How to Quit a Job

Credit @philip

My son’s beloved preschool teacher unexpectedly quit before Christmas. We live in an expensive area of the country and, understandably, it turns certain industries into revolving doors of employment. Who can live in the Bay Area on small salaries? Not many.

Though this is a really logical problem, her departure was a total shock to the community. I try not to coach people who aren’t paying me (and I often fail miserably!) but I felt compelled one day while I discussed her departure with the school administrator.

“I know it’s a surprise,” I said gently. “But I have to say, no one teaches people how to quit jobs.”

Except, in my work, I do. Whenever someone tells me they’re thinking about quitting their job, I tell them to stop the presses. I tell them to sit quietly and make a bucket list of everything they’d want to do before they left. Is there a skill they wanted to grow? A colleague they’ve always wanted to collaborate with? A client they wanted exposure to, a new responsibility to learn, some professional development opportunity within reach?

Make the list. Then, pursue the list.

See, you don’t have to change everything to change some things. We think we need to change employers because we aren’t actually parsing out the problem. Identifying what you want helps you raise your hand for those opportunities.

(By the way, half the time when you ask for the thing you want, you get it. I KNOW! It’s highly possible that you can get what you’re hungry for without changing who gives you a paycheck.)

While you’re identifying what you want, I will plant one more seed — are you changing jobs when you really should be changing apartments? Are you trying to fix your marriage by quitting your job? Make sure you’re trying to solve the right issue. You’d be surprised how often we solve the wrong problems because we’re afraid of conflict and Big Conversations.

Still think you need to quit? Time for a plan. (Incidentally, Monteiro has some good thoughts about giving more than 2 weeks notice. I totally agree.)

I have long advocated for the concept of alumni when it comes to former employees. If departures are handled well, there is no reason anyone needs to be angry and bitter. The work is simply no longer a match. (UNCLICK)

To the best of your ability, leave like a future alumnus. When I left my job before starting Plucky, I had to quit 12 times. That is not a typo! My departure conversations were with a variety of leaders, some happening in the office and some in nearby coffee shops. Whether you’ve had a rich growth path or a broken, bumpy road, it’s a unique moment to be grateful and say thanks. You learned something in that place.

Like with everything in life, you can’t control how someone else hears your words — but you can make the effort to be honest and real.

Once you work out a departure timeline, prepare yourself for a breakup period. Even in the most graceful of exits, it will happen because both sides start to retreat, pulling back from each other to blunt the pain. This is emotional survival at its best; it’s really normal. There will be a time months from now when you can come back to the office for a visit and all sides will be genuinely happy to see each other but first you have to get through an ending.

For, dear readers, the grace with which you deliver quitting news (or receive quitting news, for that matter) speaks volumes about your character. Don’t quit like a resource; quit like a human being. The way you handle moments like these in your career — the ones no one ever teaches you about — have huge potential for your legacy.

After all, it’s a small world… and your industry is even smaller.

Are you a manager who fears an employee quitting? Great. You’re a prime target for Plucky manager training in NYC this summer. We will talk about how to monitor your team members so you’re not caught by surprise and how to have hard conversations. Join us!

Diversifying the Career Race


I’m training for a 5k. I told my 4-year-old a month ago that I was starting to practice running so I could run a race before the summer.

“Are you going to win the race?” he asked. I told him no, that I wasn’t going to win and he looked sad.

“Maybe you’ll win, mom! Maybe you’ll be the fastest!”

I told him that it was ok by me if I didn’t win because that isn’t why I’m running the race. He was confused. Why would someone run a race if they didn’t want to win?!

That’s how my preschooler walked right into a lesson on managers and career path.

Why would a person run a race if they’re not trying to win? Oh, I don’t know. TO GET IN SHAPE? For the experience of seeing your family waving and cheering for you? To prove to yourself that you have stamina and discipline? To be among other people trying their best at something, to observe strangers cheering for strangers? (I get choked up just thinking about how sweet that is, humans yelling positive things at other humans who are trying. GAH.)

The general societal view of career path is that promotions into management mean winning. You start in the weeds, build expertise… and one day you’re asked to be a manager. Success! Now that’s news your mom can brag to her friends about!

Except that is super-busted.

Management should not be positioned as the reward for doing incredible work. It is one direction that employees could go in, one among many. As they move through their careers, they may dip in and out of management roles or avoid them entirely, depending on what the organization needs and what each person is hungry for. Does your employee want to work with humans, facilitating their growth and building team the way you build a product? Then by all means, move her into management.

But if an employee is reluctant to trade her expertise for a new currency, invite her to run a different race. Guide her to lean into being an expert in the field. Coach her to become a speaker on a topic that everyone else is avoiding. Identify a role that complements her life outside work so she can climb mountains on the weekend.

I know many miserable people who have the title they always wanted. Be the company where success isn’t about one path; choose the multitudes. It’s more authentic, it’s more interesting and it saves everyone from anxious competition for limited supply. There is space for all of us to succeed without one-dimensional wins or giving out participation trophies.

Because some of us are in it for a different kind of trophy.

Is one of your employees well-suited and hungry for management? Send them to Plucky’s manager training in NYC this summer. We’ll cover what success looks like as managers, how to talk about career paths on small teams and beyond. More details here!

Stuff the Envelopes

(courtesy a-evans)

In my first job out of college, I worked for a non-profit school. As part of my role I had to produce a quarterly newsletter that would be mailed to all 500 families. This meant that once a quarter, I picked up boxes (upon boxes) of the newsletter at our printer, labeled big envelopes and then stuffed them. It took a day or two; at the end I’d load everything up and drive it to the post office.

It was really brainless work.

There are aspects of our early jobs that we celebrate leaving because we are not robots: making photocopies, stuffing envelopes, filing, answering phones. Careers take off, responsibility shifts, experts and managers are born. Jobs beyond paper cuts sound like victory.

I coach managers and leadership teams in this zone. These people have tight schedules. They fly from meeting to meeting, pitches to 1:1s, sometimes still doing billable work along the way. Sometimes they are so tightly bound that they’re still checking email while we talk. (I can tell, folks. I can tell.)

I believe in them. They are trying hard and without exception, they are hungry to do good work. But one of the challenges with leadership is that you are asked to be hungry all the time. Managers rarely attend meetings because they’re always leading them. How fantastic! And how exhausting.

“Balance” is a word often used in the relationship between work and non-work hours. But you can’t just run out of gas at work and refuel totally at home; you need some balance during work hours, too — especially as you head deeper into management.

How, Jen, how? Aw, I got your back, managers.

1. Don’t delegate all envelopes. As you gain more responsibility, you’ll be asked to delegate and this is really important. Your success as a leader depends on your ability to value your time and make good choices about what should stay on your plate. That’s not an ego thing, that’s math.

So although you should delegate tasks that are best done by others, keep one or two small, mindless things on your plate for sanity reasons. Invoicing? Wiping down the whiteboard at the end of the day? Literally stuffing envelopes? Let yourself do these tasks a few times a week so you balance the intensity of your job with quiet moments that let you rest.

2. Follow. I don’t believe you can be a strong leader if you are never a follower, just like I don’t believe you can be a good teacher if you are never a student. I get my best ideas for teaching workshops when I’m a student in a yoga class or observing my son in his preschool classroom because I’m forced into follower empathy. I remember what it’s like to only understand part of the presentation, the anxiety of asking questions or group dynamics that are invisible to the leader. Practicing following makes you more helpful the next time you’re in the front of the room.

3. Use your emergency brake. Look: every once in a while, you need to bail and often it’s not as dramatic as you think it will be. A few weeks ago I canceled my first two calls so I could eat breakfast quietly at a diner with a cup of coffee. They were easily rescheduled and I showed up for my 10am in a MUCH better place than I would have otherwise.

I get the guilt that comes with canceling. But if you are going to be a royal pill in the next meeting, much better to reschedule while you take a walk than railroad all of your reports.

Because your reports are watching you, buddy. They’re learning from you. When you take good care of yourself, they see that workplace balance is possible for them too. You’re more relatable, more human and more engaging in meetings when you can admit the boundaries of leadership.

We can change the craptastic reputation of “managers” if employees are not always conflating leadership with stress and unrealistic expectations. You sanitize that word by leading by example. Management can be hilarious, inspiring and a privilege! So pull up a chair and ask the next generation of managers to pass you some envelopes.

Are you a manager? Are you craving envelopes to stuff because you’re a little worn out? Join us this summer in NYC for Plucky manager training. I promise to hold the room and let you practice following the whole time.