This is a significant hurdle on the road to financial freedom. : Most businesses make it past that crucial first year by finding investors while controlling costs tooth and nail. “If you want to find financial freedom, you need to retire all debt — and yes that includes your mortgage,” O’Leary told CNBC CMCSA, +0.40% Your personal break-even, that moment where, like a business, you’re going to thrive or fail, is age 45, he says. It’s a tall order. Huge numbers of baby boomers are hitting 65, an estimated 10,000 of them a day.