Planning Your Career Transition Project When You Don’t Know What You Don’t Know: A Discovery-First Framework

The Planning Performance Domain: Creating YOUR roadmap instead of following someone else's GPS

I studied so many success stories.

I mapped out timelines, created detailed trackers, analyzed what worked for other entrepreneurs who'd made the corporate-to-business leap. I had plans within plans, backup strategies, milestone markers based on what I'd learned from people who'd "done it right."

Then reality hit.

What took someone else 3 months was taking me way longer. What they accomplished in their first year, I was nowhere near achieving in mine.

Every milestone I missed felt like failure. Every delayed timeline felt like evidence that I was doing something fundamentally wrong.

The question that haunted me: Am I behind schedule, or am I just on MY schedule?

Turns out, I was trying to use someone else's GPS to navigate my own completely unique path.

The Planning Performance Domain Reality Check

In the PMBOK 7th Edition, Planning is one of the 8 core Performance Domains because you need some kind of roadmap to get anywhere meaningful with your projects to deliver value.

But here's where we may not be reading between the lines: You have to tailor the kind of planning you’re doing to the overall context of the project.

Some projects may have precedent, historical data, similar initiatives to reference, and standard timelines based on past performance, to name a few. We can apply a predictive planning approach to these.

Career transitions? They’re by definition unique, significant, risky, and novel. An iterative or incremental planning approach is more suitable here.

When you're building something that's never existed before, your specific business, your unique career pivot, your particular set of circumstances, predictive planning methods, no matter how appealing, are counterproductive.

You're not planning a project. You're planning an exploration.

“You’re not behind. You’re on YOUR own path—and your plan should reflect that.”

The Comparison Trap

We all know success leaves clues, right? So naturally, I consumed every story of people who'd made similar transitions:

• "I built my email list to 1,000 subscribers in 3 months"

• "I replaced my corporate income in 6 months"

• "I launched my course and made $10K in the first month"

• "I grew my social media following to 5,000 in 90 days"

I treated these like universal timelines instead of personal data points.

What I didn't account for:

• My starting knowledge level vs. theirs

• My available time and resources vs. theirs

• My industry and audience vs. theirs

• My learning style and pace vs. theirs

• My life circumstances vs. theirs

• My risk tolerance vs. theirs

I was planning my career transition from corporate to entrepreneur using someone else's variables.

For inner stakeholder dynamics that shape those variables, see my Stakeholders piece: The Stakeholder I Wasn't Prepared to Manage in My Career Pivot Project: Myself.

The "Am I Behind?" Anxiety

Six months in, the questions started:

• "Should I have more subscribers by now?"

• "Why is my content not getting the engagement theirs did?"

• "Am I moving too slowly?"

• "Did I not plan enough or did I plan too long?"

• "Should I be further along than this?"

But behind compared to what? There is no universal timeline for career transitions. There's no standard benchmark for "where you should be" at any given point.

Yet I kept measuring my Month 6 against their Month 6, forgetting that we started from completely different places, with different resources, facing different challenges.

I was worried about not knowing if I was heading in the right direction without someone else's timeline to validate my progress.

The ADAPT Framework for Career Transition Planning

After months of struggling with comparison anxiety and missed milestones, I realized I needed to apply an adaptive planning approach, the same one we use in project management for exploratory, uncertain projects, to my career transition.

The ADAPT Framework helps you plan for discovery instead of just execution.

A - Assess Your Unique Baseline

PM Concept: Baseline Creation

Life Application: Map YOUR starting point, not someone else's

Goal: Stop comparing your Month 1 to anyone else's Month 1

Predictive planning mistake: Assuming everyone starts from the same place

Adaptive planning reality: Your baseline is completely unique

Create YOUR Starting Point Assessment:

Skills Inventory:

• What expertise do you already have?

• What transferable skills can you leverage?

• What's your natural learning pace for new concepts?

Resource Assessment:

• How much time can you realistically dedicate?

• What's your financial runway?

• What network and connections do you have access to?

Constraint Mapping:

• What are your energy patterns and limitations?

• What family or personal responsibilities affect your schedule?

• What's your risk tolerance and comfort with uncertainty?

My Unique Baseline Example:

When I started, I had:

• 20 years marketing experience (but in a different industry)

• PMP certification and other corporate training (but no business building experience)

• Full-time availability (but with other responsibilities)

• Comfortable with uncertainty (but needed some structure)

• Financial runway (but limited network in new industry)

• Strong writing skills (but perfectionist tendencies that slow publishing)

  
  

This baseline meant my timeline would naturally be different from someone who:

• Started with an existing audience

• Had extensive experience with content creation

• Was comfortable publishing imperfectly from day one

• Had a large network in the target industry

D - Direction Over Destination

PM Concept: Vision vs. Fixed Scope

Life Application: Plan for flexible direction, not rigid outcomes

Goal: "I'm moving toward X" instead of "I will achieve X by Y date"

Predictive planning (execution-focused):

• Known outcome, plan the steps to get there

• Historical data to estimate timelines

• Clear metrics and benchmarks

• Linear progression toward defined goal

Adaptive planning (discovery-focused):

• Directional outcome, discover the specific path as you go

• No historical data for YOUR specific situation

• Learning metrics alongside performance metrics

• Iterative progression with constant course corrections

Example Shift:

Before (Predictive): "I will have 1,000 email subscribers in 6 months"

After (Adaptive): "I will focus on building an email list while learning what content resonates with my audience, adjusting my approach based on engagement data until I reach 1,000 subscribers."

Before (Predictive): "I will launch my course and make $10K in the first month"

After (Adaptive): "I will create a minimum viable course, test with a small audience, iterate based on feedback, and discover what pricing and format work best for my specific market"

The Direction vs. Destination Mindset:

Instead of asking: "Did I hit my numbers?"

Ask: "Am I still moving toward my overall direction? What did I learn that should influence my next steps?"

A - Anticipate Unknown Unknowns

PM Concept: Risk Management & Contingency Planning

Life Application: Build buffers for things you can't predict

Goal: Plan for the fact that surprises WILL happen

What I Planned For (Known Unknowns):

• Learning curve for new skills

• Time to build audience

• Income variability during transition

• Need for new systems and processes

What I Didn't Plan For (Unknown Unknowns):

• How perfectionism would slow my progress

• The emotional energy required for constant decision-making

• How my previous industry experience wouldn't transfer as directly as expected

• The time needed to figure out my unique voice and messaging

• Health issues that would derail productivity for months

  
  

You can't plan for what you don't know you don't know. But you can plan for how you'll respond when unknown unknowns emerge.

For a deeper dive on mapping and managing uncertainty itself, see: How to Manage Uncertainty When Your Career Transition Project Goes Off-Script.

P - Progressive Elaboration

PM Concept: Rolling Wave Planning

Life Application: Plan in waves, adding detail as you learn

Goal: Monthly/quarterly plan reviews that adjust based on new information

Adaptive planning: Create directional 12-month vision, detailed 3-month plan, very detailed 1-month plan, then adjust monthly based on what you learn

Rolling Wave Planning in Practice:

12-Month Vision (High-Level Direction):

• General direction you're heading

• Core values guiding decisions

• Major milestones you're working toward

• Success indicators (not rigid metrics)

Quarterly Strategic Plan (Medium Detail):

• Specific focus areas for next 3 months

• Key experiments or tests you'll run

• Resources you'll need or develop

• Major decision points coming up

Monthly Tactical Plan (High Detail):

• Specific actions and deliverables

• Week-by-week priorities

• Concrete metrics to track

• Review and adjustment points

Monthly Planning Review Questions:

• What did I learn that I didn't expect?

• What assumptions proved wrong?

• What's working better/worse than anticipated?

• What new information should influence my next month's focus?

Quarterly Strategic Review Questions:

• Am I still moving toward my overall direction?

• What major course corrections does new information suggest?

• How have my goals evolved based on what I've learned?

• What unknown unknowns have emerged that need integration into future planning?

T - Track Learning Metrics

PM Concept: Multi-Dimensional Measurement

Life Application: Measure learning & discovery, not just outcomes

Goal: "What did I learn?" matters as much as "What did I achieve?"

Track These Alongside Outcome Metrics:

• Skills Developed: What can you do now that you couldn't do before?

• Experiments Completed: How many things have you tried and learned from?

• Course Corrections Made: How well are you adapting when things don't go as planned?

• Problem-Solving Wins: What challenges have you figured out how to navigate?

• System Improvements: What processes are working better now than they were before?

• Assumptions Tested: What did you believe at the start that proved wrong?

• New Insights Gained: What do you understand now about your path that you didn't before?

What I'm Learning About Planning in Real Time

Some months I feel incredibly behind. I see someone else hit a milestone in 3 months that's taken me 8 months to approach.

Other months I realize I'm exactly where I need to be. The extra time I spent figuring out my unique approach created something more authentic than if I'd rushed to match someone else's timeline.

Most months it's about recalibrating. Adjusting my plans based on what I've learned about my own pace, preferences, and circumstances.

The "behind schedule" anxiety disappears when you realize you're not behind - you're just on your unique route. My 8-month milestone might be more solid than their 3-month milestone because I had to figure out what works specifically for me, what will result in the desired outcome, and deliver the value I'm looking gain from my career pivot.

Planning for discovery requires different metrics than planning for execution. Instead of "Did I hit my numbers?" it's "Did I learn what I needed to learn to make the next decision?"

The best plans for career transitions are flexible frameworks, not rigid schedules. Structure that can bend without breaking when reality introduces variables you hadn't considered.

Your Turn: Planning Your Career Transition Project Audit

Direction vs. Destination Check:

• Are you planning for a fixed destination or a flexible direction?

• How could you reframe rigid goals into learning-focused intentions?

Comparison Trap Assessment:

• Whose timeline are you using to measure your progress?

• What variables make your situation different from theirs?

• How could you establish your own baseline instead of using someone else's?

Unknown Unknowns Preparation:

• What buffers have you built in for things you can't predict?

• How do you currently handle plan disruptions - as failures or as information?

• What systems do you have for incorporating new learning into your plans?

Progress Tracking Audit:

• Are you measuring learning and development, or just outcomes?

• What evidence of progress might you be overlooking because it doesn't match traditional metrics?

• How could you celebrate course corrections and adaptations as planning wins?

The goal is to become really good at creating and adjusting your own roadmap as you discover what works specifically for you.

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Next up in the Performance Domains series: Project Work - "The Daily Reality of Building Something New (When Every Day Feels Like Flying the Plane While You're Building It)."

Following The Intuitive PM Approach™? I'm sharing real-time how I'm tailoring and applying project management principles and strategies to my own career transition.