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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When Saving Money Starts Getting in the Way of Living

May 21, 2026
Key Takeaways Saving money is important, but constantly postponing meaningful experiences can leave you financially secure and personally unfulfilled. Fear, habit, and identity often play a bigger role in spending decisions than numbers do. A healthy financial plan should support both your future security and your ability to enjoy life along the way. Imagine you’ve saved diligently for decades. You have a healthy income, growing retirement accounts, manageable debt, and investment balances that continue climbing year after year. Yet, somewhere in the back of your mind, a voice keeps saying, “Not enough.” So you hold off on the vacation or skip the kitchen renovation. You tell yourself you will spend more freely later, once things feel more certain. You keep asking yourself the same question, “Can we really afford this?” Sometimes the answer is yes by every objective financial measure, but emotionally, it still feels uncomfortable. For years, personal finance advice has focused heavily on the dangers of overspending. Save more. Spend less. Delay gratification. Avoid lifestyle creep. That advice absolutely matters. Many people would benefit from stronger saving habits. But there is another side of the equation that does not get discussed enough. Some people become so good at saving that they forget what the money was for in the first place. Am I Saving Too Much?  This question sounds almost absurd, and many people feel uncomfortable asking it. In our culture, saving is viewed as responsible and disciplined. Spending often gets framed as careless or indulgent. So when someone continues accumulating wealth year after year, nobody really raises concerns. But over-saving can create its own problems. We have worked with people who consistently save large percentages of their income while postponing almost everything meaningful to them. They delay vacations. Put hobbies on hold. Continue working in stressful jobs long after they financially need to. They keep waiting for some future point where they will finally feel safe enough to enjoy what they built. The challenge is that “enough” can become a moving target. As portfolios grow, lifestyles usually grow too. Concerns about inflation, healthcare costs, market volatility, taxes, and longevity all start competing for attention. Even financially successful people can develop a persistent fear that one wrong decision could jeopardize everything. That fear is often emotional rather than mathematical. In many cases, the numbers support far more flexibility than the person believes. The Psychology of Saving Money Saving behavior is deeply tied to emotion, identity, and the stories we tell ourselves about security. Understanding why you save the way you do is the first step toward making more intentional choices. Fear of running out is one of the most powerful drivers. Even people with substantial assets can feel that their wealth is fragile, particularly if they grew up without financial stability or lived through a major market downturn. The brain tends to overweigh dramatic losses compared to equivalent gains, which means the emotional pain of imagining a depleted account is often disproportionate to the actual probability of it happening. Habit reinforcement plays a significant role as well. If you spent 30 years in accumulation mode, consistently saving and reinvesting and growing, your financial behaviors became deeply ingrained. Transitioning from saving to spending, even intentionally, and when the numbers support it, can feel wrong at a gut level. The habits that built your wealth can work against you when the time comes to use it. Societal pressure adds another layer. High-earning professionals are often surrounded by messages that equate financial discipline with virtue. Spending on yourself can feel indulgent or even irresponsible, even when it’s neither. There is a difference between careless spending and deliberate investment in your own well-being, but the cultural script often blurs that line. For business owners and dual-income households, there is also the identity piece. When so much of your sense of self is tied to building, growing, and accumulating, shifting toward enjoyment requires a genuine psychological reorientation, not just a new budget line. Values-Based Spending Over-saving isn't fixed by spending more randomly. What actually helps is spending with intention — putting money toward things that genuinely matter to you. This is what we mean by values-based spending : aligning how money flows with what you care about. The exercise starts with a conversation about what you want your life to look like. Not the life you think you should want, and not the life your parents had or your colleagues' project, but the experiences, relationships, contributions, and comforts that would make your days feel meaningful and full. From there, a good financial plan becomes a permission structure. When your advisor can show you, concretely, that your goals are funded and your risks are managed, spending stops feeling like a threat to your security. It starts feeling like money doing what money is supposed to do. Values-based spending also helps you stop spending on things that don’t matter to you. Many high earners discover that their default expenditures have drifted away from their priorities over time. Redirecting those dollars toward what genuinely matters often feels better than a raw increase in spending. Signs You May Be Under-Living Financially A few patterns tend to show up repeatedly among chronic oversavers: You feel guilty spending money even after careful planning. Your savings goals continue increasing without a clear reason. You postpone experiences you deeply want because you “might” need the money someday. You struggle to define what financial freedom would look like for you. Your net worth keeps growing, but your day-to-day life feels largely unchanged. You continue working at a pace that negatively impacts your health or relationships, despite already being financially secure. None of these automatically means you are saving too much. But they are often signals worth examining more closely. Practical Steps to Align Your Money With Your Life Making the shift from over-saving to purposeful living does not require a dramatic overhaul. It starts with a few honest conversations and a willingness to examine some long-held assumptions. Start by revisiting your retirement projections with a financial advisor. Ask specifically what your models say about your ability to spend, not just your ability to accumulate. Many clients are surprised to find that their plan supports significantly more lifestyle spending than they had assumed. Build a "permission budget" for discretionary spending. This is not a ceiling on enjoyment but a deliberate allocation toward experiences and priorities you have identified as meaningful. Giving yourself explicit permission to spend in certain areas, backed by a sound financial plan, reduces the guilt that often accompanies even well-deserved expenditures. Consider what you are waiting for. If the answer is a number that keeps moving, or a level of certainty that financial markets will never provide, it’s worth exploring whether the hesitation is financial or psychological. A good advisor can help you separate the two. A Healthy Financial Plan Should Support Your Life A strong financial plan should create confidence, not permanent deprivation. Saving diligently is important, but there is also value in recognizing when enough may already be enough. The goal is for your spending to reflect your values, your priorities, and where you are in life right now. Because eventually, there has to be a point where the money begins serving you instead of the other way around. If you’ve been wondering whether your saving habits still align with the life you want to live, we’d love to help you think through it. At Five Pine Wealth Management , we help clients build financial plans that support both long-term security and meaningful living today. Call us at 877.333.1015 or email us at info@fivepinewealth.com to start the conversation. Frequently Asked Questions (FAQs) Q: Why do I feel anxious spending money even when I can afford it? A: Spending anxiety is often tied to the psychology of saving money. Past financial stress, market downturns, family experiences, and years of disciplined saving can condition people to associate spending with risk, even when their financial plan supports it. Q: Can over-saving negatively affect your quality of life? A: Yes. Constantly delaying travel, hobbies, family experiences, or personal goals in pursuit of “more” can lead to burnout, stress, and missed opportunities. Financial security matters, but so does enjoying the life your money was meant to support.

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.