Retirement Planning as a School-Focused Entrepreneur

Of all the financial fears that kept me awake during my transition from school employee to entrepreneur, retirement planning was #2, right behind salary. We talk about irregular income and startup costs, but there's something particularly unsettling about watching your future self lose their safety net in real-time.

For 28 years, I lived in the comfortable rhythm of automatic retirement contributions. My first school was incredibly generous, with 11.5% of my salary automatically deposited into retirement accounts every month, and I barely noticed because I never saw it. My second school wasn't quite as robust, but it was still excellent. Month after month, paycheck after paycheck, that TIAA-CREF money accumulated while I focused on work.

There's something beautifully mindless about employer-sponsored retirement plans. The money vanishes before you can spend it on something else. Your future self is fed first, automatically, without requiring any willpower or financial discipline from your present-day self.

Then I hung out my shingle.

The retirement money I'd already saved didn't disappear; let me be clear about that. Those years of contributions were still there, still growing (or shrinking, depending on market conditions). But that steady, reliable contribution stream? Gone. Completely.

The silence was deafening. No more automatic deposits. No more employer matches. No more contributing to my future without thinking about it. Suddenly, retirement planning became an active choice I had to make every month, competing with business expenses, irregular income, and the thousand small costs of entrepreneurship.

I'm fortunate to be contributing to my retirement again now, but it took time to get there. And even now, it's different. When cash flow is tight, that retirement contribution becomes optional in a way it never was when HR handled it automatically. The temptation to skip a month, or three, is real.

This isn't necessarily good or bad. It's just a fact. However, it's a fact that needs to be factored into your equation when considering whether to leave the security of school employment.

Some months, when client payments are delayed or when I'm investing heavily in business development, I miss that automatic pilot terribly. In other months, when business is good, I can contribute more than any school has ever matched. The irregularity is both a curse and an opportunity in entrepreneurial retirement planning.

If you're contemplating this transition, factor this reality into your planning. Build retirement contributions into your business model from day one, even if they start small. Consider working with a financial advisor who understands irregular income. And don't let the fear of losing automatic contributions keep you from making a leap that could ultimately give you more control over your financial future.

Your 65-year-old self is counting on the decisions you make today, whether you're working for a school or running a business that serves them.