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How to Take the Leap and Quit Your Job: The Best Way to Celebrate Leap Year 2020

Celebrate Leap Year With a Career Leap of Your Own

Since this is a blog all about career satisfaction, and today is Leap Day, I thought there was no better place or time to write about how to take the leap and do the one thing that some of you need to do in order to find that career satisfaction: quit your job.

February 29th comes around once every four years, so there’s something special about it. Does a Leap Year really mean we get an extra day to do whatever we wish? Well, that depends on how you look at it. Does it add an extra day to your life? No. But does it add an extra day to 2020? It sure does. That means we get 366 days this year instead of 365 days to reach our goals. If you’re unhappy at your job or unsatisfied in your career, that means you have an extra day to make some changes and take a leap.

What can you do with those extra 24 hours of 2020 (which can be spread out over as many days as you want), to reach your goals and make a career change?

When I was contemplating my own career change in 2018, I relied on so many resources to help me make the decision and finally take the leap. Here, I highlight my absolute favorites that I hope will help you figure out your next steps, too. What better way to spend your bonus 24 hours this year than on yourself, figuring out your future?

Resources That Helped Me Take the Leap and Quit Biglaw

From books to articles to podcasts, these are the resources that helped me the most when I was thinking about quitting Biglaw but didn’t know how and needed inspiration. I didn’t know anyone who had quit Biglaw without a “good reason” (to go to another job, to raise their kids, etc.) and I desperately wanted assurance that I wasn’t crazy for thinking about quitting my Biglaw job with no “good reason” and no plan.

A simple internet search will lead you to thousands and thousands of articles and books about how to quit your job. Some of these will give you advice about how much money to save up before you quit or how much notice you should give your employer, and while those resources will offer some helpful tips, they weren’t the ones that really addressed what I was struggling with.

I needed to know the unknown – what was going to happen when I quit and was I crazy for wanting to do so? What helped me the most at this time were the stories of other people who had made the leap and landed on their feet.

Reading and listening to a combination of these resources is what gave me that assurance and the courage to finally take the leap and quit Biglaw, and I’m so glad that I did.


1. Career Change, Joanna Penn

This book is chock full of tips and a step-by-step roadmap on how to quit your career (not just your job). If you hate your job (Part 1), want to improve your current situation (Part 2), and need to know how to change your career (Part 3), this book is for you.

2. When to Jump: If the Job You Haven’t Isn’t the Life You Want, Mike Lewis

This book won’t help you come up with your own plan, but it will offer plenty of inspiration, in the form of stories from others who’ve successfully done it, to take a leap and quit your job. The people profiled come from all walks of life so you’ll be sure to see yourself in one (or more) of them. It might just surprise you who. I felt the most connection to Rashard Mendenhall, a former NFL star who left it all behind at the peak of his football career to become a poet and a writer, so you never know whose story will inspire you.

3. Leap: Leaving a Job with No Plan B to Find the Career and Life You Really Want, Tess Vigeland

A combination of the practical and the inspirational, this is a memoir and guide to leaving – or rather, leaping from – a traditional corporate job without a Plan B. You’ll probably relate to her fear about leaving it all behind and the uncertainty of what she was leaping toward, and will take inspiration from the fact that she did it and came out even better on the other side.


1. Lisa Hoashi’s Story: Lisa was unhappy at her corporate job, so she packed up her apartment, quit her job, and set off on a year-long sabbatical that she never returned from. Sounds perfect, right? It wasn’t without missteps and hardships, but it all got her to where she is now and is an inspirational story for anyone else in a similar position. (Bonus: if you relate to Lisa’s story, she also hosts the podcast “Leap Like Me” that I reference below.)

2. Quit Without a Plan: If you (like me) need evidence or proof that it’s going to all work out, unfortunately, I’m here to tell you that that doesn’t exist. What does exist, though, is evidence of other people who have quit and how they’ve succeeded. This article highlights sixteen of those people and gives some great advice, like how you can use your lack of a plan to propel you forward instead of holding you back.

3. Familiarize Yourself With the Sunk Cost Fallacy: Are you frozen in place because of all of the time and/or money you’ve invested in your career? If you’re a lawyer, don’t you have to be a lawyer forever? If not, wasn’t law school and all of that money you paid (and are probably still paying in the form of student loans) a total waste? Law school is the perfect example of a sunk cost. It’s already been paid for and can’t be recovered. Instead of basing your decisions on sunk costs and letting those hold you back, you should be making your decisions based on what you want for your future. This article explains the concept a little more and will maybe wake you up and make you realize you can make a change, even if you are experiencing the sunk cost fallacy.


1. Leap Like Me with Lisa Hoashi:

Lisa interviews others who have taken career leaps and personal leaps. It’s pure inspiration for how you can do it, too, and I dare you not to find at least someone’s story that you can relate to!

2. Lessons from a Quitter with Goli Kalkhoran:

I was initially drawn to Goli, a former Biglaw lawyer, because she was an example of the type of “quitter” I wanted to be. I love how she’s taken the concept of being a quitter and turned it from something negative to something positive. She interviews not just former lawyers, but others, too, who have quit their jobs and moved on to something more fulfilling.

3. Why Not Now? With Amy Jo Martin:

A little bit of woo-woo and a whole lot of positivity (the perfect combination for a podcast, in my opinion), Amy Jo has the credentials to back up her advice (she started her own major PR company and represented the likes of Shaq and The Rock before she took a step back from it). Amy Jo interviews people and hosts solo episodes all based on the question: Why not now? What’s stopping you from taking the leap and quitting your job now?

My MVP: The One Book That Deserves Its Own Category

The resources above are all great, but if you are going to look into just one resource, read This Time I Dance, by Tama Kieves. Of all the things I read and listened to (and I devoured these and many more leading up to quitting), this was the one that made everything click for me.

Tama is another former Biglaw lawyer who left the law after a few years of practice and is now a life coach. She’s hippy and spiritual, and that might not be your vibe. But she is a fabulous writer and there’s something about how she retold her journey from the law to finding what she loved that just sparked something deep inside of me and finally helped me decide to leave Biglaw (even if I didn’t take the leap right away).

Even if you don’t read Tama’s book, do yourself a favor and ask yourself this one question to get your leap year journey started (it’s the question that Tama’s friend asked her when she was hating her Biglaw job and in the middle of a career crisis):

“If you’re this successful doing work you don’t love, what could you do with work you do love?

Take the Leap This Leap Year and Quit Your Job or Career – Even If You Don’t Feel Ready

If you feel stuck at your job or in your career, there’s no reason why you have to stay. We’re all looking for something different to help us figure out our next step. Hopefully, there’s something in one of these resources that strikes a chord in you and helps you take the next step and make your own leap, even if you don’t feel ready, because something good is definitely waiting for you on the other side.

How do you plan to spend your extra 24 hours of this Leap Year 2020? Will you use them to work on your own career leap? I can’t wait to hear all about it!

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