How to Get the Guts to Actually Quit Your Job

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Quit Your Job

January 1 of this year was my very first day of self employment, a move I’d been planning for more than six months. I was all excited and feeling sparkly on that day, but to be honest the few days that followed were a little rough.

I went from being elated to scared to death, even though I knew my business income was solid and had been for six months prior.  I remember e-mailing John after feeling particularly anxious about my business income asking him, “Is this normal? Will this feeling go away?”

Of course, over time, many of my worries about self employment have been put to rest. I’ve learned that as long as I continue to work hard, things will fall into place. Just when you think it’s going to be a low month, something interesting happens like a post going insanely viral or someone asking for an interview. Other times, you’re waiting on someone to pay you or someone drops off the face of the Earth after they seemed really interested in your services.

Despite all the ups and downs, actually quitting your day job to pursue your dream is something that can’t be beat. Not everyone gets the opportunity to do it, but if you want to quit your job, here’s how to find the guts to hand in that two weeks notice:

1. Prepare Your Mind to quit your job

If you think the switch will be seamless, think again. Sure, there’s a lot of planning you should do. You’ll need to get your finances in order. You’ll need a solid plan of how you’ll make an income. It would be very beneficial if you already had the clients and contracts in place and just needed more time to add to it. By doing these things, you can make your move as seamless as possible but realize you’re going to have those moments of fear. Prepare your mind, and it won’t be nearly as shocking.

Side note: I was the most panic stricken on January 15. That was the day I usually got my paycheck (I got paid once a month) and of course it came and went without a nice, solid direct deposit. These moments will come and go but they all pass. Just keep working hard, keep pushing yourself to the edge, and you will be rewarded.

2. Align yourself with people like you

I’ve learned that being an entrepreneur is a personality type. There are just some people who aren’t happy unless they have about 10 projects going on at one time and business ideas swirling around their heads constantly.

When you talk to other people in your field who have the same goals and who made a similar leap, you get inspired and realize that you can quit your job too. Before I made my switch to self-employment, blogger friends of mine, Holly and Michelle, had done the same thing just a few months before and John was already a veteran. Reading about their journeys and seeing them work in the same field and make it happen gave me the confidence to do it myself.

3. Don’t listen to the naysayers

If you are ready, if your life is as prepared as it can be for the switch, what are you waiting for? It won’t be hard to build up the courage if you get pumped up about the freedom that’s just around the corner. Don’t listen to the naysayers. This journey is about you and your dreams. If we can do it, so can you. I promise!


Are you thinking about quitting your job? What’s holding you back? If you quit your job, what would you do instead to earn income?


Photo Courtesy of: Arya Ziai

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Catherine Alford is the go to personal finance expert for parents who want to better their finances and take on a more active financial role in their families.


  • FI Pilgrim says:

    I hope to follow your lead next year Cat, although with a slightly different emphasis. Thanks for writing about your “job-less” experience!

  • debt debs says:

    I can’t give up the security of that paycheque right now, but maybe when I get closer to retirement I will happily make this transition. It is encouraging to see you full time bloggers make a go of it.

  • I considered quitting my job for months before I finally did it. I just finally snapped one day. I’m so glad that I didn’t listen to all the naysayers. It was the best decision ever!

  • This is awesome Cat. Quitting my job is something I’d love to do in the near future but it scares the hell out of me. It’s good to know that fear is normal. I’m trying to get my online income to a level that I’m able to take make that switch. Hopefully in a year or so. We’ll see…

  • Michelle says:

    Great post! I worked on being as prepared as I could to quit my job. I eventually just had to force myself to tell my boss because I knew that was the only way I could do it.

  • Great tips, Cat! I haven’t quit my job, and actually never will (at least to be self-employed), but I feel like these are good tips for those moving to another traditional job as well!

  • Deacon Hayes says:

    I quit my job a year and a half ago to work for myself full-time and it is the best decision that I ever made. There is nothing else I would rather be doing!

  • You definitely can’t listen to the naysayers, especially since there are SO many more of them than the supporters and the biggest ones are probably related to you. If you feel something passionately and know in your heart that it is the right thing to do, then you need to trust your heart. It’s usually right.

  • Hey Cat, we have the same quit date! I actually quit January 1 this year and felt a lot of the same jitters you did. It took a few months, but that all went away. I love your plan. I think the most important part for me was drowning out the naysayers. Thanks for the great read.

  • Totally agree, dude. People get stuck in these jobs they hate and they can’t seem to get the balls to get out! They end up wasting their lives unhappy in these jobs. I think the third part is the most important — don’t listen to the “you shouldn’t” “you can’t” “I woudn’t” “you’ll never make it” people!!

    • Cat says:

      Yeah exactly! Worst case scenario you have business troubles so you go back out and get a job. For hustlers, the job hunt is not as hard as it is for others.

  • I definitely don’t have a problem with needing the “guts” to quit my job; I have a problem with having the same secure income and the same prospect for much higher income. My career job is relatively secure, transferable to other companies, etc. I would need a side hustle to literally explode to justify quitting.

  • One thing I’ve learned about quitting your job is that the type of organization you work for and position you hold may dictate a different approach to how you break the news. But generally, it’s best to schedule a meeting and let your boss know in person. It just makes a better impression and it shows respect, self-confidence and that you have strong interpersonal skills.

  • Noz says:

    Great article. Helps inspire the courage to do what your gut’s been screaming for you to do. But the fear of leaving a well paid job, with all the benefits and perceived security is overwhelming. When I actually envision handing in my resignation I am gripped with anxiety. And this despite the fact that my side hustle earns over 2x what I make at my current job. What the hell is wrong with me?! Need help getting over the edge!!

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