Updated on 07.05.17

Planning Ahead for Extended Leave, Financially and Professionally


Whether you’re considering a sabbatical or you’ve been forced to take extended leave due to a family or medical emergency, there are considerable challenges to overcome. While it doesn’t do any good to worry and stress about all the details, it also isn’t wise to just shrug your shoulders and assume everything will “work itself out.” In both cases, the best course is to plan ahead. With careful preparation and innovation, that trek through South America isn’t out of reach, and staying home with a new baby for an extra few months won’t lead to financial ruin.

That’s why we wrote this piece – to guide those facing the prospect of extended leave through the process of preparing financially and professionally. The goal is to make it through (and even enjoy) extended leave without returning to a mountain of debt and a career that’s in shambles.

Here’s what we will cover:


Understanding Extended Leave

What Is a Leave of Absence?

Extended leave is a term that is used to describe a particular type of “leave” which is short for “leave of absence.” The State of Washington defines a leave of absence as a period of time in which you aren’t performing job duties, but “the employer-employee relationship is continued, and you will be reinstated in the same or similar job when the leave expires.”

How Is Extended Leave Unique?

For the purpose of this guide, extended leave differs from regular leave or vacation in that:


Reasons for Extended Leave

There are lots of different reasons why people might need or desire extended leave, but they can be broken down into three categories.




How to Prepare for Paid and Short-Term Leave

Know the Law

Depending on your unique situation, your employer may or may not be required to grant you a leave of absence. It’s important to know where you stand legally so you can use the correct approach. For instance, if your employer is legally required to grant you leave, you might broach the subject by saying something like, “we both know that you have an obligation to grant me leave for this circumstance, and I want to talk about how we can work together to make sure my critical job duties are taken care of while I’m gone.” If your employer isn’t required to grant you leave, explaining the circumstance and the timeframe involved, and then asking (not demanding) for approval is much more appropriate.

The Family Medical Leave Act (FMLA)

Not every employee is eligible for FMLA leave. To start with, if your company doesn’t have 50 or more employees within 75 miles of your job site, it isn’t required to comply unless it’s a government agency (including public schools). Additionally, you must have worked for your employer for 12 or more months and averaged 24 hours per week during those months to be covered.

Note: Seasonal workers are covered since the 12 months do not have to be consecutive, but you cannot have taken a break in employment for more than seven years. Also, airline flight crew members have special rules.

The maximum amount of time that may be taken under the FMLA in a single 12-month period is 12 weeks (except for Military Family Leave). However, certain situations may allow you to take that time off in smaller chunks, or even work out an arrangement that involves working part-time.

The reasons for taking FMLA leave are limited. Below is a summary of some situations that are covered:


State Law

Always research your state laws as some may be more generous than the FMLA. For example, several states require certain types of employers to provide paid leave in specific situations such as the birth of a child.

Research Your Company’s Policies

Depending on your employer and your benefit package, you may be entitled to a certain amount of paid or unpaid leave for certain situations. For example, government agencies tend to have strict rules about when leave will or will not be granted. Some companies may even have a sabbatical program or other programs of which you are not aware.

If you aren’t sure how to find out about your company’s policies, email or ask your supervisor or HR department. Knowing your employer’s policies and history with granting leave will give you leverage (or at least a starting point) when you apply.

Communicate Well

Who to Ask

If your company has an HR department, correspond with a representative to determine what the application process looks like. If you work for a smaller company, you should approach your supervisor or boss directly.

How to Ask

Even if your employer is required to give you a leave of absence, it’s helpful to initiate the conversation with humility and look for common ground. Remember: The idea of an employee leaving, even for several weeks, can be stressful for your supervisor – be sure to take that into account and let him or her know that you will be doing everything in your power to make sure your critical job functions are still accomplished.

Communicate with Co-Workers

While you don’t need to give your fellow employees all the details, you should let them know when you will be leaving and when you expect to be back. If your absence will impact their job functions, be sure to do everything you can to set them up for success.

Utilize Applicable Parts of This Guide

While we won’t go into depth about planning ahead for paid and short-term leave, certain aspects of Parts 1 & 2 (which are written to prepare for extended leave) may also apply to this type of leave. Overall, the amount of planning and preparation that is necessary has a lot to do with the length of time for which you will be gone, and whether you will be drawing pay during that period of time.

Part 1: How to Prepare Financially


The first step to preparing financially is to make sure you have a clear, accurate budget. That process can be broken down into three major steps that are discussed below.

Determine Your Current Monthly Spending

Before you decide how much you need to save for your leave, determine how much you spend each month right now. If you have a frugal budget that you stick to, then you are set. If not, now is the time to begin. Start by tracking expenses and determining where each dollar is going. It’s also necessary to break down your spending into categories so you can see how much you are spending on food, how much you are spending on gas, etc.

Identify “Problem” Areas

Most people have certain a type of spending that are more difficult than others to control. Common problem areas include eating out, clothes shopping, entertainment spending, etc.

Once you’ve identified those areas, the next step is to consider strategies to reduce your spending. One such strategy is the envelope system which curtails spending by moving to a cash-based budget. The cash is deposited weekly or monthly into envelopes, and once it’s spent, no more can be used that week or month for that type of spending.

Create a Detailed Budget

After you’ve decided how to limit the spending in any problem areas, you can finish your budget. Remember that your total spending in your budget needs to be less than your income. The more you limit your spending, the quicker you can save for you extended leave. Be sure to track your spending (weekly or bi-weekly) to make sure you are on track.

Start Saving Now

While you can’t change the past, you can start saving now. If your leave is for an emergency or situation with inflexible timing, you shouldn’t get discouraged if you don’t have a large amount savings built up. Instead, choose to start saving immediately – even if you have never been successful, there are steps you can take to reach your goals.

Determine How Much You Need to Save

What will your monthly budget look like while you are on leave? Are there expenses like that will increase? For instance, if your employer covered certain benefits (like dental insurance or your life insurance premium), will you be required to pay for those while you are absent? Also, consider if your leave will necessitate more expenses than your lifestyle does. Prescription costs and travel expense are two examples that might apply depending on the reason for your leave.

You should also factor in expenses that will decrease while you are on leave. For example, if you are travelling the world, your day to day living expenses might be less in third world countries than in the U.S. If you are staying home with a newborn, will you have the time to buy in bulk and cook at home, or will you be able to save on childcare costs for your other children?

Another piece to consider is whether you can make a small income while on leave. Here are a few ways you might be able to make some extra cash:

  • Babysitting
  • Driving for a ride-share company
  • Teaching English while overseas
  • Renting out your house while away for an extended excursion

Not only do you need to determine your monthly spending and potential income while on leave, but you also need to factor in the necessity of an emergency fund. If you are cutting unnecessary expenses from your budget to facilitate your leave, you won’t have the wiggle room that you did before you tightened up your budget. If you don’t have an emergency fund, unexpected bills or expenses could ruin your plans or lead to severe financial hardship.

Consider Ways to Increase Your Ability to Save

The most straightforward way to create savings is to lower your monthly expenses. Here are a few ideas:

  • Pay Off Debt: If your extended leave is a voluntary decision, it’s wise to prioritize paying off debt before your leave. Of course, a car or house might be a longer term debt that isn’t realistic to pay off quickly, but eliminating credit card debt will free up a surprising amount of your budget.
  • Trim the Fat from Your Budget: Try frugal strategies like taking a lunch to work instead of eating out, making coffee at home instead of stopping by the coffee shop everyday, and evaluating every purchase on the basis of whether you actually “need” the goods or services (or if you just “want” them).
  • Give up Recurring Expenses: Consider working out at home or opting for Netflix instead of cable. The more recurring expenses you take out of your monthly budget, the more savings potential you develop.
  • Make Drastic Changes: If the situation requires to save up a significant amount quickly, you might have to consider some serious lifestyle changes. For example, you might need to sell your newer SUV and buy an older commuter car or get a roommate.
  • Find Ways to Earn Extra Income: Selling items you don’t use is a good place to start. You could also work a side job on nights or weekends. If you live in a large city, using your newer vehicle to drive for a ridesharing service can turn your liability (car payment) into an asset.

Adopt a Savings Strategy

A couple of good ways to save include setting up automatic transfers to a separate savings account (don’t touch that account until your leave), or using a savings jar. Seeing your money grow in front of your eyes can be a great motivation to save.

The Snowflake Method is another popular strategy. Whenever you don’t spend money that you budgeted for an expense, transfer it into savings or put it in the jar. The idea is that multiple tiny additions add up to a large amount and build momentum towards your savings goal. For example, whenever you skip the morning latte and opt for a home-brewed cup, you can deposit $4.50 into your savings account. The key is to take money that you budgeted for expenses and put it into savings on a daily or weekly basis.

Part 2: How to Prepare Professionally

How to Apply for Extended Leave

Depending on the size and structure of your company, who to talk to and how you approach the conversation may be different.

If Your Company Has a Human Resources (HR) Department

Start by requesting information about the company’s policies regarding extended leave (Step #1 below), and find out how specific aspects of pay and benefits would be handled (Step #5 below). Determine who to submit your request to, just be sure to follow Step #3 (speaking to your supervisor), before you go over his or her head to apply for leave.

When you correspond with HR, be vague about your reason to request information. It would be wise to hold off on informing them that you are planning on applying for leave. For instance, you could write an email that says something like, “I would like to know if the company has any policies or history regarding taking a leave of absence outside of what is legally required.” If prompted for more information, you can respectfully decline by saying, “I’m not ready to discuss personal matters at this time. I’m simply interested in knowing what the company’s policies are concerning a leave of absence.” Additionally, ask any specific questions regarding paid or unpaid leave that you may have.

If Your Company Doesn’t Have an HR Department

Ask your supervisor or manager who you should speak with to find out about the company’s procedures regarding leave. Depending on the structure of your company, the owner or hiring manager might be the person to whom you need to direct your request.

Step 1: Investigate Your Company’s Policies

Determine if your company has established policies that relate to the type of leave that you are needing or wanting to take. If your company has policies in place, adhere to those guidelines. If not, determine who you will need to speak with to secure permission to take extended leave. The sooner you know your company’s policies and history with leave-taking, the better you can plan.

Step 2: Consider How You Will Respond If Leave Is Not Granted

If your employer outright refuses your requested leave, how will you respond? If you are willing to resign, or you have no other option but to take the leave (if it’s a medical emergency that’s not covered by FMLA, for example), do your best to make your transition as smooth as possible, and discuss the possibility of rehire in the future.

If you aren’t willing to resign, consider your response should your employer refuse. You should be ready to suggest alternate plans, including:

  • Delaying Your Extended Leave: Are you willing to put off your leave to a time that would be more beneficial to your employer? For example, if you are planning a sabbatical, delaying by an additional six months may allow your manager to train someone to cover your job responsibilities while you are gone.
  • Working Part-Time: If you’re taking leave to deal with a family emergency that’s not covered by FMLA, you may be able to handle your family responsibilities while working part-time at your job for a period of time.
  • Working Remotely: If you are planning on staying home with an infant past the allotted time frame or traveling out of the country, can you still perform limited job functions from a laptop and use video calling to attend meetings?

Step 3: Speak to Your Supervisor

If the appropriate person to request leave from is not your immediate supervisor, consider giving him or her a “heads up” before you apply. Give a brief snapshot of your reason for the request and the potential timing – this will prevent your supervisor from being blindsided by an email from HR and will ensure that he or she isn’t misinformed about the circumstances surrounding your leave.

Step 4: Apply for Leave

After determining the correct procedures (or who to speak to if there aren’t any) be sure to start the application process as soon as you decide to take the leave.

There are two schools of thought regarding how employees should approach this conversation. The first is to have a face to face meeting where you outline your reasons for taking the leave, and what you are willing to do to make the transition as smooth as possible. This is followed up by an email outlining the reasons and formally requesting the leave.

The second approach involves first sending an email outlining your reasons for leave, what you would be willing to do to ease the transition, and when you would potentially return, and then having a conversation. This tactic gives your supervisor or HR representative time to process your request. Your in-person meeting can then focus on the specifics of your potential leave and strategies for ensuring that your job functions would be handled while you are away.

Regardless of which option you choose, be sure your conversations and correspondence have these characteristics:

  • Well Timed: Be strategic by scheduling the meeting at a time when your boss won’t be overly stressed. For instance, if your supervisor or manager has an important end-of-month deadline coming up, consider working to help achieve the goal, and then schedule the meeting at the beginning of the following month. Also be sure to indicate how long the meeting could take. For example, don’t ask for a quick 15-minute meeting before lunch – communicate that you need a more realistic amount of time to discuss an important matter.
  • Respectful: Always start by asking (rather than telling) – give your employer the chance to freely grant leave before discussing what recourse you will take should your request be denied.
  • Thought-Out: It’s not optimal to approach your employer and say something like “I kinda think that I want to take leave at some point in the future, but I’m not totally sure. How do you feel about that?” Be ready to clearly explain why you want leave, when you want it to start, and when you plan on returning to work.
  • Transparent: Your employer will appreciate knowing why you need to take leave. Be honest about your reasons and don’t try too hard convince your employer that it’s necessary. That can come off sounding insincere. That being said, you also should be careful not to share too much either. Your employer doesn’t need to hear the whole story about your messy divorce, or why you feel so burnt out. Give an overview of the situation and only include pertinent details.
  • Positive: Be sure to mention the benefits of taking an extended leave. While there might be less-than-optimal circumstances behind your request, there’s always at least one or two positives that you can highlight. For instance, If you want to take a sabbatical, you can explain that there are benefits to both you and the company. When you return you will be refreshed and refocused, which will help both your productivity and the way you interact with those around you. If you need to take extended leave to rehabilitate from a substance addiction (and you or your employer isn’t covered by the FMLA), you can speak to the increased level of productivity you will have when not struggling with addiction on a daily basis.
  • Accommodating: Consider the ramifications of taking the leave you are requesting – who will fill in for you? What critical job functions will need to be handled by someone else during your absence? Let your employer know that you are willing to work with them to make sure your absence isn’t detrimental to the company. Suggest a couple strategies for dealing with any obstacles, but also ask for his or her input as to how you can prepare your co-workers and managers for your absence.

Step 5: Discuss the Specifics

While this might require a separate conversation, be sure to get answers to any questions you have as far in advance as possible. Also be sure to confirm the details (like when your leave will start and end) with your management.

Some questions to ask might include:

  • Who should you periodically check-in with to update your timeframe for return?
  • If you have equity, will it continue to vest while you are on leave?
  • How will your benefits be handled (such as health insurance, life insurance, etc.)?

Getting Ready for Leave

Document Your Work

Create to-do lists, manuals, and whatever else is necessary to carry on your work in your absence. If you plan on being available should your replacement have any questions, make sure to set up boundaries for how and when that should happen. For instance, you might notate something like, “Feel free to call between 10 and noon if you have urgent questions. If the matter isn’t urgent, send an email instead.”

Communicate with Your Co-Workers

Be sure to tell your fellow employees what you want them to know about why you are taking leave. If you don’t shape the narrative, they will assume motivations and reasons that may not be accurate. Also, inform them of the status of any critical projects, and be sure to discuss what you can and will do to minimize the impact of your absence.

Inform Affected Customers

Let your customers know the general timeframe of your leave, and who they can contact while you are away. Set up automatic voice and email responses that direct customers to the person they can contact.

Don’t Burn Bridges

One of the most important pieces to successfully navigating extended leave is to make sure you don’t burn any bridges. Do your best to leave on a positive note, and if there’s any relational tension, be sure to resolve that as much as possible before you leave.

While on Leave

Since it can be difficult to walk away from unfinished projects, you may have to resist the temptation to stay involved with work. Unless you’ve specifically indicated that you will finish up certain tasks or projects while on leave, stay as hands-off as possible.

What you can and should do, is maintain and develop relationships with your co-workers. If you are going to be travelling, you can document your journey and interact with fellow employees via social media. Getting coffee or drinks with a few co-workers every once-in-a-while can really help to ease your transition back to work when the time comes.

Additionally, keep your employer informed of your timeline for return. Let them know that you are serious about returning (if you are). If your return date changes, be sure to inform your contact as soon as possible. If you decide not to return, be direct with your employer and explain your reasoning as soon as possible. This will increase your chances of being rehired in the future, or at least the potential of receiving a positive reference down the road.

Return Well

Don’t assume everything will be the same as when you left. Approach your first day back from leave in the same way you would approach the first day at a new job. Don’t come back and immediately start throwing your weight around. It’s important to communicate your appreciation to those who filled in for you while you were gone. Keep in mind that you may have to navigate some resentment at first. For instance, co-workers might say something like, “While you were off traveling the world, we were stuck here filling in for you.”

Take Action

While the idea of taking extended leave can sound daunting at first, developing a solid plan of action can put it within reach. Whether it’s your choice, or it’s forced upon you, plan ahead, and the obstacles can be overcome. Start preparing now. After all, the sooner you begin, the more prepared you will be for your extended leave.

About this resource:

Created on: December 02, 2016

Updated on: July 05, 2017