How to Make Smarter Financial Decisions Before and During Retirement

Most retirees spend decades saving, only to realize the hardest financial decisions start the day they stop working. As we approach the end of 2026, the stakes for your retirement income stream have never been higher. I’m Mike Heatwole, CFP®, and in this video, my wife Lana and I give you an insider look at how our family-owned firm, The Dala Group, helps clients navigate the complex “trough years” between early retirement and the start of Required Minimum Distributions (RMDs). We’re currently seeing a major shift in Roth IRA conversion strategy 2026 year end planning. With the landscape of the tax-efficient retirement withdrawal sequence 2026 evolving, simply following the “taxable first” rule could be a $100,000 mistake. I’ll break down how we evaluate Social Security timing for high net worth retirees and why we are already preparing our clients for the Medicare Part D 2027 plan changes that were just announced. Whether you’re worried about the 2026 TCJA tax sunset estate planning strategies or just want a clear path to creating a tax free retirement income stream, this conversation is for you. As a family business based in Hoffman Estates, Illinois, we don’t just look at spreadsheets—we look at the legacy you want to leave. From managing IRMAA surcharges to navigating the new OBBBA senior deduction, I’ll show you how we integrate taxes, investing, and estate planning into one cohesive strategy. Watch until the end to see how we’ve built The Dala Group from the ground up to protect what you’ve spent a lifetime building. Trying to make smarter decisions about retirement, Social Security, taxes, investments, or your financial legacy? I’m Mike Heatwole, CFP®, Founder and CEO of The Dala Group. Our team helps retirees and pre-retirees navigate the financial decisions that matter most before and during retirement, including Social Security filing strategies, retirement income planning, RMDs, QCDs, Roth conversions, tax planning, estate planning, giving to family,