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Unlimited Leave: Five Steps to Maximize a Valuable Benefit


I have read articles claiming unlimited leave is a scam, costs the employee money, results in less actual leave usage, is a new mechanism to work employees to burnout in a corrupt capitalist society, and more.


These claims are right, if you are taking leave incorrectly.


However, if you use your unlimited leave correctly, you enjoy more time off than other Americans (and Europeans, if you feel comfortable doing so), increase the value of your time by increasing your hourly wage, and even improve systems and productivity at your place of employment.



1. Set a minimum leave goal.


The most obvious way unlimited leave becomes a negative is when employees do not use it. Paid time off is typically paid out if you leave an employer with unused leave. Unlimited leave is not paid out when you terminate employment because it is not quantified at all. This means if you do not take any leave, you get zero benefit out of unlimited leave because money cannot substitute for the leave.


But time is a more precious resource than money! The way to realize the value of unlimited leave is similarly apparent: You need to take more leave.


While the existing capitalist society does not automatically make unlimited leave a scam, it can trigger guilt that prevents folks from adequately using the benefit, making the benefit counterproductive. If you wrestle with these guilty feelings, remember that leave is as much a part of your compensation as your pay. If you would not turn down $100, do not turn down leave.


Even folks who recognize leave as compensation can struggle with how much leave to take when guidelines do not specifically provide 10, 15, or 20 days. Since your employer does not provide a benchmark, make your own! If you are extremely guilt-ridden and new to unlimited leave, start slow. Use your previous job or a competitor’s leave policy as a reference point, and set a goal to take at least as many days of leave as you would get if you worked for another company in your field. For example, if you work at Large Bank ABC as an associate with unlimited leave and associates at Large Bank XYZ have 20 days of leave each year, set a minimum leave goal of 20 days of leave.


Then take at least 20 days of leave. No excuses.


Want to step this up a level to really get value out of your unlimited leave? My minimum leave goal is 30 days. Those 30 days do not include the eleven paid federal holidays I receive, volunteering in the community, or bereavement leave. It does include the hours off when I take a half day to drive to Baltimore to see the Red Sox play. Taking breaks is healthy, and having the flexibility to use leave on half days for local events rather than saving every hour for a big trip decreases stress around saving and calculating leave.


If you are curious, I exceeded my 30-day goal last year. I have taken 13.5 days of leave so far in 2023 (including today), and I will be up to 16.5 by the end of the week. So far, I am on track!



2. Do not ask to take leave.


But my boss won’t let me take leave.


That is the biggest excuse when I suggest the minimum leave days approach. It has a solution that is simultaneously easy and difficult: Never ask permission. Instead, inform employers about leave.


If you have unlimited leave, you are probably an adult. (If you are 16 with unlimited leave, you are awesome. Please take over writing some of these articles because you are more ambitious than me.) Leave is provided to allow you time to prioritize your life before work during work hours because work is just something you do while life is your actual purpose. It does not matter what kind of personality your boss has, how shy you are, your extremely important role on a project, or if taking a hard stance triggers anxiety. You have to learn to inform your employer that you are taking leave.


Informing is easier when you plan in advance, so start there. If an employee tells an employer that they are taking leave for a week in six months, there is no emergency deadline or pressing issue that an employer can use to justify apprehension. Leave that is planned in advance is leave that an employer can plan around when scheduling deadlines and events.


Informing does not mean writing a curt email saying, “I am taking leave, and you cannot stop me!” Informing does mean sending calendar invites, adding leave to team calendars, and noting your absence on any process and planning tools that are pertinent to your work. Share with your supervisor as well as your team members so they can all plan for your absence.


When you are the first one on the leave calendar, nobody can say no. Additionally, planning in advance for longer periods of leave is also respectful so folks can figure out coverage plans and plan their leave for different times than yours. Planning in advance saves every office stress. And it allows you to use more leave.



3. Comply with any policies.


While I have “unlimited leave,” my employer still has some policies about how to use this leave. Regular personal leave may not exceed three weeks. (The company has other types of leave, like parental leave, that are not subject to this restriction.) Additionally, any leave over two weeks requires approval.


Given these policies, I keep my international vacations to a two-week maximum since I choose to inform when I am taking leave and do not care to navigate an approval process. However, I may use the “approval” avenue to use the full three-week maximum for a future important adventure. Either way, I recommend sticking to the rules on this one. Since unlimited leave is already a valuable benefit that provides much more freedom than most folks enjoy, working within its requirements is possible.


Aim for an ambitious level of leave while respecting the barriers the employer prioritizes. You will be a happier employee without the stress of provoking your employer, and your employer will have no reason to criticize the amount of leave you take.



4. Plan for your absence.


I already mentioned that scheduling leave in advance helps facilitate informing your employer rather than asking, but planning goes farther than scheduling. My supervisor and coworkers truly forget that I take approximately double the amount of leave as those around me because I create plans for how work will continue in my absence.


First, I reach out to a couple of my coworkers to cover my simple daily activities. As someone who helps a lot of folks with just about every IT and data issue they encounter, my return on investment is that everyone is willing to cover my simple tasks when I go on vacation. If you wonder about whether you could receive similar coverage from your coworkers, start working to become an indispensable employee.


Next, I acknowledge any large periods of leave (i.e., one week or more) well in advance and shift the schedule to accommodate my pre-planned leave. Owning your team’s calendar makes this easier, and allows you to do this on a greater scale. However, even if you do not control your larger team’s calendar, you can bring up your leave months in advance with the 1-4 people you work closest with on a daily basis to shift your specific priorities outside of your leave.


Finally, I create systems to facilitate coworkers who have to pick up any unforeseen responsibilities in my absence. This includes writing Standard Operating Procedures, creating websites that quickly guide folks to the correct points of contact for certain issues, and setting the basic away email to list the main folks that are covering my work.


I may be in Turkey right now, but my work is getting done as if I were at my computer in DC.



5. Say yes to more leave.


When you have a discrete leave allowance, you may plan your year and determine how you will use those 15 days: five for a beach week, four over the holidays, three for your friend’s wedding and wedding-related events, and two for shorter weekend getaways or half days.


But then your sister gets engaged, and her wealthy fiancé invites the whole family to Mallorca, all expenses paid, for a week to celebrate in July! Or you win free World Series tickets to games one and two, but the World Series is across the country and would require you to take at least three days off to attend both games!


Those are both quite spectacular, but the unforeseen once-in-a-lifetime events will appear. Your best friend decides to elope in Mexico and asks you to be the witness. Your brother gets divorced, and you just want to be there for him. Your child is in college and makes it to the national competition in whatever sport they play.


With unlimited leave, even if you already met your minimum leave goal, you get to say yes.


When I had limited leave, I had a spreadsheet to figure out how to stretch it as far as possible. I returned from Boston on the 5AM flight, changed in the airport, and arrived in the office (luckily one metro stop from the airport) at 7:30AM. My lack of leave often caused sleep deprivation. I also spent work hours finagling in my leave spreadsheet to figure out how to maximize the inadequate leave I had. By contrast, I arrive home from Turkey on Thursday, but I am not working on Friday because I do not want to work after flying home from Turkey!


To add even more incentive, each time you say yes to more leave, you actually increase your effective hourly wage. How? Your effective hourly wage is your salary divided by all the hours you work in a year. Keep the same salary, decrease the hours worked, and your hourly wage rises.


Take more leave, make more money every minute, and enjoy your life.

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