Raymond Akiiki

The 5 to 9 Job

Society EN ↓ 156 episodes

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.

Author

Raymond Akiiki

Category

Society

Podcast website

podcasters.spotify.com

Latest episode

Jun 22, 2026

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Episodes

Bet on Yourself — It's the Safest Risk You'll Ever Take 22.06.2026

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 have—you. We talk about self-investment, personal growth, learning new skills, taking ownership of y...

The Most Important Question You'll Ever Ask Yourself 15.06.2026

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 single grand discovery, but something that evolves as we grow and experien...

Live Before It's Too Late: The Three Regrets That Matter Most 08.06.2026

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 relationships, and not allowing yourself to be happier. We discuss why so many people spend their lives chasing...

The Comeback Mindset: How to Turn Setbacks Into Power 03.05.2026

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 last…resilient people do. We talkabout: What resilience really means (it’s not what you think) The mindset shif...

You’re Living Someone Else’s Life…Here’s How to Take It Back 26.04.2026

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 around you. And beforeyou know it, you’re living a life that looks fine on the outside—but doesn’tfeel ri...

When Life Hits Hard: Building Grit and Resilience 19.04.2026

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 intentionally build. Because success isn’t born in comfort. It’s forged in difficulty. Inside this episo...

The Truth About Vulnerability and Strong Relationships 13.04.2026

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 distractions, surface-level networking, and curated personas, realconnection has become rare. Many of us strug...

Design Your Day, Design Your Life | The Power of Routines 06.04.2026

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 future… or slowly keeping you stuck. If you’ve ever wondered how high performers manage packed calendars, mu...

The Breakthrough You Want Starts in Your Mind 30.03.2026

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 . Because whether we realize it or not, we’re all leaving a legacy already. Even doing nothing… is still...

Master the Art of Storytelling (Even If You’re Not a Speaker) 23.03.2026

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. Because here’s the truth: You don’t need to be an author. You don’t need a TED Talk. You don’t need a...

Cold DMs Don’t Work — Here’s What Does The 3 Rules of Networking That Changed My Life 16.03.2026

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. Because real networking is about: Building genuine relationships Giving before you get Creating mutual val...

If Your Kids Can’t Speak to Their Grandparents, We Failed 12.03.2026

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 uncomfortable truth: If we don’t intentionally pass down our culture, our kids might not even be able to sp...

Your 5 to 9 Is More Important Than Your 9 to 5 08.03.2026

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 a.m. That’s 16 hours. Sixteen hours where: You build. You recover. You reflect. You grow. You design...

5 to 9 Diary: Discomfort, Fate & Betting on Yourself 04.03.2026

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 — even when you don’t understand it yet Why something as simple as getting organized can quietly transf...

This Is How You Survive When Life Hits You Down 01.03.2026

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 Why Hard Seasons Create the Strongest People Life Knocked You Down? Here’s How You Get Back Up More poe...

This Is What Actually Matters at the End of Your Life 22.02.2026

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 . Because whether we realize it or not, we’re all leaving a legacy already. Even doing nothing… is still...

The 3 Rules of Building Authentic Relationships That Changed My Life 15.02.2026

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 relationships that naturally open doors, create opportunities, and compound over time. Why networking matt...

How Gratitude Unlocks Happiness and Opportunity 08.02.2026

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 wait for life to get easy. It trains your brain to see what’s already working — even when things feel...

The 5 Podcasts That Will Make You Smarter in 2026 (I’ve Tested Hundreds) 02.02.2026

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 personal growth. After filtering through the noise, I’ve narrowed it down to five podcasts that consistent...

5 to 9 Diary: Discomfort, AI, Poverty & Betting on Yourself 28.01.2026

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 9 Job , I talk about: Why everything might happen for a reason , even when it doesn’t make sense yet H...

How to Build Unshakable Confidence (Even If You’re Shy) 25.01.2026

🎙️ 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 learned. Nobody starts confident. People build it through: Action Repetition Showing up Failing and trying agai...

5 to 9 Diary: Uncomfortable Questions, Personal Truths, and Where My Head Is in 2026 21.01.2026

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 what I’m still trying to figure out. I don’t expect you to agree with everything. In fact, I’d prefer i...

Let Go to Grow: The Episode You Needed Today 18.01.2026

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, and designed to help you finally release what’s weighing you down. Raymond opens the episode by asking t...

5 to 9 Diary: Life, Business, AI & Being Human — My Most Honest Episode Yet 14.01.2026

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 across the full spectrum of life and work. No structure. No pressure. Just real thoughts that might be...

The Hidden Rules of Office Communication (No One Teaches You) 11.01.2026

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 that don’t embarrass you, and how to carry yourself with confidence in any office or formal environment. I...

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