I ran Liles Law as a side hustle for eight years before I made it my full-time practice. During those years, I asked myself "Is it time yet?" more times than I can count.
If you're asking yourself the same question, here's what I've learned, both from my own leap and from working with hundreds of founders making theirs.
There's No Perfect Moment
Let's get this out of the way. There will never be a moment when leaving a steady paycheck feels completely safe. If you're waiting for the fear to go away, it probably won't. The goal isn't to eliminate the risk. It's to make the risk manageable.
Questions to Ask Yourself
Is there consistent demand? One great month is exciting. Six or more months of steady clients or sales is a pattern. Look at your numbers over time, not just your best month.
Do you have a financial cushion? Many founders aim to have several months of personal living expenses saved before they leave a job, plus enough to cover business expenses. The right number depends on your situation, so talk to your accountant or a financial advisor.
Is your side hustle limited by your time? If you're turning away clients or can't grow because you only have nights and weekends, that's a strong sign. For me, my side hustle was taking up all my extra time, bleeding into the time I typically spent making dinner or attending my kid’s soccer practice. The business had simply outgrown my evenings.
What will you lose besides your paycheck? Think about health insurance, retirement contributions, and other benefits. Have a plan to replace them.
Is your business ready to be a real business? Is it set up with the right legal structure? Do you have contracts in place? Is your brand protected? Those things matter even more when your livelihood depends on them.
Check Your Employment Agreement Before You Go
This is the lawyer in me talking, but it's important. Before you leave, review any agreements you signed with your employer. Look for non-compete or non-solicitation clauses and confidentiality obligations. Also look for any provisions about who owns ideas or work you create while employed. You don't want a surprise claim from your former employer right as your business is taking off. I often help clients with reviewing these agreements before they take the leap.
Consider a Gradual Transition
Quitting doesn't have to be all-or-nothing. Some founders go part-time, take a contract role, or set a firm exit date six months out to give themselves time to prepare. A gradual transition can ease the financial pressure while you grow.
Trust Yourself
If you've done the math, built the foundation, and you still keep thinking about it, it may be time. Making the leap was truly one of the best decisions I ever made, and I've helped so many founders do the same.
Regardless of what you ultimately decide, I’m cheering for you.
