Working a Second Job - Part II
Guidance on Working Two Remote Jobs, or Progressing Your Side Project While 'Working'
Part 2 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
Read Part I
Choose a side project rather than a second job
A 'Husband' and a 'Boyfriend'
Tenure
Remote
Promotion Track
Working Hours and Workload
Relationships
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 below 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.
A Second Job? Or a Side Project? (Choose the Side Project)
If you have not read Part I we would recommend that you do so first before continuing.
We provided a general overview of several principles that could assist you while working two remote jobs or starting a side project.
The previous note considered side project interchangeably with a second job, however there are several important differences and considerations for you.
From first principles: we hope that you are in a fortunate position where you have a job. If you do not have a job, at all, - do your best to get one (i.e. see BowTied Fox's guide)
Secondly if you have a choice between a second job or starting a side project (business), chose the latter. BTB and others have outlined the rationale previously and you will sidestep many challenges discussed below and elsewhere in this note.
If you are considering what to do for a side project see BTB and BowTied Opossum's guide.
Our current thinking is that while not ideal, a second job can help you transition toward the skills and confidence that you will need to manage your own consulting / services business, which you can then transition to a more scalable model.
If you are (fortunately) able to start a side project many of the principles we discuss will still be applicable.
If, after careful deliberation, you (still) choose to work a second job, the are still several considerations.
A Husband and a Boyfriend
When choosing to work two jobs we recommend taking great care to assess and design your first job, and even greater care to select your second job. A single 'upstream' decision here can often save multiple 'downstream' decisions and accompanying mental effort and stress.
In our view, a best case scenario is to have a 'Husband' and a 'Boyfriend'
The 'Husband' is an existing, remote full time role where you have tenure, experience, networks and some political capital.
The 'Boyfriend', is a new remote role that could be either part time or contract (or is your own side project). The 'Boyfriend' knows of your 'Husband' and is accommodating to unforeseen demands, snap meetings, crises and busy periods.
Other alternatives are two or three Boyfriends. Two Husbands may prove more difficult to manage and you will see a lot less 'slack' or tolerance in your system when friction and drag inevitably sets in. The need to preserve secrecy from both parties also places additional demands on you.
First, let us review the 'Husband'.
We would not recommend working a second job unless you first have the 'Husband' job secured and have the elements below either set up or thoroughly assessed.
Tenure
At a minimum we would recommend *at least* 6 months tenure with your Husband before considering another job (your own side project you can start immediately however!). This gives you time to pass probation and begin assessing how the other factors below can work in your favour.
Remote
If your job is not remote, or requires some onsite / in office time, amusingly you may be perceived as more productive and loyal by simple virtue of physically sitting in a seat. Efficiency touches on strategies here such as second laptop (often justified by "IT problems" or specialist software) or a mobile phone and a blue-tooth keyboard. If your physical office set up is not a cubicle farm make use of break out areas, quieter spaces, empty meeting rooms and so called "collaboration zones"
Regarding "blue collar" or service jobs, one advantage here is that the job is constrained to physical premises and it less likely to encroach outside of your working hours. The main considerations here will be your shift and commute times. If fortunate, you may have opportunities to work a second white collar job while at your blue collar / service job during down time. Your commute time is also an opportunity to write or dictate and could be ideal to use as for a review and closure transition.
There is potentially an argument here for doubling down on a non-remote job, however remote work can completely eliminate commute time and offers you more flexibility in structuring your day. If your current workplace does not offer remote work refer to Tim Ferriss' "The Four Hour Work Week" (from which several core concepts have been adapted. Poorly) for the specific section on work remote ("Disappearing Act").
Transferring offices / cities may immediately accomplish securing remote work arrangements. Remember: if one person in your team is in a different office, then remote work is occurring.
Amusingly, we know of at least one case where an Ibank (0) employee transferred offices and then simply stopped attending. Both office sites assumed he was at the other location, where instead he was physically working another corporate job on their premises. His absence was not detected for multiple months.
Even if your current role does not offer, and will not offer, work remote we would not recommend immediately changing employers to secure a remote work environment. You must first assess your environment.
Promotion Track
BTB has written about this at length (From memory: position yourself to be in the top 25% of performers; enough for a promotion, but not the top performer to whom significantly more additional work be assigned).
Generally, we would recommend assessing the promotion track for it's ability to offer you a higher salary, more autonomy, discretion and flexibility and opportunities for delegation. All factors that you can use to your advantage to scale your side project.
Depending on structure, promotions can also give you more visibility within the organisation, potentially offering a slight hedge against being terminated (but it's a very, very weak effect) but also potentially increasing your workload.
A potentially controversial disclaimer. From our exceedingly poor memory BTB was writing in the context of finance / tech / sales careers where there are high base salaries and significant differences in salary between promotion levels (i.e. Associate to VP / VP to Dir. Etc) - for those in industries with sub 200k USTT annual salaries the promotion effects on salary are likely to be smaller.
Our recommendation here is to asses based on opportunities for you to scale your side project (see below). We would never recommend turning down a promotion just to work a second job and for our readers in China we would not recommend 躺平.
You will need to weigh the time and effort required to join, and stay, on the promotion track (visibility, contributions, office politics), against the flexibility and benefits it can offer you in relation to your side project. Control over your time and schedule is critical.
If you are not in the top 25% and have been overlooked for promotion there may be good news hiding in plain sight. While your termination risk may have slightly increased, you may also have opportunities to build and design an environment away from managerial supervision and corporate expectations - the modern workhouse does after all need workers.
Working Hours and Workload
Obvious, yes, but also begin assessing how feasibly they would support your other endeavours in the future. We may partly address this in later notes.
Note the email / messaging flow, note when calls and meetings are (panic) scheduled and note periods of relative calm and quiet. Are you required to do late night calls with the Centre of The Known Universe (generally New York or London) and are then given a 'pass' to be online a bit later the next day (or not!)? On a week to week and month to month cycle begin developing a sense of key events and key time periods (i.e. Q2 and Q3 buying push; school holidays, EOFY).
Start snuffling and testing the perimeter - when does your absence go unnoticed or unremarked, what "minor" issues can you ignore and allow to resolve themselves within several hours. If you were going holidays tomorrow what would you not respond to?
Begin also assessing the type of work that you do relative to others in the organisation.
An excellent niche here is technical work that only you understand (note that even basic 2013.xls skills are often beyond the understanding of some employees in some companies), with the best case scenario here being duties that are overlooked, or considered painful and time consuming. The goal being of course to provide cover to allow you to inflate timelines or to streamline and build systems to free up your own time.
Relationships
Your relationship with your immediate manager is of most importance. Working two jobs can often necessitate being less 'responsive' and visible within the organisation and the strategies discussed in Part I of this note are often in direct opposition to how most workplaces function.
Best case is that you have a good relationship with your direct manager that trusts you to 'get on with it' and is more focused on your deliverables. In the event that your perceived performance slips you also be less likely to proceed to sanctions as quickly (ie. Counselling, performance improvement plans, termination). In a new job in a new company the reverse is true during the initial probation period. Ideally you have also cultivated good relationships with senior stakeholders and high performers within the organisation.
More broadly you will also have a read on which projects and initiatives are just the 'flavour of the week', which will be cancelled, which will blow out their timelines and which appear to have indicators of early success.
Concluding Thoughts
Hopefully from the brief overview of the above elements it is now clearer why we would not recommend immediately starting a second job or changing employers to go remote to then start a second job. All of the elements listed above are currently known factors (for now) moving to a new employer will require you to re-establish these.
Some caveats however. Depending on your personal situation it may be worth changing jobs to go remote to start a side project. It may also be the case that your own review of the elements above determines that currently a second job is not feasible at this time.
If nothing else the principles here and in later notes can support you to effectively dispatch your workload and leave mental space and resources for your to work evenings and weekends to progress yourself.
Part II took a little longer than we would have liked - some structural issues that we had to work through.
As always comments, criticism & questions welcome -
Great stuff. Keep it comin'