How’s your five-year plan holding up? If you’re like many of us, you either (1) don’t have one anymore, (2) had one and watched it unravel in slow motion, or (3) are squinting at it now thinking, “Who was I when I wrote this?”
There was a time when the five-year plan was the gold standard of being “put together.” A beacon of ambition. A tidy bullet-point list that promised structure, security, and forward motion. Graduate by 23. Land the dream job by 25. Find the person. Buy the home. Launch the business. Save the nest egg. Have it all figured out by...what, 30?
But then came life—messy, unpredictable, growth-filled, and occasionally disorienting. And after a curveball year (or three), I started to wonder:
Does a five-year plan still make sense in a world that rarely goes according to plan?
What Is a Five-Year Plan?
Traditionally, a five-year plan is a personal or professional roadmap. It outlines where you want to be in five years and what steps you’ll take to get there. Common categories include:
- Career goals
- Financial milestones
- Health & wellness
- Relationships & family
- Lifestyle changes
- Personal development
It’s future-focused and often structured like a checklist.
And while there’s nothing inherently wrong with setting goals (structure can be empowering), the old-school version of the five-year plan tends to assume life will unfold linearly—that effort + time = predictable results.
But life? Yeah… it doesn’t always do straight lines.
The point? Five years is a long time in human years. And your plan needs to leave room for the unexpected.
My Five-Year Plan, Before and After
Let’s just say that five years ago, I had a color-coded, spreadsheet-enhanced vision of the future. I’d mapped out everything from job titles to zip codes. Then came the detours:
- An unexpected layoff
- A health scare in the family
- A pandemic (because, of course)
- A long-term relationship ending
- New values emerging I didn’t see coming
Suddenly, the five-year plan felt more like a ghost of who I used to be than a guide to where I was going. And that’s when I realized something big:
A plan is only as helpful as it is flexible.
The Pros of Having a Five-Year Plan (Yes, There Are Some)
Let’s not throw the whole concept out the window. When done thoughtfully—and with room for real life—a five-year plan can still be a useful tool.
Here’s what it can do:
Provide direction without dictating your worth
Having a loose idea of where you’d like to head can help you make aligned decisions, even if the exact path shifts.
Act as a values mirror
Planning forces you to reflect on what actually matters to you. Not what Instagram says. You.
Create micro-motivation
Setting long-term intentions may give daily tasks more meaning, even the mundane ones (hello, budgeting or that online course).
Boost your sense of agency
In chaotic seasons, having goals may help you feel like you’re steering something—even if it’s just your next small step.
Where the Five-Year Plan May Fall Short
The problem isn’t the plan. It’s what we expect from it.
Here are the most common pitfalls:
It can become rigid and self-punishing
When things don’t go as planned, it’s easy to internalize that as failure—when in reality, life was just being life.
It often ignores personal evolution
You are not static. What you want at 25 may not be what lights you up at 30—and that’s not flaky, that’s growth.
It may be built on outdated expectations
Sometimes we make plans based on cultural timelines or what our parents/friends/society expect—rather than what feels right for us.
It doesn't account for uncertainty
Job markets shift. People leave. Cities change. Pandemics happen. Life happens. Plans that don’t make space for that tend to break.
According to research, people who were more adaptable in their goal-setting tended to experience higher life satisfaction—especially after unexpected life events.
Rethinking the Plan: From Static Blueprint to Living Framework
What if we didn’t toss the idea of a five-year plan—but just redesigned it?
Here’s how to think of it as a living document rather than a static contract:
1. Start with feelings, not outcomes
Instead of “I want to be a manager at X company,” ask: “How do I want to feel in my work/life five years from now?” Fulfilled? Financially secure? Creative? At peace?
This reframes the plan from “achieve X” to “build a life that feels like Y.”
2. Use flexible milestones
Replace rigid deadlines with adaptable checkpoints. Try quarterly or annual goal themes like:
- This year, I want to explore new career paths.
- This quarter, I’ll focus on financial wellness.
- In the next 6 months, I want to invest in my relationships.
3. Build in regular “revisions”
Schedule an annual “plan review” like a date with yourself. Ask:
- What still fits?
- What feels outdated?
- What surprised me this year?
Plans that evolve are more likely to stay relevant.
4. Leave room for the plot twists
Think of your plan like Google Maps—you can still get to your destination even if you take a different route (or decide to change the destination altogether).
What To Ask Yourself Before Creating (or Reworking) a 5-Year Plan
Want to get clear without locking yourself into a version of the future that may not fit later? Try these grounding questions:
- What kind of life feels meaningful to me right now?
- What do I want more of—energy, connection, creativity, time?
- How do I want to grow over the next few years?
- What’s no longer serving me?
- What values do I want my choices to align with?
Let the answers guide your next steps—not your Instagram feed, your resume, or someone else’s timeline.
The Daily Spark
1. You’re not behind—you’re becoming. No plan can measure personal growth, healing, or how hard you’ve worked to stay soft in a tough world. You’re doing just fine.
2. It’s okay to outgrow your old goals. A goal that no longer fits isn’t a failure—it’s feedback. Adjust accordingly.
3. Plans should serve you, not stress you out. If your five-year plan feels like a performance review instead of a guiding light, it might be time to soften it.
4. Small pivots can change everything. Don’t underestimate the power of revising just one part of your plan to better reflect your now.
5. Leave space for the good surprises. Some of the best things in life won’t be on your plan. Stay open. That’s where the magic lives.
Maybe It’s Time to Make Peace With Planning Differently
So—does having a five-year plan still make sense?
Yes. And no. And maybe not in the way we thought.
Because the truth is, you can hold vision and flexibility at the same time. You can dream big while leaving room to shift. You can plan for your future without forgetting to live your present.
What matters most isn’t having a flawless five-year plan—it’s being honest enough to know when it’s time to revise, bold enough to release what no longer fits, and compassionate enough to believe that your journey still makes sense… even when it doesn’t look like the version you once sketched out.
After all, the best plans aren’t about predicting life. They’re about supporting who you’re becoming as it unfolds.
And that? That’s a plan worth holding onto.
