15 Things I’ve Learned in the last 15 Years as a Retirement Planner

Many aspiring retirees think of retirement like a finish line. But the most successful retirees treat it like a new chapter, one they get to write with freedom and purpose.

You can have $5 million and feel uncertain - or $500,000 and feel content. Security isn’t just about savings; it’s about knowing what you need and why.

Once the paychecks stop, time becomes your most valuable currency. The happiest retirees have plans for their days, not just their dollars.

Some people fear they’ll never ‘fully retire.’ But that’s not always a problem; for some, a hybrid retirement is the objective. The best outcomes after a long focused career often include meaningful part-time work, volunteering, or creative projects.

It’s not about the age; it’s about the preparation. Clarity gives you options. Rushing into retirement without purpose can be just as dangerous as retiring too late. We discuss planning for retirement more in depth HERE.

Most people think of taxes as an April issue. But the biggest tax savings happen years in advance - especially when it comes to Roth conversions, RMDs, and Social Security planning.

Trusts and wills are important - but your family also needs a clear explanation of your wishes, your values, and where the keys are (literally and figuratively).

One’s excited; the other’s nervous. One wants adventure; the other wants simplicity. The best plans include space for both dreams, and time for conversations before the leap.

Without good health, all the money in the world can feel meaningless. Prioritizing wellness is a form of wealth preservation.

Every year, someone tells me: “We should have done that 5 years ago.” If you have the resources and the dream, don’t wait for a perfect time because it rarely comes.

Chasing returns becomes less important in retirement than creating stability. You want a portfolio that helps you sleep at night, not one that keeps you up.

What they value: clarity, communication, and intentionality. What they fear: confusion, surprises, and conflict. Good planning is a final gift of love.

You don’t need every dollar to work as hard as you did. Keeping 6-12 months of cash reserves can be the glue that holds a plan together. Money itself may not bring more happiness, but the margin of safety that a cash cushion provides sure does.

The retirees who feel most confident aren’t the ones who ‘know everything’ - they’re the ones who built a team: planner, CPA, attorney, family. Don’t walk the path alone.

It’s not a light switch - it’s a dimmer. It evolves. Your goals will change, your needs will change, and that’s okay. The key is adjusting with intention, not fear.