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

3 thoughts on “An Independent Venture: Flexible Working Arrangements – Not Working

  1. I remember going through a similar thought process when I was gearing up to leave my full-time job. I was too junior to take a leave of absence, not essential enough to negotiate working from home regularly, and didn’t see any viable options for part-time work.

    Before I decided to leave, I put all my hopes into early retirement, reading blogs like Mr. Money Mustache and Mad Fientist. I made spreadsheets calculating when I could retire depending on how much I could save and how cheaply I could live. It made me feel better temporarily, but I realized that even if I could retire by 35 I would still have to endure 10 years of working a job I hated, and in the prime of my life!

    That said, I still read those blogs on occasion and I like their approach to finances. I recommend reading up on the Roth conversion ladder if you’re interested in saving more for retirement that you can access before you’re 60.


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