Retirement: Stop Planning the Exit, Start Planning the Life

When we ponder retirement - we’re masters at planning our exit, but surprisingly vague about what happens after. We’re so focused on what we’re retiring from rather than what we’re retiring to. The real goal isn’t the escape itself - it’s creating a life of genuine freedom, growth, and meaning on the other side. And here’s the plot twist - much of this post isn’t about retirement at all. It’s about what to do while you’re still working.

Sure, we all have those fantasies during rough meetings: “Finally, I’ll write that novel!” “I’ll learn to play jazz piano!” “I’ll travel the world!” But how many retired folks do you know who are actually doing these things?

Let’s explore retirement holistically - beyond the spreadsheets and financial calculators - to understand what really makes for a fulfilling next chapter.

• The Great Fallacy: Work Isn’t Your Prison
• The Map: Navigating by Autonomy, Mastery & Purpose
• The Side Quests: Starting Adventures Before The End Game
• The Journey: Embracing Life’s Next Phase
• The Hero: Crafting Your Post-Work Identity
• The Treasure: When F-You Money Sets You Free
• The Health Bar: No Extra Lives in This Game
• The Dragons: Five Myths That Keep You Chained
• The Scrolls: Wisdom From Fellow Travelers

The Great Fallacy: Work Isn’t Your Prison

“If only I didn’t have to work,” we tell ourselves, “I could finally do all those meaningful things.” But we tend to shorten this to just “not having to work,” forgetting the crucial second half about doing meaningful things. This reveals the dangerous assumption: that work is what’s keeping us from living our best lives.

But work isn’t a prison - it’s often a structure that provides significant growth, connection, and purpose. This begs the question: If work truly prevents you from pursuing what matters, why wait for retirement? The same forces that hold us back now - procrastination, fear, inertia - don’t vanish when we stop working. Without work’s built-in structure, they often become more challenging.

The Map: Navigating by Autonomy, Mastery & Purpose

When we talk about retirement, we’re often focused on what we’re retiring from rather than what we’re retiring to. The real goal isn’t retirement itself - it’s achieving AMP: Autonomy, Mastery, and Purpose.

• Autonomy: The freedom to choose how you spend your time and energy. This goes beyond financial independence - it’s about having control over your life’s direction.
• Mastery: The opportunity to continue growing and developing skills that matter to you. Retirement shouldn’t mean stopping learning - it’s about choosing what you want to master.
• Purpose: A reason to get up in the morning that aligns with your values. Work often provides this by default - in retirement, you get to choose and craft your own purpose.

Work naturally provides us with identity and purpose - through our roles, our impact, and our daily interactions. While we’ll need to consciously rebuild these elements in retirement, that’s not a bad thing. In fact, being intentional about where we get our AMP while still working can make the transition much smoother.

I’ve seen the power of AMP both in my own career and in leading others. In my current role, I’d happily do about 70% of my job even if I didn’t need the money - that portion aligns perfectly with my values, challenges me in the right ways, and gives me the autonomy I crave. The other 30%? That’s why they call it work - and why they pay me. You can see how these principles play out in leadership in my manager book, and their impact in the kind words shared by my teams on LinkedIn. The catch is, you can’t really find a job that’s just the good parts. The key is maximizing the ratio of energizing work to draining work, both in your career and in retirement.

Financial independence is just a tool that enables AMP - it’s not the end goal. The money provides the foundation, but AMP provides the fulfillment. As you plan for retirement, consider how each decision supports or detracts from these three core elements.

The Side Quests: Starting Adventures Before The End Game

Retirement isn’t about quitting work—it’s a chance to transform your daily life. Don’t wait until retirement to start your hobbies. Begin now to discover what sparks joy, fuels creativity, and builds meaningful connections. Whether it’s art, sports, or learning new skills, integrating hobbies now lays the foundation for autonomy, mastery, and purpose in your future.

The Journey: Embracing Life’s Next Phase

The decision to retire triggers a complex emotional journey. It’s not just about leaving a job; it’s about transitioning to a new phase of life that can bring up feelings of excitement, anxiety, loss, and liberation all at once.

The Hero: Crafting Your Post-Work Identity

For many of us, especially in tech, our work forms a significant part of our identity. Who are we when we’re no longer defined by our profession? This section explores building a multi-faceted identity that transcends our career.

As we transition from our professional identity, it’s important to focus on what we’re moving toward, not just what we’re leaving behind. The key is finding new sources of meaning and purpose that align with our values and aspirations.

The Treasure: When F-You Money Sets You Free

These terms are often used interchangeably, but they represent different concepts and life choices. Financial independence gives you options, while retirement is just one of those options.

As you approach financial independence - that “fuck you money” level of savings - something interesting happens: the anxiety about job security starts melting away. That nagging fear of losing your job (which is often more imagined than real) fades, freeing you to focus on the aspects of work you genuinely enjoy. It’s like getting a new job without changing companies - suddenly you’re doing it because you want to, not because you have to.

The FIRE (Financial Independence, Retire Early) community has evolved to recognize different paths:

• FIRE: The traditional approach of aggressive saving and modest retirement
• Fat FIRE: Higher savings enabling a more luxurious retirement lifestyle
• Obese FIRE: Substantial wealth allowing for significant discretionary spending

The Health Bar: No Extra Lives in This Game

There’s an old saying: “A healthy person has a thousand wishes, a sick person has only one.” Just like we save money for retirement, we need to save our health. But unlike a 401(k), your health account has mandatory withdrawals that you can’t control. Every day, whether you like it or not, you’re spending from this account. And just like unexpected market crashes, you’ll face major unexpected health withdrawals whether you’re ready or not.

Think of your physical health like compound interest - small, consistent investments early on yield massive returns later. But also like money, you can’t wait until retirement to start saving. The “health debt” you accumulate in your working years will need to be paid back, often with steep interest.

Remember: You can always earn more money, but you can’t earn more health. Make those deposits while you can.

The Dragons: Five Myths That Keep You Chained

Let’s debunk some common misconceptions about retirement and explore what modern retirement really looks like.

Common myths include:

• “Work” is preventing you from doing the things you love
• You can self-motivate yourself easily
• You won’t experience a decline in social interaction
• You automatically have enough meaning and structure
• Retirement means stopping completely

The Scrolls: Wisdom From Fellow Travelers

The resources and related content have been integrated throughout this post as summaries above. Each section contains relevant links and summaries to help you explore these topics in more depth.

The Four Enemies on Your Journey

Just as every hero faces obstacles on their quest, the journey to a fulfilling retirement has its own adversaries.

Parallels between retirement and being a solpreneur

The themes of self-motivation, creating structure, and maintaining purpose that we’ve explored here overlap significantly with other life transitions. For a related perspective on building routines and finding motivation without external structure, check out Herman’s post on staying motivated as a solo creator.