How to Know If You're Ready to Leave Your 9-5 and Go All In on Your Side Hustle If you're considering leaving your 9-5 to go into entrepreneurship full time, this guide will help you learn how to assess your business's profitability, secure a financial cushion, create a strong support network and develop a backup plan so you can take the leap with confidence.

By Jason Miller

Key Takeaways

  • If you think you're ready to leave your 9-5 and pursue your side hustle full time, ask yourself these three important questions honestly.
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Ask yourself, why do you need to quit your 9-5 to go full-time into your side hustle? How will quitting help you and what is your motivation to do so? In the U.S., 28% of people state that becoming their own boss is their top motivator to go all into their side hustle.

Maybe you have another reason for wanting to leave your job for entrepreneurship. You could want to make more money or spend more time working on your own business. If you think you're ready to leave your 9-5, ask yourself these three important questions honestly.

Related: 44 Side Hustle Ideas to Make Extra Money in 2023

Do I have a proven business model that's been tested?

Nearly 50% of businesses fail within their first five years of operation. This isn't to discourage you and in fact, can be used as motivation instead. Knowing this and learning from other businesses can help you minimize risks and figure out what your competition will be like.

Making about two-thirds of your full-time job's salary for about a year at your side hustle is a good place to start on deciding if you're profitable enough to quit your job. You should also be using the money from your job to put money aside for emergencies. Running out of cash is one of the top reasons businesses fail so by having a cash cushion you'll be able to give your side hustle the time and attention it deserves to succeed. Everyone's expenses are different, but for me, I would want at least 6 to 12 months of savings.

If it's one thing I've learned, owning a business affects you mentally, emotionally and physically. And on the days that don't go as planned, you're going to have to stay strong and positive. By becoming bogged down with a few bad weeks here and there, your productivity will slide and you'll lose your motivation. That's why I preach business is less about motivation and more about consistency. Anyone can be motivated for a short period of time. But putting in constant effort even on the hard days, will separate the side hustlers from the full-time business owners.

Do I have support?

It's important to remember starting a business isn't just hard on you as an entrepreneur, but it's going to be challenging for your whole family. At least at the beginning, you may have less time and energy to spend with your spouse or kids and you'll need your spouse's support to do that and to get through business challenges. If you're spending more time on your business, your spouse may need to do more work at home or even have to work more hours to offset the financial responsibilities temporarily. Have you thought about how else quitting your job would affect your family? How would you deal with things like healthcare and benefits or daycare?

Getting support from people who've been in your shoes can make all the difference on your entrepreneurial journey. Whether you're in a course and leaning on your teacher and peers for advice or other business owners in your industry, it's important to be open to feedback and to handle criticism with an open mind. When I was younger and didn't want to ask for help, I quickly learned how leaning on others for support was so important, especially when starting.

Related: Can You Turn Your Side Hustle into a Business? Consider These 3 Things.

What's my backup plan?

This one is controversial and can be a hard pill to swallow because many entrepreneurs see it as allowing yourself the option to fail or quit. But I think it's important to be realistic especially when you have other people counting on you to be the provider. That's one reason I always suggest not to burn bridges with former employers.

Tell senior management about your plans first so they don't receive the news from one of your peers. Give your full two weeks' notice, or whatever your contract states. If you're in a management role, you may want to give more notice and let the company decide what they would prefer. Continue to show up and do your work to the best of your capability. Now isn't the time to slack. It not only says a lot about your character if you continue to show up with integrity, but it also ensures you're not putting extra pressure on your team. And avoid gossip and avoid speaking badly about the company or any employees. Doing this will also help keep your leave on a positive and friendly note.

There are no real rules to follow when you're ready to go full-time into your side hustle because we're all different and so are our situations. I'm just giving you guidelines so you can start asking yourself the important questions to know if you're ready to leave your job. But if you think you're ready and you have a proven business model that's been consistently bringing in cash, have the right support, and have a backup plan, you're on your way to successfully quit your job and go all into your side hustle.

Jason Miller

CEO of the Strategic Advisor Board

Jason Miller is a seasoned CEO with an overwhelming passion to help other business owners and CEOs succeed. He was nicknamed Jason “The Bull” Miller because he takes no BS and no excuses from the people he serves. He has mentored thousands of people over more than two decades.

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