5 Ways to Leave Your Job Gracefully & Like A Boss


At some point in your life you are going to leave your job.

Every job has its halflife; a period of time in which the perfect opportunity loses its sheen and becomes another day at the office. (That is, unless you’ve truly found your calling. For which, I commend you…)

For example, a few years ago I worked in sales. In the beginning my daily routine was challenging and consisted of cold calling and upselling.

Because I had minimal experience with either, I had to learn from the ground up. While I was articulate and likeable over the phone, my delivery was not perfect. So every day I devised to beat the number of open prospects and closed sales I got the previous day by working on how I pitched my company’s products to others. Over time I increased our revenue by leveraging this product knowledge…

But it was slow at first.

Before I had a roaster of frequent customers, I had to develop relationships with purchasing managers in order to build trust (a little Shakespearean B2B courtship).

But I had a goal.

At its peak, I came to work with the same level of enthusiasm and perseverance each day. I was satisfied with my role. Week to week, I could see my professional growth in action.

I rewrote my pitch several times and then stuck with the one that produced the best results.

I grew a higher tolerance for rejection (hang ups) and even minimized the amount I received as I got better with pitching.

I anticipated all of the possible roadblocks to closing deals and had an answer for each one.

I even took on roles outside of my job description (unofficial bookkeeper for a few months) and mastered new software in the process (Magento, Microsoft Dynamics GP, Braintree), etc.

But after nearly 2 years, the well went dry.

The well is my role in sales and the water symbolizes the fuel it had given me every day. The passion, energy and euphoria.

Quite simply, there was no more room for growth. And before you ask if I tried to articulate my desire for growth to management, I did.

My routine became so predictable that all of the roads formed through neuroplasticity (via Wired) had been worn into a dirt path. I wasn’t learning anything new.

So, when I was in a good position, I left.

It was not an overnight decision (i.e. I left when I was in a good position). There was a great deal of preplanning that went into it.

To help you gauge your own security with your current role, I have devised a 5-point checklist on when and how to leave your job gracefully. This list is followed by a few tips on how NOT to make your grand exit.

Got any more? Feel free to share.

  1. No More Juice


A good day’s work will always come with a bit of stress. But a job should never become so routine that it feels like a chore. Or a bore.

If there is nothing else motivating you to get up every day, save a paycheck, I would reevaluate your position’s long term benefits. Personally, I aim for roles that are challenging; that will take some time to master and thus I will learn from every day. But I am also working on aligning myself with organizations whose work I support. Being passionate about a company’s offerings, mission or some other key aspect of what they do is essential to your overall sense of well-being and purpose.

Note: A job can be repetitive but not feel repetitive. The point at which repetitiveness becomes a depressing stagnation depends entirely on your own feelings. Are you passionate about what you do? If so, then the fact that it’s repetitive does not mean much.

However, understand that these feelings develop over time. Like water that gradually gets hotter, a job that was initially be “great” might turn into something else altogether later.

2. Money in the Bank

It goes without saying, regardless of how we feel about our jobs, we should never blindly leave one without having a safety net in place. An emergency fund is the backup plan you need to comfortably search for better-fit roles on your own terms. Ideally, you want to be job searching while you are employed. But everyone’s circumstances are different. Essentially, you want to save up your own cost of living (via Ally Bank) over the X amount of months that you will be searching for a new position. Rent + Groceries + Bills + Transportation (to interviews)..

The general rule of thumb is to have funds saved for at least 6 months to a year. Also take into account how long it has taken you to find a new role in the past.

3. Have Another Job Lined Up

Not so fast.

While most people are quick to start applying to new jobs, it is important to focus on the quality of roles that you are applying for. If you were unhappy in your last position, sit down and brainstorm what sort of roles you are interested in now.

What about your last role made you unhappy? Was it your job description or the industry sector?

Does it make sense to apply for the same role with a different company? If you are an unhappy burger-flipper, will a change of scenery really make a difference? Perhaps. But don’t make a mad dash towards your next gig. It’s not a race.

4. More Valuable Ways to Spend Your Time

The difference between a career and a job is passion.

If you are spending huge chunks of your time at work daydreaming about what you could do with all of that time — Start developing your app ideas into MVPs, finally get your small business off the ground, or taking courses to further develop your skillset, analyze the time that goes into your job and determine if the time you have left to devote to other things is truly worth it.

If not a part of your long-term career goals, your job should help you with your financial obligations while you pursue mini goals that will help get you to where you want to be; Until you can make your career your 24/7.

5. Too Attached/Afraid to Leave

Lastly, if you have found yourself in the grips of fear, unable to leave your job because you are not sure you can navigate the same rocky terrain to find a new one, you probably have an unhealthy attachment to your work and insecurity about your employability that is keeping you from growing.

Provided you have that safety net (new job or money) and a plan, take a chance and roll the dice. Have confidence in your skills and abilities.

Now for the Don’ts:

As for things you should definitely not want to do if you are preparing to exit from your job:

Don’t Burn Bridges. No matter how you felt about your job, leave as graciously as possible.

You don’t want to find out your last employer from Save-A-Lot is a 2nd degree connection with the technical recruiter from your dream company. Never give anyone a reason to give you a bad review. Edit: Though I’ve seen quite a few thought leadership pieces from folks on LinkedIn who think otherwise, and have recently come upon this quote:

“One of the hardest things in life to learn are which bridges to cross and which bridges to burn.” ~Oprah Winfrey

So, I am willing to admit that my thoughts on this subject may just my millennial optimism. I haven’t experienced the horror stories of employment yet. But anyways, my gut feeling tells me that departing from roles as gracefully as possible will benefit me down the road…

Don’t Ghost . If you haven’t already, offer to connect with your employers and coworkers on Linkedin. You never know when you might need their help or expertise in the future. (But, of course, this depends on the nature of your relationships).

Don’t Clock Out & Never Return. Give 2 weeks notice. Don’t just walk out the door. Follow through until the end. (Or, if you absolutely can’t give 2 weeks notice, at least call and say so?)

Don’t Do Anything illegal. Duuuh.

Lastly, Don’t Apologize…Expressing gratitude and giving ample notice ahead of your departure is a must. But you do not owe anything outside of that. Don’t let things linger. If it’s time to move on, move on. Never say, “Sorry” for doing something that is in your best interest.