Dot Your I’s, Cross Your T’s, And Get Paid

An independent professional in my network recommended I watch a talk by Mike Monteiro called “F*ck You, Pay Me” when I asked for advice on contracts and client relations. Whether you’re freelancing, consulting, part-time, or full-time, the advice given applies to any contract you sign related to your professional skills. Below is a summary of the video and I’ll also cover how this can apply to a full-time position.

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An Independent Venture: Freelancing, Contracting, and Consulting – Oh My!

Recap: Traditional full-time work isn’t a good fit. This is a post exploring what the more flexible, self-employed work options look like.

choices decision doors doorway
Photo by Pixabay on

All of the different types of work discussed here have these things in common (except Startups):

  • Not working full time for a specific employer
  • Define a fixed amount of work or time doing work for another company or person
  • You are responsible for managing and reporting all of your taxable income
  • A ramp up time of at least a month before you start getting income
  • Full responsibility for equipment, resources, and software for work
  • Choice of how much to work in a day, week, year, or month

Note: I phrasing these from the perspective of a software developer.

Another Note: You can mix, match, and combine any or all of these options.



What’s different about freelancing?

  • Projects can be very short
  • Clients are often individuals or small companies
  • Complete control over how much you work and what work you do

Money Matters

Minimum time to profit: You can pick up a freelance job the same day you decide to freelance.

Minimum time commitment: Jobs can range from a few hours of work to several months or years of work.

Income variability: Highly variable. You can control this more with contracts that require deposits before project work or payment upon receipt of milestones in a project.

On the Job

Getting work: Networking, freelancing sites, classified sites, your dad’s golf buddy’s nephew’s small business.

Types of work: Work ranges from very small specific tasks (write a script) to large scale projects (build an e-commerce website).

Types of client relationships: Highly variable. Some clients will be ignorant of what your work is and demand impossible tasks with impossible timelines for nothing. Other clients will understand your industry skill sets and value you fairly. Good news: you get to pick your clients.

Is it for you?

Ideal for people looking for:

  • Variable length projects
  • Low in-person interaction and minimal interaction overall
  • No “sales”


  • Market dependency: demand and rate will vary depending on where you are getting work
  • You need to take extra care to protect yourself from bad clients
  • It will take time and effort to increase your profits, though you will be able to make some money quickly



What’s different about contracting?

  • Work contracts with a single employer
  • Employer sometimes handles taxes and administrative tasks for you
  • Time based rather than task based
  • Consistent income

Money Matters

Minimum time to profit: This is the same amount of time it would take to find a job posting, apply, interview, and get your first paycheck. About 1 to 2 months.

Minimum time commitment: Short contracts are about 3 months.

Income variability: Stable. You’ll be paid regularly as part of the contracting work.

On the Job

Getting work: This type of work can be found on job-boards and through recruiters. There are also agencies and contracting companies but you can fall into being a full-time employee of those companies rather than working for yourself.

Types of work: This is most similar to regular full-time work where you have a set of responsibilities rather than a specific project. You’ll often be working full-time but part-time contract positions do exist. Similarly, a lot of these request on-site contractors but some can be remote.

Types of client relationships: Very similar to employer-employee relationship. You’ll often be talking to recruiters and “contingent staff managers” as your hiring clients but you will be working with a team manager for day to day work. Your clients in this case will be medium to large sized companies looking for “contingent staff” to temporarily bulk up their workforce.

Is it for you?

Ideal for people looking for:

  • A regular work routine with a single company with consistent pay
  • A fixed term full-time employment with a clear end date
  • More security provided by the hiring company
  • Less administrative work
  • Working on teams with other people


  • You may not be seen as “equal” to full time employees
  • You can’t choose your hours
  • You may not be able to choose your location


What’s different about consulting?

  • You own your own business
  • You need to sell and market your products to potential clients
  • Your client relationships may be longer term with many repeat clients

Money Matters

Minimum time to profit: 6 months or more. You will need to build up a business, advertise your services, come up with portfolio data, and identify clients you can sell to.

Minimum time commitment: 1 – 2 years. You can be a consultant for 1 month but you’d ideally want clients that are looking for longer engagement of your services.

Income variability: Moderate. If you have long term clients, you will see some stability in income but depending on how consistently you get clients, it could be more variable.

On the Job

Getting work: networking, former employers, friends of friends… of friends

Types of work: Bigger projects with longer term or permanent involvement. Permanent involvement might mean that you are available to provide support work for a defined fee after the initial project contract is done.

Types of client relationships: Your goal is to have repeat clients and a steady flow of new potential clients. The clients will often be businesses and not individuals. You’ll be offering a complete and self-contained service to them. Ideally they recommend you to other businesses or return to you for more business.

Is it for you?

Ideal for people looking for:

  • Work scoped to a specific skillset
  • More decision power over how work is done
  • Lots of interaction with clients
  • Potential for expanding into hiring other people to work with you


  • You need to have marketing and sales material publicly available
  • You need to be comfortable doing sales to sell your consulting services
  • A miscalculation at the beginning of creating your value proposition and selecting your clients could result in the wrong clients or no work at all


What’s different about starting up your own business?

  • You own your own business
  • You are not dealing with clients but trying to engage customers instead
  • Marketing and sales comes after development and is targeted at groups of people rather than specific individuals
  • You are selling a product, not a service or a skill
  • There are significantly more administrative tasks to consider

Money Matters

Minimum time to profit: Months to years depending on the type of product you are selling. If you are building a simple phone app, it could be weeks or months. If you are building  website or service, it could be months or years.

Minimum time commitment: This one is tricky because you want your product to last long enough to make money. I’m going to throw 2 years out there as a minimum.

Income variability: Technically, the income isn’t variable since you won’t have any income fairly consistently until your product is out in the market and people are buying it. Often you’ll get a single lump sum investment and then nothing again. However, there are some ways to get variable income as you are developing. These are things like Kickstarter and Patreon.

On the Job

Getting work: You make your own work.

Types of work: You decide what work you are doing but be prepared to do everything from janitorial work to client calls to bug fixes for your business.

Types of client relationships: There are no clients; there are only customers.

Is it for you?

Ideal for people looking for:

  • A way to share a great idea they have with the world
  • Complete control over an entire product including inception and maintenance
  • A long term investment that might turn out to be extremely lucrative
  • Lots of variety in their work tasks


  • Your idea has to actually be good and you must be able to execute well
  • Market competition for your specific product or lack of demand
  • Inability to monetize in a way customer are willing to pay
  • Due to the long term investment, lack of follow through to completion


An Independent Venture: Sales?

I was at a software conference and met up with someone in marketing. I asked Marketing Friend for advice about how to negotiate sales and land clients for my business. Here is a digest of the advice she gave me.

It Turns Out There Is Something In A Name

First things first: how do people know you? Not only that, once they know you, how do they remember you? Despite what certain inventors of English literature may write, there can be quite a bit in a name.

  1. You need a name
  2. Your name should be associated with you
  3. Your name should be memorable

You might think (1) is a little silly but at this point in my business I had no name so I was confronted with an existential crisis every time someone asked where I worked.

If you have a larger company, you may not want to  associate it directly with yourself but rather with what your company identity is. I work on my own so I can make the company name more personal. If you can find a personal trait to coerce into a memorable and catchy name, you can create something that helps people remember both you and the company.

Example: If you have a common name with an alternate spelling, use the corrective phrase as a title. This is contrived but if your name is “Joan” but spelled “Jone” then you can have a company named “J number one” or “J – 1, 2, 3”. This is both personalized to you and helps your clients associate you and your company together.

Bad Example: I have a silent ‘d’ in my name, which Marketing Friend noticed right away. She said, “Call your company ‘With a “D.”‘ For what I hope are obvious reasons, I’m not going to go with that one. It would definitely be memorable though. Not safe for work reference.


A.K.A. Gathering Competitive Information

You will win bids and you will lose bids. Every win is an opportunity to strengthen the positive aspects of your sales and every loss is a way to identify gaps and shrink them. When you lose a bid, take the loss gracefully and use this opportunity to get information about the winning bid from your formerly potential client. This will almost be the only time you’ll get this information because you’re playing on guilt in the client. Remember this needs to be done as an immediate reaction to the rejection of your bid.


Client: “Hi Alacritical, I just wanted to follow up to say we’ve decided to go with another consultant for this project.”

Me: “I understand and I’m glad you found someone you want to work with. If you don’t mind my asking, what about that team made them stand out to you?”

This can be a fishing expedition but I hope to find out about what the competitors bid is and whether they had some marketable edge over me.

Sell Like A Vampire Hunter: Straight Through The Heart

It turns out humans aren’t robots. It can be disappointing news, but there you go. We have feelings in addition to logic and often we aren’t aware of how this affects our decisions when we think we’re being logical. That’s a whole other discussion though. When you are telling a story, making a joke, or selling anything, you need to hook that emotional part of a person and show them how what you are saying relates to them. Once you’ve got that attachment, you can let that robot logic make the decisions and spit out all the data and numbers you want.


  • A sales pitch is a story
  • A story has a beginning, middle, and end
  • The beginning draws people in through emotion and a clearly identified challenge
  • The middle describes an action in response to that challenge
  • The end is how that action resolved the challenge and addressed the emotion at the beginning


You want to pitch a service where you audit a cloud software system and identify cost savings areas. What are the different parts of this story?

  1. Emotion: You’re looking to play on the fear of losing money, the pressure of increasing profit margin without increasing resources, and the avarice of taking more money home
  2. Hook: Build your hook with a clear definition of the challenge and emotion. This means using language that evokes emotional responses. “Are you sure you could see the invisible leaks draining your infrastructure funds?” “Do you find yourself squeezing your budget for more research funds? Look no further than your own infrastructure as a bounty of potential savings.” “What would you say to boosting that profit margin with some simple streamlining techniques to your infrastructure?”
  3. Action: Describe what action you can take to solve this problem and address that emotional response you just played on. “We will use our team of skilled infrastructure engineers to dive into your infrastructure to deeply understand what your needs are. We can always find ways of lowering costs without lowering quality, engineering happiness, and ease of maintenance.” Note the continued used of evocative language. Also note use of the second person voice. You want your client to feel like this is something you’re doing just for them even if we all know that’s not true.
  4. Happily ever after: This is where you can start throwing in some data. Talk about success stories and what they got out of your services. “As a result of this work, we’ve empowered small and large businesses to re-invest almost 25% of their previously wasted infrastructure funds into innovation and growth.” Perhaps with a strong implication that we can do this for you too.

I personally don’t like the part of sales where I need to use emotionally charged words or topics to trigger attention or attachment but the good news is, this works for telling jokes and making effective presentations too. Check out TED talks and other advertisements to see if you can identify each of the components of the story they’ve created.

Client Communication Guidelines

Good news, you did the sales part and now you can just relax and treat clients like a regular person? No. It’s not going to be as much of an effort but you need to respect that they are running their own business and they are the center of their own universe. What does this mean?

  • Do not sound like you’re reciting a one-size-fits-all response. Personalize to show that you are making this proposal for them specifically. “For you, I recommend…”, “Something that will work well for your system…”
  • Do not use jargon. Use simple and direct communication. Take a look at the way they do news bulletins on television and how they can be understood by most high school students without difficulty.
  • Spend time focusing on making sure they see you understand the problem and are there to help them cope with it instead of throwing a solution at them and walking away.
  • When proposing alternatives to a solution or suggesting a solution to a separate problem you have not been asked to solve, always empower the client to make the decision. Present your suggestion in a way that highlights the differences (i.e. even if the change isn’t visual, a visual difference is easier to understand). Propose objectively and respect their choice.
  • See if you can connect with individuals closest to the problem to gain the best level of understanding. This can also smooth some turbulence caused if you indirectly create work for others before you’ve talked to them about the work.


There were a few phrases that, as a “radically candid” person, seem okay but Marketing Friend told me to adjust:

  • “Renegotiate” should be “Modify” – renegotiate is scary and will lead people to close down and back away despite its accuracy.
  • “You can’t afford me” should be “This isn’t a good fit” – Being a woman in tech, I’m repeatedly told to assert my value. Just not with clients it turns out.
  • “You say you can’t afford me but I guarantee I’ll do a great job and it will be worth it” should be “I really want to work with you on this project; don’t let money stand in the way” – This communicates that you are committed to doing a good job on the project but also that you’re not just selling the service, you’re selling your emotional investment as well. Thus, selling your heart.

Notes on Being a Woman in Business

We hear a lot about how gender stereotyping harms women in business, politics, the home, and basically everywhere. However, there are some ways women can leverage this in sales.

It is more acceptable for women to show emotional and caring according to gender stereotypes. As a result, women can show much more emotional attachment to potential clients and highlight their caring and supportive strengths as an asset. If you can find someone who can do the job and actually cares about how it affect you, why wouldn’t you choose them?

This is not to say you should sell your heart to these companies. When you genuinely are interested in delivering a service and want to show you care, do so. This is about letting that extra bit come out in your sales.

Example: Say, “I love the ideas and innovation you’re bringing to this market and I want to be here to support you through building this vision” instead of “I find your ideas and innovation interesting and I’d like to contribute”

Now, this is a touchy subject. I’m not saying men can’t do this. They can. However, due to the unfortunate restrictive bias of gender stereotypes (remember, they’re not good), men may be seen as weaker for showing this kind of emotion. Weaker means less trustworthy to some people. It’s unfair. I’m sure men all over North America are just crying themselves to sleep at night with that extra $0.20 on the dollar they make over myself and other women.

Note: I did intentionally choose an article that both explained and contradicted that number for maximum fairness to everyone.

The End

Remember, these are just notes and ideas from me and my marketing friend. Everyone works differently and all I can hope is that trying this out will make a few more interesting blog posts to write.

An Independent Venture: So Long and Thanks for All The Fish

If you’ve ready some of the other posts on my blog like this one or this one, you might wonder “why didn’t you quit?”. Short answer: quitting is hard. I only have myself and two cats to support and there’s already a migraine inducing list of things to consider. I can only imagine how much more challenging it would be for someone with a spouse or children to support as well. For what it’s worth, I will go over considerations I have in mind when quitting, whether I have a job to jump to or not.

Health and Well-being


There are a few things to consider about vacation if you have any left at the time you are planning to leave.

Cashing Out: Does your company pay out any remaining vacation left that you haven’t taken? If not, then you may want to take that paid vacation time before leaving.

No Extension Policy: Your company may have a policy where you cannot extend your time working for the company by taking all your remaining vacation within some number of days of you quit date. Even when I worked at a company with this policy, it wasn’t enforced.

Health Insurance

End of Coverage Date: A lot of companies pay for their employee health insurance monthly and typically you are covered from the 1st of the month. This means that if you quit on the 1st, you are covered for the full month without being employed. Unless there’s a good reason not to, try to quit after and as close to the first as possible if you need to stay in the US after quitting.

FSA: If you have a Flexible Spending Account, you will lose all the money when you quit because your health plan will change. Need a new pair of glasses or were you considering Lasik? Use up that FSA before you leave.

HSA: If you have a Health Savings Account, you can keep it open and keep the money in it. However, you may be responsible for the monthly fees to the bank. Check those out with your HSA provider to see if you’re willing to keep those up. Alternatives for this include rolling your HSA funds into an IRA. You would need to check with your HSA provider first. If you plan to leave the Unites States, you will need to pay the penalty to withdraw all the money if you don’t plan to leave it in the states.

COBRA: When you quit you’ll get a letter about COBRA. You can enroll in continued coverage with your employer’s health plan for a limited amount of time. Usually this is expensive. Plan to research this along with your other health plan options before quitting.

Fitness and Education Benefits

If you company has fitness or education benefits like paying for a gym membership, you will not only see your membership end but you may need to pay back some money. Double check the policies to see if you need to pay money back and how much. Similarly, check to see at what point your gym membership will be cancelled. Maybe you can spend more time at the gym after you quit if it continues.

Employee Assistance Program

Many more companies are offering something called an Employee Assistance Program or EAP. This offers some small number of appointments for free with a therapist or psychologist. Feel free to pass this up but there are some therapists that specialize in life transitions and career planning. If you want to chat with someone about quitting and bounce your ideas off them, a couple of free session before actually making the change might keep you more sane during it.


Before losing contact with your physicians or other medical providers, make sure you have their contact information to retrieve records in the future. Similarly, request any necessary vaccines and proof of vaccination before losing health coverage. Also another potential way to drain that FSA money if you want a yellow fever vaccine, for example. Do also have a printed copy of your prescriptions to make it easier for any new physicians in any country to resume your medical care.

Money, Money, Money

You will have all kinds of money implications including but not limited to:

You can go very deeply into all of these so I will try to boil them down as much as I can:

  • If you received any bonuses, check to see if you need to pay them back and how much you need to pay back.
  • Have enough money to cover your living expenses in savings for at least 3 months. There are many resources online that can help you understand what goes into that number or if 3 months makes sense for you. Example.
  • If you have stocks awarded from your company, check what their vesting dates are and how much you will lose. You will lose all unvested stocks.
  • Opening new lines of credit may change if your company has an agreement with banks to provide discounts or other advantages to it’s employees. You may want to carefully plan for any new lines of credit you’ve just opened or plan to open to see if you benefit from using the company benefits.
  • Taxes! We love taxes! If you make a decent salary and get stock from your company, you deeply fear selling your stock due to the jump in your tax bracket for that year. The plus side of being unemployed? Lower income. Consider planning to sell stocks or otherwise liquidating assets during the time you are unemployed to keep your taxes low.



If you have a Green Card or a visa (not the credit card), you may not know when you will stop being allowed to work in the US. For visas, it varies based on the visa type. Check your visa type and it will specify for how long you may remain in the US before you must leave and reenter. For example, H1B – you must leave within 60 days and re-enter on a visitor visa if you want to come back without another work visa.

Green cards are more interesting. You may be abroad outside of the United States for 1 year and re-enter without needing to report your absence or lose the card. You may additionally request another year to extend your absence from the US to 2 years but any longer than that and you lose the card. If you don’t request and extension, you will lose the card after 1 year away. How do they tell when you’re away? I have no idea. You can try to game this system but the consequences are extended periods of being banned from entering the US if you lose that game.

Finally, if you have dependents on your visa, they will face similar status changes and risks as you do.


If you would like to move to another country, state, or city with your animals, make sure you have copies of their vaccines and medical records before moving. If you have young animals that are still considered babies of their species, there are different import/export laws for them. Even in other states or cities they may have different banned breed lists, animal registration policies, or spay neuter policies.

Nice to work with you; let’s stay in touch

Giving Notice

Check about your company policies around resignation. Many tech companies use “at will employment” contracts which means we can quit whenever we want. However, if you want to stay in the good books of your employer, find out what the unofficial guidelines are. If you are not able to ask anyone at work, websites like Glassdoor or Blind (if you can sift through the toxicity) discuss these topics for each company.

There is a stereotype of “2 weeks notice”. Do not assume that your company follows that. Typically you want to budget enough time to tie up loose ends for work but not enough time for them to give you more work. Further, when hearing that an employee is leaving, some managers will choose to pile on the work even harder to get the most out of them before they leave. Be ready to say no if this happens to you.

Finally, and perhaps most importantly, some companies will require you to leave immediately under company escort out of the building if you disclose you are leaving to work for a competitor. Make sure you moved your office couch out before you give your notice in that case. Make some excuse about getting it reupholstered with Pokemon fabric or something similarly question blocking.

Staying in Touch

There are a few different ways of staying in touch with people. My favorite is using LinkedIn. This allows me to give my contact information out to people and still being able to control who I accept as a contact.

Using your email address is up to you but I find that people rarely reach out that way. LinkedIn is far less personal and lacks commitment enough that people are more likely to use it. Similarly, Facebook or phone numbers are also a little too personal and you might find out about that secret crush the guy near the printers has had on you and wish he didn’t just get your phone number. If you do prefer phone and want to keep your personal number private, Google Voice numbers are another way to share numbers and maintaining control over who can reach you. They are also another way to maintain contact with those in the US if you are not going to be in any particular country after quitting.

How to do the quitting

After having gone over all these really painful planning and paperwork points, what about the actual conversation with your boss? You will need to stay tuned for another blog post on that topic!

Explanation of title.

An Independent Venture: Flexible Working Arrangements – Not Working

In the previous posts about finding ways to create more mental space for yourself around work, I looked at working from home and working less. These things weren’t solid options for me so I started looking into what my options were for not working for short or long periods of time.


If you are a full-time employee of a North American company, you probably have vacation. There are different types and lengths of vacation available:

  • Accruing vacation: You will gain an amount of vacation each pay period and you will need to build up “savings” in order to spend them.
  • Lump sum vacation: You will get a fixed amount of vacation per year at the beginning of each calendar year.
  • Unlimited vacation: You can take all the vacation you want as long as your deadlines are met.

Unless you have unlimited vacation, typically in tech I see people get 2 – 3 weeks of vacation to start off and that grows as your tenure increases. Usually you need to work at a company for 5+ years to gain an extra week of vacation.

At most companies I’ve worked at, the official line is that vacation is tracked and you need to report your vacation when you take it. Unofficially, most managers I’ve had don’t care too much about the reporting as long as you don’t take vacation too often or too long. Personally, I feel uncomfortable with this type of undefined vacation policy and struggled a lot to understand what was okay and what wasn’t. Most managers will not give you any clarity of how much is unofficially okay so it’s very subjective.

Vacation is all fine and good but for me, 3 weeks isn’t enough. Due to family obligations, I am asked to spend 1 to 2 weeks on family per year. This became more important when family members became ill. During those years I was lucky if I could spend any of my vacation time on myself and would be guilt ridden if I did, thinking that I was missing my last chance to see a loved one. In “normal” years, I would still spend a week with relatives leaving 2 weeks for myself during the year. My choice would then be between spending 2 weeks in an interesting country far away or taking little vacations here and there. Unfortunately, I wanted both and to get 6 weeks of vacation was basically impossible.

Wait a second – what about that “Unlimited Vacation”? From those I have spoken to that work in the unlimited vacation companies, people are not encouraged to take vacation and enter into a competitive “I take less vacation than you” environment. You also end up back in that situation of uncertainty where if you aren’t explicitly told what’s okay, you default to taking no or little vacation. In theory, it is a good idea but it practice it doesn’t work as well as it sounds.

So, vacation is nice but not enough on it’s own.

Sabbatical or Leave of Absence

Often companies will offer leaves of absence or sabbaticals. I’ve more often seen these called “Leave of Absence” or “LoA”. The policies typically include the time you have to work for the company before you can apply for one, the length of time you can take, and how long you need to wait until you are eligible for another.


You may apply for a leave of absence after 2 years of full-time employment. A leave of absence must be greater than 2 weeks and less than 3 months. You may only take 1 leave of absence per 5 years of employment.

In addition to meeting the tenure and length requirements, you typically need the approval of your manager, your director or vice president, and HR. These absences are always unpaid. The only people who I’ve seen take these leaves are those who are quite high in the organization either as developers or managers (senior level).

Why didn’t I take this option? I would still be restricted by my company’s moonlighting policies so I’d be limited in trying out building my own software. Additionally inn my personal history, once I leave something I rarely want to go back so I decided I’d rather quit and score a signing bonus for another job than take 3 months off and go back to my old job. This wasn’t appealing to me so I passed on it.


We all know that one day we’ll have amassed enough money when we’re in our 40s if we’re lucky or 60s if we’re average to stop working and enjoy senior’s discounts. Many companies provide 401ks that allow you to build up this dream. Unfortunately, there are several types of investments called “55 and a half” money where you, unsurprisingly, need to be over 55 to start collecting. The point is: I’m going to have to wait several decades for this to be technically valid unless I save millions on my own.

Several companies also offer aggressive 401k catching up so you may be able to build up enough money to retire in a short number of years if you’re near the end of your working years. I, on the other hand, have quite a few working years to go. It is a risky choice to choose to manage your working time and income because you may never know if you’ll run out of money or become irrelevant. Your company often covers disability insurance as well. Taking this all into your own hands is a huge risk and very scary for some people. However, I am unhappy enough working for one of these large tech companies that I am willing to take that risk. We’ll see what happens.

Next Up: How to quit

An Independent Venture: Flexible Work Arrangements – Working Less

In the previous post I talked about working from home and keeping the approximate same hours. Below I’ll talk about the ways I looked into working different hours or less hours.

Flex Time

This a really popular option among tech and non-tech companies. The way it works is you work an extra hour for 8 days and you get the 9th day off so you keep your average of 80 hours per 2 week period. This doesn’t work in tech.

Flexible work arrangements typically require either hourly work or a fixed frame of time where you are working. In tech, full time employees are intentionally not hourly so they can be asked to work extra hours and the company pays the same salary either way. Similarly in tech, companies offer core hours and flexible start and end times otherwise. You can do 7 – 3 or 9 – 5 or 11 – 7. Due to this pressure to work long hours and a lack of consistent work time, flex-time tends not to work. Managers are happy to have you work an extra hour a day but you can’t have an extra vacation day.

Exception: The only exception to this is if you are on-call or supporting a customer product and you are asked to work nights or weekends. In these cases, I’ve been told to take the corresponding amount of time off that I worked.

Part Time

You’ve probably wondered if you could work 4 instead of 5 days a week and just get paid 20% less. Why not have a long weekend every weekend? This would be the thought process that lead me to ask about part-time arrangements.

I have seen part-time arrangements put in place at some of the old tech companies and some of the new ones, for young and old, for test and dev, for women and men. So what does it take to get in on this and what does it look like?

Here are some of the examples I’ve seen:

  • Highly valued software tester was going to quit to be a full time mother and she was convinced to work 3 days per week
  • Highly valued developer with PTSD was allowed to work 4 days per week and work from home 2 days of those 4 days per week
  • A full team was working part time to investigate the impact of offering this option: each member worked 4 days per week for 6 hours per day

When I asked about how I could get in on this, both the examples and the management gave the same response: you either need to be a superstar at this company for 5+ years or you need to be a lab rat. I was neither unfortunately so this wasn’t an option for me.

Being part-time outside of being a superstar or a lab rat means that you have to sacrifice benefits such as health care or other company programs like parking discounts or gym memberships. Health care is quite pricey and it does grind away at your self-esteem when you are treated as less than your peers even though you put in the same rate of effort, just for less time.

As a note, there are plenty of articles that explain why 8 hours per day is a recipe for stress, physical exhaustion, and just an unproductive worker. Example: work less hours

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Shared Worked

This is a really unusual option that I haven’t seen in play before. I’ve only seen reports of it.

The way this works is you have two people who can work a particular position. They will together do 1 person’s worth of work for 1 person’s pay. Typically these two people need to apply for the position together as if they were a single person and then work with the hiring manager to outline how they can split their responsibilities. I’ve only seen this proposed for managerial positions where 1 person would do a lot of coaching and career development and the other would do project management.

In order for this to be successful, you need to first find a person that has complementary skills to your and who you can work with closely. Next you’ll need to do the hard part of applying for jobs together and convincing your prospective employers why two people are better than one. Given how people are happier and more productive when they work fewer hours, you might actually be able to do this fairly effectively. Similarly, if you have a managerial position that involves a lot of travel, you might be able to make a good case for it.

As far as engineering positions go, I have never seen this before. I suspect this might have a lot to do with engineers having too many responsibilities or too few. If you manage code, deploy, test, debug, devops, design, planning, interviewing, and mentoring, it becomes hard to group those into equal parts without creating two separate roles. Similarly, if you only code and test, you will become too narrowly scoped if you only do one or the other. That’s my theory anyway.

Unfortunately, it looks like the “work less” options are all bust. Next up are ways you can take time off.

An Independent Venture: Flexible Work Arrangements – Working from Home

Continuing with this series of posts, I’ll describe some of the flexible work arrangements I’ve investigated. Thus far, I’ve explained that once I determined that my job was the main source of my unhappiness in life, I started researching how to change it.

I was working in a large tech company that was typical Monday to Friday, 7 – 9 hours of work per day. This company offered me all of the benefits of working for a large, established company that was successful enough to liberally fund its development groups. Given that this was a very comfortable position, I started off looking at ways I could make it work for me but also change the situation. Previously, I described ways of making small changes to your work life to reduce stress without any significant job changes. The changes here are more significant and will require working with your managers or potentially your HR department.

Working at Home

If you find that you are unhappy at work either because of your commute, your coworkers, or the work environment, you can look into working from home. This can take a few different forms and which works best will depend on the problem. Here are a few things I’ve tried.

Work from home in the morning to reduce commute stress

I noticed that my commute was causing me some stress, especially on days with bad weather. My commute time would go from 1 hour to 1.5 hours. Sometimes I’d be squished between smelly commuters in an overheated bus. Or stuck waiting on an off-ramp for 30 min. I decided I could try to change this by working from home in the mornings just until after rush hour and still make it in time for team stand-up.

I approached my boss about this asking if the work arrangement would work. Since no one in that team booked meetings before stand-up unless absolutely necessary, the arrangement had no problem and I got the green light immediately. Here’s a comparison of what changed:

  • Work start time: 9 am → 8 am
  • Commute time: 1 – 1.5 hours → 40 min to 1 hour
  • Commute method: Bus or car → car
  • Daily cost: Bus (free) or car ($20) →  car ($20)
  • Likelihood of finding parking in my building: 100% → 0%

Did this work? No. I exchanged my commute stress for more costly commuting and stress finding parking. Interestingly, I later found that if I rode a motorcycle, I would get free, guaranteed parking. Unfortunately, that does have an increased risk of death. [Disclaimer: I currently ride a motorcycle to work from time to time when I want to come in late]

Let’s try a different tack.

Work from home to avoid going to and being at work

Since working part of the day didn’t work out, I upgraded to trying out the full day. It turns out a lot of people like working from home or at least not having to work from their desk. Several of my teams have had a policy where if you don’t have meetings in a day, you don’t need to be in. Virtual stand-up was supported on these teams. Generally, I made use of this as often as I could, which was probably 2 – 3 times per month.

When I approached my managers on each new team and described my circumstances with stress and work, they said they understood and wished they could accommodate me. Usually they would say I could work from home if there were no meetings but I had to be at work during team meetings. On some teams they said they didn’t trust that the team would be productive if everyone started working from home (apparently the natural escalation from accommodating my needs is that everyone is going to want to work from home).

I decided to talk to HR about what I could do to force the issue. I did have a doctor or two that could certify that I have a need to reduce my exposure to stress at work so I could swing it if needed. HR at more than one company said that I could go the medical route but if my manager wasn’t willing to support the accommodation, my performance would suffer.

Conclusion: this is a good option but ultimately not in my control.

Can I just work from home all the time?

I never tried this. If working for myself doesn’t work out, this is what I’ll be aiming for. So, why didn’t I try this out?

Doing a fully remote job is definitely on my radar. One of the catches I’ve noticed about some remote jobs is that they require you to be at an office from time to time. This can range from once a year to once a week. Depending on your location and life situation, this can be challenging.

For my next venture of working for myself, I will primarily focus on working at home and going to meet clients when necessary. This won’t be easy or simple. I will need to make sure not to fall into the traps of working where I live like getting distracted by my cats, sleeping in too late, or just not being in the right mindset. There will likely be a post from me on that topic later on.

Next up: An Independent Venture: Flexible Work Arrangements – Working Less