This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.com

Let’s be honest—most of us don’t plan our careers. We react to opportunities, chase what looks good on paper, and hope it all somehow adds up.

But if you want to stop winging it and start steering it, you need a strategic career plan—think of it as your personal GPS—connecting where you are today to where you want to go, so every step actually moves you closer to your goals.

Take my client Jerry. He wanted a seat in the C-suite and his mentor told him an MBA was key. So, Jerry applied to several Ivy League programs—his heart set on Stanford. When he got the rejection email (ouch), his mentor called in a favor to get feedback. Turns out, Jerry’s résumé lacked a “big win.” He needed something to help him stand out from the crowd.

So, they got to work. Over the next year, Jerry led a project that showed real leadership and delivered major results. He reapplied—and this time, he got in.

That’s the power of a strategic plan. It keeps you focused on the long game, helps you adapt when things go sideways, and reminds you that progress isn’t about overnight wins. It’s about intentional, sustained effort that pays off over time.

So stick with me — we’re going to unpack what made Jerry’s plan work—and how you can use the same approach to shape your next chapter. I’ll walk you through what to include, what to avoid, and how to shift from letting your career happen to actually running the show.

Key Elements of a Career Strategic Plan

There are four key elements to building a strategic career plan:

* Clarify Your Vision and Purpose: What does success actually look like for you? Think of vision as your destination and purpose as the engine that drives you there. Are you motivated by creativity, leadership, or making an impact? Getting clear on this gives your decisions direction and keeps your goals aligned with your values.

* Create Goals and Objectives: Big dreams need small, specific steps. Goals are the big-picture outcomes (like “Become a VP within five years”), while objectives are the measurable action steps that get you get there (“Lead three cross-departmental projects in the next 18 months”). Think of goals as the headline, and objectives as the fine print that makes it real.

* Conduct a SWOT Analysis: Before you map any move, know your landscape. What are your Strengths, Weaknesses, Opportunities, and Threats (SWOT). This snapshot gives you the lay of the land – where you shine, where you can grow, and what’s happening around you that might help or hinder your progress. This step grounds your plan in reality.

* Identify Milestones and Metrics Milestones mark your key moments like completing a certification, landing a leadership role, publishing an article. Metrics measure your impact like boosting team performance by 20% or expanding your network by 50 new contacts. Tracking both keeps you honest, motivated and clear on your wins.

What’s important to remember is that a strategic plan isn’t chiseled in stone. It’s meant to evolve as you do. New data, experiences, and insights will keep shaping it—and that’s a good thing. I like to revisit these headline elements at least once a year to see what needs a tweak or a course correction.

Case Study: Jerry’s Strategic Plan in Action

Let’s revisit Jerry—the C-suite hopeful we met earlier. When we last left him, he’d just turned a Stanford rejection into a powerful lesson about clarity and perseverance. Now let’s look at how he built his strategic career plan step by step, using the same four elements we just covered.

Jerry wasn’t chasing a title for ego’s sake. He wanted to lead in FinTech because he cared deeply about access. His moonshot was to make wealth-building tools available to everyday people—even those who could only invest fifty dollars at a time. That was his vision and purpose: to use leadership as a way to open financial doors that had long been closed.

To move that vision into motion, he needed clear goals and objectives. The first was straightforward—earn an MBA from a top-tier program. But the how mattered just as much as the what. With his mentor, Jerry broke the big goal into smaller, actionable steps: identify a visible project that could showcase leadership, deliver measurable results, and strengthen his MBA application.

Next came his SWOT analysis. Jerry’s strengths included sharp analytical thinking and the ability to navigate complex systems. His weaknesses? He hadn’t yet proven his leadership impact on a major stage. Opportunities included his mentor’s network and a company ready for fresh ideas. The threats were real too—fierce competition for top MBA programs and limited recognition at work. Seeing it all laid out helped him target where to take bold, meaningful action.

Jerry launched a cross-departmental initiative to improve client onboarding—a persistent problem in his organization. It wasn’t easy. He had to rally skeptical teammates, make tough calls, and stay centered when the project hit turbulence. But he tracked milestones and metrics religiously: monthly progress reviews, measurable efficiency gains, and client retention rates. By year’s end, his team improved onboarding efficiency by 30% and cut costs across departments.

When Jerry reapplied to Stanford, he had a story worth telling—one that blended purpose, proof, and progress. His essays weren’t about ambition; they reflected alignment. He didn’t just get in. He stepped into his next chapter with a renewed sense of confidence and a clear direction for the impact he wanted to make.

Jerry’s plan wasn’t perfect—it evolved as he did. But that’s the beauty of having a strategy rooted in purpose. It gives you something solid to lean on when things change, and a clear way to measure progress when doubt creeps in. His story is proof that when you approach your career with curiosity and intention, even a setback can become a step forward.

Bottom Line

A strategic career plan isn’t about predicting every turn—it’s about creating a framework that keeps you aligned with your purpose while staying open to change. When you take time to clarify what matters most, set meaningful goals, and check in with yourself regularly, you stop drifting and start leading. Progress may not always be linear, but with intention behind it, it’s always forward.

If someone came to mind while you were reading this—please send it their way. You never know the impact a well-timed message can have.

* How to Move Ahead in Your Career

* What are the Seven Big Mistakes of Goal Setting?

Perks for Paid Subscribers

Moonshot Mentor paid subscribers get weekly journal prompts to spark personal and professional growth, guided meditations to help them center, reflect, and reset, plus exclusive career development and career grief workshops that build clarity, resilience, and momentum.

Journal Prompts

Here are 4 journal prompts for paid Moonshot Mentor subscribers. These questions will help you clarify your career vision, strengthen your strategy, and stay connected to what truly matters as you move forward.

What’s Your Next Career Move? 🚀

Powered by Wave AI