Ask Yourself These 2 Questions Before You Quit Your Full-Time Job for Your Side Gig
Written by
Jordan Rosenfeld
Edited by
Molly Sullivan
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Turning a side hustle into your full-time career is a common financial dream for many Americans. Rising living costs, stagnant wages and the appeal of being your own boss have pushed more people than ever to wonder whether now is the moment to make the leap. But quitting your job too early can create long-term regret, lost income and unnecessary financial strain. That’s why Wayfair co-founder Niraj Shah suggested making what he calls a “no-regret decision,” a choice where even if your business doesn’t take off, you’re still glad you tried.
According to Shah, that decision starts with asking yourself two core questions about your business and your financial readiness. If you’re thinking about going all-in on your side gig in 2026, check out his suggestions.
1. Is Your Side Gig Strong Enough To Justify the Risk?
The first question Shah asked is about the business itself. He recommended you look closely at your side gig’s real-world progress, not just your hopes, and ask a realistic question: Has this business grown enough to be worth your full-time focus?
That means looking at actual performance metrics. Are you bringing in consistent revenue? Do you have regular, repeat customers or a reliably growing client base? Has your side gig reached a point where devoting more time to it is the only thing holding it back?
Many entrepreneurship experts recommend not quitting your day job until your side gig earns as much as two-thirds of your full-time income and shows staying power. Others say you should know your next three to five growth steps and have proof your product or service solves a real need.
Some indicators your side gig may be ready for full-time focus include:
- It earns meaningful, recurring income each month.
- Customer demand is steady or rising.
- You know your cost structure and how to scale.
- You’ve tested your business model beyond friends and family.
- You already struggle to keep up while working full time.
If your business feels fragile or unpredictable, that’s a sign you’re not ready yet.
2. Are You Financially Prepared To Take the Leap?
The second question Shah asked is more personal: Can you afford to take this risk? Shah stressed that financial readiness is just as important as confidence in the business itself.
The reality is that many people quit too soon and end up returning to jobs they don’t want because they ran out of cash long before their side-gig-turned-business had a chance to grow.
Most financial planners recommend having a padding of six to 12 months of living expenses, plus an additional cushion for early business costs. That includes rent, utilities, food, insurance, loan payments and anything your household relies on. If your family couldn’t weather the slow months, or a worst-case scenario, it’s not safe to quit.
If savings alone can’t support you, some entrepreneurs rely on temporary help from family, small personal loans or early-stage business financing. However, be sure you have a plan. Don’t rely on chance.
Consider the ‘In-Between’ Options
Quitting doesn’t have to be all or nothing. Shah suggested negotiating reduced hours or creating a flex schedule if your employer is willing to work with you. A four-day work week or part-time arrangement can buy you the breathing room to grow the side gig without giving up financial stability.
Another option is outsourcing small tasks for your side gig to free up your limited time while still keeping your day job.
These hybrid approaches won’t work for everyone, but they can help bridge the gap between dream and reality without taking a reckless leap.
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