How to leave a job—Gen Z/Millennial Edition

Oct 17, 2019 · 8 min read

I’m both demographically and spiritually on the Gen Z/Millennial border, and a few weeks ago I made the very tough decision to leave my job. In fact, I’m writing this in between jobs now. The full context isn’t very interesting — the company treated me very well throughout my time, there wasn’t a single coworker in the office that I disliked working with, and my day-to-day work was far from being the worst day of my life, every day.

Anyway, I’m here to share the story of leaving my job, and advice on how one should do it in this day and age, based on actions I took. But first —

Why finish strong?

One of the guiding principles that my parents raised me on is based on the saying, “Never say that ‘from this water I shall not drink’”. It has its equivalents in other languages, stood the test of time, and its real-life application in this context is that you never know who you’ll work with or seek help from again, so it’s generally better to not burn bridges with your employer or coworkers.

If you are a good engineer or career climber in a highly-demanded profession, chances are that you don’t get your job from “applying online”. You get jobs by networking, you prove that you are a valuable addition to whatever team you’re on, that people love working with you. My belief is that if you come off as lazy, incompetent or just a bad teammate, you prune potential “nodes” in your network, “branches” of serendipity die completely, and you’re cutting your future self off from what could be fantastic opportunities. In fact — the opportunity for which I’d left my job in question — is the result of a fantastic working relationship that I built up with one of my former colleagues.

The easy choice to make when your foot is out the door is to “check out” and do just enough work to not get fired. That is okay, and it’s what most people do, but you run the risk of pruning those nodes, or even ruining the company if it is a small startup.

I’ve found that some of the following advice makes particular sense for leaving a startup, where departures can be felt the most, and even negatively impact the value created by that company in the form of second- and third-order effects: reverse network effects (people leaving when they see others leaving), key-person risk, slower product-to-market time, processes grinding to a halt, coordination problems left to an uncontrollable explosion.

Silicon Valley S4E10 spoiler: Jared, Pied Piper’s COO, “quits”. Richard leaves a truck containing critical objects open as they drive off, leaving said objects strewn across the road to Stanford. “This wouldn’t have happened if Jared were still here,” says Dinesh (iirc).

So with that context and guiding motivations, here are some tips for leaving your job in the most polite and reasonable way, that will be both good for you and the firm:

Leave with another job in hand.

Or minimally, at least a few months of “personal runway”. It seems financially irresponsible to leave without another job in hand, unless you just can’t take it anymore or the circumstances demand that you voluntarily leave ASAP (I’m sorry that sucks).

Leave after your stock options vest (if you’ve determined that you might exercise them).

Enough said. Who knows the hundreds of thousands of dollars (and well, taxes) you could miss out on if you leave before the closest equity grant date?

Leave at the beginning of the month if you plan on taking some time off.

Most company insurance policies should cover you till the end of the calendar month as the fees are typically deducted from your salary at monthly pay periods. A single accident during your time off can financially wipe you out. You don’t think it could happen to you, but I’ve had friends get into life-threatening accidents from skiing and ATVing, which are, you know, conceivable leisure activities during one’s time off.

View from my ATV near SLO. The speedometer is cropped out, so I may or may not have captured this while it was moving (I really can’t remember).

Be prepared for both financial and non-financial counteroffers.

Employers recognize (after the fact, sometimes) that their employees will leave for a better financial and/or day-to-day environment. Sometimes this results in a raise in cash or equity, a change in title, movement across teams. I received an interesting proposition:

I had recently gotten a raise, so I wasn’t expecting to get another one. Instead, I was given an opportunity to be on a different team (a greenfield development team led by the founding CTO, no less). In fact, it was suggested that I push my start date at my new gig by a few months, work on the greenfield team, and decide then whether to stay or to leave for good.

(Founders with key employees leaving: this might also be a creative way to get employees to stay and provide value for a bit longer!)

But my suggestion is to have conviction when you decide to leave. Even if your employer convinces you to stay, the promised new circumstances might be different than you expected. In a particularly toxic environment (not true of the one I left), others may have already written you off from their plans and trust may have been eroded. As a result of either of those, or your growing resentment towards the firm for making you stay, your motivation and thus efficacy may have been depleted without realizing it. Not to mention, if you had followed the first bit, “Leave with another job in hand”, the bridges you could have burned at the next job.

Tell them in person with an appropriate amount of notice.

Make sure your manager, tech leads, etc. are the first ones to know you’re leaving, and at least with two weeks notice. It’s the respectful thing to do. Gauge how critical you are to the organization — during your time, were you “someone who can take an idea from conception to life”, or in Keith Rabois words, “a barrel”? A core contributor? A line cook? A pencil pusher? — and from there, decide how much more than two weeks you should notify your manager and team. Not to brag, but I gave three weeks notice. (It is conceivable to me that you would experience a reduction in planned responsibilities and expectations as soon as you give notice to the team — I’ll leave those implications to be considered by the reader.)

Tell those people in person. Ultimately on the morning of my announcement, I scheduled a GCal invite named “sync” with my manager, my tech lead, and one of the founders with whom I had a close working relationship with. The description of the event was, “Sharing some news with the team”. Which is pretty much the professional equivalent of your partner saying “We need to talk”. To be fair, I couldn’t think of a better way to put it, but at least the obviousness diffused a bit of the tension I carried before the meeting.

The alternative to setting up a separate meeting is to say it during a regularly-scheduled one-on-one between you and your manager. I would’ve done that, but I wanted everyone to be in the room.

From The Genealogy of the Gervais Principle, which is just a portion of a brilliant body of work. If you read too much into The Gervais Principle, my recommendation is to read Showstopper! The Breakneck Race to Create Windows NT and the Next Generation at Microsoft, which was the antidote for me.

Keep track of everything you were responsible for, and find potential candidates to take them on.

The corollary to this is to proactively schedule a transition meeting with affected parties and prepare a document to keep yourself and others accountable.

The name of the document I made was called, “[My Name] Transition Plan”. And inside it was a complete list of the responsibilities that I’d picked up over the months. For instance:


This is a random tip if you’re leaving a high-growth startup, especially if you designed a lot of processes: along the lines of “continuing a machine”, writing process down could be the highest leverage thing you do.

Give tactful and honest feedback during your exit interview

This might get the most pushback. Some on the side of the employee say that there is nothing to gain from providing criticism during your exit interview. However, I’m of the opinion that it’s better to give organizations the opportunity to change for the better, and that it might make the environment better for those remaining. It’s reasonable to have been more reserved while employed. But the exit interview is a fresh and perhaps final touch point between you and the firm to tactfully provide your perspective and reasons for leaving. If you are respectful and the firm doesn’t take it respectfully, then it may not have been a great idea to be at the firm in the first place. Fortunately, my firm had given me the space and the psychological safety to share the feedback I had.


For better or for worse: the norms for company loyalty — especially among Gen-Z/Millennial knowledge workers — are changing. From a recent survey of me and my peers, our revolutionary late-stage capitalist battle cry sounds like: “We want impact, ownership, social status, mission, and the wifi password! When do we want it? After I finish my avocado toast!”

As business, technology, and communication processes become modularized and people get the ability to work from anywhere with an Internet connection, the market of employers to happy, productive employees may become more “efficient”, and so knowledge work may eventually sustain a gig economy-like structure. Average employee tenure trends over time hint at this. Articles written by other people have analyzed these trends in more depth. Ultimately, companies should have a continuity plan in the event of a key person’s departure, or some playbook for damage control.

I began this post with my argument for why finishing strong is a win for both the firm and your future self, and then I shared a bunch of practical tips (that I’ve acted on myself) for finishing strong. Hope you found this interesting, and feel free to reach out to me on Twitter.

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Written by


software engineer • more at • literally GPT-2 sponcon • Texas '18ish ➡️ SF

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +787K followers.


Written by


software engineer • more at • literally GPT-2 sponcon • Texas '18ish ➡️ SF

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +787K followers.

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