The Magical Benefits of the 'Quitter's Mindset'
People & Culture

The Magical Benefits of the 'Quitter's Mindset'

Ellen Chisa is a renowned product leader and blogger who quit Harvard Business School to try something new. It worked wonders. Here's what happened.

Ellen Chisa knew she had to quit Harvard Business School. She looked out the window, and back down to her desk where a full-time offer letter from Lola sat, awaiting her reply. It didn’t matter that she’d only finished her first year. Or that most people she asked said it was a mistake. She knew it was time to make a change, and she did.

Chisa made the decision fast, but not rashly. It wasn’t the first time she had quit (and it wouldn’t be the last), so she had a framework to think through it:

  • She didn’t know what she wanted to get out of the Harvard experience, so she didn’t know how to prioritize her classes. There was missing context.
  • She would've definitely chosen the Lola opportunity over HBS had it arrived earlier. This she knew stone cold.
  • The Lola role would give her an experience she had prioritized for a long time — the ability to grow a product team.
  • She could always go back to HBS. There would be no chance to join Lola at such an early stage again.

This is how Chisa’s brain works — in systems and lists. She uses them to steer her life, personally and professionally, and it lets her spot patterns. In particular, knowing when to quit and when to say no has made a massive, positive difference in her trajectory. It sounds counterintuitive, but these decisions have made her career as an influential product manager and blogger possible. Here, she shares her best advice on when to quit and say no, and how to use the space this creates to do what truly matters.

The Little Known and Vastly Underestimated ‘Quitter’s Mindset’

“Leaving Kickstarter was so much harder than leaving Harvard,” says Chisa, who was a leading product manager at the crowdfunding company. “When you love your co-workers and your office and the work you do every day, it’s nearly impossible to leave. But working there became core to my identity, and realizing that is when I knew I had to let it go.

She became so attached to the company that she was nearly convinced she couldn’t do anything else. She’d joined because she's passionate about helping people support work they care about. She expressed that through building a more personal discovery experience (letting people find the projects they most identified with) and that work was done. “I kept thinking, ‘How am I ever going to do anything as good as this again?’"

I had to quit to put myself in a position to believe in myself.

She also felt the creeping stagnancy that comes with being unwilling to change the things she had already built. “When you work for 8 months on a project, it’s hard to go back and change it even if you have a hunch that you should,” she says. “That’s when you know you’ve stopped seeing things with fresh eyes.”

These were the two indicators that pushed her to leave Kickstarter, but there are several other key lessons she’s learned about when and why to quit, and what to do next:

When You Can’t Fix It

It turns out it is possible to know too much. When you get too ingrained in one role, you start developing blind spots. You might know intuitively that something's broken, but you won’t be able to see truly original solutions.

“At Microsoft (where she started her career), I would get migraines all the time because I knew things were suboptimal and needed to change,” says Chisa. She spent a lot of time pondering how she could make things better in her role. What would that look like? “I looked at all the answers I was coming up with and realized I was only trying to make change within the structure that already existed. It was time to go.”

Don’t get Hijacked by Impatience

Labeling what you’re feeling as impatience is the first step to avoiding this mistake. You might have a lot of different feelings that make you want to quit — antsiness, an unsettled stomach, FOMO, envy, dread. Make sure that these aren’t impatience in disguise, says Chisa. Why are you really feeling this way? Ask yourself these questions:

  • Am I not learning new things? Is that my fault or my company’s fault?
  • Do I disagree with how my co-workers are doing things? If yes, have I truly tried to change their minds?
  • Do I trust the leadership here?
  • Do I feel blocked, and if so, why do those roadblocks exist?
  • Have I given myself enough time to adjust? To learn? To find the right advocates/mentors/teachers/allies?
  • Is it just that the honeymoon has worn off and the real job has started?
Early in my career, I thought this gut feeling of impatience was always right, but that’s definitely not the case.

“Sure, there are sometimes reasons to leave a company after 8 days because it was sold to you entirely differently during the interview process, or it’s a clear mistake," says Chisa. "But the more common flip-side is that you might hate a new job for the first three months or even a year only to have it actually turn into what you wanted.”

She’s spent a lot of time studying and speaking to fresh graduates who are just joining the workforce. It turns out that most people simply have a very tough first year. “They aren’t used to sitting in a chair all day. They’re used to cram cycles, not a sustained cadence of things to do. It can be really disillusioning,” she says. “And the ugly truth is that this isn’t just about recent grads. Every new job environment has a different cadence, different demands, personalities that might make you want to quit, no matter where you’re at in your career. That first year can be brutal and deceiving.”

When you start feeling unhappy in your work, you owe it to yourself to get specific about changes you could make for it to get better, and to develop your own innovative solutions and experiments to try. No matter how warm and fuzzy the culture, your co-workers and boss are not therapists, says Chisa. It's not their job to respond to your discomfort.

“You'll succeed if you get yourself to focus," she says. "Figure out and write down exactly what kind of work you want to do. Is that valuable to your current company? If not, keep looking. If so, what argument can you make to your boss to pivot in that direction? You’d be surprised how many mature professionals haven’t really thought about this with any depth or rigor.”

When you ask for a change, always frame things positively. Don't say, 'My job is terrible! X, Y and Z must change.' Go in there and say, 'I see a new opportunity for us...'

Set a Deadline for Yourself

If you suspect you want to quit at some point (even far in the future), set a deadline just for yourself to step back and reflect. It could be the beginning of the next quarter, the next year, or even at a certain age (I’ll think about this when I’m 30, for example). It can be arbitrary. The milestone is what's important. Treat it as a trail marker to double-check that you're on the right path in life.

“When I was at Harvard and I started wondering if it was really for me in my first month there, I actually put an event on my calendar for March that said, ‘Do you have a really great group of friends yet?'” says Chisa. “That was the only way I thought it would pay off to stay and not quit that first year. It also took the weight of the decision off my shoulders so I could breathe easier and process things better. In March, I did, and I laughed at how much time I had spent worrying about the decision in September.”

It can be really handy to have forcing functions scheduled for the future. It allows your brain to work through questions and problems subconsciously without putting a ton of pressure on you to know what you want right then, she says.

Remember, You Own Your Story

A lot of people are discouraged from quitting even when they should because they’re worried about ending on a sour note. “Let’s say the worst happens and you really do depart without doing everything you wanted to do, or in a way that feels like you disappointed people. Unless you really torched critical relationships, that doesn’t mean your experience there was a wash,” says Chisa. “You have to fix your eyes on what you want to learn next, not what you failed to accomplish in the past.”

The way you tell the story of this experience will no doubt change over time, and you can decide proactively to change it. It doesn’t have to be a story of failure or missed opportunity. It can be about where you were at that stage of your career. What your personal best was given your education and experience.

Chances are in 10 years, you’ll have a great deal of empathy for yourself and what you were capable of doing back then.

So why agonize over it in the present, or worse, let it dissuade you from making a positive change now?

“When I left Microsoft, I felt much differently than I did five years later, and even that was radically different than how I feel about it now,” says Chisa. “I went from devastated to bitter to fine to even grateful for lessons learned. You don’t need to tell a bunch of people how you feel or why it’s fine. You don’t need to get into all the details of your transition — even in job interviews — all you need is a clear, accurate narrative that you know you control. Maybe it’s just, ‘It was my time to move on, I’m still processing it and learning from it.’ That’s just fine.

Saying No with Grace and Certainty

Saying 'no' is a tool to do the few things that matter to you very well.

“It took me an embarrassingly long time to say 'no' with any confidence,” says Chisa. “In high school, you’re successful because you take on and do so much. But that’s not what makes you a success — or even an interesting person — in adult life.”

Most people have their full-time jobs and one or two other things they like to focus on. This sounds limiting, but it’s both true and fluid. Your job can change and your external interests can change. Nothing is permanent. And missed opportunities always make way for others.

Saying 'yes' too often comes at the detriment of the things you love to do,” says Chisa. “You can’t say you’ll sleep less, because then your thinking will be worse. Everything impacts something else. Tradeoffs are necessary, but they’re also your tools for building a life you actually want.”

At work in particular, it’s really easy to get bogged down into day-to-day tasks. But you won’t grow if you don’t carve out time to prioritize where you want to go next, what you want to learn, and how to help your teammates think through the same thing. You have to take time out from fighting fire after fire to see the big picture, and that occasionally means letting some fires burn.

So how do you make these calls? Chisa has some ideas to offer:

Abide By the 80% Rule

The rule is: I can only let myself work at 80% my full capacity at any given time.

This has been a huge source of success for Chisa, but it requires saying no a lot. It's powerful because it let’s you say yes to the most special, biggest needle-moving one-off opportunities that come your way.

“An incredible woman engineer I had long admired emailed me out of the blue one day to ask if I could refer any interesting people for a dinner she was hosting,” says Chisa. “I had the time to do it, so I did, and ended up getting invited to the dinner myself. And since I had the time to go, I ended up meeting all of these big name product managers and writing an article on the discipline of product management that turned into one of the most important things I’ve ever written. It all stemmed from having that time.”

Opportunity compounds.

The greatest example of the 80% rule in her life is that it allowed her to start writing.

“I was sitting around on a Saturday morning and thought, ‘What if I wrote down all the email newsletters I subscribe to in a list and published it?’” So she did, and to her surprise, over 100 people read it over the next few days. “I was so shocked, that I thought I’d write something else, and I ended up building a bigger and bigger audience. Now my writing has made a bigger difference in my career than my product work, and I would have never started if I was constantly engaged wall-to-wall with other things.”

Saying No Helps You Trust Yourself

This is something Chisa also discovered during her time at Microsoft. When she first started, there simply wasn’t that much work to do. “It was actually stressful to have so much free time,” she says. But then she taught herself to cook. She started going to the gym. She spent more time with friends and got involved in a variety of activities.

“I feel like I was forced into free time and got to see everything that blossomed from it,” she said. “It’s interesting. Before that, I never really trusted myself. I always assumed if I had time off I would watch Netflix and do nothing. I learned that when I had time to myself I could be even more thoughtful and productive.”

Now without the benefit of quite so much free time, Chisa knows that saying ‘no’ will provide her with the fallow periods she needs to remain creative and think about what new things she wants to try and learn. Without saying no, she’d surely overextend herself and lose the ability to really strategize her next moves.

Saying No Reveals Your Strengths

When you give yourself permission to say no to everything that doesn't truly appeal to you on a gut level for an experimental trial period, you can start to recognize patterns. For Chisa, she realized that she didn’t like massive events and parties with tons of people. “When I don’t know anyone and have no specific goal in mind for events like that, it’s really exhausting for me,” she says.

Saying no to things that sapped her energy prompted her to be really honest with herself about her strengths, abilities and dislikes. “I always try to make sure the things I do give me as much energy as I’m putting into them,” she says. “Those are the things I want to say yes to. For example, a lot of people feel exhausted and stressed out by writing. For me, that’s a regenerative activity. I learned that about myself when I started paying attention to the things I said ‘no’ to.”

If you’re going to experiment with saying ‘no’ more often, it’s valuable to record data. What types of events do you get the urge to decline? What requests from others? Why? Write these things down to get a better sense of your personal landscape. What do these things have in common. Where do you always say yes? Why? This is one of the best ways to find work and relationships that truly fit you. Of course, you always want to keep trying new things and growing, but if you're looking to prune back or re-invest your efforts, this is a good way to find out how.

Finding the Space to Create Your Ideal Fate

Chisa has a concept she calls “Ideal Fate” — it’s that life you could have where you wake up every day excited about what you need to do. How do you define it for yourself? Think about the average day you’d want as part of this fate, and get really detailed about writing it out. Writing things down always helps process them on a deeper level, in her experience.

“In my average day, I’d like to wake up without an alarm, have time to write, and then alternate between working with people and working on my own ideas,” she says. “I’d like to do my best work before 4 p.m. because I know I start to be less mentally productive later in the day and I want high-quality social time.”

When she got specific about the look and feel of her ideal life, she knew she needed to have a job where she’d get to shape her own schedule.

If you have a job that doesn’t fit the rhythm with which you want to live your life, you should commit to learning what you can from the experience so you can ultimately move on to something that does.

Sometimes it’s not that easy to visualize an Ideal Fate, especially if you have no practice. A good place to start is conducting a life audit, Chisa says. Here's how:

Make Your Own Heat Map

One way to figure out what you want in your life is to physically stake it out. Get two different colors of Post-It notes and a Sharpie.

Start with one color and write down specific things that are on your mind. For example, Chisa jots down ideas she wants to write about, but also bigger concepts, like her concern over a lack of artistic outlet or things in her life that have recently changed. “The important thing is not to judge anything that you’re writing down,” she says. “Nothing should be good or bad. Just what’s top of mind for you. Just get it all out of your brain.”

Once that’s done, try grouping your Post-Its into common buckets. Maybe you’ll have a health bucket with any fitness goals or concerns. You might have a technical skills bucket with a new programming language you’re learning, etc. Take the other color Post-It and label these groups with this umbrella theme. You’ll probably end up with two or three major themes at the end, and having this macro view will help you see theareas that deserve your focus. (Think of the Pareto Principle, where 20% of what you do actually deserves 80% of your energy. This is a smart way to find your 20%.)

For Chisa, whenever she’d run the exercise, she’d notice she was creating a lot of Post-Its around writing and speaking goals, even though her primary occupation was product management. “It was really helpful to see some of these areas of emphasis emerge,” she says. “Even if you don’t know where to start to get better or achieve a goal, it’s so critical to see what’s truly important to you.”

She suggests selecting one personal goal and one practical goal from what you’ve mapped and pursuing next steps over the course of a time-bounded three or four month period. To get better at speaking, she met with people in her life who she knew were good at it and picked their brains. She also focused on an intermediate step she identified in her Post-It exercise: Responding better to perceived criticism — a stumbling block standing between her and freely writing and speaking on topics that matter to her. She might not have discovered that one without the exercise, or knew that it was blocking her larger goal.

The Wisdom of Others

“It’s always helpful to ask someone who you really respect in your field what you can learn to make a bigger impact in your work,” says Chisa. “Very few people ask that question, but would get incredible answers back if they did. You don’t have to ask people who are far senior to you — just someone with experience equal to or greater than yours. You’ll almost always be surprised by what they say.

To get better at growth marketing, one of her past areas of interest, Chisa scheduled a number of informational interviews with growth marketers in her network. In addition to interviewing them about their experiences, she also asked them each to provide a list of resources she should read to get a better grasp on the field. This paid major dividends, and quickly.

Extract as Much as You Can from Your Current Role

“One of the best things you can do is figure out what your company is best at,” she says. “The reason I started writing more seriously is because it was a value that was really celebrated at Kickstarter. Good writers were really championed within the organization, and I was always around a bunch of people who were really good at it — people I could rely on to grow myself.”

She helped others do the same. One of the most talented community managers at the company expressed interest in product and shadowed Chisa opportunistically. She also used their time together to ask many questions about community dynamics and best practices. “Learning from your current environment doesn’t have to be a big dedicated effort,” she says. “Just take the time to really think about what you want to learn next and identify the people who can help.”

Prompt Yourself to Take Action

Kickstarter also encouraged Chisa to do a lot of personal research. At one point, she was looking into different writing tools for a work-related project and she stumbled upon the app Day One.

She’s now set it up to prompt her every day at 1 p.m. to write down her thoughts. This, more than anything, has helped her build her writing habit and stick with it.

“Most days I write things I don’t publish,” she says. “Sometimes I write some raw, personal things. Some days I write about things I see happening in tech. If I feel really strongly about something or I like the direction it’s headed, I might turn it into a public post.”

The important thing is having a regular prompt. A lot of people never write because they’re waiting to have a good idea. What they don’t know is that the simple act of typing or writing the words will help them connect thoughts and lead them in new directions toward the right idea. Things very seldom dawn on your without putting in some pre-work.

Using prompts isn’t just a tool for writers. Anything you want to practice, or any mental or physical muscles you want to build, can benefit from scheduling regular time to make it happen. Rain or shine. No excuses.

Reframe Regret

“It might sound cliche, but a big question you should continually ask yourself when faced with any opportunity is if you’ll regret not taking action,” says Chisa. “When you’re 70, how will you feel about having not done whatever it is?”

She goes a step further, abstracting the action from herself to gain more clarity. “Whenever I wonder if I should write something or not, I ask myself, ‘Would it have helped me if someone else would have been brave enough to write this two years ago?’ Asking if I would have benefited from someone else doing something always leads me to taking selfless action. And it also gets me to do the harder things I might shy away from otherwise.”

She uses a similar technique when deciding what she wants to do or learn or where she wants to go next. “This might sound odd or even counterproductive, but I take time to write down what I’m jealous of. Who are the people I’m jealous of? Why? Because of their jobs? Their experiences? What are pieces of writing I’m jealous of? What do all of these things have in common?”

She channels her envy into positive action. If someone else did something that inspires jealousy, there’s usually no reason she can’t do it too. Maybe she didn’t know she wanted it until she saw it on someone else’s LinkedIn or Facebook. This has actually served as the launch pad for many of Chisa’s dreams and adventures.

Something as innate and strong as jealousy is a voice that should be listened to as long as it's motivating.

Do the Next Right Thing

“When you’re young, it’s easy to get paralyzed by worry that you’re a sham, that you’re not keeping up, that you don’t have the title you deserve or you’re not making enough money,” says Chisa. “But it turns out the best way to solve all of these problems is to just start doing.”

But don’t try to do it all at once. Make your goals small enough to be manageable. Full reinvention is impossible. Instead, it’s the gradual product of small wins against small goals that help you gain personal momentum.

Even if what you want to do is big — solve a major problem, start a company, make significant impact — you want to focus only on that one next step.

“Think to yourself, what is the smallest unit of achievement in the right direction? Maybe it’s shipping a product that makes you proud,” she says. “Shrink your goals down to the one thing that makes immediate sense. Then find the next thing. Then the next. When you connect the dots, you’ll see how far you’ve come.”