Day 23 Transcript
NOTE: Today’s transcript is followed by an AI prompt that can be used with your AI provider of choice. Just copy and paste it into ChatGPT or Perplexity and it will help you answer today’s questions for your specific side hustle… the way a human teaching assistant would help you in an Ivy League university. If you’re eager for more on today’s topic, I’ve included a Secret Dessert Course at the very end — a bonus section that isn’t directly covered in today’s video but has a lot of value practical, hands-on value. That dessert also comes with its own AI prompt.
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Part 1: Enter Super Skill #3
Welcome to week 4, Day 23 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to build a business that’s meaningful, impactful, and profitable. Our topic today– effective delegation– making you less of a control freak. Not a lot less. Not like a control hippie. But maybe a control knob… if you’re British. Anywho…
Most of us start out believing that if we want something done right… [exhale]... yeah. That means most of us are wrong. It’s a trap. It sticks you with all the work you shouldn’t be doing… burning your most valuable resource—your time—on tasks that coaches say “don’t move the needle”-- they do– they just aren’t the best use of YOUR time.
So today’s questions are designed to help you confront your own resistance to delegation.
Question 1. What’s one task you keep doing yourself—even though you know you shouldn’t—because you’re worried about the outcome if someone else takes it on?
Question 2. If you had an extra hour every day because you delegated one thing, what would you do with that time?
And bonus question– #3: Who’s the last person you trusted to handle something important for you, and how did it go?
If you do it right, delegation isn’t just about offloading work. It’s about reclaiming the other two super skills: focus and prioritization. It’s about reclaiming your time and your energy for the things that only you can do. It’s about making your hustle sustainable—so you don’t burn out before you even get to the good part.
Part 2: 💼 Employ a Delegation Matrix: Today's Ivy League MBA Skill
“...founders who are control freaks convince themselves that only they can do things that are 100% right… and what makes it tricky is that they’re actually right. But they’re answering the wrong question. The right question is– can that task be done at say 80% right without negatively impacting clients? And the answer to that for most things is abso-@#$ing-lutely.”
Day 23, Part 2 of Lunch Break Millionaire– where we turn whatever you're eating for lunch into an Ivy League MBA degree. Today’s meal? Nachos– tacos pequeños! Perfect for sharing as long as the other person doesn’t keep licking their fingers.
Today’s Ivy League MBA skill is what’s called a delegation matrix— one of the most practical and widely taught frameworks out there. It builds on what’s called the Eisenhower Matrix– you can look that up– but it basically adds layers for clarity and scalability. Don’t freak. I’ll explain how it works.
First– you define the task you’re going to delegate. What exactly needs to be done? What are the inputs, the outputs, the success criteria? In the corporate world we call that an SOP– a standard operating procedure. Others call it operational playbooks. That is the first step.
Second– you assess the task’s importance and urgency. Is it a high-impact task that only YOU can do, or is it something that could be done by someone else? This one’s tricky because founders who are control freaks convince themselves that only they can do things that are 100% right… and what makes it tricky is that they’re actually right. But they’re answering the wrong question. The right question is– can that task be done at say 80% right without negatively impacting clients? And the answer to that for most things is abso-@#$ing-lutely.
Ok. Third step of the process– you identify the right alternate person to do the task. Who has the skills, the capacity, the motivation to take this on? And if the answer is no one, can you hire someone?
Fourth– You set clear expectations for that person/task. What does success look like? What are the deadlines, the check-in points, the communication protocols?
And fifth– the really really hard part–- you empower and trust. You give them the authority and the resources to get it done. And you step the hell back and let them own it.
That 5 step process is how you grow your hustle. Not from a sales perspective. From an operational perspective. Your goal is to create a culture from day 1 where delegation is encouraged– where it’s rewarded, where it’s refined over time.
If you need to control something, control that. Because that’s how you hustle smarter.
Part 3: Reduce the Cost of Doing It All
“...never ever ever delegate a job you don’t know how to do yourself.”
This is Day 23, Part 3 of Lunch Break Millionaire. This is the segment where we #BuildinPublic– where I answer the daily questions every hustle should– using the MBA skills we just learned– and showing my work– sharing how I’m building my hustle from scratch-no filters, just the real journey. You don't need to actually like or subscribe. I'm not doing this for the clicks. But if you’re leveling up from other creators you follow or know, introduce us. I want to learn from them and help them level up, too. We all deserve better than just making rich people richer.
Ok. Let’s look at how delegation plays out in a real-world side hustle. And it can’t be my current hustle because I’m still flying this one solo. Free climbing as the adrenaline junkies like to say. So I’ll use my experience from past hustles.
The core idea here is simple: your time is your second most valuable asset– after your incredible good looks. And the only way to scale your impact is to stop trading your hours for dollars. That’s scalability 101. You need to build systems and teams that let you focus on what are called “high-leverage activities”—That’s a fancy way of saying “the things that only you can do.”
For instance, can you as the founder– as the person who designed every last dimension of the product you’re selling– can you provide the best possible support on the planet for that product. Hell yeah! And guess what– if you do, you’re choosing the privilege of customer support emails over getting more customers. That’s a bad use of your time. Customer satisfaction is important but not urgent for me to do personally. Hell, I even enjoy it. So delegation isn’t just “what don’t you want to do?”
The other big learning from my past hustles– and my day job– never ever ever delegate a job you don’t know how to do yourself. I believe that so strongly that if I hire an expert from the outside to do something that I don’t know how to do, I pay them to teach me. I’ll never do it as well as them but I’ll manage my hustle– my day job– better because we took the time.
Delegation without curiosity– a giant nope. Delegation without empathy – nope. Delegation without active listening… you see where I’m going. I’m applying last week’s trust-builder mindset to my internal operations.
The result? I get a ton of back hours every week to focus on the things no one else can do like me– growing my hustle faster. And the side-benefit: my stress levels drop. My team feels valued. My freelancers feel valued. We’re all more invested in each other’s success.
This is the essence of delegation done right: delegate the things that don’t require your unique skills, so you can invest your energy where it matters most. That’s how you hustle smarter.
Prompt #1 - Make Your Hustle Scalable and Sustainable
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Prompt #1 - Make Your Hustle Scalable and Sustainable ○
Today, you’ll learn how to delegate effectively—so you reclaim your time and energy for the work that truly matters. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in leadership, team dynamics, and operational excellence:
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and creating environments where trust and empowerment thrive.
- **Professor Francesca Gino, Harvard Business School:** Expert in decision-making, motivation, and the science of trust in organizations.
- **Professor Adam Grant, The Wharton School, University of Pennsylvania:** Specialist in productivity, teamwork, and building high-performing cultures.
**What Today’s Coaching Will Help You With:**
You’ll identify tasks you’re holding onto out of habit or fear, learn how to delegate with confidence, and discover how letting go can make your hustle more scalable, sustainable, and stress-free.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **What’s one task you keep doing yourself—even though you know you shouldn’t—because you’re worried about the outcome if someone else takes it on?**
- Be honest about what’s holding you back from letting go.
2. **If you had an extra hour every day because you delegated one thing, what would you do with that time?**
- Think about the high-impact work you could focus on instead.
3. **Who’s the last person you trusted to handle something important for you, and how did it go?**
- Reflect on their strengths, your process, and what you learned from the experience.
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### Step 2: MBA Skill – The Delegation Matrix
Today’s MBA lesson is about using a delegation matrix to grow your hustle:
- **Define the Task:** What exactly needs to be done? What are the inputs, outputs, and success criteria?
- **Assess Importance and Urgency:** Is this a high-impact task only you can do, or could someone else do it at 80% right without hurting the business?
- **Identify the Right Person:** Who has the skills, capacity, and motivation to take this on? If no one, can you hire or train someone?
- **Set Clear Expectations:** What does success look like? What are the deadlines, check-in points, and communication protocols?
- **Empower and Trust:** Give them the authority and resources to get it done—then step back and let them own it.
This process helps you build a culture where delegation is rewarded and refined, not feared or avoided.
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### Step 3: Coaching & Delegation Action Plan
After you reply, I will use the writings of Professors Edmondson, Gino, and Grant to:
- Help you identify the tasks most ripe for delegation and the fears or habits keeping you from letting go.
- Guide you in designing clear playbooks and expectations for each delegated task.
- Suggest ways to build trust and psychological safety so your team or partners feel empowered to take ownership.
- Offer strategies for monitoring progress and giving feedback—so you can delegate with confidence, not anxiety.
- Share real-world examples of how delegation unlocks growth, reduces burnout, and makes your hustle more resilient.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your delegation challenge.
- I’ll help you refine your approach, suggest next steps, and offer practical tips for making delegation a core skill in your business.
Secret Dessert Course
Delegation is mostly about buying your time back to multiply your impact and your peace of mind. There are too many easy/cheap digital virtual assistants out there to still be doing everything yourself. So today’s dessert course is a step-by-step plan to onboard, delegate, and empower others (especially virtual others) so you can focus on what only you can do.
Prompt #2 - Treat Yourself to a Virtual Assistant
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Prompt #2 - Treat Yourself to a Virtual Assistant ○
**Today’s Focus: Delegation for Virtual Assistants**
**Ivy League MBA Coaching by:**
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and team empowerment.
- **Professor Francesca Gino, Harvard Business School:** Expert in decision-making and organizational trust.
- **Professor Alison Wood Brooks, Harvard Business School:** Specialist in communication and emotional intelligence.
**What This Prompt Will Help You With:**
You’ll design a process for onboarding and delegating to virtual assistants or remote contractors, making delegation seamless, scalable, and stress-free—so you can reclaim your time and energy for high-impact work.
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### Step 1: Onboarding Blueprint
**Instructions:**
Create a simple onboarding document for your virtual assistant. Include:
- **Welcome message and your core values**
- **Overview of your business and goals**
- **List of key tools and logins (with security notes)**
- **Contact info and preferred communication channels**
- **Schedule for check-ins and feedback sessions**
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### Step 2: Task Handoff Process
**Prompt to Design Your Handoff:**
For each recurring or one-off task you want to delegate:
1. **Describe the task clearly:** What needs to be done, step by step?
2. **Define success:** How will you know it’s done right?
3. **Set expectations:** What’s the deadline? Who checks the work?
4. **Provide resources:** Are there templates, scripts, or examples?
5. **Offer support:** Who can the assistant ask for help?
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### Step 3: Empowerment & Trust Building
**Reflection Questions:**
- **What’s one task you’ve been avoiding that a virtual assistant could take off your plate?**
- **How will you build trust with your assistant—through clear communication, feedback, or autonomy?**
- **What’s one way you can empower your assistant to make small decisions without asking you?**
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### Step 4: Feedback & Continuous Improvement
**Action Plan:**
- **Schedule regular check-ins to review progress and give feedback.**
- **Ask your assistant for suggestions on how to improve the process.**
- **Celebrate small wins and acknowledge their contributions.**
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### Step 5: Coaching & Insights
**After setting up your process, reflect:**
- **What surprised you about delegating to a virtual assistant?**
- **How has delegation freed up your time or mental energy?**
- **What’s one habit you’ll build to make delegation a regular part of your workflow?**
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**How to use this prompt:**
Copy and paste these steps into your favorite journal or AI assistant. Use them to onboard your next virtual assistant or remote contractor.