Lab Notes #1 - Strategic Planning Like a Rebel

Objective

To create a roadmap (aka a strategic plan) that identifies key milestones that will take me from where I am to where I want to go.

Question

Can I create a strategic plan that provides inspiration and direction without igniting my spirit of resistance?

Materials

• My iPad
• Notion
• Claude (my favorite AI assistant)
• A willingness to wreck a template

Problem

You know that feeling when you pull on a pair of pants that technically fits but just doesn't feel right? The waist hits at the wrong place to look or feel good. The length is all wrong for your legs. On someone else, they might be the perfect pants, but not on you.  

That's the best analogy I can think of for how it feels when I try out popular productivity tips and project management systems.

I get why SMART goals (Specific, Measurable, Attainable, Relevant, and Time-bound) work for other people. I understand why having an accountability partner can help others achieve their aims. I appreciate the value of making a five-year plan and doggedly sticking to it. Objectively, I see the value and appeal of these tools. But they've never worked for me.

In my professional life, I've used Microsoft Teams, Discord, Trello, Monday, and ClickUp to manage projects. While these systems have helped me successfully coordinate events, marketing campaigns, and design projects for my teams, they've never worked for me. I always ended up keeping track of my own to-dos using a hodgepodge of handwritten notes and task lists.

Discovering Gretchen Rubin's Four Tendencies Framework (a tool for understanding how you respond to expectations—yours and others) clarified why I couldn't find productivity tips and project management software that fit me. I'm a Rebel, someone who resists inner and outer expectations.

As Gretchen explains in her Rebel Tendency Report, "Rebels place a high value on authenticity and self-determination, and bring an unshackeled spirit to what they do. Rebels work toward their own goals, in their own way, and while they refuse to do what they're supposed to do, they can accomplish their own aims."

Yeah, that about sums up my working style. My approach to life has essentially been to rise to the challenge in front of me:

• I wanted to join a writers' group in college, but my university didn't have one, so I founded a student organization to create one.
• I wanted a flexible career that would allow me space to write and pursue creative projects, so I established a hybrid career working part-time training and managing product demonstrators and part-time as a freelance copywriter.
• I wanted to move back to a big city (after being laid off from my product demonstration job), so I networked with my friends until I found someone to stay with and a job in a big city that led my career in a new direction.

On and on, the list could go charting my unconventional career filled with many highlights, setbacks, successes, and failures, but with no clear direction. While I love the fact that I've been able to fit so much into 37 years, as my 40th birthday approaches, I want to start connecting the dots and achieve some longheld goals:

• Becoming a published writer, not just a copywriter
• Launching a newsletter-based publication of my own to share my writing, marketing resources, and build a community of creatives and entrepreneurs
• Finishing and selling the memoir I've been working on off and on for years
• Improving my physical fitness and managing my weight to prevent developing diabetes and other medical complications that run in my family

When I heard Todd Schulkin on Happier in Hollywood making the case to Liz Craft and Sarah Fain that even creatives could benefit from a strategic plan, I felt like he was speaking directly to me. I also knew that if I approached it the wrong way, it would backfire, and I'd end up further from my goals.

Process

So, I pulled up a chat with my favorite AI assistant, Claude. I'd started a conversation with him the month before to brainstorm creative, Rebel-friendly strategies to help me balance my workload, family obligations, and goals. That chat had inspired me to get back to the gym after a two-month hiatus and re-establish a creative routine after taking a sabbatical from writing and web design for a year. I felt confident this version of Claude could help me develop a strategic plan aligned with my Rebel tendency.

The back-and-forth conversation sparked by my request for help developing a Rebel-friendly strategic plan for myself led to the creation of my Momentum Map in Notion. (Of course, the copywriter in me had to rebrand "strategic plan" to something more catchy and less corporate.)

My Momentum Map runs from July 2025 to July 2028. It's broken down into three phases: Foundation Building (July 2025-July 2026) > Growth & Expansion (July 2026-July 2027) > Authority & Impact (July 2027-July 2028). It runs from July to July because my birthday is July 1st. I've long considered my birthday New Year's for me. Under each year are Primary Goals, Key Milestones, and Tactics.

As Todd recommended, there is a SWOT (Strengths, Weaknesses, Opportunities, Threats) section under the long-term planning map. My favorite part is the last section: my quarterly action plan. It's broken down into months with a unique theme for each, a primary and secondary focus, and a step-by-step strategy.

Real-World Testing

You might be thinking, Wait, it's not even July yet. So, are you waiting to follow your Momentum Map until your birthday? Good point, and No. Start dates, deadlines, these are all flexible to me. The two bonus months between when I first created my Momentum Map (at the end of April) and its official start date (July 1st) have been a time for trial and error to test tactics, redefine my vision, and refine my timeline.

I've taken my own advice to wreck my template to make it work for me. Over the last two months, it's changed a lot.

Originally, my quarterly plan was broken down into months and a week-by-week strategy. I quickly realized that doesn't work for me. I'm a sprinter, not a marathoner. One week, I can cross off two or more steps, while the next week, I might cross off none. So, I changed "Week-by-Week Strategy" to "Step-by-Step Strategy." That way, I could keep the steps in place that would help me visualize my route but eliminate the unrealistic timeline.

Under each month in the quarterly plan, I also added:

My Base Camp (flexible, supportive systems)

• Monday Coworking Club - External structure without rigid accountability
• Sprint/Rest Week Cycling - Working with my natural energy patterns instead of forcing consistency

Gears I'm Test Driving (experimental productivity tactics)

• Daily Options Menu - Choice-based scheduling that gives me flexibility while ensuring key areas get attention
• Weekly Non-Negotiables - Essential tasks I commit to completing each week, but with the freedom to choose when
• Catalyst Challenges - Monthly creative experiments designed to spark growth and keep momentum fun

The creation and launch of Unboundium has been the biggest change to my strategic plan and the greatest delight. I had planned to launch a different type of newsletter and a separate platform for sharing and selling creative resources and flexible marketing tools, but clarity sparks creativity.

After I created my Momentum Map, I thought it could be a nice gift for the Happier in Hollywood Facebook group if I made a version for others with tips for all tendencies. As I worked on that, I developed another tool for myself: the Clarity Console. A daily dashboard in Notion to execute my quarterly action plan.

Using the Clarity Console everyday—to capture ideas, keep my momentum going, and add to my "Done" and "Needs Doing" lists—got me thinking about how it might benefit others. I thought, I bet there are Rebels, creatives, and entrepreneurs like me who are frustrated that it's so hard to find flexible systems and tools that are designed with us in mind. Maybe I could share this, too!

The ideas kept flowing and growing until Unboundium was born.

Conclusion

In just two months, my Momentum Map has propelled me towards my long-term goals while also sparking the creation of new tools, projects, and communities. I hope the Momentum Map I've made for you—with Scout's tips and tactics for all four tendencies—will be as helpful for you as it has been for me. But, remember your mission—should you choose to accept it—is to wreck this template.

Lab Notes are usually exclusive to Innovators and Pioneers, but this foundational resource will be available to all subscribers as our gift to the community.