“Which Account Do I Pull From First?” A Guide to Smarter Retirement Withdrawals

March 26, 2026

Key Takeaways


  • How you withdraw retirement income is just as important as how much you've saved.

  • The order you pull from accounts can significantly impact your tax bill over time.

  • A coordinated strategy helps your portfolio last longer and behave more predictably.

  • Withdrawal planning works best when it's aligned with your broader financial plan, not handled account by account.

You've spent years saving for retirement.


But when it comes time to actually use that money, the strategy isn't always as clear.


While saving is important, just as important is how you'll turn those savings into income. And decisions like which accounts to draw from first or how to manage taxes can have a real impact on how long your money lasts.


A thoughtful withdrawal strategy helps you create reliable income, reduce unnecessary taxes, and avoid costly mistakes along the way. 


Why Your Retirement Withdrawal Order Matters


It's tempting to assume you can just pull from whichever account is most convenient. And honestly, in the short term, that works fine.


Over a 20- or 30-year retirement, though, the sequence of your withdrawals shapes your tax bracket every single year, your Medicare premiums, the growth potential of your remaining accounts, and what you eventually leave behind for your family.


Your retirement accounts aren’t taxed the same way:


Traditional 401(k) or IRA

Tax-deferred, owing ordinary income tax on withdrawals

Roth IRA

Tax-free, no taxes on qualified withdrawals

Taxable Brokerage Account

More favorable long-term capital gains rate when holding investments for a year or more

Traditional 401(k) or IRA Roth IRA Taxable Brokerage Account
Tax-deferred, owing ordinary income tax on withdrawals Tax-free, no taxes on qualified withdrawals More favorable long-term capital gains rate when holding investments for a year or more


A thoughtful withdrawal strategy draws from each bucket in a way that keeps your taxable income as smooth and low as possible throughout retirement.


The Traditional Withdrawal Order (and When It Makes Sense)


For many retirees, the conventional wisdom goes like this:


1. Start with taxable accounts

Brokerage accounts and savings are often tapped first because the growth in these accounts is taxed annually anyway, and using them first lets your tax-advantaged accounts continue to grow undisturbed.


2. Move to tax-deferred accounts next

Your traditional IRA, 401(k), or 403(b) accounts are next in line. Withdrawals here are taxed as ordinary income, so drawing on them in a thoughtful, measured way helps you avoid unnecessary jumps into higher tax brackets.


3. Preserve Roth accounts for last

Roth IRAs aren't subject to Required Minimum Distributions (RMDs) during your lifetime, and withdrawals are tax-free. Letting your Roth sit and grow as long as possible tends to pay off, both for you and for any heirs who may inherit it.


This framework is a reasonable starting point, and for some retirees, it works well.


But it's not a universal rule.


Where the Traditional Order Falls Short


Here's a scenario we see fairly often.


A client retires at 63 with most of their savings in a traditional IRA. They draw from their taxable accounts first so their retirement savings can continue growing.


But by the time they hit 73, their IRA has grown large enough that the required distributions push them into a higher tax bracket than they were in at the start of retirement.


Throw in Medicare surcharges (called IRMAA), and what felt like a smart, conservative strategy in their 60s has created a real tax burden a decade later.


That's why we often recommend a more nuanced approach—one that considers what your tax picture looks like across your entire retirement, not just in the first year or two.


Tax Diversification and the Case for Blending


A blended decumulation strategy, rather than a strict withdrawal sequence, often serves retirees better than following one account type at a time. The goal is to keep your taxable income in a range that helps you stay below the thresholds that trigger higher tax brackets, IRMAA surcharges, and heavier taxation on Social Security benefits.


Here's a practical example:


If your expenses can be covered by a mix of Social Security and modest IRA withdrawals that keep you in the 12% tax bracket, you might also consider doing some Roth conversions that same year. You'd move money from your traditional IRA to your Roth while your tax rate is still low.


Yes, you pay the tax now. But from that point on, your Roth grows tax-free, and your future RMDs shrink.


It takes careful planning and realistic income projections, but for many retirees, it's one of the most effective tools available.

This is where many retirees run into trouble.
They've saved enough for retirement, but their withdrawal strategy wasn't designed as part of a larger plan.
➡ See how a comprehensive retirement plan comes together

The Behavioral Side of Withdrawal Strategy


We've covered the math, but there's a human side to this that doesn't get talked about enough.


A lot of retirees feel hesitant to touch certain accounts, especially ones they spent decades carefully building.


We've worked with clients who had more than enough saved but were pulling too little, simply because spending down their IRA felt uncomfortable. That emotional hesitation sometimes led them to draw from the wrong accounts for the wrong reasons.


Having a clear, written withdrawal plan takes that pressure off. When you know which account you're pulling from and why, you're less likely to second-guess yourself when markets get bumpy or make reactive moves that throw off an otherwise solid plan.


Think of it as guardrails: a defined spending amount, a clear account order, and a scheduled check-in to revisit when things change.


There’s No One-Size-Fits-All Answer


The right withdrawal sequence depends on things specific to you: how much you have and where it's held, your expected income in retirement, when you plan to take Social Security, whether you have a pension, how your state treats retirement income, and what you'd like to leave behind.


A strategy that's a perfect fit for one person can create real headaches for another. That's why this is one of the first things we talk through with clients who are getting close to retirement—and one we revisit as things change.


If you're within five to ten years of retirement and haven't mapped out a withdrawal plan yet, now is a good time to start. Before RMDs kick in is often when you have the most flexibility to plan.


We'd love to walk through what this looks like for your specific situation.


Reach out anytime at info@fivepinewealth.com or call 877.333.1015.


Frequently Asked Questions


Q: Does my withdrawal order change if I have a pension?


A: Yes, it can. A pension provides guaranteed income, so you may already be covering a good chunk of your expenses before touching your investment accounts. That changes how aggressively you need to draw from tax-deferred accounts, and may create more room for Roth conversions early in retirement.


Q: How does Social Security timing affect my withdrawal strategy?


A: If you delay Social Security to boost your monthly benefit, you'll need to cover living expenses from your portfolio in the meantime. That gap period is often a smart time to draw down traditional IRA balances at a lower tax rate, before Social Security income pushes your taxable income higher.


Q: Can my withdrawal order affect my Medicare premiums?


A: It can. Medicare uses your income from two years prior to set your Part B and Part D premiums. A large IRA withdrawal that bumps your income above certain thresholds could mean higher premiums (IRMAA surcharges) two years down the road. Keeping those thresholds in mind when planning withdrawals can help you avoid some unwelcome surprises.

Five Pine Wealth Management is a fee-only, fiduciary financial planning firm based in Coeur d'Alene, Idaho. We work with individuals and families across the country who want thoughtful, personalized guidance — without the conflicts of interest that come with commission-based advice.


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What's Inside Your 457? (And Why It Matters More Than You Think)

April 30, 2026
Key Takeaways Your 457 should work alongside your pension to support your overall retirement income plan. Many 457 plans are set on autopilot, but your investments shouldn’t stay that way as you near retirement. Understanding what you're invested in helps you make better decisions when markets move. Turning 50 is your signal to review your 457 more closely so you can check your contributions, risk level, and how it fits with your pension before retirement gets too close. Like many first responders in Washington and Idaho, you probably have a pretty solid grasp of your "Plan A." Between the WA LEOFF Plan 2 or ID PERSI, you’ve spent your career earning a guaranteed monthly pension. It’s the foundation of your retirement — the steady paycheck that arrives regardless of what the stock market does. But then there’s that "other" account. The one you’ve been tucking money into every pay period through deferred compensation. In Washington, it’s usually the Washington State Deferred Compensation Program (WSDCP); in Idaho, it’s often the State of Idaho 457(b) Plan. When we sit down with firefighters and police officers who are within 10 years of their "end of watch" date, they usually know two things about this account: how much is in it and that they’re glad they started it. But when we ask, 'What is that money actually doing?' — that question usually gets a pause. If you’re 50 or older, it’s time to move past the "set it and forget it" mentality. Let’s take a look at how your 457 works and how to make sure it’s working for you. 457 Plan Investment Options  Unlike your pension, which is managed by the state, your 457 is a “defined contribution” plan. That means the outcome depends entirely on how much you put in and how those funds are invested. A 457 plan is just a container. Think of it like a toolbox. What matters is what’s inside the box. Your account isn’t sitting in cash (at least it shouldn’t be). It’s invested in a mix of underlying funds, usually including: Stock funds (equities): These are your growth engines. They tend to go up over time, but they can be volatile. These could be U.S. stock funds or international funds. Bond funds (fixed income): These provide stability and income, but with historically reduced long-term returns. Stable value or cash equivalents: Lower risk, but also lower growth. Most public service 457 plans in the Northwest offer a menu of these options. Some people choose to build their own mix, while others choose a single “all-in-one” fund and let it do the work. This brings us to the most common choice we see… What is a Target-Date Fund? A Target-Date Fund (TDF) is designed to be a one-stop shop. The “date” in the name is the year the fund assumes you will retire. If you plan to hang up the uniform in 2030, you’d likely be in a 2030 fund. A TDF automatically shifts its risk level as you get closer to that date. This is called the glide path . When you are 20 years away from retirement, the fund is aggressive. It buys mostly stocks because you have time to recover from market crashes. As you get closer to the target year, the fund manager automatically “glides” the investments away from risky stocks and into “safer” bonds and cash. TDFs are built for the “average” American worker who relies solely on Social Security and a 401(k), but you aren’t the average worker. You have a LEOFF or PERSI pension. Because your pension acts like a “super bond” (stable, guaranteed income), being too conservative in your 457 might hinder your growth. Conversely, if you’re planning to retire at 53 (common for LEOFF 2) but your fund is target age 65, you might be taking way more risk than you realize. It’s also important to note that two funds with the same year, for example, 2035, can have very different levels of risk depending on the provider. One may still hold 60% in stocks near retirement, while another might be closer to 40%. How Risk Changes as Retirement Approaches In your 20s, 30s, and even early 40s, “risk” is your friend. Risk is what grows a $50,000 account into a $500,000 account. However, as you approach the age of 50, the definition of risk changes. That’s because you’re entering what we call the “retirement red zone,” roughly five years before and five years after your retirement date. This is when: Your portfolio is at its largest You have less time to recover from downturns You may soon rely on the money for income We look at two specific types of risk for our clients: Sequence of Returns Risk: The risk that a market crash occurs just as you start taking withdrawals. If the market drops 20% the year you retire, and you start pulling money out to travel or pay off the mortgage, your account may never recover. Inflation Risk: If you get scared and move everything into the “Fixed Account” or “Stable Value Fund,” you might not lose money, but you’ll lose purchasing power. If your account earns 2% but the cost of living goes up by 4%, you’re technically getting poorer every year. Finding the “Goldilocks” zone — not too hot, not too cold — is the primary job of a pre-retiree. The Age 50 Checklist Once you’re in your 50s, it’s time to stop running on autopilot and take a closer look at your 457. Check Your “Catch-Up” Options In 2026, the standard 457 contribution limit is $24,500; however, once you’re 50, you can add an extra $8,000 in “Age 50 Catch Up” contributions. Even better, if you're within three years of your normal retirement age and haven’t maxed out your contributions in previous years, you may be able to contribute up to double the normal limit ($49,000). This is a massive boost for your savings. Diversify Your Tax Buckets Most first responders have their money in a Traditional 457, meaning you get a tax break now but pay taxes when you take the money out. Both Washington and Idaho offer Roth 457 options. With a Roth, you pay the tax today, but the money grows and comes out tax-free. For high-earners who expect their pension to keep them in a higher tax bracket during retirement, having a “tax-free” bucket of money can be helpful. Coordinate With Your Pension If your LEOFF or PERSI pension covers 70% of your needed income, your 457 can afford to be a bit more aggressive in fighting inflation. If you plan to use your 457 to bridge the gap until you collect Social Security, that money needs to be protected differently. Let’s Take a Look Together At Five Pine Wealth Management, we work with first responders in Washington and Idaho who are approaching retirement and want clarity around their financial picture. We understand how LEOFF Plan 2 and PERSI fit into the bigger picture, and how your 457 can support the retirement you’ve worked hard to build. If you’d like help understanding what you’re invested in, we’d be happy to take a look with you. You can email or call us at 877.333.1015 to schedule. We’d welcome the conversation. You’ve spent your career looking out for the community; let us help you look out for your future. Frequently Asked Questions (FAQs) Q: Is a Target-Date Fund enough for my 457 plan? A: For many people, it is, but as you get closer to retirement, it’s important to review whether the fund’s risk level matches your timeline and overall financial picture. Q: Is there a penalty for taking money out before age 59½? A: No. Unlike a 401(k), the 457 plan has no 10% early withdrawal penalty if you leave your employer, making it an ideal tool for first responders retiring in their early 50s. Q: Should I choose a Target-Date Fund or build my own portfolio in a 457? A: Target-date funds offer simplicity, but building your own portfolio allows for more customization. If you have a pension that already provides a stable income, building your own could be a good option.

He Had $1.1 Million and Almost Went Back to Work. Here's What Changed

April 22, 2026
Key Takeaways A portfolio designed for accumulation may carry too much risk, or the wrong kind of risk, once you stop contributing. When two spouses are at different financial life stages, their investment strategies should reflect that difference. A Roth conversion strategy during the years before required minimum distributions begin can meaningfully reduce your long-term tax burden. Rob spent 30 years building a picture-perfect financial foundation for his retirement. He maxed out his 401(k) and stayed disciplined through market downturns. By the time he retired from a long career in plant management and HR, he had a nest egg most people only dream about. But then retirement arrived, and with it came a new kind of anxiety. Rob spent all those years learning how to build wealth, but never how to draw it down. The accumulation phase was clear, but the decumulation phase is far more complex and far more personal. Rob had hired a financial advisor when he retired, hoping for guidance through that transition. Instead, he got portfolio management and investment decisions without the broader planning context he needed. That relationship didn’t last a year. And that’s when he and his wife Christie, came to Five Pine. The Numbers Behind the Plan: When They Started Today Rob’s age 57 63 Investable assets $1.1 million $2.5 million Net worth — $3.5 million Primary challenge No decumulation plan, Comprehensive plan in place heavy pre-tax exposure Key strategies Portfolio redesign, Ongoing tax planning, Roth conversion planning rebalancing When Saving Well Isn't Enough When we first met Rob and Christie, a few things stood out right away. Rob was recently retired with $1.1 million in investable assets (the vast majority of it in pre-tax retirement accounts). Christie, about ten years younger than Rob, was still working and earning a high income as a part-owner of a small business. They were a dual-financial-life household: one person winding down, one still in full accumulation mode. Rob’s most pressing concern was straightforward to state but harder to solve: how much could he spend without putting their retirement at risk? He wanted to travel, renovate the house, and buy a new vehicle without second-guessing himself. But after those decades of saving, spending felt foreign, even a little reckless. He had seriously considered going back to work, not because he needed to, but because he felt he couldn’t trust the numbers. Underneath that, a long-term tax problem was simmering. With most of their savings in pre-tax accounts, Rob and Christie were looking at significant required minimum distributions (RMDs) starting at age 73. And Christie, likely to outlive Rob by a meaningful margin, would eventually face those distributions as a single filer at higher tax rates. They weren’t in trouble, but without a plan, they were heading toward unnecessary complexity and tax liability. A Plan Built for Retirement, Not for Accumulation We started with the full financial picture. Before we touched the portfolio, we built a comprehensive financial plan and stress-tested it against different market scenarios, spending levels, and timelines. Once Rob saw the projections running out over a 30-year horizon, his hesitation about retirement began to lift. The plan gave him the number he needed and, more importantly, the confidence to trust it. From there, we redesigned the portfolio to match Rob’s phase of life. He had come from a Dave Ramsey background and had always preferred an all-equity approach: aggressive, growth-focused, and straightforward. That served him well during the accumulation years, when he contributed every month and had decades to recover from downturns. But in retirement and drawing from the portfolio regularly, it introduced more risk than his situation warranted. We restructured his holdings to roughly 60% equities, 25% fixed income, and 15% in alternative investments, specifically private credit funds and private real estate. The alternatives were a meaningful addition. They could potentially carry lower price fluctuation than publicly-traded assets and have the ability to generate distributions, which may potentially help support spending needs without forcing untimely equity sales. Christie's accounts, meanwhile, stayed aggressive. She's still contributing through her employer plan, still has years of earning ahead of her, and has time to weather market swings. Finally, we put a Roth conversion strategy in place for the years ahead. Timed to begin when Christie retires, the strategy takes advantage of a window when their income will likely be lower, but before RMDs kick in and before Christie potentially files as a single filer at higher tax rates. Converting pre-tax dollars gradually reduces the accounts that will eventually be subject to mandatory distributions, potentially saving hundreds of thousands of dollars in taxes over time. From Hesitation to Confidence Rob came to us considering whether he needed to keep working. He left with a plan that showed him that he didn't. Once the plan was in place, Rob and Christie started making the most of their years together, international sailing trips, travel they had put off, and experiences they had earned. A health scare along the way reinforced what the plan had already made clear: the goal is to fund a life worth living while you're healthy enough to live it. On the investment side, market volatility became an opportunity rather than a threat. When markets dropped sharply during a period of economic uncertainty, we rebalanced, selling fixed income to buy equities at a discount. As markets recovered, those moves contributed meaningfully to their overall growth. Five years in, their investable assets have grown from $1.1 million to $2.5 million. Beyond that, Rob and Christie have referred five family members to Five Pine, a reflection of the trust that developed alongside their plan. In Christie's own words: "Ben and Jeremy are honest, approachable, and very professional. They take great pride in getting to know clients and listening to each individual's goals. Honestly, they are the best fiduciaries I have ever worked with, by far." Your Decumulation Strategy Starts Before You Retire Rob's story is more common than most people realize. Disciplined savers often arrive at retirement without a spending plan, a tax strategy, or a portfolio suited to this new phase of life. If you're within five to ten years of retirement (or already there), it's worth asking whether your current advisor is doing comprehensive planning, including tax planning for retirement, or simply managing your investments. Over the course of a long retirement, that distinction can determine whether or not you’re equipped to tackle retirement with confidence. We'd love to help you find your number. Email us at info@fivepinewealth.com or call 877.333.1015. Let's talk.* Frequently Asked Questions (FAQs) Q: When should I start building a decumulation strategy? A: Ideally, five to ten years before you plan to retire. That window gives you time to gradually reposition your portfolio, identify potential tax issues before they become expensive, and stress-test your spending assumptions while you still have income coming in. Q: What role does Social Security timing play in a decumulation plan? A: Claiming Social Security early locks in a permanently reduced benefit, while waiting until 70 can increase your monthly payout substantially. The right timing depends on your health, other income sources, and whether a spouse will eventually depend on your benefit as a survivor. Coordinating with your Roth conversion strategy is also worthwhile, since both affect your taxable income. Q: What happens to my decumulation plan if the market drops early in retirement? A: This is often called the sequence of returns risk. A significant market decline in the first few years of retirement can have a lasting impact on a portfolio, because you're withdrawing funds at lower values. A well-designed decumulation strategy accounts for this by maintaining a portion of the portfolio in less volatile assets, so you're not forced to sell equities at a discount to cover living expenses during a downturn. *Names have been changed to protect client privacy*