Working a Second Job - Part III
Guidance on Working Two Remote Jobs, or Progressing Your Side Project While 'Working'
Part 3 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 and II
Recap: A Husband and a Boyfriend
Selecting the Boyfriend
Size and type of company
MNC / Enterprise
SME
Family Business
Start Up
Scale Up
Working Hours
Type of Role
Managing the Boyfriend
Don't Tell the Husband
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 Parts I and II we would recommend that you do so first before continuing
In Part I we provided a general overview of several principles that could assist you while working two remote jobs or starting a side project.
For Part I we considered a side project interchangeably with a second job, however there are several important differences and considerations for you. Part II discussed this in more detail and, while recommending that your efforts be focused on starting a side project, began providing an outline of what to consider before commencing a second job.
We also introduced the concept of a 'Husband' and a 'Boyfriend'. To briefly revise:
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.
In our view, this is the best case scenario for managing two jobs.
At this time we do not recommend two Husband jobs. We do not have experience with this and in our view the resources required to manage and coordinate would far exceed a single Husband job and a side project(s).
Having said this it is our understanding that BowTied Brazil is currently working two remote sales jobs so individual skill sets and temperaments can offer different roadmaps here!
We have also heard of an individual working three (!!!) full time Husband jobs, however they have a specific technical skill set and their market is currently characterised by a lack of mainstream understanding.
Two Husband jobs may obviously offer short term a significant boost in USTT, however if you are seriously considering this we would recommend again revisiting Part II of this note first to assess your current job.
Selecting The Boyfriend
After the assessment of the Husband Job discussed in Part II, the selection of your Boyfriend job is the next most important step.
The Size and Type of the Company
We will provide a brief overview of several different types of companies. There is a very broad range here, and in our view your focus instead should be on the definitions and boundaries of your role (including the working hours).
Large MNC or Enterprise
Generally we would see these used as Husband jobs (our experience) rather than Boyfriend jobs.
They're potentially less wiling to overlook your Husband job, be less open to part time or ad hoc / flexible arrangements and more likely to insist on stricter compliance measures.
In our view you probably better off either avoiding them completely, or approaching a specific business unit from a contracting or vendor perspective. Some parts of the business could be high churn, or could scale up (and down) with short term contractors, offering you an opportunity.
The benefits of the MNC / enterprise for you is generally their scale and their inertia. Size and scale often means there's often plenty of vacancies and once you're in, plenty of downtime to assist you to manage your existing Husband job. This can be hard to identify and assess from outside of the organisation however. The inertia often means that temporary decisions, like hiring you for a contract, can often persist for far longer than they would in other companies.
We would also consider government or semi-government as similar in this category, while opaque and slow to hire, depending on the circumstances however they can suddenly find budget for short contracts to address specific issues. With the help of inertia this then becomes a longer term fix.
SME
Keep an eye out for these.
You're potentially attractive to an SME as a (semi) experienced professional offering a skill set that they otherwise may not have, or may not be ready to commit to full time.
There's really wide variation here (see below), so similar to an MNC look for really well defined roles within specific areas.
On a side note, it also goes without saying that you want to avoid any company with so called 'productivity tracking software'. Our understanding is that modern applications will not only assess time logged in, but will build a measure of 'intensity' based on page activity, eye movements and facial expressions.
Again, we have less experience here with this section, but our guts suggest that SMEs may actually use these types of software more than large enterprises (who have a more mature, older, broader compliance / ER framework already in place). We may update this section at a future date once more credible information comes to light.
Family Business
Tends to be on the smaller side of the SME. Here you will likely be bringing a new skill set that doesn't otherwise exist in the business.
As an example, in smaller family companies you likely be the only person that does marketing, and are likely the first marketing hire, and you'll be taking over and consolidating and number of piecemeal marketing initiatives that have historically sat with different people who never quite understood it.
This can potentially come with a large education piece as often the business doesn't know what it wants, or needs and definitely doesn't know what it doesn't know. Expect challenges managing misaligned stakeholders with difficult / emotional relationships and environments that can lurch between highly collaborative to autocratic within a few minutes.
Start Up
In our view, these SMEs are distinct from Scale Ups (below). A Start Up is the real deal cash flow impaired boot strapping circus held together with duct tape and undiagnosed personality disorders (not necessarily a bad thing). While unstable these are an accessible option for a Boyfriend job, however care must be taken regarding the nature of the work and setting boundaries (see below).
You are likely to be very attractive to the start up as a (semi) experienced professional offering a skill set that they otherwise could not attract or afford full time.
In dealing with Start Up our recommendation is to set very clear expectations around payment and payment terms. Avoid compromising your rate / salary. In some situations you may be offered equity or be considered a part time employee (or co-founder !!) with a traditional vesting cliff toward equity (ie. 1 + 4). Here you need to carefully consider that the promised equity may be worthless, revoked or diluted.
Consider having clear go / no go guidelines in place and exit gates in your arrangements. Leave immediately if they're not going to pay you or if previously agreed arrangements begin to change.
Scale Up
In our view, a Scale Up is a Start Up that has secured funding (perhaps up to and including several series B rounds) that still choose to present itself as a start up. Beware of entrepreneurial chic and Town Hall meetings where the ex-Ibank(0) founders attempt to commune with the shade of Steve Jobs.
They will typically have a longer cash flow runway than a scale up and should be able to pay their people consistently and on time (On a side note: perhaps no longer! We suspect that there's more than a few zombie start ups that are in for a shock once the VC flow stops)
Again, you are likely to be attractive to them as a (semi) experienced professional offering a skill set that they otherwise are not ready to commit to full time. You will also represent a fairly light opex that they can scale up and down. Over time however you will need to manage them (see below) as they look to "evangelise" their mission and bring you onboard the "Rocket Ship" and they will be looking to discuss your commitment to them.
Working Hours (again)
Following on from Part II, By now you should have a good idea of the periods of time in your Husband job that you can quietly re-purpose with minimal impact.
You are now looking for a suitable Boyfriend job that will fit mostly within these periods.
Consider the timezone that your Boyfriend job operates in, and if relevant, the timezone that their clients / customers and stakeholders operate in. Obviously an overlap or a bad match could potentially overwhelm you with co-occurring busy periods and competing demands for meetings.
Look for opportunities to be strategic here, as both jobs are ideally remote you may be able to leverage time zone differences or simply starting earlier to give yourself a block of several productive hours.
Type of Role
This is probably the most important factor for you to assess
You're looking for something that will be feasible and sustainable for you to do while managing your Husband job and other commitments. There is an also an argument here that you could use your Boyfriend job as a means of gaining or practicing an additional skill set that will later support your own projects.
In our view, the best case scenario here is a role that is completely performance based, requires minimal engagement with stakeholders / peers / managers, is asynchronous and has a high degree of flexibility regarding timelines and deliverables. Or better yet; does not deal in time sensitive work at all!
Work that is time sensitive such as sales, account management, customer service is best avoided if possible.
This type of work has a habit of encroaching past the time allotted for it and it is tempting to either quickly reply and close the loop or to check it at intervals elsewhere in the day, inviting the dreaded context switching and multi-tasking.
If it not possible to completely avoid this type of work (or it is a strength for you) our recommendation is to set hard limits upfront around the hours where you will contactable for this and clearly communicate this.
Otherwise there will be an expectation that you are available and contactable.
A clear hand off process for any 'live' matters is recommended as well (see Part I of this note for closure processes and use this as the foundation for a strong, explicit handover process).
Educate your environment or you will risk being overwhelmed by constant requests that "will only take a minute"
Phrasing similar to this may assist.
"I'm happy to support you with account management - however I'm really concerned that if I get caught up at my Husband Job (probably don't refer to it as that) something will slip and damage your brand. How about I deal with anything between 9 - 11.45 and I'll hand off you to daily at 12 noon via a call / summary message".
Managing the Boyfriend
Even though the Boyfriend is aware of the Husband and is more accommodating to your situation there may be considerations you need to manage. After all, in their mind you're not 100% committed to the Husband - would you do the same to them?
Here are some phrases / wording that may assist. A lot depends on your situation.
"The husband is a dead end / no opportunities - however I need to stay until milestone (i.e. Participation bonus, end of a project / commitment)"
"I'm at the top of my pay grade already and my boss has been there since the wheel and the fire - this gives the opportunity to build something new with you"
"Honestly I'm in an ok seat, but the extra effort to get promoted would just mean more politics - I'd much prefer to stay hands on progressing real projects and learning"
"I am really interested in the opportunity and growth here - while you scale I'll stay flexible / part time / consulting until milestone when I can transfer over to you fully etc. "
“I'm looking forward to coming over full time to you, however this is prevented by [personal circumstances] (if a trusted associate), lets review in n months - this way you get my expertise, and we can assess if this is the right long term fit.”
“My deliverables for you will be asynchronous and can be done remotely. I'll be reasonably available if you have questions. My recommendation here is that you actually keep me part time / freelance as there's not quite enough for me to warrant full time yet. Let's review in...”
Of course, working on your own side project completely sidesteps issues with the Boyfriend.
And finally:
Don't tell the Husband
The Husband job is unlikely to respond positively to news of your new boyfriend so we would recommend not disclosing this. Even if working a second job is not strictly prohibited by your contract or code of conduct there is likely to be adverse consequences.
Depending on the job this could involve discussions with HR, compliance and your manager and even if you are able to successfully argue that you are only volunteering temporarily on a side project for a friend (for example) it will likely impact your standing with the job.
Remember that your contract is overruled the employment law in your local jurisdiction and the feasibility of aggressively prosecuting breaches. Later sections of this note will discuss ways to minimise detection, and if you've followed our recommendations around appraising your Husband job and carefully selecting a Boyfriend job then these steps will have already reduced your risk of discovery.
Finally out!
Thought we could turn this one around quickly (no) - but got rebuilt quite thoroughly with some structural issues and expanding on a few sections. Quite a few sections sent over of Part IV where they're much happier.
As always comments, criticism & questions welcome -
If you're on the bird app feel free to drop by as well
@BowTiedHippo_
Part IV is now published.
https://bowtiedhippo.substack.com/p/working-a-second-job-part-iv