The Work Optional Plan: What Pre-Retirees Need Beyond a Magic Number
Summer has a way of changing your perspective.
Maybe it's a Tuesday afternoon on the patio. You're reading a book you haven't had time to open in months. Maybe you're out on the golf course, hiking a trail, sitting by the lake, or having lunch with friends in the middle of the day.
For a moment, you get a glimpse of what life could look like with more freedom.
Then reality kicks back in.
Most people spend decades chasing a retirement number. They tell themselves, "Once I hit $2 million..." or "Once the house is paid off..." or "Once I can replace my paycheck..."
But here's what I've seen over and over.
People reach the number they thought would make the decision easy, and they're still not sure they're ready.
Because retirement readiness isn't just a math problem.
It's a design problem.
The number matters. But the life matters more.
The Myth of the Retirement Magic Number
We're obsessed with retirement numbers.
Financial headlines love them because they're simple. "$1 million." "$2 million." "Here's what you need to retire comfortably."
It makes for a great headline.
It just doesn't tell the whole story.
A retirement number gives you permission. It doesn't give you a plan.
I've met people who could retire tomorrow but keep working because they don't know what comes next. I've also met people with less than they thought they needed who retired confidently because they had clarity about the life they wanted to build.
The difference wasn't just the balance sheet.
It was the vision.
If you've never thought about what retirement actually looks like, reaching your number can feel less like crossing a finish line and more like standing at the starting line wondering where to go.
Five Questions That Matter More Than Your Retirement Number
Before worrying about whether you've saved enough, spend some time thinking about what you're actually saving for.
1. What does Tuesday at 2 pm look like?
Many careers provide structure without us even realizing it.
You wake up with a purpose. Your calendar is full. People need you.
Take that away overnight, and many retirees find themselves asking, "Now what?"
What time do you wake up?
What fills your mornings?
What gives you a sense of purpose?
Retirement isn't just about having free time. It's about knowing what you'll do with it.
Many people find purpose in their work. I’ve seen people continue working long after they could afford to retire because they couldn’t picture what Tuesday at 2 pm looked like without it.
2. Who do you want to spend time with?
Work naturally creates community.
When work goes away, those relationships often fade faster than expected.
Who are the people you want more time with?
Family? Friends? Former coworkers? A volunteer group? A golf league? Your church?
Relationships don't automatically get stronger just because you have more availability.
Like anything else, they require intention.
3. What's your retirement income flexibility plan, not just your withdrawal plan?
One of the biggest misconceptions about retirement is that it's an all-or-nothing decision.
It doesn't have to be.
Maybe you consult a few months each year.
Maybe you teach.
Maybe you take on projects because they're interesting, not because you need the paycheck.
Work optional doesn't mean work never.
It means having choices.
Ironically, many people enjoy working more once they no longer have to.
4. Where do you actually want to live?
Retirement often changes how you think about home.
Do you want to stay close to family?
Spend summers somewhere cooler?
Become snowbirds?
Downsize?
Travel for extended periods?
These decisions affect far more than your lifestyle. They influence taxes, healthcare, housing costs, and ultimately how much money you'll need.
5. What will your retirement lifestyle actually cost?
This is where the financial planning starts, not where it ends.
These questions aren’t a substitute for the numbers. They’re the foundation the numbers should serve.
Too many people pick a retirement number first and hope it supports the life they want.
I'd rather work backwards.
Figure out the life you want to live.
Then calculate what that life actually costs.
Your retirement number shouldn't come from a headline.
It should come from your life.
Try the Summer Preview Test
Summer offers an opportunity to experience what retirement could actually feel like before making a permanent decision.
Take a week or two off.
Not to catch up on projects around the house.
Not to answer emails from the lake.
Actually unplug.
Pay attention to what you naturally gravitate toward.
Do you enjoy slower mornings?
Do you miss solving problems?
Do you get restless after three days?
What activities energize you?
What feels missing?
At the end of that time, ask yourself a few questions.
What parts of the week would you want every week? What surprised you? Did you miss solving problems, or did you enjoy having nowhere you had to be? And if this became your normal life, what would you change?
The answers are often far more valuable than another online retirement calculator.
Of course, reflection only takes you so far.
Once you have a clearer picture of the life you want to build, that's when the numbers become meaningful.
Where the Financial Plan Fits Your Work Optional Era
This doesn't mean the numbers don't matter.
They absolutely do.
You still need a plan for income, taxes, healthcare before Medicare, Social Security timing, investment risk, and all the moving pieces that come with retirement.
But those decisions should support the life you want to build.
Not replace it.
A financial plan isn’t the destination. It’s the infrastructure.
It's the bridge that gets you where you want to go.
And a good advisor doesn't simply tell you whether you can retire.
They help you understand your options.
Sometimes that means retiring earlier than you thought.
Sometimes it means working longer—but for reasons that align with your goals instead of your fears.
The goal isn't to stop working on a particular date.
The goal is to have the freedom to choose.
That's what being work optional really means.
Start With the Life
This summer, don't start with the spreadsheet.
Start with the life.
Picture that Tuesday afternoon again.
What are you doing? Who are you with? Where are you?
Once you know the answer to those questions, the financial planning becomes much clearer.
The number gets you to the starting line. Designing the life you want is what comes next.
Not sure what your Tuesday at 2 p.m. looks like yet? That's exactly the conversation we enjoy having with people.
David Drumhiller, CFP®, BFA™, AAMS®is a financial advisor with nearly 20 years of experience helping individuals and families prepare for retirement. He specializes in tax-efficient retirement income planning and comprehensive wealth strategies. David holds Series 7 and 66 registrations and is licensed in WA, OR, and ID, and across the nation. A Washington State University graduate, he lives in Pullman with his wife and enjoys travel, barbecue, and Cougar Athletics.