Life is full of milestones—some predictable, some unexpected—but many come with a hefty price tag. Whether it’s sending your kids to college, celebrating a major anniversary, or preparing for life after your career, the only way to prepare is to map out what’s coming down the pipeline.
In my own life, I encountered a year where several major events collided: my 25th wedding anniversary, my daughter’s high school graduation, and her first year of college. I could see it coming a decade in advance, and I knew that if I didn’t plan for it, I’d be scrambling to cover expenses. So, I made intentional financial choices to ensure I had extra income that year—whether it was for a graduation party, an anniversary trip, or tuition payments.
Anticipating Your Big-Ticket Years
Take a moment to reflect on the major expenses looming in your future. Maybe you have a child starting college in 2027 or perhaps two in college by 2028. These are not just theoretical future costs; they are real financial obligations that need a structured plan.
Instead of averaging income projections over five or ten years, break it down year by year. Ask yourself: What revenue will actually be realized in each calendar year, and how does that align with my specific financial obligations?
More Runway = More Flexibility
Many of our clients operate in a world where salaries are just one component of their income. Some own businesses, in which they have surpluses, debts, and occasional deficits that impact their personal finances. Many others are executives who receive significant (yet variable) compensation through bonuses and equity.
While we don’t want to live in fear of every possible risk, we do want to operate from a plan that gives us more runway to prepare–and lower the risk. Take the two examples above. I’ve known business owners who didn’t hit their profit goals and had to re–adjust their kids’ expectations around college. I’ve also known executives who planned on selling vested stocks, only to have the stocks be in a slump when their cashflow needs came.
The common factor in all of those cases was that they hoped to find the cash nearly all at once as the need arose.
The Power of Strategic Planning
So, how do you plan effectively? Start by mapping out your income and expenses on a year-by-year basis. Instead of relying on broad estimates, use real numbers to forecast how much you’ll need for significant milestones. Overlay that with your personal financial timeline so you can make proactive decisions rather than reactive ones.
Financial stability isn’t about luck—it’s about preparation. By identifying your big-ticket years early and structuring your income accordingly, you can navigate life’s financial peaks and valleys with confidence. The earlier you start planning, the more flexibility you’ll have when those costly moments arrive.
This is an exercise we encourage all of our clients to do with us. Together, we can take an inventory of your financial world to help match your priorities with your cashflow.
We’re always here to help you Envizion More–and plan for it.