When planning, differentiate the 'roadmap' from a simple to-do list. The roadmap should outline 5-7 major strategic shifts or capabilities you need to acquire—such as building a personal brand or mastering paid ads—not just the daily tasks required to get there.
Combat strategic complexity by creating a one-page plan. This document connects your highest-level vision and values to tactical quarterly goals in a clear cascade (Vision -> Strategy/KPIs -> Annual Goals -> Quarterly Goals). This simple, accessible artifact ensures universal alignment and clarity on how individual work ladders up.
A product roadmap's value is in the planning process and aligning the team on a vision, not in rigidly adhering to a delivery schedule. The co-founder of Artist argues that becoming a feature factory focused on checking boxes off a roadmap is a dangerous trap that distracts from solving real customer problems.
When a product team is busy but their impact is minimal or hard to quantify, the root cause is often not poor execution but a lack of clarity in the overarching company strategy. Fixing the high-level strategy provides the focus necessary for product work to create meaningful value.
Effective planning requires two distinct phases. First, brainstorm ambitious goals without limitation (e.g., start a YouTube channel). Second, in a separate step, select a focused list of 2-3 core offers that will generate the majority of your revenue. This prevents confusing audience-building activities with direct moneymakers.
This framework provides a structured approach to planning by answering five questions: What's our aspiration? Where will we play (ICP)? How will we win (pillars)? What capabilities do we need? And what management systems (budget, headcount) are required?
Large goals are paralyzing without a clear path. Instruct an AI to take your five-year vision and break it down into a logical sequence of yearly, quarterly, and weekly milestones. This ensures you do the right things in the right order, preventing wasted effort and making the goal approachable.
Robinhood is shifting its planning process to focus on what will be announced at its next public product keynote. Instead of setting abstract internal goals, this aligns the entire company around concrete, customer-facing deliverables and creates a powerful, immovable deadline for shipping.
The most valuable professionals are neither pure visionaries nor pure executioners; they are "step builders." This means they can understand a high-level strategic vision and then map out the granular, sequential steps required to achieve it. This skill is critical for turning ambitious goals into reality.
To prevent rigid plans that break, maintain consistency in your high-level strategic pillars for the year. However, build in flexibility by allowing the specific tactics used to achieve those pillars to change quarterly based on performance and new learnings.
Traditional business planning focuses on financial targets. A more powerful vision includes the desired state of client acquisition, such as shifting from outbound prospecting to a 90% inbound model. This re-frames vision as an operational and lifestyle goal, guiding your strategy more effectively.