Ask Zoe


February 7, 2024

Should I quit my job?

Take your time, plan your next move — and never resign on a bad day

Zoe Hewitt

5 min read

I think I want to quit my job but, without another role to go to, the unknown is scary. What are my options and what advice can you give me on making the leap?

Decisions to move on are rarely easy, especially if you have built up tenure at a company. In tech, career trajectories run at accelerated speeds. The sense of team culture plus mission is often so strong that deciding to leave can be uncomfortable, emotional and — understandably — scary.

Worry can stem from many places: where the next opportunity will come from, how soon you’ll find it, what your exit will look like to the market, how your skills/experience will translate and whether you’ll ever find a place as good as your last one. This bundled fear, however, can prevent us from making sound career choices. Clarity of thought around why, when and how to move on is paramount. 

Maximise your current situation

Your first option is to stay by finding an alternate path, role or focus at your current company. There are highs and lows working for a fast-moving business and sometimes the feeling of wanting to quit reflects a temporary “stuckness”.


Moving past that requires a degree of situational awareness — is it the company you want to leave, or the role/project/team you find yourself in?

Switching cost is a real consideration, especially if there is strong alignment between what you’re great at, what you care about and what the company needs.

Before you leap, make sure you've mapped out any avenues of change that could reignite learning and satisfaction. Leave no stone unturned in reshaping your internal path — and never resign on a bad day.

When to know it’s time

The tough reality in startups and scaleups is that there isn’t an abundance of alternate role destinations to make a lateral move. The earlier the company, typically the leaner and flatter. Internal opportunity is constrained compared to working in a corporate environment. Without this option, you may be faced with no other but to look elsewhere. 

The most common reasons I hear for wanting to leave a company are: your personal learning curve starts to taper off; the business has outgrown you (very common for early employees); mis-set expectations over role scope or company growth upon joining, or a toxic team culture.

All of these can lead to unfulfilment valid enough to look elsewhere. 

If you find yourself in one of these situations, I encourage you to ask: what is the opportunity cost in staying? In other words — what is the value of the unseen missed opportunities if you remain at your current company.

This is hard to know without another role to compare against, but you should think about your time as being the most valuable and finite career-building resource that you have. Be aware of the “sunk-cost fallacy” at play — the tendency to stick things out because we over-value the irrecoverable time and effort that has already been invested into something.

This can lead to faulty career decision-making that hinges on the past, rather than rationally planning for the future — for example, a reluctance to leave a company because of your tenure, despite knowing you are not set up to thrive there.

These are tough decisions to make. But bending the arc of your career doesn’t happen without hard decisions. Every career transition I have made has felt uncomfortable in one way or another. The leaps that make us feel most discomfort are usually the ones that pay off.   

So you’ve decided to leave — what next?

Overcome psychological barriers to opportunity. It’s very normal to attach our identity and sense of purpose to the places we work, making it hard to psychologically detach when we decide to leave. Worry builds through negative thinking caused by unhelpful cognitive biases like catastrophising (“if I leave, no one will want to hire me”) and fortune-telling (“I’ll never find something great”).


This can lead to an unhealthy cycle of pessimism that impacts confidence and undervalues your skills, experience and expertise. Instead, focus on positive storytelling about your time at your last company, the impact you had and your core strengths. Be both courageous and optimistic.

Think like a designer. One empowering mindset I like to reference is the idea of being the “creative agent“ in your career. This concept is discussed at length in Designing Your Work Life by Stanford’s Bill Burnett and Dave Evans — a great read on how to apply design-thinking principles to your career.

With the belief that you can design the work life you want, you are able to replace fear with the “builder“ mindset that designers possess.

Thinking of your career as a product can provide an instant outlook switch: designers love problems and are really good at reframing them to become better problems to solve. Behaving like a designer helps you run a better discovery process by ideating options and prototyping your next move, helping you generate a set of actions to test out.

Expand your aperture. The best operators are typically heads-down focused on driving results and so pay little attention to external opportunities. This can make the world of opportunity feel really small when you decide to leave a company. Free up some time and energy for interaction with your wider network and the people who could be useful sounding boards as you figure out what comes next.

This doesn’t have to be people who can connect you to a job — in fact, broadening your set of experiences is the best way to start. It’s good to have some sense of direction, but don’t overplan networking. Act curiously, ask questions and start road-testing some of the new storytelling that you have been working on. 

Quit well. Resignation doesn’t have to be a powerless last resort. Burnett and Evans stress that quitting should be seen as a purposeful choice and a positive, generative experience. Your exit story is just as important as the new one you’re about to write, particularly in the tech ecosystem where references carry a great deal of importance. Plan to handover well, with good documentation for your successor and aspire to leave the company in a better place than when you found it. Reputation and relationships outlive jobs, and careers are long.

With a rational, optimistic and proactive approach, I’m confident that moving from the familiar to the unknown can become less scary. Life is too short to spend time in the wrong environment!  

Zoe will be answering questions from Sifted readers each month. Have something you want to ask? Reach out at

Zoe Hewitt

Zoe Hewitt is VP of talent at Sequoia.