The Strategic Planning Series for 2026, Week 4
Week 4: Work & Career Positioning
Building Who You're Becoming
I've reached the top of my teaching career. I'm good at it. It's comfortable, stable, and enjoyable.
I love my job. But I'm not satisfied with the growth opportunities my role provides anymore.
So I'm transitioning into coaching and writing. Not because teaching failed me. Because that's who I want to become next.
But that's just my path.
You might love your current role, business, or career path. You might not want to change anything about it.
What matters more is who you are becoming through your work.
Does your work give you opportunities to become the person you want to be?
We did identity work in week one. We spend the majority of our waking lives at work. Our careers are extremely formative to our identity growth. Here is how the two connect:
Week 1: Who you're becoming as a person.
Week 4: Whether your work supports that growth.
I have a great career that I love. I still show up with enthusiasm and perform well. I'm also building leverage in areas that move me toward who I want to become.
That's what this week is about.
The Framework
Strategic work planning has five parts:
Reality Check
Strategic Direction (Work vs Identity)
Leverage Focus
Year-End Objective
Guardrails
This isn't necessarily about career moves. It's about growth, leverage, and alignment.
Part A: Reality Check
Before you plan anything, get honest about what's happening right now. You need to know where you stand before you can decide where to apply pressure.
Answer these:
What about my current work still energizes me?
What feels increasingly misaligned or draining?
What am I tolerating that I don't want to normalize long-term?
Try to differentiate the hard or boring parts of the job from this section. All careers have hard or boring parts. This is more about your growth than about judging the job.
Part B: Strategic Direction (Work vs Identity)
You've already decided your growth path in Section 1. Does your work support that?
If the majority of our waking hours are spent at work, we had better make sure they're aligned with who we are becoming.
Answer these:
What growth opportunities would I like to have in my work this year?
Be specific. Not "more responsibility." What kind of responsibility? Not "better skills." Which ones?
Does my current role provide those opportunities?
If yes: What opportunities already exist that you're not fully using?
If no: Can you create them inside your role? Or do you need to find them elsewhere?
How do I find or make these opportunities?
That's where leverage comes in. For me, teaching has opportunities to lead, communicate, and help people. But it doesn't give me opportunities to write, coach, or build frameworks at scale. So I'm finding those opportunities outside my role.
Your version might look completely different. You might find everything you need inside your current work. Or you might realize you need to create space elsewhere.
Part C: Leverage Focus
Hard work doesn't automatically create options. Leverage does. Leverage is what expands your future possibilities. It's what makes you more valuable, more capable, more trusted.
Leverage isn’t just about leaving your job. It provides pathways forward (raise), upward (promotion), sideways (side hustle/passion project), or out (career change).
The key here is to develop tools for chapters of your life that haven’t been written yet. Growth opportunities are all around you. If you aren’t prepared, you won’t recognize them.
Pick ONE or TWO areas where you'll intentionally build leverage this year:
Skill / Craft: Getting demonstrably better at the actual work
Knowledge / Expertise: Mastery, judgment, domain depth
Leadership / Influence: People trust, decision-making, ownership
Innovation: Ideas, creation, improvement, change
Efficiency / Systems: Processes, scale, time leverage
Then answer:
Which one, if upgraded this year, would most expand my future options?
Which am I currently neglecting by default?
Important: You can't build leverage in all five areas at once. Choose your focus.
For me, it's Skill (writing, coaching frameworks) and Knowledge (understanding behavior change at a deeper level). I'm intentionally NOT focusing on efficiency or innovation right now. Those can wait.
What's yours?
Part D: Year-End Objective
You don't need a full plan. You need a clear marker that tells you whether this year mattered.
By the end of 2026, I want to be able to say:
I am demonstrably better at: ___________________________
I am more trusted or credible in: ___________________________
I have more options because I built: ___________________________
Write one statement that matters to you.
Now pressure-test it:
What would need to happen weekly for this to be true?
Examples:
If you want to be "demonstrably better at writing," you need to write 3x/week minimum
If you want to be "more trusted as a leader," you need weekly 1:1s and consistent follow-through
If you want to "have more options," you need to build visible work or relationships weekly
Am I willing to prioritize that consistently?
If not, shrink the scope. Don't abandon the objective.
Better to hit a smaller target than miss a big one.
Part E: Guardrails
Even with a clear objective, you'll drift. That's normal.
The key is catching it early.
Red flags:
What are the early signs that you're drifting from your leverage focus?
Write down 2-3 specific signals that tell you things are off track.
Resets:
When those red flags show up, what will you do?
Write down 1-2 specific actions you'll take to get back on track.
When you're drowning in work, you won't think clearly enough to figure it out.
What This Does
This framework won't tell you whether to stay in your role or leave.
It won't guarantee a promotion or a career change.
It does give you clarity on where you're building leverage and whether that aligns with who you're becoming.
Some of you will realize your current role has everything you need. You just weren't focused.
Some of you will realize you need to build leverage outside your role while maintaining excellence inside it.
Some of you will realize it's time to make a change.
All three paths are valid.
The key is knowing which one you're on and moving with intention.
I'm building leverage toward coaching and writing while staying excellent at teaching. That's my path this year.
What's yours?
What's Next
Next week: Finances & Household Economics.
Until then, work through the five parts:
Reality Check: Where am I now?
Strategic Direction: Is my work supporting who I'm becoming?
Leverage Focus: Where am I building advantage?
Year-End Objective: What marker tells me this year mattered?
Guardrails: How do I know I'm drifting, and how do I reset?
Write it down. Get clear.
See you Tuesday.
Run Your Life Like a Business: The Strategic Planning Series for 2026
This is Week 4 of 8. If someone you know needs to hear this, forward them this email.