A Financial Advisor’s Guide for Active Retirees and WA Educators in Spokane, Deer Park, and Chewelah
Picture this: A principal walks out of her school building on her last day after 32 years. Retirement party complete. Speeches given. Cards and gifts packed in a box. She gets to her car and sits there for a moment before driving away.
And she starts to cry.
Not because she’s sad to leave. She’s ready. She’s excited for this next chapter. But also… she’s not sure who she is anymore without that building, those students, those challenges that shaped every day for three decades.
This is the conversation nobody has in those pre-retirement seminars. They talk about Social Security timing and healthcare options and 403(b) rollovers. All important. All necessary.
But nobody talks about the grief.
May is peak retirement decision season – the time when educators sign contracts (or don’t) for the next school year, when businesses announce leadership transitions, when people throughout Spokane, Deer Park, and Chewelah finalize their retirement dates.
So let’s talk about what they’re actually walking away from. And what they’re walking toward.
Is retirement grief a real thing?
Yes. And it catches most people completely off guard.
Retirement grief isn’t about regretting your decision to retire. It’s about mourning the end of one identity while you’re still figuring out the next one.
You can be excited about retirement AND grieve what you’re leaving behind. Both can be true at the same time.
Here’s what people don’t expect: the grief often hits hardest a few months AFTER retirement, not on the last day. That first day feels like vacation. The third month feels like loss.
The daily colleagues who understood your professional challenges? Gone. The rhythm that organized your entire year? Disappeared. The sense of being needed, being the expert, being the person others counted on? Shifted.
Even if you were ready to leave – even if you were counting down the days – there’s still a mourning process for the parts of work that gave your life structure and meaning.
This doesn’t mean you made the wrong choice. It means you’re human.
What do retirees miss most about work?
Based on conversations I’ve had with retirees throughout Eastern Washington, here are the things people miss most – and they’re rarely what you’d expect:
The daily social connection. Not necessarily the meetings or the office politics, but the organic interactions. The person you grabbed coffee with every Tuesday. The colleague who made you laugh. The five-minute hallway conversations that broke up your day.
Work provides built-in community. Retirement requires you to be much more intentional about maintaining and building friendships.
Having a clear purpose each day. When you worked, your purpose was obvious. Problems to solve. Deadlines to meet. People who needed your expertise. You knew what you were supposed to do when you woke up.
In retirement, purpose becomes something you have to create rather than something that’s handed to you. That’s harder than it sounds.
Being the expert. For Washington educators especially, you spent years – decades – being the person with the answers. Parents called you. Colleagues consulted you. You had specialized knowledge that mattered.
In retirement, that expertise doesn’t disappear, but the regular opportunities to use it do. And that can feel surprisingly diminishing.
The structure and rhythm. School calendars. Fiscal year cycles. Project timelines. Busy seasons and slow seasons. These external structures organized your life without you having to think about it.
Retirement is entirely unstructured unless you create structure yourself. For natural planners, that sounds appealing. In practice, it can feel unmoored.
Professional identity. When someone asked “What do you do?” you had a clear answer. Teacher. Principal. Administrator. Business owner. Manager. That identity carried weight and meaning.
“I’m retired” doesn’t feel the same, especially in those first years. You’re not just leaving a job. You’re leaving an identity.
What surprised me most about retirement conversations?
Here’s what catches me off guard in conversations with people navigating this transition: how many retirees struggle with permission.
Permission to enjoy their time. Permission to spend money they saved specifically for this purpose. Permission to say no to things that don’t matter to them anymore. Permission to not be productive every single day.
Many educators and professionals I work with spent entire careers serving others, often putting their own needs last. The idea of focusing on themselves – their hobbies, their rest, their enjoyment – feels uncomfortable. Almost selfish.
Picture this common scenario: A retired couple has the financial resources to travel. They’ve talked about it for years. But every time they start to plan a trip, they talk themselves out of it. “Maybe next year.” “It seems extravagant.” “What if something happens and we need that money?”
The money isn’t the issue. The permission is.
Retirement requires a fundamental shift from “What should I do?” to “What do I want to do?” And for many people who’ve spent decades in service professions, that question is harder to answer than any financial calculation.
What won’t you miss about work
Let’s be honest about this part too. There are real reasons you’re retiring, and naming them isn’t ungrateful.
The politics and bureaucracy. The meetings that could have been emails. The decisions made by people who don’t understand the actual work. The compliance requirements that took time away from what actually mattered.
The constant demands on your time. The emails at 9 PM. The work that tried to creep into the weekend. The inability to fully disconnect because someone might need you.
The stress you carried home. Whether it was student challenges, employee issues, financial pressures, or organizational changes – the weight of responsibility that sat on your shoulders every day.
The lack of flexibility. Having to ask permission for a doctor’s appointment. Scheduling your life around other people’s needs. Not being able to take a Tuesday off just because it’s beautiful outside.
Energy spent on things you didn’t care about. Whatever part of your job felt like obligation rather than mission. The tasks that drained you rather than energized you.
You won’t miss these things. And it’s okay to be glad they’re gone.
Why do some retirees go back to work?
This happens more often than you might think, and it’s not always about money.
Some people go back because they realize they retired TO nothing. They left work, but they didn’t move toward anything specific. And after a few months of unstructured time, they’re bored and restless.
Others discover that the things they thought they wanted to do in retirement – travel, hobbies, volunteering – don’t fill the gap that work left. They miss the challenge, the expertise, the contribution.
And some realize that their identity was more wrapped up in their career than they understood. Without it, they feel like they’ve lost themselves.
Going back to work isn’t failure. Sometimes it’s clarity. And sometimes it’s the bridge you need while you figure out what retirement actually means for you.
But here’s what I notice: the people who go back to work most successfully often do it differently. Part-time instead of full-time. Consulting instead of employment. Teaching one class instead of carrying a full load. Contract work instead of permanent positions.
They’re not trying to recreate what they left. They’re selectively keeping the parts they valued while leaving behind the parts that drained them.
How do you replace structure without replacing stress?
This is one of the most important questions for early retirement.
You need some structure. Humans thrive with rhythm and routine. But you don’t want to recreate the stress-filled, over-scheduled life you just left.
Here’s what seems to work well for retirees I know in the Spokane area:
Anchor points, not rigid schedules. A few regular commitments each week that give shape to your time. Maybe that’s a Tuesday morning coffee group, a Thursday volunteer shift, a Saturday hike. Enough structure to create rhythm, not so much that you feel trapped.
Seasons rather than permanence. In work, commitments were often permanent. “I’ll serve on this committee.” “I’ll teach this class.” In retirement, you can think in seasons. Try something for three months. If it works, continue. If it doesn’t, move on.
Projects with endpoints. Instead of ongoing obligations, consider projects with clear completion points. Organize all your photos. Learn to make bread. Read the complete works of a favorite author. Train for a 5K. Build something.
Projects give you focus and a sense of accomplishment without the indefinite commitment.
Permission for blank space. This is hard for achievers, but it’s important: some days can be unscheduled. Some mornings can be slow. Some weeks can be quiet. That’s not wasted time. That’s rest. That’s what you worked for.
The goal isn’t to fill every hour. It’s to fill your life with things that matter to you.
What about the financial side of this transition?
While this article focuses primarily on the emotional and relational aspects of leaving work, the financial pieces absolutely matter.
If you’re a Washington State educator, understanding how your PERS or TRS pension works, when to start Social Security, and how to create income from your 403(b) or 457 accounts – these decisions affect your ability to live abundantly in retirement.
Healthcare coverage is particularly important if you’re retiring before age 65. PEBB continuation for WA educators works differently than private insurance or COBRA. Understanding your options and their costs is important before you retire, not after.
And tax planning shifts significantly. The income sources that seemed simple while working – just your salary – become more complex when you’re coordinating pension income, Social Security benefits, retirement account withdrawals, and possibly part-time work.
Note: This article discusses general retirement planning concepts and should not be considered personalized financial or tax advice. Before making any financial decisions, consult with qualified professionals who understand your specific situation.
But even with all the financial pieces in place, you still need to address the identity questions, the social connections, the daily purpose. Money alone doesn’t create a fulfilling retirement.
How do you build new community after work?
This is one of the biggest challenges, and it requires intentionality.
Work provided automatic community. You saw the same people regularly. Relationships formed naturally through proximity and shared challenges.
In retirement, community doesn’t happen automatically. You have to build it.
Some ideas that work well in our area:
Stay connected with select work relationships. Not everyone. But the colleagues who became real friends. Schedule regular coffee dates. Meet for walks. Keep those connections alive intentionally.
Engage in local community. Whether it’s the Settlers Day planning committee in Deer Park, volunteering at the Chewelah Arts Guild, joining a group at your church, or participating in community events in Spokane – local involvement creates connection.
Find hobby-based communities. Book clubs. Hiking groups. Photography classes. Woodworking workshops. Communities built around shared interests can create meaningful relationships.
Consider strategic volunteering. Not just any volunteer work, but opportunities that use your expertise and connect you with people you enjoy. Former educators might mentor new teachers. Business professionals might help nonprofits with strategic planning.
The key is being proactive. Community in retirement doesn’t find you. You have to pursue it.
What about the couples who retire together?
If you’re married or partnered and you’re both retiring around the same time, you’re navigating a double transition.
You’re each processing your own grief about leaving work. You’re each figuring out your new identity. And now you’re spending significantly more time together than you have in years.
This can be wonderful. It can also be challenging.
Picture this: One partner has been managing the household for years while the other worked. Now that second person is home all day, wanting to help, reorganizing things that already had a system. The first partner feels like their space is being invaded. The second feels like they’re not welcome in their own home.
Or: One partner wants to travel constantly. The other wants quiet time at home. Both thought “retirement” meant the same thing, but they never actually discussed what that looks like day-to-day.
The couples who navigate this well tend to do a few things:
They talk about expectations before retiring, not after. What does a typical week look like? How much togetherness vs. independence do we each need? What are our individual goals and our shared goals?
They maintain some separate interests. You don’t have to do everything together. Having your own hobbies, your own friend groups, your own activities creates healthy space.
They give each other grace during the adjustment. The first year of retirement (especially if you retire around the same time) is a transition for your relationship too. It takes time to find your new rhythm.
What does a good retirement look like emotionally?
This is highly personal, but here are patterns I notice in people who seem to be thriving several years into retirement:
They’ve found new sources of meaning. Not necessarily one big thing, but a combination of activities, relationships, and pursuits that matter to them.
They’ve maintained some expertise. They’re using their skills and knowledge in new ways – mentoring, consulting, teaching, creating.
They have rhythm but not rigidity. Their weeks have shape without being over-scheduled.
They’ve built community intentionally. They see people regularly. They have friendships that go deeper than surface level.
They’ve given themselves permission to enjoy what they built. They travel when they want to. They spend on things that matter to them. They live abundantly without constant anxiety.
They’ve made peace with letting go. They don’t constantly compare their current life to their working life. They’re present in this season.
That last one might be the most important. You can’t fully embrace retirement while you’re still gripping onto your work identity. At some point, you have to let go.
Not forget. Not diminish what that career meant. But release it enough to move into what comes next.
The Grief Timeline
Here’s something helpful to know: retirement grief often follows a fairly predictable pattern.
Months 1-3: The honeymoon. This feels like an extended vacation. You’re sleeping in, tackling projects, enjoying freedom. The grief is usually minimal here.
Months 4-8: The valley. This is often when the grief hits. The novelty has worn off. You’re realizing what you’ve lost. This can feel surprising and unsettling, especially if the retirement itself was a good decision.
Months 9-12: The emergence. You start finding your new rhythm. New interests develop. New connections form. The grief doesn’t disappear completely, but it becomes less dominant.
Years 2-3: The settling. Most people feel genuinely comfortable in their retirement identity by this point. They’ve built a life that works for them. The grief is largely resolved.
Knowing this pattern can help. When you hit month five and you’re feeling unexpectedly sad, that’s normal. It doesn’t mean you made a mistake. It means you’re human and you’re grieving the end of one chapter while you’re still writing the next one.
Moving Forward
If you’re approaching retirement from a career in education or another field that’s been central to your identity, take the emotional transition seriously.
Yes, get the financial pieces right. Absolutely work with someone who can help you work towards optimizing your pension, Social Security, tax strategy, and retirement income. Those pieces matter.
But also give yourself space to grieve what you’re leaving. Permission to not have it all figured out immediately. Grace to try things and change your mind. Time to discover who you are in this new season.
The goal isn’t to retire FROM work. The goal is to retire TO something – a life that’s intentional, connected, meaningful, and abundant in the ways that matter to you.
You spent decades building financial resources for this season. Don’t forget to also build the emotional and relational resources that make those finances meaningful.
Ready to Plan Both the Financial AND the Emotional Transition?
If you’re a Washington State educator within a few years of retirement or an active retiree navigating this transition, I’d be honored to help.
At Deep Creek Financial Planning, we address both the numbers (pension coordination, tax planning strategies, feasible withdrawals) and the bigger questions (What do you actually want this life to look like? What matters most to you now?).
Because retirement done well isn’t just about having enough money. It’s about living abundantly with both resources and purpose.
Schedule a 30-minute Discovery Call
Learn more: DeepCreekFinancialPlanning.com
Serving active retirees and WA educators throughout Spokane, Deer Park, and Chewelah.
To your abundant life,
Caleb Stapp
Securities and advisory services offered through LPL Financial, a Registered InvestmentAdvisor, Member FINRA\SIPC. Deep Creek Financial Planning is not a registered broker-dealer or investment advisor.
This article provides general information about retirement planning and emotional transitions and should not be considered personalized financial, legal, or psychological advice. Before making any financial decisions, consult with qualified professionals who understand your specific situation. Past performance does not guarantee future results. Client stories and quotes are compilations and not from any one person.
