The 5 to 9 Job
by Raymond Akiiki
Welcome to The 5 to 9 Job—my journal on growth, failure, and figuring life out. I started this show because I felt this deep need to help people like me…People trying. Failing and rebuilding. The idea was to use the hours between 5pm to 9am to grow. Slowly, my vision expanded and I wanted to do it all, to build a platform to raise others, reflect and share my interests and soon I hit a wall. Now It’s back to the basics; fewer better episodes. Each week, I share a few reflections, conversations, and stories from guests so make sure you don’t miss out on any episode.Welcome to my workshop.
Episodes
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Bet on Yourself — It's the Safest Risk You'll Ever Take
In this episode, we explore a simple but powerful idea: the best bet you can make is on yourself. Life is uncertain, every path carries risk, and there are no guarantees whether you choose safety or ambition. So if you're going to take a chance, why not invest in the one asset you'll always...
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The Most Important Question You'll Ever Ask Yourself
In this episode, we explore one of the most important questions a person can ask: "Why am I doing this?" Whether it's your job, business, relationships, goals, or daily habits, understanding your "why" gives meaning to the effort and direction to the journey. We discuss how purpose isn't always a...
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Live Before It's Too Late: The Three Regrets That Matter Most
In this episode, we explore the powerful lessons from The Top Five Regrets of the Dying by Bronnie Ware. Rather than focusing on all five regrets, we dive into the three that seem most relevant to modern life: not having the courage to live true to yourself, losing touch with meaningful...
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The Comeback Mindset: How to Turn Setbacks Into Power
Life doesn’talways go your way. Sometimesthings fall apart. Plans fail. People let you down. And you’re left wondering…what now? In thisepisode of The 5 to 9 Job, I’m diving into one of the most importantskills you’ll ever need: resilience. Because thetruth is simple: Tough times don’t...
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You’re Living Someone Else’s Life…Here’s How to Take It Back
Are youliving your life…or just going through it? In this episodeof The 5 to 9 Job, I’m diving into something that quietly controlseverything: your vision for your life. Becausehere’s the truth… If you don’t create a vision for your life, someone else will. Your job. Society. Even the people…
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When Life Hits Hard: Building Grit and Resilience
Life isn’t always smooth. Careers stall. Dreams feel distant. Self-doubt creeps in. And sometimes, it feels like the storm won’t pass. In this episode of The 5 to 9 Job, Raymond breaksdown what it really means to develop grit and resilience — not as motivationalbuzzwords, but as skills you can...
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The Truth About Vulnerability and Strong Relationships
Relationshipsshape everything. Your growth. Your resilience. Your confidence. Your opportunities. In thisepisode of The 5 to 9 Job, Raymond explores what it truly means to buildauthentic relationships — the kind that uplift you, challenge you, and standthe test of time. In a worldfull of...
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Design Your Day, Design Your Life | The Power of Routines
Design Your Day, Design Your Life | The Power of Routines Most people think success comes from motivation. It doesn’t. It comes from structure. In this episode of The 5 to 9 Job, Raymond breaks down the real power behind routines — and why your daily habits are either quietly building your…
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The Breakthrough You Want Starts in Your Mind
When your time is up, what do you want to be remembered for? That’s a heavy question — but it’s one we can’t afford to avoid. In this episode of The 5 to 9 Job, I reflect on legacy — not in terms of money, titles, or achievements, but in terms of impact, character, and how you make people feel....
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Master the Art of Storytelling (Even If You’re Not a Speaker)
Everyone loves a good story. Movies. Books. Conversations. Stories are how we connect, inspire, and make sense of the world. In this episode of The 5 to 9 Job, we break down the art of storytelling — and how you can use your everyday experiences to connect, influence, and leave a lasting impact....
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Cold DMs Don’t Work — Here’s What Does The 3 Rules of Networking That Changed My Life
Networking can change your life faster than almost anything else. But most people are doing it completely wrong. In this episode of The 5 to 9 Job, we break down what real networking actually looks like — and why it has nothing to do with collecting business cards or sending random cold DMs....
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If Your Kids Can’t Speak to Their Grandparents, We Failed
Have you ever realized you’re friends with someone simply because you speak the same local dialect? It sounds small — but it’s deep. In this episode of The 5 to 9 Job, we talk about culture, language, identity, and something that’s slowly disappearing without us noticing. Because here’s the...
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Your 5 to 9 Is More Important Than Your 9 to 5
Most people obsess over their 9-to-5. But the real transformation? It happens in the 5 to 9. In this foundational episode of The 5 to 9 Job, I break down what this concept really means. Not just the trendy “5 to 9 before your 9 to 5” productivity wave — but the entire window between 5 p.m. and 9...
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5 to 9 Diary: Discomfort, Fate & Betting on Yourself
This is one of those raw bonus episodes. No tight structure. No polished framework. Just thoughts I’ve been wrestling with lately — about life, discomfort, identity, poverty, AI, and betting on yourself. In this episode of The 5 to 9 Job, we unpack: The idea that everything happens for a reason —...
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This Is How You Survive When Life Hits You Down
Got it 👍 — same exact system. Here are 5 click-bait / podcast-optimised title options + 1 clean episode description for The Storm – Cultivating Grit and Resilience. You’re Not Weak — You’re Just in a Storm This Is How You Survive When Life Hits Back Grit Is Built in the Storm, Not the Sunshine…
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This Is What Actually Matters at the End of Your Life
When your time is up, what do you want to be remembered for? That’s a heavy question — but it’s one we can’t afford to avoid. In this episode of The 5 to 9 Job, I reflect on legacy — not in terms of money, titles, or achievements, but in terms of impact, character, and how you make people feel....
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The 3 Rules of Building Authentic Relationships That Changed My Life
Networking can change your life faster than almost anything else — but only if you do it right. In this episode of The 5 to 9 Job, I break down what real networking actually looks like. Not collecting business cards. Not awkward cold DMs. Not “using” people. This is about building authentic...
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How Gratitude Unlocks Happiness and Opportunity
Today’s episode is a short one — but it’s powerful. We’re talking about gratitude. Not the Instagram-quote version, but the real kind: gratitude as a practice, not a reaction. If you’ve been feeling stuck, overwhelmed, unmotivated, or just off, this episode is your reset button. Gratitude doesn’t...
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The 5 Podcasts That Will Make You Smarter in 2026 (I’ve Tested Hundreds)
In this bonus episode of The 5 to 9 Job, I’m breaking down the best podcasts you should be listening to in 2026 — based on real listening time, not hype. In 2025 alone, I spent over 400 hours (almost 18 full days) listening to podcasts across business, psychology, health, relationships, and...
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5 to 9 Diary: Discomfort, AI, Poverty & Betting on Yourself
This is one of those bonus episodes where I just sit down and share what’s been on my mind lately. No scripts. No big structure. Just thoughts, questions, lessons, and a few uncomfortable ideas I’ve been wrestling with — about life, mindset, discomfort, and the future. In this episode of The 5 to…
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How to Build Unshakable Confidence (Even If You’re Shy)
🎙️ What Confidence Really Is Confidence is not noise. It’s not being the loudest person in the room or pretending you know everything. True confidence is quiet. It’s walking into a situation and knowing: “I’ll figure this out.” Just like walking, talking, or riding a bike — confidence is…
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5 to 9 Diary: Uncomfortable Questions, Personal Truths, and Where My Head Is in 2026
This is one of those bonus episodes where I just sit down and talk. No script. No clean structure. Just the ideas, questions, and lessons that have been living in my head lately. Think of it like us having a long conversation — I’m unpacking what I’ve been learning, what I’m struggling with, and...
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Let Go to Grow: The Episode You Needed Today
In today’s episode, Raymond breaks down one of the most transformative habits you can build: the ability to let go. Whether it’s past mistakes, relationships that drain you, or beliefs that limit your future, holding on keeps you stuck — letting go sets you free. This episode is gentle, honest…
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5 to 9 Diary: Life, Business, AI & Being Human — My Most Honest Episode Yet
This is one of those honest, freestyle diary episodes — the kind where Raymond sits down, opens his mind, and shares the lessons, observations, fears, wins, and breakthroughs from the week. From growth and iteration, to empathy, to listening better, to unfair advantages and AI, this episode moves...
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The Hidden Rules of Office Communication (No One Teaches You)
In today’s episode, we’re doing a 5 to 9 review of your 9 to 5 — the small communication habits that make you look professional… or completely lost. Raymond breaks down the unspoken rules of workplace communication: how to talk to your boss, how to lead people below you, how to write messages…
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5 to 9 Diary: Burnout, Red Flags & My Inner Villain
Today’s episode is a raw one — a true 5 to 9 Diary entry. Raymond opens up about burnout, recovering from loss, relationship red flags, communication flaws, and the uncomfortable realization that sometimes… he’s the villain in his own story. This isn’t a themed episode. It’s the messy, honest,...
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When You Feel Stuck in Life: Why It Happens & How to Move Again
Today’s episode dives into a feeling we all know too well: being stuck. Not unmotivated. Not lazy. Just… stuck. Working hard, doing everything “right,” but still feeling like your life isn’t moving the way you hoped. Raymond opens up about his own journey—from comparing himself to others after...
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The 2025 Season Finale: Gratitude, Growth, and What Comes Next
🎙️ Season Finale Reflection In this episode, Raymond closes out the 2025 season of The 5 to 9 Job with gratitude, honesty, and a grounded mindset heading into 2026. No pressure. No perfect plans. Just perspective. A fast year A heavy year A revealing year It wasn’t just “character building.” It...
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Your Network Is Not Your Net Worth — Unless You Fix This
In this episode, Raymond breaks down one of the biggest traps young professionals fall into: confusing volume with value when it comes to their network, followers, clients, and connections. He dives into the dangerous lie of “network as much as possible,” exposes why being everywhere can actually...
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Happy Holidays from The 5 to 9 Job
In this short holiday episode, Raymond shares a personal message about slowing down, being present, and not letting small frustrations steal the joy of Christmas. No productivity hacks. No pressure to “optimize” your break. Just perspective. Raymond opens up about how hard it is to intentionally...
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The 9 to 5 Trap: Office Politics, Bad Bosses & Boundaries
What We Cover How to lead without a title: Influence > authority How to negotiate a raise: Homework + receipts + confidence The dark side of money: It amplifies who you already are Office politics 101: Play smart, not dirty How to say no without losing your job: Boundaries = survival Honest…
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5 -9 Diary: Why Your Relationships Are Falling Apart — And How to Fix Them Fast
What You’ll Learn Why working too much destroys relationships — and how to fix it How to command respect in any room The truth about confidence (and how to build it from zero) How to be liked without being fake or a people-pleaser Why most managers fail — and how not to become one How “bad…
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You're Not Busy — You’re Disorganized.
Most people wake up, grab their phone, reply to messages, react to the world, and then wonder why they’re overwhelmed, drained, or feeling stuck. But here’s the truth no one wants to hear: 👉🏽 If you don’t plan your day, someone else will. Your boss. Your friends. Your emails. Random...
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5 - 9 Diary: How Most People Lose Their Dreams After Work
Most of us finish work exhausted… but what happens after 5 p.m.? You get home, you tell yourself you’ll rest “for a bit,” and suddenly… it’s midnight. Netflix is still asking if you’re alive. TikTok thinks you died. And you realize you just lost four hours of your life. Here’s the truth: 👉🏽…
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How to be there for people without losing yourself
I’ve always been a giver—emotionally, financially, mentally. I love being there for people I care about. But at one point in my life, it started draining me. So I did what the internet tells you to do: “Protect your energy.” But I went too far. Way too far. In this raw, honest episode, I open up...
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Why I Almost Quit This Podcast… And Why I’m Still Here
I wanted to stop this podcast. Not in a dramatic way. Not because things were falling apart. Just… quietly. I planned to pause for a long time — maybe months — but somehow I only took a few weeks off, and today, I found myself recording again. And that made me ask myself: 👉🏽 Why am I still…
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The Power of Your Absence: Reclaim Your Worth and Stop Proving Yourself
Do you constantly feel like you’re performing—at work, socially, even in your own life? I know I did. I spent months trying to prove myself, seeking validation, and living on edge, until I discovered a life-changing truth: your worth isn’t determined by anyone else. In this episode of The 5 to 9...
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Why You Should Care (And How to Do It Without Losing Yourself)
For years, I wore “I don’t care what people think” like a badge of honor. I thought it was confidence. I thought it was freedom. But life humbled me. I realized I wasn’t being confident—I was slowly becoming cold, distant, and disconnected from the people and opportunities that mattered. In this...
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Reach Back and Pull Someone Else Up: Denzel Washington’s Lesson on True Success
How do you measure success? Not by the money you make, the titles you earn, or the stuff you accumulate. Denzel Washington reminds us: “You will never see a U-Haul behind a hearse.” You can’t take it all with you. True fulfillment comes from impact—using your skills, your talents, and your...
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5 To 9 Diary: Hallucinating Customers, Pleasing Women, and the Fight Against Fake Productivity
This bonus episode is different. It’s raw, unfiltered, and straight from the notes on my mind lately: A dream that made me question how ready I am for my family to hear everything I say here. Slipping back into an old version of myself—cold, distant, but highly productive—and whether that’s...
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How To Play The Long Game — Patience in a Fast World
We live in a world obsessed with quick wins—overnight fame, fast money, instant success. And honestly? It’s not even our fault. The world has changed. Success is everywhere—more billionaires, more creators, more people “making it” than ever before. But here’s the trap: when you see success...
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Don’t Waste Your Life: Lessons from Steve Jobs
What would you do differently if today were your last day? In this episode of The 5 to 9 Job Podcast, we explore the third and final story from Steve Jobs’ legendary Stanford commencement speech—the story of death. Jobs shares how a cancer diagnosis forced him to confront his own mortality and…
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Your Future Self Is Waiting — Here’s How to Meet Them
Who is the person you want to become in 5 years? 10 years? In this episode of The 5 to 9 Job Podcast, we dive into the powerful practice of visualizing your future self—not as wishful daydreaming, but as a strategy for clarity, discipline, and action. By consistently picturing who you want to be,...
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Why You Should Embrace Failure (Denzel Washington’s Lesson)
Failure isn’t the opposite of success — it’s the path to it. In this episode of The 5 to 9 Job Podcast, we explore Denzel Washington’s powerful philosophy of falling forward. Behind every success story lies a trail of setbacks, rejections, and struggles. What separates winners from quitters is…
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How to Stop Letting Fear Control Your Life
Fear isn’t just yours — it’s everyone’s. In this episode of The 5 to 9 Job, I get raw and real about my own fears — from the worry of failing in business, to the fear of being a bad dad one day, to the quiet voice that whispers: “What if you’re not enough?” But here’s the truth: fear is normal....
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Why Losing Something Could Actually Be What You Need
What happens when the world’s most visionary founder gets fired from his own company? In this episode, we revisit Steve Jobs’ legendary 2005 Stanford commencement speech — the story of love and loss. Jobs built Apple from his parents’ garage into a $2 billion giant, only to be forced out at 30....
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5 To 9 Diary: Why I Turned Down Another Job (Even When I Needed the Money)
This bonus episode is a mix of updates, reflections, and big ideas that I’ve been wrestling with lately. From why choosing the hard road now creates an easier life later, to how to prepare for life’s unpredictable seasons, to saying “no” when a job offer threatened my integrity—even though I…
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Dreams Need Goals, Not Just Hope
In this episode, we dive into Denzel Washington’s unforgettable message on the power of failure, discipline, and purpose. Too often, fear keeps us from chasing what we’re passionate about. But failure isn’t the end—it’s the process. Denzel reminds us that dreams without goals are just dreams,...
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Reflections After 100+ Episodes
This episode is different—it’s not about business, real estate, or even motivation. It’s about why this podcast exists in the first place. After more than 100 episodes, I felt the need to step back, reflect, and re-center on the vision that started The 5 to 9 Job: creating a space for people who...
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Steve Jobs on Following Your Curiosity and Dealing with Uncertanity
“You can’t connect the dots looking forward; you can only connect them looking back.” In this episode of The 5 to 9 Job, we break down one of the most powerful stories from Steve Jobs’ 2005 Stanford commencement speech—the calligraphy class that changed everything. From dropping out of college to...
About this show
Welcome to The 5 to 9 Job—my journal on growth, failure, and figuring life out. I started this show because I felt this deep need to help people like me…People trying. Failing and rebuilding. The idea was to use the hours between 5pm to 9am to grow. Slowly, my vision expanded and I wanted to do it all, to build a platform to raise others, reflect and share my interests and soon I hit a wall. Now It’s back to the basics; fewer better episodes. Each week, I share a few reflections, conversations, and stories from guests so make sure you don’t miss out on any episode.Welcome to my workshop.
Hosted by
Raymond Akiiki