How to leap: advice on quitting your job


I grew up in a risk adverse, immigrant culture in which the idea of finding the work you loved was always counterbalanced by the idea of having a stable, steady career. When you’re young and uncertain, the easy choice is the one right front of you. It’s the path you fall into out of convenience, as in: This is what I did for two summer internships, so, this is what I’ll continue doing. Or: This job has good benefits, salary, and will make me feel like a real adult, so I’ll take it until I figure things out

But what happens, months or years later, when you realize that you wake up every morning to just “get it over with,” so that you can come home, eat dinner, unwind for two hours, and then do it all again the next day? What happens when you’re just living for the weekends, and after your weekends disappear, your Sunday evenings culminate in a predictable rhythm of small, existential crisis? What happens when each day feels like it’s slowly deadening your soul, but you feel too drained to do anything about it?

It doesn’t matter how you ended up here. What matters is that it isn’t where you really want to be. What matters is the fact that you can do something about it. In this post, I’ll write about two big things, drawn from my personal experiences (quitting my job and starting my own studio) and working with coaching clients through their career changes.  

Part 1 - Deconstructing what’s holding you back
Part 2 - 5 things you need before quitting

Part 1 - What's really holding you back? 

First, imagine your ideal career situation or longer-term goal— something that deeply excites you. It could be as vague as a warm feeling of fulfillment, accomplishment, or creative nourishment, or as specific as a particular role in a particular company. Paint it in your head clearly, and then ask yourself: what’s stopping me from actively pursuing this (or similar situations) with everything I’ve got? This is different than the question of “what’s stopping me from attaining this,” because it focuses just on you, and not external circumstances. Listen to what you hear in response. 

When I asked myself this question, my first thought jumped to my company-paid health insurance and my company-owned computer, then to the voices in my head reminding me of my inexperience and inadequacy when it came to design, and to running a business. My mental walls were made from my fears of “not ready enough,” and maybe even “never ready enough.” 

The thing to remember is that our mental walls were built by us, and no one else. Meaning that we can choose to take them down, too. I’ll briefly discuss 3 mental walls: uncertainty, fear, and inertia. 


Uncertainty is not knowing what you want, except knowing that it isn’t this. It is feeling directionless and adrift, with your head spinning with infinite options. It is not knowing what to expect of the future, and instead seeing it as a big, gapping void. 

A wise friend told me once: the future is only scary because it’s so abstract, whereas the present is concrete and tangible. In this situation you only have two choices: stay as you are (in paralysis), or take a deep breath, step into the unknown, and see what you can learn from it. The only way you can become at peace with uncertainty is to lean into it. Resolve to explore what you want to do with your life. Be brave enough to say, “I don’t know what’s going to happen, but I would like to find out.” Approach it with an open attitude of experimentation, and be willing to learn from it. 


Fear is a vague, amorphous thing that, like uncertainty, seems daunting because its boundaries are so unclear. To take the power away from your fears, the key is to be extremely specific with articulating what they are— the equivalent of shedding a flashlight on the monsters in your closet. Usually, “fear of failure” is the common problem, but even that is too vague. What does “failure” mean to you, exactly? 

So when it comes to taking your big leap, what is the thing which is most scary to you? What—or who—are you really afraid of?  

An example: Me quitting my job to start my own design and coaching studio. 

  • My shallow fear: I was terrified of not having a stable source of income.

  • My deeper fears: I was afraid of realizing, slowly, over six or eight months, that no one valued me enough to pay me, and that affecting my self-worth. I was afraid that, with unstructured time all by myself, my anxieties would consume me, and I would drown in a negative cycle of self-loathing.

Once I was able to articulate my specific, deeper fears, I was able to look squarely at them to say, no, these aren’t actually valid concerns. Not only is it completely hyperbolic, but knowing myself, I would never let myself feel that way. 

Being articulate and specific also means that I can set up structures for myself to help prevent the thing which I fear— in my case, doing all I can to get clients, structuring my time, and nourishing myself. 

The most realistic worse case scenario

What also helps in dealing with fear is to think more concretely about your most realistic worst case scenario. Realistically speaking, what is the worst thing that could happen to you? How bad/impactful is it really? Would you be able to recover from it? How much effort would that recovery take? 

For me, my worst case scenario is that I deplete my savings and end up back where I started right after graduation: jobless, and with an empty bank account. In other words, I didn’t have very far to fall, which was incredibly comforting. I said to myself: if this fails, I would just get a job and count this whole thing as a valuable learning experience. 


The rule of inertia says: once things are going one direction, it takes extra effort to change course. Keeping things the way they are is easier than starting over. Small details suddenly enlarge and seem really daunting: like where will I get health insurance, how will I break it to my boss, what will I tell my family? Ignore those details. It’s just your mind telling you that you’re afraid. 

The good thing with inertia is that it works the other way around, too. You just need to find what most excites you, and do more of what gives you momentum. For me in my journey into self-employment, what gave me momentum was taking evening design classes, and consuming everything I could— books, podcasts, e-courses— on building a business, then talking to people about it, then sitting down and making concrete plans. 

Brainstorm— what gives you momentum? Try those things. Soon, inertia will be working for you. 

In summary: 
At the root of your paralysis and inaction are the three mental walls of uncertainty, fear, and inertia. But the way to deconstruct those walls— not just deconstruct, but dissipate into thin air- is by taking small, tangible steps towards your goal. 

Start with something small— reading a book, setting up a meeting, talking about it with someone you trust— then let each step lead to something bigger. Each action will build your confidence, until one day, the “big leap” will just be another small step in the forward direction of your life. 

Part 2 - 5 things you need before quitting

It is easy to quit your job when you have another job lined up, much harder when the next thing is uncertain and hazy. Maybe you fit into one of these situations: 

1. Quitting a job because you’re unhappy, but you’re not sure what to do next
2. Quitting your job to start your own business
3. Quitting a job to focus on developing your skills, or even going back to school.
4. Dropping out of grad school to look for an industry job 

Whenever you’re on the brink of a big change, it’s easy to get caught up in the details, and make long to-do lists of things you “must do” before you feel “ready.” But, as I’ve gradually learned, “not ready” is a trap, an ever-expanding hole that swallows you because it runs on perfectionism and fear. Take a step back and ask yourself: what are the bare bones of what I need before I quit? 

Here’s my list of 5 essentials: 


First, you need to define what your goal is. Is it to find a new job that will make you happy? Learn new skills in preparation for a career change? Embark on a personal journey to find out what you want to do with your life? Build your own business and be self-employed?  Whatever goal you choose, you must be 100% committed to doing whatever it takes to make it happen. You must want it badly enough that you’d be willing to spend mornings before work, evenings after work, weekends doing it. 

My recommendation: try pursuing it outside of your day job, and see how committed you feel. Are you nourished and energized and excited, so much that you need very little motivation to keep going? I took design classes and started working with coaching clients while I was still at my day job, and I would wake up at 6 am every morning (even weekends) because I felt so excited. 

Before you take the plunge, you need to understand what you are giving up— stable income, sense of security, social approval— and you need to be completely convinced that it’s worth it. You need to feel that taking this next step is not only beneficial, but it’s absolutely necessary. It must feel so true in your bones that your confidence won’t be affected by any lukewarm responses you get from other people. Having resolve will also help you get what you need before you quit— for instance, it’s easier to save money when you know what you’re saving it for. 

Because if you’re not convinced that this is the right next step, how will you convince other people? One foot in and one foot out won’t get you very far. For further inspiration, read and reread this quote by Goethe.   

A plan  

You don’t need a week-by-week plan stretching out into the next year, but you do need a general sense of direction, a list of few big things that you’ll be tackling, and a specific idea of how you’ll be spending your days. If you’re quitting your job to figure out what you want to do next, then you should have a list of things you’ll be exploring to test your interests in various fields— classes you’ll be taking, people you’ll talk to, self-reflection practices you’ll do. Perhaps this post about the job search process could help. If you’re quitting your job to start your own business, you need a plan for branding yourself, doing marketing, and finding clients. 

A key component of your plan is the question of how you’ll structure your time— what will you do every morning, afternoon, and evening? How will you make sure you’re making the best use of your time and energy, and applying yourself fully to meet your goals? I wrote a post about daily routines for creative professionals (but really, for any self-employed professionals), and if you need help, write me, and I'll see if I can help. 

A financial cushion

Some people work well under immense financial pressure— they see it as having a fire to their butt— but I prefer a longer-term approach. I wanted to build my business thoughtfully and sustainably, instead of being desperate for any form of work just so I could pay the bills. So I worked hard to save, and I quit my job with 6-8 months of living expenses. 

How much you need depends on what your next step is, and whether you want to find other forms of income, like taking a part time job. But be realistic about how much you need to feel safe and secure. When you’re already doing something scary, it’s best to prepare for yourself a basic safety net so that you’re pursuing it with excitement and positive energy, instead of with fear and desperation.  


You don’t need approval from everyone in your life, but you do need a few people — maybe even just one or two people— who believe in you, and who are willing to push you. You need a few people you can go to when you’re feeling self doubt— because that will happen— and a few people who you can bounce ideas off of and work things through with. 

Sometimes it’s also nice to be part of a community of people who are supportive of each other— whether it’s in-person or online. It will require that you share your journey and vulnerabilities, but oftentimes, you’ll be surprised by how people respond. Taking big leaps like this isn’t easy, and most often, people will respect you for your courage. 

I’m not sure I would’ve found the momentum to quit my job— at least not so quickly— if it weren’t for a few very specific conversations I had with people in my life, and since then, I've surprised by the support I’ve gotten from my wider network. 

One thing I’ve noticed: sometimes it’s hard to get the nourishing support you need from your closest friends— at least initially— because they are your peers in similar life situations, and they will be afraid for you. Just like they are afraid for themselves. The advice we give is more often than not, a reflection of our own situations.


Quitting your job to find something more fulfilling means you’re giving up a lot of stability, and embarking into a world of unknowns. It’s natural to feel afraid and anxious, but we can’t let those feelings be our roadblocks. You have to get out of your own way, and to do this, you need to continually nourish and care for your well-being. This is why nourishing yourself is at the center of my ingredients for creative professionals

Nourishment might include: 

Remember that you are not a tool for your own ends, so you must not treat yourself like one. You are running a marathon, so not only is self-nourishment good for your soul and your happiness— therefore a worthy end in itself— it’s also the most efficient way for you to reach your goals; far more efficient than working until you drop, and beating yourself up about it. 

(Update, Jan 2019: I’m working on a project all about building nourishing practices into your everyday routine, called Camp Kening).

The iron gate that become glass

Let me leave you with a metaphor. 

After I quit my job, I felt like I had walked through a momentous threshold— a metaphorical gate. Back when I was behind the gate, packing my bags, getting ready to embark on my journey, the gate felt impenetrable; in my head, it was made from iron-wrought steel with spikes and guarded with armed men, and I was terrified.  

Now, writing to you from the other side, I look back at the gate, and I’ve realized that it was all an illusion— the iron gate is actually a sliding glass door. I can see right through it into my past. 

I see my past self standing there with her bags, and I think: if only she knew that she could walk right through. She doesn’t have to feel “not ready;” she doesn’t have to be afraid. 

I’ve walked right through, and nothing bad happened. 

And so can you.