Our Process

Our Holistic Retirement Planning Process

Retirement confidence doesn’t happen by accident. It’s the result of a coordinated plan, built around your full financial picture and designed to evolve with you.

At Sailwinds Financial Strategies, we use The Bucket Plan® holistic planning process tailored to your goals, income needs, tax situation, and values as our guide to providing exceptional outcomes. The output of that process is a comprehensive plan that covers each of the Five Pillars of Holistic Wealth Management. Every step using The Bucket Plan® is purposeful, and every recommendation connects to the bigger picture.

What Is Holistic Retirement Planning?

A holistic financial plan goes beyond your portfolio. It factors in every dimension of your financial life, coordinating each area so that your decisions work together rather than in isolation.

Many advisors treat income, risk management, healthcare, tax strategies, estate and legacy planning, and investments as separate conversations. We treat them as one, grounded in The Bucket Plan®. That integration is what allows us to identify inefficiencies, find ways to help reduce your tax burden and protect your income, and create a full-picture plan that reflects your life.

The Bucket Plan®: The Holistic Framework at the Heart of Your Retirement

The Bucket Plan® is a time-tested philosophy that organizes your assets by purpose and time horizon rather than leaving your savings in a single pool exposed to the same risks at the same time.

With The Bucket Plan®, instead of watching one large portfolio rise and fall with the market and wondering whether you can afford your lifestyle, every dollar has a defined role. You know what you’re spending today, what is positioned to replenish your income in the near term, and what is working toward your long-term future. That type of clarity can change how retirement feels.

The Now Bucket

Your Now Bucket holds the assets you need in the near term, typically covering one to two years of living expenses. These funds are kept in stable, liquid vehicles, not subject to market swings, so you always have reliable income available regardless of what markets are doing. This bucket is the foundation of your retirement security.

What it helps protect you from: Needing to withdraw income during a downturn and the damage that forced selling at the wrong time (sequence of returns risk) can do to a long- term portfolio.

The Soon Bucket

Your Soon Bucket holds assets you’ll need over the next 5-10 years, generally your intermediate horizon. These funds are invested more conservatively than your long-term assets but with enough growth potential to keep pace with inflation and replenish the Now Bucket over time. As the Now Bucket is drawn down, the Soon Bucket is adjusted to refill it systematically.

What it helps protect you from: Running through long-term assets too quickly or keeping growth-focused investments in overly conservative strategies longer than needed.

The Later Bucket

Your Later Bucket holds your long-term growth assets, the portion of your portfolio with a time horizon of ten or more years. With the Now and Soon Buckets providing for your near and intermediate income needs, these assets have time to ride out market volatility and pursue the growth required to fund the decades ahead. This is where your wealth does its long-term work.

What it helps protect you from: Market downturns forcing changes to your long-term strategy, and the slow erosion of purchasing power that comes from keeping too much in conservative growth containers for too long.

Our Four-Step Planning Process

Before we begin, we always schedule a brief introductory call. This is a pressure-free, no- obligation conversation to make sure we’re the right fit for each other. If we are, we move forward together through four clear steps.

Step 1: Discover

Where You Are Now

Understanding you is our priority: your goals, your concerns, your lifestyle, and what a confident retirement looks like to you. If you have a spouse or partner, we ask that they join as well. We will cover:

Income sources
Assets and beneficiaries
Tax picture
Unique circumstances, like a late-career transition, or partner protection needs
Lifestyle considerations
And more

Step 2: Design

Where You Want to Go

In our second meeting, we dig deeper into the details. We analyze your cash flow, net worth, and tax situation, and we begin mapping a path forward. We help you clarify and prioritize your goals, from travel and lifestyle spending to legacy intentions and healthcare needs.

We look across your accounts to understand your current and future tax exposure, and we start identifying the strategies, including Roth conversions, bracket management, and withdrawal sequencing, that can help reduce your lifetime tax burden.

Step 3: Deliver

Your Holistic Plan

Here, we present your personalized Bucket Plan. This is your full retirement roadmap: a clear, coordinated strategy that accounts for your income needs now, in the next ten years, and beyond.

You’ll see how your investments are allocated across time horizons, how your tax strategy is structured to protect more of your income, and how every piece of your financial life, from protection and legacy to Social Security and Medicare, fits together into a single plan built for your future.

Step 4: Dedicated Partnership

Ongoing Service and Support

Delivering your plan is the beginning, not the end. After implementation, we continue as your dedicated planning partner, monitoring your strategy and adjusting as life changes. We review your plan regularly across all five pillars of holistic wealth management and stay ahead of any changes in tax law, Medicare, Social Security, and market conditions that could affect your strategy.

Dive Into the Philosophy Behind The Bucket Plan®

To gain a deeper understanding of the retirement planning philosophy that guides our process, we encourage you to explore The Bucket Plan®: Protecting and Growing Your Assets for a Worry-Free Retirement. Written by Jason L Smith, this book expands on the strategies we use to help clients create sustainable income, navigate market uncertainty, and pursue retirement with greater confidence. Paired with the personalized guidance you’ll receive from our team, it offers valuable insight into how The Bucket Plan® can support a more flexible, lifestyle-focused approach to retirement planning.

Ready to Begin?

The best retirement plans create confidence not just on paper, but in daily life. The first step is a conversation. We’ll learn about your goals, walk you through our approach, and help you decide whether Sailwinds is the right fit. No pressure, no obligation.

Book My Complimentary Strategy Call

Frequently Asked Questions About Tax Management in Retirement

A standard portfolio treats all your assets as a single pool, leaving you to wonder whether you can safely withdraw from it at any given time. The Bucket Plan® gives every dollar a defined role based on when you’ll need it: near-term income in the Now Bucket, intermediate income in the Soon Bucket, and long-term growth in the Later Bucket. This structure helps provide income reliability, reduce the impact of market volatility, and protect against sequence-of-returns risk.
Sequence-of-returns risk is the danger that poor market performance in the early years of retirement, when you are actively drawing income, can permanently impair your financial picture even if markets recover later. Because withdrawals during a downturn can lock in losses, timing matters as much as average returns. The Bucket Plan® helps shield against this by positioning your short-term income needs to be covered by more stable assets, so long-term growth assets don’t have to be sold at the wrong time.
Absolutely, we encourage it. Retirement planning touches both of your lives, and we want to make sure both voices are heard. This is especially true for LGBTQ+ couples and partner care situations, where protection and legacy planning often require more specialized attention.
Tax management is woven into your plan from the start, not added as an afterthought. In the Design step, we map your current and future tax exposure across all accounts. In the Deliver step, your Bucket Plan includes a coordinated withdrawal strategy built to help reduce your lifetime tax burden. And in the Dedicated Partnership phase, we monitor your tax situation year-round through The Tax Management Journey®.

Ready to See How It All Fits Together?

Every situation is different. Schedule a conversation and let's explore how holistic, tax-focused planning could work for your retirement.

Book a Complimentary Strategy Call