What You ACTUALLY Need to Do Before Leaving Your 9 to 5 - Jenna Kutcher

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What You ACTUALLY Need to Do Before Leaving Your 9 to 5

Jenna Kutcher 

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With entrepreneurship generally comes leaps of faith coupled with a lot of fear. I can remember the fear that came as I was planning and preparing to ditch my corporate salary and leave behind my 401k and I can tell you it was borderline crippling fear. 

If you’ve ever had the desire to launch your own business or take a side hustle and turn it into a full time career, I’m here to champion you 100% of the way. Taking a side hustle to a full-time gig is an enormous and sometimes scary undertaking but also a huge adventure to finally go for your dream full steam ahead.

If you want to leave your full-time job or steady income behind, whatever that may look like, to go for a different dream and goal, and to launch or scale your own thing, there are a few important and smart steps that will make the transition a) way less scary, b) way more motivating, and c) a whole lot more well-thought-out, so that you aren’t freaking out in a year if things aren’t going well or a challenge crops up that you didn’t expect.

This episode is for those who feel sort of stuck between clocking hours for someone else when they’d really rather be spending that time and energy building something of their own. I know the temptation of just wanting to go all in right away—but let’s pause and walk through a few smart steps you can take right now, so that when it IS time to quit your job, you are fully prepared for the leap and know exactly where you’ll land.

Responsible logistics

If you currently have a salary and health insurance and a 401k, then you’ll want to make sure you can replace those things or have a plan surrounding those big topics before going full in on your side gig. If you currently freelance or work part-time jobs that don’t provide these types of benefits, it’s still smart to try to get a plan in place for your future and your health… AKA, setting up retirement savings and health insurance if possible.

I remember I had sat down with an accountant (the same one I use to this day) and I hadn’t made a single penny yet but I asked all of the questions about taxes and paying myself and what I needed to prepare for expense wise and it gave me the ability to start to plan out based off of what I would actually need with certainty. I also waited until Drew and I were married and he had secured a stable job to switch to his health insurance and had contacted an investor who my accountant referred to help me with the retirement piece. While these initial steps required an investment on my end, I acknowledged the importance of having a well thought out plan and it helped to give me the clarity to set the right goals of when I would be able to go full time. 

How much money do you need to make?

When I decided I was going to pursue photography, I first made sure I was making the same amount per year in my photography business as I was in my salaried job. Now, this is NOT totally necessary for everyone. In fact, you may not need nearly as much as your salary pays you, or you might need more than it currently provides. This is where determining your “enough” becomes extremely crucial, and it’s the first thing you should do as you prepare to eventually leave your 9 to 5.

For me, at the time, the $50,000 salary was what we needed to pay bills, create a savings, pay off my student loans, and live comfortably and so my goal in my head was to match that, making it a worthy decision to go all in. For the first few years of my business, I paid myself that same amount even though my income was growing. It allowed us to save even more money and reinvest into the business and it kept us living under our means without changing the lifestyle we had grown accustomed to. I am so thankful the extra money didn’t burn a hole in my pocket and that it allowed us to save! By year three my business was bringing in 6-figures, but I continued to pay myself that same $50,000. 

If you’re not quite sure how much you need or what to shoot for, go back to episode #312 of the podcast, I did a full episode all about how to define your enough, and it’s worth a listen as you begin to navigate what yours looks like. In short, though, your enough point is just the overarching level of success that you can realistically achieve and would be pleased to reach. 

So this COULD be the same number as your current salary… or maybe you could make $10K less a year and still afford your needs and desires just fine and be perfectly content. This number isn’t based on emotion, it’s based off of an actual equation that gives you the clarity of what you need to be shooting for. It’s based on your values surrounding money, time, and effort, and it allows you to say “no” to the wrong opportunities while preserving your best “yeses” for the things you value the most. 

Retirement savings and healthcare insurance

There are good options for entrepreneurs for each and it’s important to research and seek out the best option for your needs and goals before choosing your route. And please, please, please don’t just assume either thing can wait until you feel more “steady” in your business. I think our brains often trick us into that thought that once I have XYZ, I’ll start to save or create my plan, but any financial advisor will tell you that saving for retirement now, as soon as you possibly can.

If you can find a trusted advisor to help you set up either a solo 401k or a Roth IRA that you can contribute to every month, even if you’re not able to max them out right away, just contributing something will begin to set you up for a better future and the ability to retire comfortably someday. Remember, if it becomes a part of your habit and you have it auto draft the money so you don’t even see it, it’ll be set aside and your lifestyle will likely adjust to help that remain a priority. 

For us, health insurance was a big piece of the puzzle. With many of my family members working in the medical field and after being voted “most accident prone” in my graduating class, I knew that having medical insurance was important for me to secure before going full time. Keep in mind, this was a decade ago so the opportunities have changed around healthcare but it’s important to note that there are also a lot of healthcare plans and opportunities for self-employed people out there. 

For the first few years we relied on Drew’s insurance but once he joined the world of entrepreneurship, we had to find a new way. I know healthcare plans vary state to state, but for any of you who live in the U.S., we’ve been a part of the Christian Healthcare Ministries ever since I became an entrepreneur and absolutely love it.

It’s a more budget friendly solution for healthcare because it’s actually not insurance. Instead, it’s a cost-sharing system or coop where members can submit their medical bills and costs, and other members help to pay for them. It’s an accepted form of coverage via the government and a lot of my friends and family members have switched to it. You can also write off the amount to spend on it each year since it’s technically a non-profit. 

Savings is key

Now, I know we already covered your enough point and what your side business should be bringing in before you go in on it full-time, but I’d also recommend putting aside any extra income that you can for a few months in order to pad your savings should an emergency come up. I was super thankful that I was able to save all of the money I had coming in from the photography business while working my full-time gig to build up some savings. Doing that allowed me to reinvest in the must-haves that I needed in order to launch my business and get it to a point that made me confident to make the leap.

If you have a side hustle on top of a more consistent income, my best advice is to save every penny that side hustle is bringing in and wisely reinvest in the must-haves. Don’t get used to that extra spending money or it will make it even harder to make the leap for you. Try to be conscious of setting aside as much money as you can manage to build up a savings account that will help give you the confidence to leap without worrying too much about money. 

The personal finance tracking app, Mint, advises that you save at least 6 months of living expenses before quitting your job. I personally think that’s a pretty conservative amount, but if you CAN save that much or already have that much in savings, bravo! By all means, go for it. But in general, I personally believe 3 to 6 months of living expenses should be plenty should any kind of emergency or slow season arise in your business.

Things to do

Whether you’re a coach or a consultant, a personal trainer or an artist, a course creator or a social media manager on the side… there are a few things you can do to set up your side business to be successful before you take it full time. 

One of THE most important steps you can take is setting up a few streams of revenue in your business. While it might sound overwhelming, it’s a way to ensure that you have more than one way to make money. After last year, we learned that the world can shift in a matter of days and we need to be resilient and adaptable. It’s much easier to be both of those things when you aren’t reliant on just one thing to make an income. 

Having more than one way to generate money is something to be thinking of and planning for. It doesn’t mean you need to have 101 different offers and products and services for your target clientele… in fact, I’d recommend just having at least three and trying to make each of them different price points so you can reach and serve more people and so you have options based on the current market, economy, or needs of your clients. 

Some other ways to add more revenue streams also include: sponsored content with brands you love, sharing affiliate codes for products you love, or selling merchandise of some sort. Just keep in mind that selling products introduces a few new pieces to the puzzle, like figuring out where to host your shop and how to ship or deliver items to customers, but it can be a great extra revenue stream once you sort out those details. These days the ease of use makes it a lower barrier to entry in starting up other means to generate income. 

Email list setup and warmed up

Trust me when I say, one of my biggest business regrets was waiting years to start my email list. You want to have an email list up and running well before you leave your full-time job so that you can be speaking to and engaging with your target audience, aka turning them into a “warm” audience that knows and trusts you and will be more willing to buy from you, too. If you create an email list that is focused on serving before you have anything to sell, you’re building an audience that will be eager to support you when the time comes to launch. 

I always say this, but it’s important: email lists are THE best way to build a strong community and connect with your target audience. I consider social media the hello, the handshake, the “how ya doing?!”… but email marketing is the long walk on the beach and candlelit dinner. It’s where you can speak DIRECTLY to your audience, share important stories, wins, and lessons, and it’s the spot where you don’t have to compete with literally thousands of other voices a la social media. 

The marketing gurus behind OptinMonster shared in a blog post that for every $1 spent on email marketing, $44 are made in return. That’s a pretty big deal if you ask me. Plus, 59% of people say that marketing emails influence their buying decisions. So… the bottom line is, if you aren’t emailing your target audience and focusing on your email list, you’re probably not optimizing your reach and your revenue as effectively as you could!

Work-from-home-for-yourself life

For starters, make sure you have a place in your home that you can actually focus and get work done if you won’t have a dedicated office space outside of the house. It doesn’t need to look like a gorgeous, Pinterest-worthy home office with a dedicated room, desk, and workspace, but you should try your best to set up somewhere productive and conducive for getting into your flow state when you do sit down for work. My first office was in our spare bedroom of our apartment. We fit our desk from college in there and I added a few photos and motivational quotes and voila! I officially was someone who worked from home. 

You might be overwhelmed by the freedom of your days at first, and that’s completely normal. I remember when Drew would come home from work and wondered out loud why I didn’t unload the dishwasher or do the load of laundry in the laundry room but I had to set up boundaries for myself to separate work and life and stay focused. It’s important to figure out what that balance will look like for you as you begin your new full-time endeavor! 

Focus on figuring out what times of the day are most productive for you and what your preferred work style is. For example, batch working might not be your thing, but instead you might LOVE time blocking. Maybe you prefer to take calls on Mondays and do admin work on Tuesdays and then leave Wednesday through Fridays for client work or project expansion. Lean into those habits that work best for you, and pay attention to what doesn’t. You’re going to have the full freedom to choose your schedule and routines, and that is a beautiful thing.

The Big Picture

I know it might sound cliche, but every moment of preparation matters and is leading to something so important. Going for your dreams is a BIG deal, and doing your due diligence to get there and secure your finances and future means that you have the wherewithal, gumption, and endurance to really rock this entrepreneurship life.

But I won’t lie, getting your ducks in a row is no easy or even very quick task. It might take you 6 months, a year, or even a little longer. But if you can prepare well and wisely, you’ll feel so much more at ease and confident when you finally do feel ready to step away from your 9 to 5. 

And when you do? Then it’s go time, and your past work life will feel like a distant memory in no time at all. Congrats for going for it, and I am so excited to cheer you on toward the finish line! Or, is it really the starting line? Either way, I know you can do this, and do it well. Keep going!


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  1. Alexandra says:

    Great overview of logistics to cover before quitting a 9-to-5 job! However, please BEWARE that “health care sharing ministries” is NOT health insurance! In fact, it’s a very risky option compared to the Affordable Care Act or other private healthcare providers. I encourage any listeners/readers to search and watch “Last Week Tonight, John Oliver, Health Care Sharing Ministries” video on YouTube) for we-researched coverage on this topic when considering entrepreneurship healthcare options.

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