Feeling frustrated with your 9-to-5 job can make you want to quit and pursue your dream business. But when is the right time to make that leap? What factors should you consider?
If you’re not sure, read about someone who became a full-time entrepreneur here.
My husband criticizes me for replying with a question when asked one. But this approach helps clarify my thoughts before making decisions or choices. So I request you to ask these questions to yourself before leaving your 9-to-5 job.

What is your strategy?
Strategy is a vague term. But who you want to become as a brand shows you the roadmap, guidance, investment, and the patience you need. I learned this secret from Seth Godin. Have a strategy that aligns with your traits. For example, last week, I wrote an article collaborating with another wedding vendor. Because, empowering others is one of my traits. When your company values match your personality, it’s easier to think, write, and reach your goals. So, ask yourself who you want to become.
How disciplined are you?
Disciplining oneself is easy in a comfortable life with paychecks every 2 weeks. Your discipline not only shows in how fast you reply to your lead. But, how motivated you are on sales pitches even when there is no cash flow. If you have 4 hours each day for your side hustle, how many days do you spend on routine tasks? This includes cold calls, emails, writing, and planning content. I batch-cook my breakfast to save time. It’s the same coffee-flavored protein drink with chia seeds that I’ve had every morning for the last 3 months. This doesn’t change my breakfast budget nor consume energy to think beyond that.
Can a coach discipline you? May be. But, hiring a business coach is not what you do after quitting your 9-5 job. You make money, feed the business and ensure it is scalable without you . If it is not scalable without you, it could be a lifestyle business. Those business models are hard to sell when you no longer want to run it.

How much is the profit and not the revenue from the side hustle?
If you watch online business videos, many focus on revenue, not profit. Profit shows if you can stop using your personal funds or if your business needs more time. Remember, some business models take longer to become profitable. As a solopreneur, aim for profit margins over 85% in service-based businesses. If you rely on labor, profit margins will vary based on labor and operational costs. In short, don’t quit before analyzing your profits for at least a year. This way, you’ll have seen both the worst and best seasons in the past 12 months.
How seasonal is your side hustle?
Wedding businesses, tourism, and hospitality are seasonal. If your side hustle is in this area, look for ways to boost sales all year before quitting. A wedding florist can sell flowers to corporate clients. They can also provide them to funeral homes. This strategy creates steady income from different sources. So, focus on finding a B2B market to enter. There you will find sustainable opportunities. Corporates always need reliable vendors.
Who brings money to the table if not your business?
In the USA, it’s best to have one steady 9-to-5 income. Use the other income to test business ideas. This way, the pressure to earn eases while you learn your business model. Sit down with your partner and look at both bank statements. Review your finances together. Make a list of expenses you can cut. For example, I last bought shoes in 2022. Identify expenses you can change from must-haves to nice-to-haves. This talk brings clarity and allows time before you go full-time with your business. Have honest conversations about money and expenses. Also, plan for tough times. Set aside emergency funds.
What is your mindset about uncertainty?
Your mindset is like a smile. It spreads. One of my uncles called to thank me last week. I was surprised and I asked why. His answer made me smile. He decided to become a realtor in the USA. I inspired him to push beyond his 9-5 job. When we talked about side hustles, I was struggling with mine. But my mindset was strong. Remember, you only need a game plan once. Then, you can focus on the right efforts. Also, as Alex Hormozi says, the goal of your first business is not to get rich. It’s to get good. Everyday you curate your business in different forms. For example, preparing a detailed questionnaire for your customers adds quality to your deliverables.
What is your baby situation?
Babies are precious but need a lot of care. If you don’t have family nearby, you’ll need daycare or a nanny. While America loves pregnant women, that support often fades once you become a parent. In my experience, there’s never a perfect time to have a baby and start a business. Both come with surprises, even with a good plan. As a mother, even when someone else cares for my baby, I still worry and miss him. Motherhood can be chaotic, which affects my side hustle. The one decision my husband and I cherish is sleep training our baby. It has changed everything, giving us peace of mind and time to regain our lives.
Conclusion
There’s no perfect moment to quit your 9 to 5 job. But don’t leave if you haven’t sold anything yet. Ideas alone don’t make money; they only feel good. Every entrepreneur is a salesperson. If you excel in sales and partner with a marketing expert, you’re set for success.
As Joshua Latimer says, we are all marketers. This is a strong idea. You market yourself at work daily. It’s not just about selling a pen. It’s about understanding who needs the pen, their pain points, and how your pen can help them.
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