Most people know they need a plan. Few have one that actually keeps up with their life. Checkpoint Planning brings structure, clarity, and a fiduciary advocate to wherever you are.
Job loss, divorce, early retirement, inheritance. The moments when financial decisions are most consequential and most often made without a plan. This is where Checkpoint Planning was built to work.
Building a portfolio aligned with your goals, timeline, and risk tolerance. Social Security timing, retirement income strategy, and ongoing investment management.
Cash flow, debt, insurance, estate documents, tax coordination. A comprehensive plan that connects every piece of your financial picture and keeps it current.
We also work with clients navigating inheritance and unexpected wealth, loss of a spouse, and career reinvention or sabbaticals.
Severance decisions, COBRA vs. marketplace coverage, unemployment, and a financial runway plan for what's next.
Retirement readiness, Social Security timing, pension elections, and building income that lasts longer than you planned for.
Settlement analysis, QDROs, tax impact, and rebuilding a financial plan that's entirely your own.
Thoughtful, unhurried decisions about a windfall: taxes, investing, and honoring what it represents.
Benefit claims, beneficiary transfers, and stabilizing finances during an emotionally difficult time.
Sabbaticals, career pivots, and equity compensation decisions when you're building something new.
We start by helping you prioritize what's most important to you today and in the future. Together we review the following areas of your financial life.
Not sure where your situation fits? The Where We Begin session is the easiest way to find out, complimentary, no obligation, 45 minutes.
Schedule Your Free Session