Issa Rae Details Biannual Goal-Setting Routine That Guides Her Expanding Career

Writer, actor, producer and entrepreneur Issa Rae follows a structured exercise twice a year to organize her priorities and track progress across her many projects. The 41-year-old creative professional, known for co-creating and starring in HBO’s “Insecure,” begins each calendar year by transferring ideas, goals and resolutions into a new notebook. Six months later she returns to the same pages to measure results and make adjustments, using the same format to keep both short-term and long-term objectives visible.

Notebook System Anchors the Calendar

Rae’s process starts on January 1, a date she informally calls her “superpower day.” She reviews previous notebooks, compiles the ideas captured during the prior 12 months and divides them into two primary sections: personal goals and career goals. The personal side typically includes three or four broad resolutions such as reading more or improving overall habits. The career section, by contrast, lists highly specific targets that address ongoing productions, business ventures and prospective opportunities. By separating these categories, Rae says she can keep professional ambitions from overshadowing individual development.

If a new idea emerges after January, Rae records it immediately to avoid losing momentum. She keeps a notebook close at hand for unplanned inspiration, noting that her strongest concepts often appear during periods of relaxation rather than scheduled work sessions. The mid-year review, conducted roughly at the six-month mark, functions as a checkpoint. During this second session she evaluates progress, removes items that no longer fit her strategic outlook and adds any fresh initiatives that surfaced since the start of the year.

Routine Supports Multiple Ventures

The system helps Rae manage a workload that has expanded significantly since “Insecure” premiered in 2016 and concluded its five-season run in 2021. Beyond acting and writing, she operates several companies: Hoorae Media, her production banner responsible for film and television projects; Viarae Prosecco, an alcoholic-beverage label; Sienna Naturals, a hair-care brand; and Hilltop Coffee and Kitchen, a California café chain. She is also slated to appear in a TurboTax commercial during Super Bowl 60 on Sunday, adding another commitment to an already full calendar.

Rae has acknowledged that she does not consider herself a natural long-term planner, making the twice-a-year exercise crucial for maintaining direction. Establishing a clear routine, she says, forces her to be deliberate about how each goal aligns with broader professional and personal aspirations. The approach reflects a discipline found among many business leaders who credit written plans with clarifying intent and reinforcing accountability.

Experts Cite Cognitive Benefits of Writing Goals

Scientific research supports Rae’s experience. According to studies referenced by the American Psychological Association, documenting objectives by hand engages memory and attention systems in the brain, increasing the likelihood that individuals will recognize opportunities to act on their plans. Recording milestones also creates an external trigger, reminding the writer to monitor progress and adjust behavior.

Prominent entrepreneurs share similar perspectives. FUBU founder Daymond John and Virgin Group’s Richard Branson have publicly endorsed the practice of writing goals, arguing that a tangible record provides focus amid competing demands. Neuroscientist and author Erin Clabough echoed this argument in a recent interview, suggesting that some people may benefit from drafting a motivational letter to themselves instead of a bullet-point list. She said open-ended statements, such as a commitment to embrace new experiences, can offer flexibility while still guiding daily decisions.

Clabough recommends revisiting self-authored letters regularly, applying incremental effort toward the stated intention. The process aligns with Rae’s semiannual checkpoint, though executed in a different format. Both methods rely on routine evaluation rather than one-time resolutions to transform abstract wishes into measurable achievements.

Balancing Specificity and Flexibility

Rae’s choice to keep personal resolutions general while specifying professional targets illustrates a common strategic balance. Broad declarations—“be better,” for example—leave space for evolving definitions of success in well-being or relationships. Conversely, a television production schedule or product launch demands precise timelines and deliverables. By distinguishing the two, Rae maintains adaptability in her private life without compromising the structured requirements of business initiatives.

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The exercise also acts as a filter. When Rae reviews her notebook on January 1, she evaluates which ideas appear attainable within the year. Some concepts move forward immediately; others remain archived until resources, timing or partnerships align. The June reassessment repeats this process, ensuring that outdated items do not consume attention and that emerging possibilities receive prompt consideration.

Application for Broader Workforces

While Rae operates in entertainment and consumer goods, the underlying framework translates across industries. Professionals in corporate environments can adopt a similar cadence: set discrete, trackable objectives at the start of the year; revisit them at a midpoint; and maintain a written log of spontaneous insights. Neuroscience indicates that handwriting in particular slows thought just enough to encourage reflection, deepening cognitive encoding of the material. Digital tools can replicate some advantages, but many experts still recommend pen and paper for maximum engagement.

Organizations may integrate the model into performance reviews, pairing individual aspirations with company metrics. Employees could outline quarterly benchmarks, then assess outcomes with supervisors mid-year. Such alignment clarifies expectations and may boost morale by demonstrating tangible progress. It also mirrors the iterative nature of project management frameworks like Agile, which emphasize constant feedback over annual evaluations.

Next Milestones on Rae’s Agenda

Looking ahead, Rae continues to expand Hoorae Media’s slate, develop consumer products under Viarae Prosecco and Sienna Naturals, and grow Hilltop Coffee and Kitchen’s footprint in California. The TurboTax advertisement airing during the National Football League championship will further raise her profile, potentially opening additional commercial partnerships. Each endeavor will occupy a line in Rae’s current notebook, subject to review when the next “superpower day” arrives.

Whether through notebooks, letters or digital trackers, Rae’s disciplined approach demonstrates how a concise, repeatable ritual can anchor complex schedules. By combining specificity in work objectives with flexibility in personal growth, she maintains momentum across diverse ventures without losing sight of individual well-being—an outcome that many professionals, regardless of industry or seniority, aim to replicate.

Crédito da imagem: CNBC Make It