I've never been very good at knowing when to call it quits.

As a leader I think this is about the toughest call to make. There's no easy time to know when to wrap it up. No matter how much you try, you'll always leave a little leftovers in the fridge for someone else to clean out. That's not a great feeling. I still get anxious thinking about unfinished business from all the jobs I've held before. But I also think an elegant "baton pass" is just about the best thing ever to witness.

Culturally speaking, we do a pretty terrible job about encouraging people to move on in the job market. It's considered a "red flag" in your resume if you switch jobs too much. And even at the moment when you decide you might need to move onto what's next, there's this presumption that you've got to keep all of those indecisive, conflicting feelings and emotions to yourself until you have a real offer from another possible employer on the table.

Unfortunately, for many of us, this means the people who know us best at work (ie: our current colleagues) are the last people we can go to for advice when in transition.

You hear stories about bosses who turn sour on their employees when they know they are looking to move on. Managers who cry when someone on their team confides that they might want to work somewhere else. Let alone the manager who has the guts to look their teammate in the eye and open the door with the honest question: "How's it going for you here, really? Do you want me to help you find something else?"

This is hard enough in the messy middle. But for people at the very top, it can feel near impossible.

Who's in the trusted circle of the CEO enough to tap them on the shoulder and invite them to tap themselves out? As a leader, how is it possible to keep doing your job of showing up while also acknowledging that you might need someone else to take the wheel for awhile?

When I worked in venture I had the unique privilege of observing about a dozen CEO transitions in startups over the years. Some easy, some hard. I'm most impressed by leaders who know themselves when they've take things as far as they can. Even better if they manage to figure that out while still reserving enough energy to find someone else to take their place.

How to Normalize Quitting

As a fractional worker, I get a lot of "at bats" at leaving jobs. I wouldn't call it "quitting" exactly. (Anyone who's ever worked with me before knows I don't exactly disappear even after going off payroll.) But it is an important transition phase in any job that I don't think gets enough air time when we talk about business.

I've noticed that there are easy quits (ie: a self-contained project comes to a close), planned quits (which often include an internal training of transition period for someone else), and there are hard break quits (the worst from a "pit of your stomach" feeling kind, where the most is left unsaid or work left unfinished).

I think we should celebrate the quits in our lives as much as we celebrate the obvious wins. A quit means a conscious choice to make a change. We can learn a lot about a person based on the things they walk away from. As a leader, I don't care if it's your all-star employee or your least favorite slacker who's walking away -- a quit always means an opportunity to bring some new energy into a company or a group of people.

Here are a few things I think we can do to make quitting a little more palatable:

1. Get really good as passing the baton. I'm proudest of the "quits" I've had in fractional work where I've been able to backfill myself before leaving. This is a skill that takes time and muscle to practice. As a leader, you need to be able to both identify your own strengths that helped you succeed in that role and also your weaknesses against the company's needs so that you can (ideally) bring in someone who can do something a little bit differently. A baton pass should never be about treading water -- you need to find someone to move things forward. Easier said than done.

2. Encourage job "lifestyle" reviews for long-tenured employees. I think startups are generally ill-equipped to manage people who stay in jobs for four years or longer. Chances are, any long-tenured employee has had one or more life changes throughout the course of their work, and there may be intangibles about the way they do work that naturally change as a result. We should normalize the idea of talking about this with trusted managers without it feeling terrifying to the employee.

3. Implement "fractional quitting" as a new work norm. When you really think about it, the very idea of "quitting a job" is as outdated as the 9-5 work life. You had to quit because you literally couldn't be in two places at once. But today, you can. Something fun I'm trying right now (which I'll write about later) is a "baton pass quit" to a trusted friend who I'm still talking with regularly even though I'm no longer working there anymore. There are obvious benefits to this across the board. They get built-in advice from someone who's "been there, done that" and you get to feel good about passing on much-needed knowledge and advice to someone who literally is in your shoes. I'd like to see a lot more companies start to encourage "fractional quits" -- save 20% of your time for your old job, at least for the first few months.

I've never been very good at knowing when to call it quits. So I'll just leave it here for now.