THE BLOG

ENTREPRENEURS

Dear Jenna: I Want to Quit My 9-5 Job

May 1, 2016

•  

DSC_1829

Dear Jenna, 

My question for you is this.. How did you gain the courage to leave your corporate job and how did you build your plan to finally make the jump? I am in the same position at 24 years old, unhappy with my role, manager, and mundane routine at my corporate job in Milwaukee. I want so badly to be my own boss but need the courage and proper game plan in order to execute!

Thanks so much!

Wanting to Leap 

Hi there, Wanting to Leap. I was excited to see your question come through, because it’s the question I get asked the most. To think about being 23 again and taking that giant leap out of the corporate world and into my own home office (or my bed!) I want to first set the stage a bit for you: before handing in my resignation letter, I had never quit a job in my life. I was terrified, I had my mom proof read it, I felt like I was going to throw up. While it’s easy to pretend it was an easy leap of faith, it was anything but that. Being three years deep into my corporate career that started fresh out of college, it was a gamble but the more that I thought about it, the more I knew I needed to go.

Before I made the leap, I did a few things to set myself up for success! 

  • I hired an accountant and filed with the state as an LLC: I wanted to be too legit to quit and make sure that I was starting out on the right financial foot and with some guidance. They have been instrumental in guiding me through each financial year of business!
  • A graphic designer helped design a logo for me: while I couldn’t afford to have a custom website, I ran a blog with this logo on it and knew that I needed to post consistent work! I made business cards, a Facebook page, and this helped establish a brand and reputation.
  • Don’t go into debt for your business, ever: I used my corporate job to help fund my creative endeavors and it was a slow process! I bought cameras from Craigslist, pinched pennies, and made sure that when I did profit, I was re-investing back into my business.
  • Leverage advertising to help find clients: I was living in a village of 1,200 people, I knew no one, I had zero connections, and I was working around the clock. I invested hundreds each month to get my name out and fill my calendar, it worked and after that first year, I didn’t have to pay to advertise anymore!
  • Fill your calendar: Before I leapt, I had matched my salary. I worked up until my wedding season started. I knew I needed 25 weddings to match my corporate salary so I hustled and booked 25 clients. That gave me the affirmation that I would be getting paid for the next year and had time to make it work! This made making the leap less risky and way easier!
  • Insurance switched to Drew’s employer: I knew I couldn’t leap without having insurance, so we switched our insurance over from my employer to Drew’s before I quit. It ended up being a giant blessing because I had to have an emergency foot surgery a month before I quit and we had double insurance! God is good!
  • Look fear in the face: It’s scary as heck, but when I realized that if I did happen to fail, I would be okay. I didn’t burn bridges, I worked hard through the end, 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.

Taking that leap will look different for everyone. For me, I needed to know the net would be there when I jumped. For some, jumping and making it happen works better. I loved the security of knowing I had a full calendar and while that letter was hard to hand in, I never looked back. In my fifth year, I still feel blessed every single morning to wake up and report to the world’s best boss (me!) My best advice is to set yourself up for success and have sound business practices in place so that you can free yourself up creatively. While photographers rock out the creative process, the business side of things is usually where the trouble occurs so make sure that you are legal, you have systems, you aren’t in the red, and you’re ready to hit the ground running and shout from the rooftops that you are a photographer!

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, and let me know how it feels when you can finally say, “I am a photographer!”

Have a question? Join my tribe to ask me! Click here to get a pep talk on Monday! 

 

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. To and Fro says:

    Such great advice. Thanks Jenna!

  2. Marie Therese says:

    Good advice! I really appreciate how you talked about being responsible and laying some netting for youself BEFORE you made the leap. It makes it more relatable and applicable. Thank you, Jenna <3

  3. Megan says:

    This is inspiring! Helps me remember patience is important when you want your dreams to become your reality. Thank you Jenna.

BINGE THE LATEST POSTS

HOT RIGHT NOW

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

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).  One of my favorite places to be is here, sharing what I'm learning with you. I'm glad you're here!

AS SEEN IN:

SEARCH

What do you want to read today?

Get My Heartfelt Worldwide Bestseller,
How Are You, 

Forget hustle harder. Want to build a vision for your life that's unapologetically true to who you are and what you *actually* want?  Here's how you start.

Screw the junk mail, I'm bringing "real" right to your inbox. Deep encouragement, tough questions, needle-moving challenges, and smart strategies to help you make your dream work. You in?

Bringing Real
to Your Inbox

Bringing Real
to Your Inbox

    Join over 1 million followers on Instagram, where I'm your mom friend with the garden who also runs a multi-million dollar business and bakes sourdough and dresses up with my toddlers between podcast episodes.

    © JENNA KUTCHER 2025

    |   ALL RIGHTS RESERVED

    |    SITE CREDIT

    |    GET IN TOUCH

    |    Legal