8 Considerations Prior To Taking The Leap

“Unless commitment is made, there are only promises and hopes; but no plans.”

– Peter F. Drucker

With the inner confidence of quitting my job and taking a sabbatical established, some planning began taking place.

I found myself relaxing in the assurance of quitting in July. Even though the end date was seemingly far off, there was a light at the end of the tunnel to work towards. I noticed positive shifts in my mood and behavior at work and at home. My mind started planning and figuring out logistics—all of what happens when you commit to change.

Here are 8 considerations prior to taking the leap, including ones that I wished I had considered in retrospect.

1) Alignment with spouse

My husband was a key part in my process from the beginning. When you’re in a committed relationship, it’s important to ensure your significant other is on board with shared understanding on expectations, timing and scope of activities in making a leap.

We aligned on mid-July timing to quit and on the following six months to be income-free from my side. We established that the goal was to leave our cushion fund and retirement accounts untouched. We determined what amount I would still contribute to household expenses during my sabbatical. We discussed the places and duration of travel plans, which were primarily on my own.

What we weren’t as prepared for was the amount of emotional support I’d need from him post-sabbatical. I made the mistake (and I’d guess it to be common for others as well) of thinking that the quitting and the sabbatical itself were the big events, when in fact they were just the beginning of many more changes and challenges to come.

2) Budgeting

The biggest consideration and inhibitor for many people are the monetary implications of taking the leap. I was lucky to have no student debt and to have been casually but regularly saving for about a year (after recovering from wedding and first home expenses) by the time I committed to taking the leap. Even though losing my income reduced our total household income by more than half, the budgeting was easier in having a partner continue to make steady income, in buying a smaller house than what we could’ve qualified for, and in generally living below our means.

In my high-level budgeting exercise, I considered the following things:

My portion of base-level housing, utilities, general living and food expenses for six months
Travel, food and activity expenses for trips to see my family and friends, attend weddings, visit Prague and a couple other places
Some buffer for fun activities, unexpected costs, transition time, etc.

Coming from a finance background, it was somewhat surprising how unconcerned I was on the details of this exercise. I simply did a rough estimate—enough for me to see it was generally feasible—and left it at that.

In retrospect, I probably would’ve factored in more funds for the time it took to explore, assess and find income streams post-sabbatical. I did have some buffer planned, but the combination of unexpected costs (from my travels and miscellaneous items such as towing fees, etc.) and the length of time it took to start finding income sources post-sabbatical drew my bank balance to levels slightly below my comfort zone.

For planning purposes, I’d reserve at the very least three months of living expenses for post-sabbatical funds, and if you’re able to swing it, up to six months or even longer. I wouldn’t have stayed at my job any longer than I did but perhaps I could’ve reallocated more funds to that bucket from another area.

3) Timing of sabbatical

Conversations with my husband and rough estimates on the budget were the main factors for the timing of mid-July. Mid-July was chosen for many reasons.

Companies often have policies on a specific date (often through the last day of the fiscal year) you need to remain an employee in order to qualify for the bonus payout. For the months leading up to mid-June, I knew my team would be swamped with year-end and next year financials. In the latter half of June, the workload relaxes for the majority of the company with off-sites, half-day Fridays and fewer priorities.

The more relaxed pace, beautiful summer weather and extra time to save up more and take care of business made my chosen leap date all the more attractive. The only other thing I’d mention was I was fully vested in my 401-k match contributions. I’d reached this status far before my quit date, but it’s another timing aspect for you to consider if your company offers this perk.

I scheduled all the physicals, allergy tests, eye exams and dental cleanings that were covered under my company healthcare insurance coverage prior to my last day. Having committed funds to my HSA account for the year, I also paid and applied for reimbursement for as many expenses that qualified. You will have more time (generally until the end of the year or even the first couple months of the next year) to submit for reimbursement, but the date of the appointment or purchase needs to be within the dates of coverage through your company. For me, I was under the company policy until the end of the month of my last day of employment.

A pro-tip is that the available funds in your spending account are based on the total amount you’ve committed for the year minus any expenses you’ve already been reimbursed, but (for most people) the contributions are from each paycheck. It’s a use-it-or-lose-it spending account, so the more of it you utilize, the better. Therefore it’s to your benefit to check that you’ve at least reimbursed yourself for the collective amount you’ve contributed from each paycheck of the year, with the possibility of getting reimbursed beyond what you’ve contributed thus far.

After reviewing the eligible expenses covered, I got new glasses and six-month supply of contacts with my updated prescription, in addition to stocking up on eye contact solution, Band-Aids, sunscreen and various other items.

5) Other intentional spending

I made a point to not spend frivolously during this time, preferring to save up as much as possible for my sabbatical.

Yet I chose to spend intentionally on certain things such as upgrading my cellphone, knowing that the better camera and features would come in handy during my travels and other adventures in this new phase of my life. I also planned on buying a new laptop (having held onto an oldie over the past 5 years), but my husband thoughtfully collaborated with other family members to gift it for my birthday. In addition to new glasses, I cut my long hair short and dyed the ends, a drastic hair change that is common for people to do when they’re ready for or going through a change in their lives.

Other than that, the wallet remained relatively closed. There were fewer trips made to the mall, morning lattes on only the super tough days, and less happy hours in the months leading up to my leap.

6) Vacation days

Most people accrue vacation days with each paycheck for the year (with potential carry-over from previous years depending on the company) and get paid out for any unused days by the last day of employment.

This is a good thing to keep tabs on, particularly if you’ve used up more vacation days than you’ve accrued and will need to pay the company back. If you have vacation days left and are in need of more funds, this is an excellent way to get more cash.

In being comfortable with what I’d saved up and fried from the hectic workload of the previous two months, I opted to take a week of vacation in early July and effectively use up the vacation days accrued by mid-July. The day I got back from vacation was the day I decided to turn in my notice.

7) Working until you leave

When I committed making the leap in May, the first couple weeks afterwards were tough. With my new level of readiness, it was a struggle to deal with frustrating situations, people or issues when I knew I was leaving in a couple months. Part of me simply didn’t care.

But the other part of me still did. As I get older, I believe more and more in always treating others with respect and consideration, even when they do the opposite. I’m for maintaining bridges when it comes to other people, because you just never know when you might run across them again. The world is truly small when it comes to who knows whom.

Instead of focusing on the fact I was leaving, I focused my energy on leaving on good terms. This helped immensely in continuing to do good work, pitching in for my team, and having (at times, even more) compassion for co-workers who called me frantically during the monthly planning and year-end periods. I also started documenting my processes and files more fully in preparation for my departure. Knowing that someone on my team would likely need to pick up my responsibilities in the gap between hiring someone new, I wanted to set up my team for as much success as I could.

I had my limits though. I didn’t need to work long hours on certain projects or special requests anymore. During busy estimate and year-end weeks, I worked as much as I needed to fully support my business teams, but I took advantage of the down periods when I could. And guess what? No one noticed. In fact, people seemed to more greatly appreciate the support and service I provided on the key items.

Even when fair and ethical intent is assumed, a company will always consider its best interests first when push comes to shove; employees should use their right to do the same. I prioritized the timing of my quit date to my advantage as detailed above, and was firm on giving the standard two weeks’ notice. Some people choose to give more notice, and depending on the situation, that may be a good thing for both parties. Other companies may appreciate the longer notice; others may escort you out the day you give your notice. In my case, I knew it would be an awkward time, and so the standard period was right for me.

8) Planning of sabbatical activities

I certainly considered many things as listed above in preparing for my leap. Yet for what to do during the sabbatical itself, I didn’t plan much of anything until the first official day of unemployment.

Part of the reason I was less concerned on the details of budgeting and planning of my sabbatical was due to the whole point of making this change. In the absence of knowing what I wanted to do, I had committed to making a change. I had no clue what I was going to do during and after my sabbatical. The plan was to—for the most part—not have a plan, to be open to exploring the possibilities.

In retrospect, this was just fine. To create space for something completely new, you have to make space first and oftentimes without knowing what is to come. Many of the plans I cooked up during my sabbatical ended up falling through. In ambiguous settings, I found that plans are useful to a certain extent, but they are easily rendered useless depending on circumstances outside of anyone’s control.

Deliberately not planning anything was easy to do in the rush of preparing for and wrapping up projects before my last day of work. As I found myself with idle time and many open possibilities beginning on the first day of my sabbatical, this ended up being more difficult for me than I anticipated.

Overall, the 8 areas of consideration listed above helped me in preparing to quit my job to take a sabbatical. In retrospect, there were a couple things I might’ve considered in more detail but I have no regrets. In making a potential leap of your own, take what’s useful for you in the list above, don’t sweat the rest and go for it!

Up next, some realizations from quitting my job.