need solid blocks of uninterrupted focus). You will need to balance the time that you're able to spend progressing yourself, against how effective you're going to be during that time, and crucially, what the consequences will be for the next day, the one after, and the coming weeks. Our recommendation here is to consider what is going to be a sustainable marathon pace for months at a time, while assessing opportunities for you to push for specific concrete wins on a daily / weekly timeframes.
The general sense from other, more successful and established anonymous cartoon animals who have grown real business is that certain step changes can occur after prolonged periods of intense effort - our reading there is that you must then assess when to maintain pace, and when to push through "filters" to achieve real results.
Your sleep and health will likely suffer working two jobs, especially when differing time zones become involved. Working both late night and early mornings will literally burn you at both ends so avoid if possible, and avoid building up a "run" of consecutive days working. It's sustainable until it isn't, and we recommend taking some time regularly to decompress and not think about work or projects. Older BTB / WSP recommendations were 3 -4 days or so to reset.
For anyone that's gone through front office Ibank(0) first year analyst programs (we have not) this paragraph may elicit amusement. Those who have worked in first / emergency response roles (we have not) will likely have interesting takes as well.
From memory BTB's advice here was to find the threshold at which you could barely function (i.e. No recollection of where you just put your house keys) and then pull it back a bit from there. This advice was tailored toward readers in their mid to late twenties. For the "older" (i.e. Over 30) readers the recommendation was to have one softer / easier year after to c. 2 years of effort.
A brief observation on working out - if this is something that you struggle with consistently, during busy periods you will start looking for reasons as to why you are too busy to make time to go work out. These periods are exactly when you need exercise the most and we recommend as best you can keeping to a fixed schedule and going for nothing else other than to try to clear your head for a bit.
Once the broad structure of your week and days is planned, we will now move forward to execution. One of the key tools that will support you is a calendar, and your calendar management practices.
Calendar Management
When working two jobs, the amount of time, care and attention spent planning and coordinating your days and weeks will additionally increase (especially if there is a third job in the mix, your side project or other obligations). Recall that one plus one is not two. Some of the risks you need to manage will be a schedule clash, a deadline or deliverable being missed, or simply not creating effective blocks for focus and progress. You will therefore need disciplined calendar management to record and block your schedule(s).
Block It In
Any appointment, meeting or activity should be immediately blocked into your calendar(s) as an event. No exceptions.
Any changes to time, duration or location should be immediately updated. If the event is not yet confirmed place an empty event as a block or a hold so as not get double booked.
Here you should rely on your system of immediately updating your calendar and should make a decision not to hold any scheduling information in working memory. If its not in your calendar it doesn't exist.
We would also recommend also blocking in personal events as well.
To maintain overall visibility we would also recommend using an aggregator calendar (ie. Google calendar, Samsung calendar, iCal /Apple Calendar) and have multiple calendars feed in. This will help you plan and manage as everything will be collated in one place for your review.
Assertive (if not downright aggressive) management of your calendar(s) will be key to successfully managing two jobs. Once you are confident that you have visibility over the major commitments and things that need to be done, you will now need to carve out time for yourself.
One feature that may assist is setting working hours in your calendar (ie. When you are, and are not available), or depending on the situation, employing the use of calendar booking software such as calendly, squarespace. There are also similar options available in the Microsoft stack (Bookings) and Google calendar bookings can be set as blocks of selectable appointments.
A core strategy to create and protect time for yourself is creating events where you invite "yourself" to events
If feasible, (remaining cognisant of who has visibility) you can even invite your different work accounts to block out the alternate calendar. Having said this we would recommend maintaining discrete psychological "silos" (see August's Q&A re separate laptops)
Alternatively you can manually block calendars with bogus appointments to hold space for your other job while preserving confidentiality. Even though these are bogus placeholders, you should still treat them as blocks of valuable time where you have an appointment with your most important client: yourself!
While you may have an option to set an appointment block as private this may raise additional questions from your workplace. Our recommendation is to either block it with a convincing cover that will withstand moderate scrutiny ("a meeting with a (semi) trusted colleague", "a medical appointment"), or simply an untitled block. Depending on your situation you may explain that you have a practice of blocking time for focusing on certain pieces of work, and that calendar blocks are not necessarily meetings, however we would lean towards creating the impression that these blocks are meetings / calls.
We would also recommend using calendar appointments as a kind of meeting file. In the event description - prepare an agenda, or place hyperlinks to key messages and documents that you will need to refer to. If you need to preserve confidentiality (i.e. A sales meeting or a difficult conversation); create an identical second booking (with no other participants) parallel to the first in your calendar and store your agenda, links and docs there.
This can help speed transitions between work contexts and reduce cognitive load as all the context and resources you need are waiting in the event description to load and refresh yourself (Some readers may recognise this as a modern adaption / variant of the oddly named "tickler file" from the GTD framework).
Timezones
When managing multiple timezones our recommendation is https://www.worldtimebuddy.com/ (no shill, no affiliate).
Its UI and design exceeds a lot of competing solutions (particularly on desktops). We now use it exclusively after several Entirely Preventable Fuck Ups in our former careers. Remember to always input the exact dates you're working with to avoid a nasty surprise with a shift to, or from daylight savings time.
A recent alternative for a mobile we were made aware of is the Savvy Time application (no shill, no affiliate). A desktop version is available, however we are yet to fully investigate and compare it to World Time Buddy. At first glance it appears to only compare a single time, rather than meeting blocks like World Time Buddy but more proactively flags the daylight savings time transition.
Finally, you should regularly review and amend your schedule. At the end of each work period and day you should review the upcoming events that you have blocked for the next day and the rest of the week. Remember when scheduling to prioritise create large blocks (2 - 4 hours) of uninterrupted time.
Your Personal Life
A potentially overlooked aspect here will be around "managing" a partner or spouse or family member (perhaps another post in of itself)
Depending on your situation consider creating a shared calendar, or sharing access to your aggregated calendar (see below). This can reduce the need for questions around your schedule and keep them passively updated
One strategy here is to give them access to your aggregator calendar via a shared calendar. At a glance, they will be able to see your schedule outside of the "core" hours of the husband job and reduce the need to text you questions
(note we would recommend discussing this with your partner first - introducing a calendar and expecting them to book time with you via a calendly link is likely to cause "issues" in your relationship, and we are no means a publication focused on relationship or dating advice.
Closing Notes
Finally you can reach us at bowtiedhippopotamus@gmail.com or on the bird app @BowTiedHippo_
Great stuff!