The Financial And Professional Moves To Make Before You Take An Extended Leave

The Financial And Professional Moves To Make Before You Take An Extended Leave

Quite often, when the topic of extended leave from one’s career comes up, it’s in the context of having children. People often want to spend a few years at home with their children when they’re young, returning to the workforce when the children are entering their school years, or even continuing to stay at home and providing a homeschooling environment.

Photo by Atlas Green via Unsplash.

That’s one big reason for such leave, but there’s another reason as well. Some people want to take a period of extended leave to build a business or chase other creative pursuits, while still others simply want an extended break.

My cousin and her husband, who I’ll call “Nina” and “Craig,” plan ahead often for extended breaks. Multiple times over the past two decades, Nina and Craig have taken time off from their careers to go on adventures. One time, they walked the length of the Continental Divide. Another time, they walked the length of the Appalachian Trail. Yet another time, they set off on a cross-country bicycling adventure. Each time, they planned ahead for the excursion, left their current positions on the best possible terms, spent a year or so on their adventure, and then went back to their regular lives afterwards.

At the same time, one of my closest friends, who I’ll call “Kevin,” walked away from his career for a two-year break during which he hoped to launch a woodworking business. During his spare time, he had developed a plan for this business, and he made financial choices along the way so that he could spend two years either making or breaking that business. Unfortunately, his business didn’t take off like he hoped and he’s back in his previous career path.

When I left my own previous career in 2008, I didn’t know whether it was going to be for an extended leave or whether it was a permanent change. I left on great terms, giving my boss plenty of notice and setting up as much documentation and information as I could before I left (I literally created a “wiki” of my work practices). I intended to spend that time focused on my family, but in the margins of that time I intended to keep building up The Simple Dollar. In a few years, it became clear that I had built something stable enough with The Simple Dollar that it could effectively become my career for a while.

What do each of these cases have in common? They all involve people choosing to take extended breaks from their career to try something different, and there are a lot of specific elements that they have in common, too, if you look closely. Here are some of the strategies that all of these stories have in common.

Build a Very Clear Budget

When you make the decision to move forward with an extended leave at some point in the future, your first step should be to build a very clear budget so that you know what this will cost. Like it or not, that’s going to add up to a lot of money. This is not a cheap proposition. Here are some things to think about while planning.

How much will you need to live on during this period? What is your true monthly cost of living? Furthermore, what money will you need to support whatever it is that you plan on working on? You can start by looking at your average monthly spending right now, then multiplying that by the length of your intended leave.

How will you pay for things like health insurance? Make absolutely sure that you’re covering irregular bills as well as the expenses that are currently covered by your employer. Walk through all of those expenses and know what you’re going to need to cover.

What about an emergency fund, so that an unexpected event doesn’t destroy all of your plans? Unexpected things are going to happen. Make sure that all but the worst events don’t derail your plans. You do that by having some significant flexibility in your budget, which means saving extra money that serves as an emergency fund.

Live Well Below Your Means While Preparing

The savings for this plan is going to have to come from somewhere, and the way you’re going to be able to build it up is by living well below your means as you prepare for the extended leave. If you can find ways to cut, say, 50% of your living expenses, then you’re suddenly able to save 50% of your take home pay.

Try all kinds of frugal strategies, even ones that seem kind of extreme. Completely cut the cord when it comes to television service. Eat all of your meals at home and take leftovers to work. Buy store-brand everything. Use mass transit to get to and from work and sell off a car if you can. Move to a smaller home or apartment. There are many strategies you can use here.

The more frugal strategies that stick, the lower your savings goal becomes as well. Remember, whenever you permanently lower your living expenses, that means that your savings goal becomes lower, too, because you’ve reduced the cost of each month that you’re trying to cover.

Have a Plan for Your Time, Too

While you’re getting your finances in order and saving up for this big idea you have, start thinking about how you’re going to spend your time, too. It’s very tempting, once you’ve taken a burden off of your shoulders, to just idle for a while, and that idling can turn into a long term pattern. If you take an extended leave and do nothing of value with it, what was the point?

If you’re going to start a business, develop a thorough business plan. Don’t just think about it. Write it. Revise it. Find mentors that will look at it and give you suggestions. A business plan is there to help you think through all of the potential pitfalls of a business idea, so take it seriously. It’s your blueprint.

If you’re going to chase a creative endeavour, treat it like “work.” Make sure that you’re planning to spend a lot of time every day on that creative endeavour. Plan those days out now. Even better, start practicing your skills now in your spare time. Make drawings, write short stories, write some code — whatever it is that you want to do, start honing the underlying talent.

If you’re going on an adventure, plan at least the framework of that adventure. When will you leave? How long will it actually take (with some extra time thrown in to handle unexpected events)? What will you actually need on this adventure? What preparatory steps will you need to take to pull it off? Make a packing list. Make a timeline of things you need to take care of. Do the thinking now so you can jump right into the “doing” later.

Don’t Burn Bridges; Do Everything You Can to Leave Them Intact

This is probably the most important principle behind all of these stories. When you step away from your current career path for an extended break, don’t burn bridges. Do everything you possibly can to step away in the most positive fashion possible.

Give plenty of notice. Don’t just show up, drop a two week notice on someone’s desk, and then stroll out the door. That will almost always harbour negative feelings. Instead, when you give notice, give plenty of lead time so that the process for finding a replacement is as clear as possible.

Document your work. Make sure that you have thoroughly documented your work as much as you possibly can, so that someone else who comes in to replace you can pick up the threads easily. Make sure to show all of this documentation to your supervisor so that they’re aware that you took many steps to make the transition smooth.

Maintain positive relationships. Even if you’re frustrated by workplace relationships, take an extra effort to make sure that they remain positive during your final months and weeks at work. Don’t leave with an angry rant against anyone, even if you feel it’s justified. Be positive with everyone in your final days. Then, try to maintain some of those relationships even after you leave, even if it’s just through social media.

Make Sure You Have a Clear Path to Return

This is the flipside of the “don’t burn bridges” strategy. You want to make sure that the door is open to your return, so take those steps now as you’re thinking about leaving.

Talk to your supervisor about the prospect of returning at the end of your timeframe. What would you need to do to maximise the chances of that return? What small steps can you take now to make it possible? What about a few steps even while you’re gone?

Don’t let your knowledge completely atrophy while you’re gone. Spend at least a little time each week keeping up to date on the changes in your field. What new things are coming down the pike that you need to be aware of? Things will change while you’re away.

Maintain those connections. One great way of doing this is to start a blog or an Instagram about your adventure and share it with your old coworkers and supervisors. This keeps you as a real presence in their lives. Tag them in your posts sometimes and respond to any comments that they leave. If you remain at least somewhat on their radar, your return will seem much more plausible for everyone.

Final Thoughts

Walking away from your career in the middle of the journey can seem as scary as possible, but if you plan for that departure carefully, don’t burn your bridges, and keep the door open for a return, you’ll find that your adventure will have a much greater chance of giving you life-changing results while still keeping a bit of a safety net in place.

Good luck in wherever your adventures may take you!

Planning Ahead for Extended Leave, Financially and Professionally [The Simple Dollar]

Trent Hamm is a personal finance writer at

This post originally appeared on The Simple Dollar.

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