Is it time to quit your job?

By: Sarah Wagner

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You’re probably feeling a little exhausted right now. Like you’re in the middle of a game of tug-of-war. On one side is your reality–your stable job that pays the bills but doesn’t light your soul on fire. On the other is your dream. It’s a little unknown and a lot of “new,” but it makes you more excited than you’ve been since you were a kid getting to stay up past your bedtime.

You’re stuck in the middle trying to give your best, feeling exhausted because it’s not really possible to give both worlds your best. I get it, because I’ve been there. Not too long ago actually. I asked myself hundreds of times, “Am I ready?” And, “How much longer can I take this?” The phrase, “If I just had more time,” rolled off my tongue on a daily basis. For me, it felt like time was standing between me and this dream, this better life I wanted for myself.

After months of pouring every bit of energy I had left at the end of the day and on the weekend into my business, I knew it was time. But my husband and I didn’t see eye to eye on the topic. If you’re in a similar position, know that you’re not alone. Countless entrepreneurs have faced exactly what you’re facing right now. Hearing from others who have gone before me, helped me make the right decision. Now I want to help you. Here are five ways to tell if you’re ready to leave your 9-5 job to focus on your side hustle and what to do if your partner isn’t on board.

1. You’ve built the foundation of your business

This may seem obvious but there are so many foundational tasks that get missed. We’re talking, corporate filings, banks accounts, brand guides, you know – all that stuff that makes your eyes glaze over like a Krispy Kreme donut. 

As someone who grew up with a dad who was an entrepreneur and a mom who was a business and accounting professor, business things came naturally for me. I also worked with many business owners during my time at the marketing agency before going full-time into photography so I just knew these things needed to be done if I wanted to run a successful business. I realized that not everyone has this background so I’ve created a check list of foundational tasks that I recommend be completed before you go full-time with your side-hustle so here are a few must-dos:

  • Open a business bank account (you never want to mix your personal and business funds)
  • Name and file your business (will you be an LLC or a sole-proprietor?)
  • Set up a system for tracking receipts and expenses – I use an excel file and then transfer everything to QuickBooks
  • Write a plan for what you would like to accomplish in the next 2-3 years
  • Start nailing down what your ideal client looks like (this may change over time but knowing who you are marketing to will help give you direction)

2. You Have Consistent Income from Your Side-Hustle

So many of us (yes me too!) operate with a “once I get this, then this will happen” mentality. But that’s not always – scratch that – that’s rarely how it works. Having extra time doesn’t mean you will have more bookings and if you’re quitting your job with this expectation, you’re taking a risk. People everywhere are saying to “jump before you’re ready.” But take note that they are referring to feeling ready. Being ready in a business sense is possible. If you have consistent bookings, and are bringing in revenue that is comparable to what you make at your full-time job, then you’re ready as long as the timing makes sense. Which leads to the next point…


3. You’re heading into a busy season

If busy season is coming and you’re already at your max for what you can take on AND you’re making comparable income, it’s a no-brainer. Now is the time to quit your full-time job. If slow season is coming, pump the brakes. The revenue is about to slow down, so use the next few months to nurture your business and work on the foundations while you continue to work your 9-5 job. These are things that will help you work more efficiently once you go full-time with your side-hustle. 

  • Do styled shoots to build your portfolio
  • Add a CRM like Honeybook (it’s only $10 a month until you hit $10k in sales)
  • Set up workflows and create email templates to help you save time
  • Build a website or an email list

Or you could just rest, because you’ve been going hard and you need rest to be able to do what you’re doing!

4. You have savings or a partner who also contributes to your household income

If your partner is the bread winner, what are you waiting for!? Jk, I get it. My husband was making double what I was making at my corporate marketing job but we still didn’t feel like it was a good idea for me to quit. We’re very financially savvy people who have been dedicated to paying off his, *cough* I mean our student loans as quickly as possible. Leaving my ‘stable’ job meant we’d be pushing back this timeline which meant we’d be waiting longer to get out of our condo and into a house to start a family.

All this being said, you have to look at your quality of life. If you are borderline miserable because you are just exhausted, you’re at risk for being burnt out before you even get started. Take a look at your expenses. Is it possible for your family to live comfortably on one income? What would you have to give up to make this possible? You have to decide if the risk is worth the reward.

If you are the sole provider for yourself or your family, you need to be a little more cautious here. There’s a lot more on the line which unfortunately means you don’t have the flexibility that others may have. An option could be to slowly work your way into going full-time with your side-hustle. Leave your 9-5 for a part-time gig to help supplement your income while you continue to build up your business. This will give you more hours to invest in your business without going all in. I also recommend having savings that could support you for a few months if your income was paused.


5. You Feel Confident in your Abilities

Lastly, you need to feel confident. Not fearless, confident! I had terrible anxiety the last two weeks leading up to my last day at my corporate job. Even with having all the right things in place, I was still scared that I could be making a premature decision. Of course there was no going back at this point so I chose to look at the facts over my feelings to cope with the anxiety (another reason why it’s important that all of the previous parameters are in place). Jordan Lee Dooley’s podcast episode on ‘When it’s Time to Let Go of a Good Thing‘ really helped me feel confident that I was making the right decision.

Confidence comes with experience, planning, and faith. If you’re lacking any of those three, I highly recommend doing a little more work before you put in your notice.

What to do if your partner isn’t on board

I think I asked my husband about 3x a week if I could quit my job. Each time he would laugh. The only problem was, I wasn’t really joking. Each time he laughed I felt like my dream was dying a little more. I was 100% confident in my ability to not only replace my corporate salary, but make MORE. I felt like he didn’t believe in me but really he just wanted what was best for us. We had different versions of what “best” looked like or could look like.

It took a lot of difficult conversations and a lot of (my) tears before we were both ready to take this leap. We have to remember that this big decision affects more than us. Maybe your parter has a dream they want to chase and seeing you chase yours causes some new feelings to arise. Maybe they’re scared of the pressure of being the main or possibly the only income provider for a while. Their feelings are valid which is why it’s important to look at things from their perspective and try to find a middle ground.

My husband and I ultimately decided that I could go ahead and quit my job, but if I wasn’t bringing in what I was making at that job, I would get a part-time job to supplement. This compromise protected HIS dream of paying off our loans as quickly as possible and also allowed me to chase mine. I was ready to bag groceries at Publix or sit at a front deck for 20 hours a week but thank goodness, God has more than provided for us. Which I believe is His reward for being obedient to the calling He put on my heart.

No matter where you are in your entrepreneurship journey, know that literally anything is possible. I hope this post has either given you the confidence to leave your job or helped you realize that you have a little work to do first. Either way, reach out and let me know. I am here to support you and I’m cheering you on!

Always remember to be smart, and dream big.

XO Sarah


Chasing Creative was founded by Sarah Wagner, a corporate marketing exec turned entrepreneur. When she’s not photographing families + couples on the beaches of Southwest, Florida, she’s teaching other photographers how to build their businesses and grow their photography skills. Learn more about mentorships and coaching call with Sarah HERE.

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