5 Lessons I Learned When I Quit My Job

Last week, I left the company that I had been a part of for nearly three years. When all was said and done, I found myself reflecting on my time with the company – both the highs and the lows; and came to the conclusion that the "difficult, but necessary decision" phrase I'd been repeating, wasn't so difficult after all. 

Don't get me wrong, the warm-and-cozy familiarity and the high of knowing the ins-and-outs of my role was enjoyable for a time, but both ultimately led the downfall of my happiness and my engagement in my role. At the end of the day, the most difficult aspect of leaving was saying goodbye to the team I'd grown to love, because despite the quirks, they felt like family.

Looking back over the last two weeks, I feel as though I've learned five valuable lessons.*
*While everyone's company, relationship with their team, boss and vendors is different, I've found a couple of these (arguably jaded) truths may haunt a majority.

1. Having "the conversation" with your boss never gets easier

In the eleven years that I've been in the workforce, I've had my share of jobs. In my younger years, I was definitely plagued with the all-too-familiar "I know everything and I deserve the world" millennial mentality, which isn't quite conducive to long-term success with an employer. Whether it stems from personal pride, not wanting to let them down, or the general awkward factor that comes a long with it, I still find it a struggle to have "the conversation" with my boss.

My greatest tip for success: follow the three c's: be calm, be courteous and be concise. Your boss doesn't need to know the ins and outs of your decision making, where you're off to next or what you think of them and their company. Show them respect, gratitude and your plan of attack in making the transition as efficient as possible and you're golden. Keep the conversation short and to the point — your boss and your anxiety-induced stomach issues will thank you for it. 

2. The environment can (and usually does) change instantly 

Whether this departure was a long time coming or something more spontaneous, you should be prepared to handle the instant change in environment like a real adult. There may be colleagues that come to resent you for leaving, whether they're jealous or upset that you're adding to their workload. Beyond that, you've begun your transition to becoming an outsider — you may not be a part of scheduled meetings, strategy brainstorms, etc. — and that's okay. Focus on buttoning up any of your pending projects, getting the new or interim staff familiar with your work and wrapping up any one-off assignments from your boss

3. You're never as prepared as you think you are

As I've transitioned into adulthood and taken on more corporate roles, I've made it a point to create guides, updated job descriptions and other documentation for my role, prior to leaving the company. For one, this helps my boss, team or replacement better understand my existing projects, workflows and daily tasks, but it also gives me time to reflect on what I've learned, and what I can apply to my resume or next opportunity.

Because my last role dealt with a complex system that I had the most experience in, I made myself available to my team to answer any questions after my departure. Even though I'm not a part of the team anymore, I still hope for the success of my old coworkers and the company. Despite spending the extra time to make sure that everything is in order, there's bound to be something that falls through the cracks. Try as we might, we're not superheroes, and it's entirely possible that minute details get missed in the commotion that is your last two weeks. 

In most cases, I'd recommend that you make yourself available, if even for a short time, to help by phone or email if needed. 

4. Fairy-tale send offs (FOR OUR GENERATION) are often just that, fables

It's time for a little truth talk: Millennials are the largest group in today's workforce — and while that may make some feel powerful, it's simply not the case. Before you come at me with flaming pitchforks, hear me out. We may think that we're rockstars, capable of conquering all and deserving of recognition, respect and cold hard cash; but I don't think we've quite earned the title just yet. Sure, there are millennials in the workplace that are visionaries, that run circles around teammates and that kill the game, so to speak — but a vast majority fall into the less-desireable category that society labels us as — lazy, entitled and foolish. Don't believe me? Look around the next time your in the office, I can assure you you're picking up the slack of at least one other twenty-something.

When it comes to parting ways with your company, I wouldn't expect cake, balloons and a company-wide signed thank you card. Because millennials are newer to the workplace, it means we're even more replaceable than other generations. Look at it this way, it would be much more difficult to fill a role of a Director with ten to fifteen years of hands-on industry experience, versus someone a few years out of college with a knack for using social media. (No offense 😇) 

If you're lucky enough to get a warm send off, count your blessings and move forward into your next chapter, humbled and ready to prove-yourself once more.

5. The dizzying array of emotions often ends with solace

Let's face it, making the decision to leave a company, finding a new role that aligns with your goals, prepping your current team for your departure and getting through all the last-minute fires is draining. The stress (and quite possibly the sweat and tears) all leads up to the moment that you walk out of the building for the last time and drive off into the sunset. This is the time to channel your inner Elsa and let it the hell go. Crank your favorite song, and ditch the stress — you're free!

Hopefully you've lined up another role prior to leaving (because adulting and stuff), so take this time in-between jobs to relax, unwind and prepare for the ramp-up of your new position. Pat yourself on the back for your wins at your last company — and more importantly, look at your areas of opportunity for personal and professional growth. Set your future self up for success and create a list of goals as you move into your next chapter.


Now, if you'll excuse me, I'm off to go soak in the Seattle sun! 😎

David Self