5 Things To Do Before You Leave Your 9 to 5

Jenna Kutcher 

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July 19, 2017


Today I am sharing the 5 steps I took before leaving my 9 to 5 job and I’m walking you through all the different things I did before taking the leap into full time entrepreneurship. A lot of times people get really hung up on when to make that transition and I want to lead you through the things I did before I was ready to hand in my two week notice and really make a go at things. I am really excited about this episode because it answers one of the questions I hear most often from entrepreneurs.

Start off on the right foot

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!

It’s tempting to think you need to invest everywhere. Check out episode 55 where I break down how to know where to invest in your 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.

Speaking of investments

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!

Start growing a following

Long before we had even conceptualized an actual business plan, we started two very important things: an Instagram account (@kickingitwithkutch) and an email list. Our first priority was to grow the following on the platforms we know best. Instagram to build the trust and personality of the business and more importantly, an email list where we could serve the clientele and eventually sell to them.

What did we do? We created two freebies for the email list: a free grocery shopping list/food plan and a weeks worth of at home workouts. Both of these were free downloads and grew Drew’s email list quickly. We set goals for subscribers and dreamt up new ways we could foster a true community before the time came to launch and offer services/products. Thinking you might eventually want to start a business? Start growing your email list and following TODAY. That way, when the time does come to launch, you have people who are already at the edge of their seats ready to cheer you on!

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! But most importantly, know your numbers. Check out my customizable pricing guide to make sure you’re not pricing emotionally and tune in to episode 56 where we break down business finances with Shanna Skidmore.

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.

Don’t use my story as a roadmap – 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 creative small business owners 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, maker, florist!

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!”

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  1. Angela says:

    This post meant so much to me today. I just had a conversation with one of my bosses this morning about resigning from my position, and I came back to desk with a podcast notification that said “5 Things to do Before you Quit Your 9-5.” I know God works in all sorts of ways and this was without question an answer to prayer. Thank you for sharing!

  2. Colleen says:

    Jenna you continue to amaze me each time I hear part of your story. The part where you went “B*lls to the wall” as you said is hard for me. I’m afraid to ask my friends to recommend me and I’m afraid I’m not good enough to do it! How did you book weddings with a $350 camera and NO lighting? That’s my biggest worry that I won’t have the right equipment for a wedding. I have a midlevel cannon right now but no professional flashes yet.

  3. Sarah says:

    This podcast was so helpful to me since I started my business two months ago. I had been praying for years about it. I still have a part time job but it was so encouraging to know that it can be done and goals/dreams do come true. Thank you!

  4. Kate says:

    Hi Jenna!

    First off, your podcast has seriously been changing my life. I am currently a PhD student who thought that continuing on in school was just the right thing to do, meanwhile my passion is in the fitness industry and my side hustle (and passion) is not getting the attention it deserves. Your experiences have given me so much positivity about my current situation and I can’t thank you enough!

    How did you find an accountant that was right for you and your ventures? Did you specifically look for an accountant that deals with small business ventures or LLCs?

  5. Michelle says:

    Thank you Jenna for sharing your knowledge!! So glad I found you…awesome inpsiration and information!!

  6. Kiki says:

    THANK YOU so much for sharing such VALUABLE information with such passion, enthusiasm and care for the people you’re serving.

  7. Hey Jenna! My husband and I recently launched our own business this past year while working full time! This pod-cast was helpful to motivate us to move forward to grow our brand and hopefully/eventually move my husband to this fun time! Your insight and examples are so helpful! I’ve been catching up on your podcasts all winter! We will in MN so we can relate to the cold winters! 🙂 Thank you for all your work with the podcasts and information you bring to the table!!

  8. Laura says:

    Jenna, you’re such an inspiration! I’ve been too scared to transition to FULL time photographer for years (I always have an excuse: kids, money, time, etc.), but I am READY to commit to myself and stop half-assing it. It’s time for me to be a fierce #bossmom #bossbabe! Thank you for the amazing advice and inspiration 🙂

  9. Vittoria says:

    I have been praying for an answer.. for a light to shine on my path.. This may sound strange, but this has been an answer to one of many prayers… thank you for sharing!!!

  10. Angela says:

    Jenna, this podcast was very insightful and I enjoyed it alot!

  11. georgie says:

    this is exactly what I need to hear right now! so inspiring, i’m hoping to make the leap by this time next year, I just need to figur out a few things and learn how to believe in myself more! thanks for the motivation, love your work 🙂

  12. I love this podcast so much. I can relate to a lot of what you were talking about. I am working on taking that leap into my business. Living in Custer, a suburb of Stevens Point, I have that 9-5 job that is secure and I always know I will get paid every other Friday. We do have the double insurance and 2 pre-teen girls. I have been praying about this for a long time, to which I think the prayer team at church is just ready to push me to jump. Thank you for being so honest and open.

  13. Marianne says:

    Hi Jenna… I’m listening to you for the 1.time and you made me think one more time about what it is that I want.
    I am a Danish woman, living and working in Germany . I’m turning 52 in 3 weeks and I’m starting to question my life and if I’m doing the right thing with my life.
    Thank you for putting a couple of things straight for me. Love from Marianne

  14. Gina Santoro says:

    Thank you for empowering women enturopueners! I am about to make the leap and I am so stoked to hear any advice about it all!!! Thank you for this!!

  15. Alex says:

    Jenna! This particular post has kind of clarified for me where I am on this path, so thank you for telling it like it is. I am currently at ground 0 on this girlboss journey, but according to your survey, am a move-making maven ; D Photography has been a hobby of mine since high school, but I dream about making it a career. Most content I can find is how to launch from side hustle to full time career, but I’m trying to figure out how to even gain traction and muster up a side hustle. Where to start?! Do I pour all my energy into honing in on my craft, gathering skills until I feel confident in sharing it? Do I start sharing the amateur photos I have as a brand? That can’t be good for business! Do I start an actual business? Do I establish the brand first? How do I make a social media page or website for a business I don’t even have?! Do I start ‘practicing’ on people other than my own family for free? Any sense of direction would be so appreciated as I know you’ve been sitting in this exact spot before.

  16. […] How do you keep your flow between your 9 to 5 and your businesses? […]

  17. Mimi says:

    Just this week I’ve been so worried about my future, whether I should graduate from college and take the leap or work immediately to a 9 – 5 job. I don’t think the routine of this type of job is wrong or bad, I just think it’s not for me. I really want to have my own business and crave being my own boss, so a huge THANK YOU, for inspiring me to follow what I believe works best for me and since I study communication I CAN see a bright future ahead <3.

  18. Canitha Raynor says:

    This was great… I have been wanting and saying I’m going to do this thing for over a year now….. I dont want to wait any longer. I see so many people these days stepping out and accomplishing what they want. I have to do it!

    Thanks for this cast

  19. Wow! Just wow! Thank you so much for sharing your journey!

    I recently launched my blog that I have been thinking about for over a year. I finally got up the courage, but I’m a free spirit without a plan. I’m bettering myself by learning all about becoming more organized and in charge of my life.

    I really like how you shared actionable steps that I can include in my plan. I have been focusing on growing a following for my site, and I will be creating some opt-in freebies for my subscribers.

    Keep up the good advice!

  20. Leah says:

    Jenna! This was a phenomenal podcast! Thank you for sharing your story and for being a sounding board for my goals and dreams.

  21. Lauren says:

    Hey Jenna!
    I’ve been listening to the podcast for awhile but came upon this one just today. I was looking for and needing encouragement as I embark on my new journey. Which as the days go on I’m realizing more and more that God has called me to create my own path in the form of a business. I’m very excited but I’m also scared that maybe people won’t be interested. But as you said what’s the worst that can happen? You fail and you get back up. Not damaging in the slightest. Thank you for sharing your story. Cheers to being kickass girl bosses!

  22. Devon says:

    Thank u so much for your episode on how to leave your 9to5. I just listened to it and I feel so inspired. I Invision my future life without doing to commute to work and doing my passion! I’m an artist at heart and want to do it fulltime. I do have a business accounting background that makes me think rationally about the Big picture. Your steps give me some goals to work towards this goal. Thanks again for doing this podcast. I’m sure I’ll listen to it again. I want to check out a few more of yours first. ❤ Sincerely, Devon

  23. Wow!
    Get out of my head Jenna!
    I have been thumping this question around in my head for two years and counting. Fantastic! What a great blueprint. No matter how close the boat gets to the doc, I still have to take that leap of faith to step off. Thanks girl

  24. Jenna, you lit a fire 🔥 in me, I so want to retire in the next 1 1/2 yrs, and so worried about whether I will have enough income. I am really struggling to building my business to that level. Thank you so much. Pat 😍😍

  25. Lori says:

    Thank you so much! Very helpful and very inspiring ❤️

  26. Jessica says:

    I want to thank you for this podcast it was trully useful! Most of the things you find online are more “romatic” but this was relevant and true stuff to take into consideration! In earky on in the transition process but this extremly help to get a clear mind of what i can do! Muchisimas gracias! Abrazos desde Perú!

  27. Carolina says:

    Hi! I just found your podcast and I’m absolutely inspired…it’s been three days on nonstop listening. Where did you start posting the freebies for Drew? If it was before creating a business, I’m assuming he didn’t have a website yet.

  28. Debora Arn says:

    This podcast has been absolutely encouraging and exactly what I need to hear today! On Monday was my last day at my corporate job and I made the leap of becoming self employed. I am very excited for this journey and your podcast ignited my fire and passion for my business even more. Thank you for being real and sharing!

  29. […] is an insane repository of useful and easy-to-implement information. Jenna covers everything from preparing to leave your 9-to-5 job to start a business to how to start an email list to how to optimize a Facebook group […]

  30. The 3 Best Podcasts For Female Entrepreneurs | commsmom.showitterra.wpengine.com says:

    […] is an insane repository of useful and easy-to-implement information. Jenna covers everything from preparing to leave your 9-to-5 job to start a business to how to start an email list to how to optimize a Facebook group […]

  31. Edward Reeves says:

    I completely agree! I believe that podcasts like those hosted by Keion Henderson have aided many people who aspire to be entrepreneurs. Do you have any thoughts or ideas about which ones are also worth listening to? Thanks!


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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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