So You Wanna Quit Your Job? Read This First

How to decide if it’s time to make your side hustle your full-time gig

“I’m so excited, I’m so excited, I’m SO… scared!” I replied with my best Jesse Spano, Saved By The Bell impression.

That’s exactly how I felt when my husband took the initial leap from his 9-5 job into his own business full-time!

I’m so excited I can finally share this with you!!!

He left his full-time job in March 2022 to open his own business! So we are now officially a fully self-employed household with two different businesses. 

Some couples have “his and hers” closets; we have “his and hers” businesses! 

You might think that because I’m a Business Coach and COO for Creatives, I’m immune to the uncertainty that comes with going all-in on a business idea. 

But promise you, I’m not. 

I understand how much courage, passion, and risk it requires to go after your dreams with 110% commitment! I’ve done it myself and witnessed several of my clients go for the gusto!

I have all the faith in the world in my husband, and I know he will rock this new venture. But, as an entrepreneur myself, I know first-hand the rollercoaster ride that is starting a business and pursuing self-employment! 

I also accept that this is naturally a whirlwind of emotions full of the highest of highs and the lowest lows (sometimes both on the same day)! Still, it’s a bet, on him and on us, that I would take any day.

So, if you are considering leaving your full-time job and pouring your time and energy into your side gig full-time– FIRST, I want to offer you my most sincere CONGRATULATIONS! This is a tremendous step in your life and your career. Whether you decide to go for it now or in the future, your commitment to your passions and your faith in yourself is something I admire deeply. 

SECOND, I want to offer you the tools that helped my family decide that THIS was the right move for us so that you can feel more confident as you make this critical choice for yourself!

In this blog, I’ll walk you through the things I recommend all entrepreneurs consider before turning their side gig into their full-time business. 

Soul Searching

So many people ask me, “When is the right time to go full-time with my creative business?” 

Honestly, only you can answer that. 

Before making any decision, I highly recommend taking some time to sit with yourself and with your family. This is not a choice that should be made in haste.

My husband and I did this before he officially put in his 2-weeks notice. To prep for this transition, we did a ton of soul-searching and prep work to ensure that we were fully informed.

After all, we have two kids to think about! And for me, it was like a flashback to a few years ago when I started my business! All the familiar uncertainty and excitement bubbled up!

In the upcoming sections, I’ll offer you some logical and personal prompts to help you decide if making the move from your 9-5 gig to your side gig feels aligned with your goals.

Burn The Boats or Hang Onto That Safety Net?

There are two schools of thought when it comes to going into your business full-time:

Burn the boats, or leap with a safety net.

Burning the boats involves going in, head first, without a backup plan. Some people find that this “all or nothing” approach positively motivates them to achieve their goals without any alternative. 

For others, however, doing something without a backup plan can be pretty terrifying and overwhelming!

Leaping with a safety net is a more conservative option that offers some extra cushion and security. With this strategy, you can build your way toward your full-time goal while ensuring your financial needs are met. Eventually, you can take the training wheels off and step fully into your business. 

For some people, this approach doesn’t push them to fully commit, and they drag their feet instead of taking action because the stakes are a bit lower. 

Neither approach is wrong, but as you can see, each has its pros and cons. You get to decide which approach to take and to what degree.

In fact, that’s EXACTLY what my husband and I did while planning for his transition into full-time business ownership. We designed a modified version that worked for us. He burned the boat, so to speak, by leaving his fulltime job, but we also kept some safety nets in place to feel supported through the process.

Here are some things to think about to weigh if the time is right and decide which approach you’d like to lean into:

  1. Make a plan.

Create a vision for this transition. Support yourself with clear goals, specific deadlines, and measurable milestones. This will help you stay on track, remain accountable, and help you gauge if and when the time is right for you. Part of this plan may also include a “worst case scenario.” What’s the WORST that could happen? If this not-so-great situation were to come up, how would you handle it (i.e. pick up a part time job?). It may sound like a bummer, but planning for the worst will help you respond if things don’t work out ideally so that you can pivot rather than panic. 

  1. Find your enough point. 

Your enough point is the amount of money you need to earn from your business to feel comfortable. This number will vary from person to person and even from one season to the next in your life and business. Consider your current salary, personal expenses, anticipated business expenses, and how much you want to work. For some, a lighter schedule is worth a reduced profit, while others would rather work more hours to hit their financial goals. No matter what feels right for you, define this in advance and reevaluate regularly. Everything beyond your enough point can be considered a bonus!

  1. Check your capacity.

Does your business add up? Before committing to your business entirely, you need to make sure it makes sense! Consider your schedule, how many “sellable” hours you can dedicate to your job, the kinds of services or products you’ll offer, and your rates. This process may require a bit of “play” to find a system that makes sense for your schedule and financial goals. 

  1. Prepare for liftoff!

What does your runway look like? If you are doing this as a side hustle, how big of a leap is it to hit your enough point? Be realistic and honest. What will change when you go full-time, and how will that impact the business?

Assessing each of these factors will help you decide if it feels most aligned to cut all ties and burn the boats or develop a slow and steady approach while holding onto that safety net. 

The Nuts & Bolts

Once you’ve done some soul searching and mapped out a plan, it’s essential that you take time to dig into all the annoying but oh so essential logistics of running a business. No, it’s not fun, and YES, I know you’d rather pour your energy into your creative work, but it’s a non-negotiable. Plus, you’ll be so grateful you took the time to cross your t’s and dot your i’s BEFORE making the official jump from side gig to full time. 

Here are the essentials:


Health insurance is the most important. Explore options in your state that will cover you and/or your family as needed. If your partner has health insurance through their full-time job, you might explore hopping on their plan or look into other possibilities. 

In addition to health insurance, business insurance is another piece to explore depending on the type of business you have and your specific needs, risks, and liabilities. 


Making money is the fun part, but you need to put systems in place to make sure you can accept money, pay your bills, and handle the financial side of your business through and through. 


  • How are you going to pay yourself and how much? 
  • Do you have an emergency fund? 
  • Do you have enough to get by until you start making money in your business? Generally speaking, it’s wise to have enough savings to cover about six months of living expenses, but talk to your accountant and financial advisor about this! 
  • What about retirement
  • Also, figure out banking and access to funds should you need it for personal or professional reasons. 

COO Tip: Typically, it’s harder to borrow money as a self-employed person, especially in the first few years, so consider what is on the horizon for you, such as buying a home or a car or taking out a small business loan. This may help you decide if NOW is or is not the best time to take your business full-time. 


You must protect your business, yourself, and your assets. Now that you are the full-time CEO of your creative business, you might need to revisit things like contracts, wills, and more. Be sure to reach out to your lawyer to see what they recommend you review or update. 

Consider Your Lifestyle

An important question to ask yourself:

 “Do I need to adjust anything lifestyle-wise to make this work?”

What does your lifestyle currently look like? Consider things you value about how you live, such as time off, your neighborhood, how often you enjoy eating out, the types of vacations you look forward to, and how much time you have with your kids, family, friends, etc. 

Are you willing and able to make changes to your current lifestyle? And if so, which things are flexible and which are you unwilling to part with?

Defining these lifestyle preferences upfront will help you decide if and when you’re willing to make a sacrifice while you get your business up and running. 

That’s not to say that you’ll necessarily need to change anything. Still, you may need to be flexible, especially early on, as your business gets its footing and becomes financially sustainable. 

Get In The Right Headspace

The last, but certainly not least, piece of advice I have for you as you decide if it’s the right time to take your side gig full-time is to do the mindset work. 

Entrepreneurship is not for the faint of heart. YOU are absolutely capable of anything you put your mind to, but YOU need to believe that is true!

Taking care of your mindset and mental health is key as you embark on this new adventure. Here are some helpful ways to support yourself mentally and emotionally as you move into a new stage of life and your career:

  1. Journal. Take time to reflect and get your thoughts out of your head and onto the page.

  2. Seek out a trusted therapist or life coach to support you. I also recommend reaching out to your support system of friends and family!

  3. Connect with other entrepreneurs who understand the unique challenges of running a business. Attend workshops, join Facebook Groups, or plug into your local creative community.

  4. Make time for your art! Allow yourself the space to create just for fun’s sake! This will help you stay plugged into why you do your work while prioritizing JOY!

You’ve GOT This!

Whatever route you decide to pursue, remember that it is YOUR choice to make. The beauty of being your own boss, whether part-time or full-time, is you get to play by your own rules, and you can change your mind at any time. I hope that as you weigh the pros and cons of taking your creative business full-time, my experiences, combined with these prompts, tips, and questions, offer you the guidance and confidence you need to take the next BEST step for you!

I know that this choice can be scary (and thrilling all at once)! If you need a sounding board or want to talk things through, I’d be glad to help. 

Click here to shoot me an email with your most pressing business questions so you can bust through the doubt and feel ready to make your next move. I personally respond to every single email that pops into my inbox, so I’ll get back to you ASAP!


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