Let's Build with Shegun Otulana

How do I know it's time to quit my job and go all in?

Published 4 months ago • 4 min read

I love it when people hustle. I’m familiar with several people, including friends, who use side hustles to supplement their income and enjoy doing it, even earning relatively good income from it.

However, my writing on this blog focuses on building great companies. I don’t discuss side hustles or ways to make money online with ChatGPT and all the other side hustle-type businesses out there. I focus on getting the right frameworks, mindset, and tactics to build high-scale businesses with significant impact beyond earning extra income.

But today, I’ll be discussing side hustles. Why?

One of the questions I often get is, “When is the right time for me to quit my job and focus on my startup full-time?” In many cases, the asker has been working on their idea as a side hustle, and they want to know if it’s time for them to go all in.

The answer to this question is a cause for debate in the startup world. To be a true entrepreneur, should you take the enormous risk of stepping away from the stability of a full-time job right out of the gate? Most investors, for example, won’t fund you if your company is a side gig. What is a founder to do?

I’m not inclined to tell anyone how to live their lives or that they must quit their day job to be a successful entrepreneur. That’s the route I took (eventually), but that doesn’t mean it’s the right thing for everyone. The risk was significant for my family – it involved credit card debt, bank debt, etc., but I had a working spouse. Everyone’s level of risk is different. Ideally, it’s great to save up enough for six months, or even better, a year’s expense before quitting your day job, especially if you have a family. Use this time of aggressive savings to validate your idea, talk to experts, study your competition, and learn from other successful founders. But don’t stay in this phase forever, using “saving up” as an excuse. Cut your living expenses down. Be aggressive and treat it as your first test.

Focus — The Superpower

If you want to build something big and grow it into something impactful, you must quit jumping from project to project and focus.

Take my journey as an example: Zertis, my first company and the precursor to TheraNest, was registered in 2004. For 6-7 years, it was a side gig in one form or another, and for various reasons didn’t get my full undivided attention. Plus, I had great jobs. Zertis became my full-time gig in 2011, and by the end of 2012, it had led to what became TheraNest. That’s the power of undivided attention.

The question of whether or not you should quit your job to be a full-time entrepreneur depends on your goals for the business. Whichever path you choose, you need to be realistic about the consequences. Here are some scenarios you need to consider.

Steady, Gradual, Longer Term Path

The truth is, your side gig will never become your main gig until you start giving it as much time as you’re giving your day job. Working on your startup idea part-time is fine, but it lengthens the time to succeed.

Of course, if you don’t mind your entrepreneurial endeavor growing gradually over time and you’re okay with it taking many years before your side gig becomes your main gig, go for it – there’s no need to change what you’re doing. It may also mean you don’t believe your idea can be that impactful.

The downside is you’re losing time, your most valuable asset. You only have so much time to reach your destination. Settle in your mind that your idea is just a side gig you give a few hours to weekly and be at peace with it. Don’t raise money or pretend you’re all in. There is a reason why VCs don’t fund side gigs: the amount of time you give to your business is a determining factor in its growth. You need to be able to make mistakes and iterate quickly, and that requires time, energy, and mental space —effort compounds.

Until the amount of time you give is impactful enough to start compounding fast, it will take a long time to be successful. You won’t enter the hypergrowth stage if you’re doing it part-time.

You Can’t Quit But Want High Growth and Impact

If you thoroughly believe in your idea and you want to grow it quickly, then you’re faced with a choice. Your first option is to quit your job and go all-in on the entrepreneurial journey. It’s a risky step, but it’s the quickest way to give your entire mental focus to what you’re doing.

If you don’t quit your regular job, be ready to work like you have two full-time jobs. There’s no way around it. You have to give your entrepreneurial journey at least as much time as you’re giving your regular job to be successful in a reasonable amount of time.

If you can’t quit your job and you can’t take on two full-time jobs, then I just don’t know how you’re going to get there fast. Yes, there are exceptions, but those are the exceptions. You’re probably not going to be an exception.

Multiple Side Hustles — The Fastest Path to Multiple Dead Ends

Whether you go all-in or stay in your job, don’t become one of those people who jump from one hustle to another, all in the pursuit of making money. They chase everything all at once and end up with nothing to show except a few crumbs here and there. If making some extra cash is what motivates you, that’s fine. But it isn’t what will help you make an impact in terms of building outsized success as an entrepreneur.


The entrepreneurial journey isn’t just about the “hustle.” It’s about focused hustle – that’s how you win. You will make mistakes. Make the mistakes quickly, learn from them, iterate, and move forward. Focus on the thing you believe in and make it happen. Make your choice and run with it.

Interested in discussing more? Join the Let’s Build Community to connect with me and other growth-minded founders.

Let's Build with Shegun Otulana

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