Upticks: 20 Years of Retirement Planning Taught Me These 5 Things
By Luke Sullivan on July 30, 2026
In this week’s episode of Upticks, Jake shares five lessons he’s learned over two decades of working with clients. They’re practical ideas, but together they reinforce an important principle: successful retirement planning begins long before selecting investments.
Start with organization.
One of the first challenges many people face is simply understanding what they own. Retirement accounts from previous employers, brokerage accounts opened years ago, multiple bank accounts, insurance policies, and estate documents often live in different places.
When your financial life is scattered, it’s difficult to make informed decisions.
Before worrying about investment performance, create one complete picture of your finances. Knowing what you own, where it’s located, and how each piece contributes to your overall plan provides the clarity needed to make better decisions.
Measure your progress against your goals.
It’s common to ask how your portfolio performed compared to the S&P 500. The better question is whether your investments are helping you accomplish what they’re intended to accomplish.
A retirement portfolio exists to support your lifestyle, generate sustainable income, and provide confidence throughout retirement. Those goals are unique to you, which means your success shouldn’t be measured against someone else’s portfolio or a market index.
A financial plan provides the benchmark that matters most.
Don’t overlook tax planning.
Investment returns only tell part of the story. How much of those returns you ultimately keep can have an equally meaningful impact on your retirement.
Tax planning isn’t a one-time conversation. As your circumstances change, opportunities involving Roth conversions, charitable giving, withdrawal strategies, and asset location should be revisited regularly. Small decisions made consistently over many years can have a significant cumulative effect.
Give every dollar a purpose.
Every account should have a clear objective. Some dollars are intended for monthly spending. Others are reserved for emergencies, retirement income, future opportunities, or large purchases.
When every dollar has a purpose, financial decisions become simpler because your money is aligned with your priorities instead of sitting idle without direction.
Often, improving a financial plan isn’t about adding something new, it’s about bringing more intentionality to what you already have.
Build flexibility into your plan.
No one knows exactly what the future holds.
Markets will fluctuate. Tax laws will evolve. Life will inevitably present unexpected opportunities and challenges.
Rather than attempting to predict every outcome, a well-designed retirement plan creates options. Flexibility allows you to adjust spending, revisit withdrawal strategies, and respond to changing circumstances without feeling like your entire plan needs to be rebuilt.
That’s one of the characteristics Jake believes separates a durable retirement plan from one that’s dependent on perfect conditions.
Better decisions—not bigger returns.
Retirement planning isn’t simply about accumulating more assets. It’s about making thoughtful decisions that support your long-term goals.
When your financial life is organized, your investments are aligned with your objectives, taxes are considered alongside investment decisions, every dollar has a purpose, and your plan remains flexible, you’re giving yourself a much stronger foundation for retirement.
To hear Jake expand on each of these ideas and explain how they’ve shaped his approach over the past twenty years, watch this week’s episode of Upticks or listen wherever you get your podcasts.
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