Retirement Planning 101: The First Steps You Should Take 

Admin • December 1, 2023

Have you ever been up against a really tough challenge? Not the kind of challenge that’s overly complicated, physically demanding, or seemingly unattainable — the kind that demands a shift in your habits and maybe even the dismantling of mental barriers to progress to the next level.

Your mind may naturally wander to things like maintaining a healthy diet or sticking to a gym routine. However, if you sit with this question, your thoughts may gravitate towards other unquestionably essential things, such as planning for retirement.

Think about it: opening up a retirement account or setting up automatic contributions, the very basics of preparing for retirement, isn’t all that challenging. Yet, many of us find excuses to put it off for another day.

“I’ll start saving when I make more money.”

“Who knows what tomorrow holds? I’m living life on my terms now, and I’ll deal with retirement later.”

“It all feels overwhelming, and I have no clue where to start.”

While those thoughts may hold some validity, they often become excuses to procrastinate on planning for something that will inevitably come. Even if we delay retirement or opt to work part-time during retirement, the fact remains that a time will come when we are no longer physically or mentally fit for employment, and the time to prepare for that day is now .

Steps in Retirement Planning

So, where do you start if the enormity of it all feels too much to handle? Fortunately, taking small steps is not only allowed but encouraged. And if you’re asking, “What are the first steps of retirement planning?” —we’ve got you covered with four steps you can start taking today! 

1. Define What Retirement Means to You

If you’re in the early stages of your career, it’s natural for your retirement goals to shift many times before you retire. However, even if you don’t have all the answers, it’s still important to think about what retirement means to you right now.

For some, retirement might mean achieving a work-optional lifestyle, meaning they have the flexibility to retire by a certain age, even if they intend to continue working because they genuinely love their work. Others may aim for a more definitive retirement age, at which point they focus on a passion project or volunteering their time.

Here are a few questions to help you start thinking about what retirement means to you:

  • What’s your ideal retirement age? ( Hint: It doesn’t have to be the traditional age of 65. You’re allowed to dream while still staying grounded in reality.)
  • Where do you want to live? Do you want to stay put, move to a tax-friendly state, or move abroad for a lower cost of living?
  • Do you have a passion project in mind, like launching a non-profit or turning your hobby into a business that you can hand down to the next generations?

Remember, it’s okay if your goals evolve with you. It’s better to adjust your goals as your circumstances and dreams change rather than do nothing because you have no vision for the future.

2. Estimate Your Anticipated Expenses

This step in retirement planning can feel hazy, given the many variables that can change between now and retirement. However, a practical starting point is assessing your current spending.

Make a list of your current expenses and determine which ones you’ll realistically maintain in retirement and which you won’t, or which might increase or decrease in retirement. Remember to factor in inflation, medical expenses, and some things you aspire to do in retirement.

Here are some questions to inspire your imagination about what you might want and need to budget for in retirement:

  • What are some things you want to experience in retirement? For example, do you plan to travel extensively while you’re still in good health?
  • Is there someone or something you’d like to financially support, such as an organization close to your heart or your grandchildren?
  • Is there anyone who would be able and willing to take you in if there comes a time when living independently becomes challenging, or do you envision a scenario where you might require care in a nursing home?

Depending on where you are in life right now, it might be too soon to have a solid answer to some of these questions. However, they are meant to get you thinking about how you may want and need to manage your finances during retirement. 

3. Assess Your Current Financial Situation

This step may be challenging because we’re shifting the focus from dreaming about what’s possible to facing reality. However hard it may be, you need to clearly understand where you are today to plan for where you want to go.

To gauge your retirement readiness, you can start with these steps:

  • List all your retirement accounts, including their respective balances and ongoing contributions.  

This list should include everything from employer-sponsored plans like a 401(k), self-employed retirement plans such as a Solo 401(k) or SEP IRA, personal retirement accounts like IRAs, and even non-retirement accounts that you’ve earmarked for retirement, like investment or savings accounts.

  • Review your investment portfolio to ensure it aligns with your age, risk tolerance, and goals. 

Some mistakenly believe they’ve covered all the bases by simply contributing to a retirement account, but there’s more to it. While retirement accounts offer tax advantages, if your retirement funds are parked in cash, your returns won’t be much different than leaving your cash in a savings account earning a meager 0.3%.

A more aggressive approach to investing is typically suitable when you’re younger because you have more time to take risks for greater rewards and recover from market setbacks. As you approach retirement age, a conservative approach may be better to preserve your wealth. 

Once you know where you stand, you can take the proper steps to move the needle in the right direction.

4. Determine What Changes Are Needed and Take Action

This step involves some number crunching to determine if you’re on the right track and, if not, how to bridge the gap. While a more in-depth approach may be required, there are many online calculators that allow you to plug in some basic data to get a general idea of your retirement readiness.

In addition to solving for your required contributions and rate of return to meet your goals, you may need to make other changes. For instance, you may need to set up or enroll in a retirement plan.

If you’re employed, start by reviewing your benefits to see what option(s) are available to you; if you’re self-employed, start comparing the various plans available to business owners to determine which best meets your business needs.

Once you’re clear on what needs to be done and you have the means to do it (even if it involves trimming some of your discretionary spending), it’s time to take action. 

Enroll in your employer’s 401(k) plan. Boost your contributions to secure the full employer match. Automate savings to your investment account. There’s no universal guide to retirement, so do what’s necessary and attainable for your circumstances.

Your Retirement Life by Design: Piecing It All Together

While we encourage you to work through these exercises individually, merging all the steps in retirement planning into a comprehensive and well-defined strategy can be challenging.  

The good news is, much like there are specialists for handling your taxes or repairing things around your home, there are retirement planning specialists , too. Retirement planning specialists like the team at Five Pine Wealth can help you develop a clear roadmap with steps in retirement planning to help you achieve your vision.

If the idea of planning for retirement feels daunting, we’d love to chat with you to see if we’re a good fit. Give us a call at 877.333.1015 or send us an email at info@fivepinewealth.com .

At this time, we’re welcoming clients in Spokane and across the nation through our virtual retirement planning services Remember, whether you do this independently or opt to team up with a trusted advisor , taking even small steps is far more valuable than taking no action at all.

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April 1, 2026
Key Takeaways Taking early withdrawals from your 457 while letting your IRA grow can help you build a more balanced retirement plan. First responders with LEOFF or PERSI pensions can use their 457 plan as a bridge between retirement and traditional retirement account access. Rolling your 457 into an IRA at retirement removes penalty-free access to funds before age 59½. Many first responders in Washington and Idaho can realistically retire early. Thanks to pensions like WA LEOFF Plan 2 or ID PERSI, disciplined savings, and a long career of service, retiring at 55 is common. If you've been putting money into a 457 deferred compensation plan, you may be sitting on a sizable balance by the time you retire. As retirement approaches, you may be wondering: “What do I do with my 457 deferred compensation plan?” Many people unintentionally make a costly mistake. They roll their entire 457 balance into an IRA the moment they retire, thinking it's the right move. It might seem logical to combine accounts and keep things simple by moving everything into one IRA. However, this move eliminates a key advantage of a 457 plan: you lose penalty-free access to your money before age 59½. Let’s look at how this works and how you can set up your retirement accounts to stay flexible in your early retirement years. Early Retirement at 55: The Income Gap Problem Whether you're covered by LEOFF Plan 2 or PERSI, retiring around age 55 is entirely realistic. LEOFF Plan 2 members can retire with a full benefit at age 53 (or as early as 50 with 20 years of service and a reduced benefit). Idaho PERSI first responders can retire as early as 50 under the Rule of 80. The years between ages 55 and 59½ are a unique financial period. Your pension might cover a portion of your income needs, but often not everything. Social Security usually starts much later, and if most of your retirement savings are in IRAs, taking out money early can trigger penalties. This is where your 457 plan can be especially helpful. Unlike most retirement accounts, 457 plans let you take out money without the 10% early withdrawal penalty once you separate from service. This rule gives you a helpful bridge between retiring and the time when traditional retirement accounts become easier to access. You lose this benefit if you move your money into an IRA too soon. If your pension doesn't cover all your needs and you rolled everything into an IRA, you might face penalties or be unable to access your money. This early-retirement gap is exactly what good 457 planning can help you avoid. 457 Plan Withdrawal Rules Once you separate from service, whether you quit, get laid off, or retire, you can start taking 457 withdrawals from your 457 plan without a 10% penalty, no matter your age. Whether you're 55, 45, or even 35, the penalty doesn't apply. If you move money from your 401(k) or another account into your 457 and then withdraw it, that money loses the 457's penalty-free status. It’s now treated like IRA money and is subject to the 10% early withdrawal penalty. Only the original 457 money stays penalty-free. You will still owe ordinary income taxes on every withdrawal from a traditional 457, just like an IRA. The key difference is that you don’t have to pay the extra 10% penalty, which can save you thousands of dollars. Should I Roll My 457 Into an IRA? Now that you know the withdrawal rules, you might be asking yourself, “Should I roll my 457 into an IRA?” This is an important question, and the answer is: it depends. Usually, moving everything at once isn’t the best idea. Many people roll their entire 457 into an IRA at retirement because it’s often suggested as a way to “consolidate” and “simplify.” While there are legitimate reasons to roll some money into an IRA, doing it all at once at age 55 means you lose your penalty-free income bridge. A few of the advantages of rolling some money into an IRA are: More investment options Estate planning flexibility Roth conversion strategies A better strategy for most first responders retiring around 55 is to split your 457 balance into two parts, or “buckets,” each with its own role in your retirement plan: Bucket 1: Use your 457 account for early-retirement cash flow. This is the money you'll live on from age 55 to 59½ (or whenever your pension plus other income is sufficient). The 457 allows penalty-free withdrawals at any time, so you control both the amount and timing of distributions. This bucket bridges the gap until your other income starts coming in. Bucket 2: Roll into an IRA for long-term growth. Once you've determined how much you need for the early years, the rest can be rolled into a traditional IRA. The IRA bucket offers more investment choices and greater flexibility for estate planning or Roth conversion. Here’s an example: Jason is a firefighter retiring at 55 from Washington with $300,000 in his 457. His LEOFF Plan 2 pension covers most of his expenses but leaves a $1,500 per month gap. Instead of rolling everything to an IRA, he keeps $90,000 in the 457, which covers about five years of that gap at $1,500/month, and rolls the remaining $210,000 into a traditional IRA. The $90,000 stays accessible, penalty-free, and the $210,000 continues to grow. By the time he turns 59½, the IRA restrictions are gone, and he hasn't paid any unnecessary penalties. Deferred Compensation Rollover: What You Need to Know If you decide to roll part of your 457 into an IRA, the process is simple. You can move your 457 into another retirement account, like a traditional IRA, Roth IRA, 401(k), 403(b), or another 457 plan. There are a few things to keep in mind: Direct rollover is the best option. Have your 457 plan send the money straight to your IRA provider. If you get the check yourself, you have 60 days to put it into your IRA, and your employer will withhold 20% for taxes. If you miss the 60-day deadline, it will be treated as a taxable withdrawal. Roth conversions are possible, but watch the tax hit. You can convert your 457 to a Roth IRA, but be careful about taxes. If you do this soon after retiring, your income might be lower, which could make it a good time for a Roth conversion. Just make sure not to convert everything at once without checking the tax impact. Putting IRA money back into your 457 is usually not a good idea. Once IRA or other retirement plan money goes into your 457, it loses the penalty-free withdrawal benefit. Only do this if you have a very specific reason. Washington's DCP and Idaho's PERSI Choice 401(k) have their own rules. Washington state's Deferred Compensation Program (DCP) is administered by the Department of Retirement Systems (DRS). Idaho first responders may have the PERSI Choice 401(k) as well as other 457 plans. Be sure you know which accounts you're dealing with before starting any rollovers. Here are two helpful resources: Washington DRS (DCP information) Idaho PERSI A Note on Taxes and Required Minimum Distributions Even if you don’t pay a penalty, you still need to think about taxes. Every dollar you take from a traditional 457 counts as regular income for that year. If you're not careful with how much you withdraw, you could end up in a higher tax bracket, especially if your pension income is already high. This is one reason the bucket approach is helpful: you can control how much you withdraw from your 457 each year and keep your taxable income in a comfortable range. It’s also important to know that required minimum distributions from traditional 457 accounts begin at age 73 or 75, depending on when you were born. Beginning in 2024, Roth 457(b) accounts in governmental plans became exempt from RMDs under the SECURE 2.0 Act. This is another reason to think about whether Roth contributions or conversions are right for you. Talk With Us Before Rolling Your 457 The 457 plan is a powerful tool, and rolling it into an IRA without careful thought means losing the feature that makes it so valuable for retirees. At Five Pine Wealth Management, we help many first responders and public employees in Washington and Idaho. We know the ins and outs of WA LEOFF Plan 2, Idaho PERSI, deferred compensation plans, and the unique challenges of retiring earlier than most people. If you're within 10 years of retirement, or if you're already retired and want to make sure your money is set up the right way, we'd be happy to help. Call us at 877.333.1015 or email info@fivepinewealth.com. Before making a decision about your 457 rollover, let’s make sure your retirement accounts are working together as they should be. Frequently Asked Questions (FAQs) Q: Does a 457 rollover to an IRA count as a taxable event? A: A direct rollover from a traditional 457 to a traditional IRA is not taxable. Q: Can I take money out of my 457 while I'm still working? A: Generally, no. 457 plans don't allow withdrawals while you're still employed, except for very limited exceptions (such as an unforeseeable emergency). The penalty-free access kicks in once you separate from service. Q: What happens to my 457 if I roll it into an IRA and then need money before age 59½?  A: You lose the 457's penalty-free protection. If you roll 457 funds into a traditional IRA, you lose the flexibility of penalty-free early withdrawals and become subject to a 10% early withdrawal penalty
March 26, 2026
Key Takeaways Your retirement withdrawal order affects your taxes, Medicare premiums, and how long your money lasts. The traditional sequence (taxable → tax-deferred → Roth) is a useful starting point, but it isn't right for everyone. Drawing from multiple account types at the same time can help you manage your tax bracket year to year. Roth conversions in the early years of retirement can reduce your future RMD burden.