How to Quit Your Day Job

Jenna Kutcher 

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January 25, 2019


I was 23 years old, shut in a windowless office, wearing red and khaki and clocking ten hour days. I was miserable, anxious, and questioning if this really was my “dream.” I get a lot of emails daily but  this is one I see the most: “How did you gain the courage to leave your corporate job and how did you build a plan to finally make the leap?” Trust me, I see you, I hear you, and I still remember those same feelings you’re facing. Perhaps you’ve been working day and night on your side hustle and would like to make it your main gig. Maybe you just know that corporate ladder climb isn’t for you. Or it’s possible that you landed what you thought would be your “dream” job and it’s turned out to be more of a nightmare.

Getting free? Putting in your notice? It’s all you dream about but you’re stuck on how to actually make this a reality, how to actually quit your day job. I’ve been there and looking back on my journey of quitting my day job, I realized I took a few major steps that I’m sharing with you to encourage and empower you to be able to make this decision, if it’s right for you, too.

Make sure your business is legit

Already got a side hustle? Collecting money for it (even if it’s $10!) If you’re running a business or wanting to start one, it’s important that you treat it like one. Make sure you’re set up for legal and financial success. Repeat after me: this is NOT a hobby. If this is going to be your income and future, let’s make sure you do all that you can now to set yourself up for success later. There’s nothing worse than getting a year or two into your business and then backpedaling because you didn’t do things right at the very beginning.

Actionable steps include filing your business with your state or getting an LLC. My best advice? Hire an accountant to get professional advice on your options, what will make the most sense for you, and the correct order in setting these things up. I also recommend opening a separate bank account specifically for your business and creating a budget. If you’re doing commissioned work or offering a service, make sure you have a solid contract that has you covered and also consider a client management system to get your workflows and processes streamlined from the start. Take these steps seriously, they require an investment up front but if you’re ready to go full time, you should be willing to invest in doing things right! I promise you’ll be so glad you did.

Fill your calendar first

A deal I made myself before making the leap was that I needed to match my salary so that I wouldn’t take a giant financial risk in order to pursue my dreams. In order to match my corporate paychecks, I needed to book 25 weddings before leaving my corporate job. I burnt the candle on both ends juggling 50+ hours a week in the corporate world and building my business in every spare hour that I had. I worked right up until that wedding season to save as much money as I possibly could before exiting.

Not every business is going to be able to book an entire year out in advance, but make sure you have a solid plan for how you’re going to replace your income if it’s detrimental in making your ends meet. Define what “enough” looks like for you, because maybe you’re willing to make sacrifices to take the leap or you are comfortable with a lower projected income at the beginning. My point is that I don’t recommend making the leap without having a financial plan and goal for your business. I wanted to protect myself from having to take any kind of work to make ends meet and be able to pursue the work I loved the most. Do everything in your power to secure clients, orders or work before making the leap to give you that extra boost of confidence when making this decision.

The big question: health insurance

It can be hard putting in your notice when you’re used to having benefits like health insurance offered through your company. If you’re married and can hop onto your spouse’s plan, make that move now so when it comes time to leave your corporate position, everything is all set and ready for you. There can sometimes be a delay in coverage, and you don’t want to find yourself without insurance, even if it’s for a limited time, so plan ahead.

If you’re like Drew and I (or single!) and are self-employed, check out Christian Healthcare Ministries and read this post all about what to do for health insurance when you’re self-employed. This has been a great solution for us as we’ve navigated that “insurance” question that can hold people back from being able to leave the security of their job.  Do your homework because you have options available to you, choose what works best for you and ensure that you are set up before you leave!

Have a backup plan

Looking fear in the face and quitting your day job can be scary as heck. A lot of times our fears can hold us back from really going for those big dreams on our hearts. I remember feeling like I was going to puke when I wrote my letter of resignation. I don’t want fear to have a grip on you, so I want you to think through what you would do if your business failed. Even if it’s not your ideal situation, sometimes having a clear vision of what would happen, what your next steps would be, can make things less intimidating.

When I realized that if I did happen to fail, I would be okay, and it took a lot of the stress and anxiety out of the decision. I didn’t burn bridges at my corporate job, I worked hard through the end and I had experience and a degree to fall back on! I had to just make the leap and know that even if “failure” occurred, I could make it work and find another job. Was that my ideal situation? No. Did I work as hard as possible to make sure that didn’t happen? Absolutely. But simply knowing I had a safety net, a “contingency plan” helped me sleep at night and gave me the confidence to make the decision to work for myself.

I am not an extraordinary case! I had zero connections, lived in a tiny village away from home, and was burning the candles from both ends working the corporate job by day and building an empire by night. Being self-taught doesn’t mean you have to be paid less and looking back, I am proud that I recognized that from the very beginning. There will be a lot of “fake it ’til you make it” moments (heck, there still are!) and a lot of days of uncertainty, but when you feel unsure of your call, remember the one who called you in the first place! You can do this, you deserve to chase your dreams, pour into yourself, invest in your business, set yourself up for success!


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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