Day 34 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: You’re the Alamo
Do you know who doesn’t burn out? People who know themselves (and their limits) well enough to ask for the right kind of help. There’s a lot in that statement. People who know themselves (and their limits) well enough to ask for the right kind of help. If you unpack all that, you come to the same conclusion I did back at MIT when I was studying burnout in grad school: everyone burns out. In some people we call it burnout. In others, tuning out… losing the plot…. going numb… quiet quitting… We call it waking up one day and realizing you haven’t felt like yourself in a long, long time. And all those labels are the ones that the work world hates.
There are ways of burning out that the work world loves because companies quietly benefit from them. Like the opposite of “quiet quitting” is called self-erasure… identity burnout… over-engagement. That’s when you lose yourself in your work so completely that boundaries disappear: you pour in more hours, more emotional investment, more identity than is reasonably sustainable, often to the point where your sense of self becomes one with your job.
Like I said, everyone burns out. And all of that is ok. It’s perfectly human… or imperfectly human. Either one.
During sales week– back in week 3– we talked about the trust-building mindset– about how you can become a great salesperson by actively listening, by exercising empathy and curiosity. And being transparent. When you think about self-care– and how important it is for founders– for everyone really– you realize that the answer starts when you focus that trust-building mindset on yourself… listening to your body… being curious about your own mental and emotional life… empathizing with yourself… which sounds a little too hippie to me… but really just means dealing with your own feelings and struggles with kindness and without judgment. And being transparent… which in this context means… asking for help… even if it’s the wrong kind of help… because you haven’t yet figured out your boundaries. The point is– always– if it's worth doing, it's worth doing poorly. Asking for help poorly leads… eventually… to asking for help effectively. Like all skills, it’s a journey.
Second time this week without upbeat music.
Welcome to week 5, Day 34 of starting your side hustle! We already took 28 Days—28 small steps—to build a business that’s meaningful, impactful, and profitable. So we’re in masterclass territory this week. It’s a bonus week! Today, we’re talking about something most founders ignore until it’s almost too late: founder self-care.
Today’s questions.
1. Where are you running on empty, and what’s it really costing you?
2. What’s one boundary you could set this week to protect yourself for the long haul?
These questions matter. The one because it forces you to take an honest inventory of exactly how much you’re running on empty. If you don’t know where you’re stretched too thin, you’ll keep draining superskills 1 and 2– focus and prioritization– on things that don’t move the needle. And the second question matters because it’s about agency. Most founders wait for permission to take care of themselves. You don’t need permission. Setting a single boundary—no matter how small—can be the difference between flaming out and lasting longer than you ever expected.
Part 2: 💼 Dare to (Self) Care: Today's Ivy League MBA Skill
Let’s pretend you’re the kind of broken that doesn’t prioritize self-care. You don’t have time for it.. All you care about is the business. That’s a very special kind of broken. And to you, I say self-care is about operationalizing your own well-being so you don’t become the bottleneck in your business. If you’re not going to do it for the right reasons, do it for the business.
Day 34, Part 2 of Lunch Break Millionaire– where we turn whatever you're eating for lunch into an Ivy League MBA degree. It doesn’t even matter what day of the week it is– we’re talking about today's Ivy League MBA Skill: self-care… so Tacos.
Let’s jump right into how you do it… and this applies to your hustle, your day job… anything you take seriously in life.
You start by noticing the warning signs—fatigue, irritability, brain fog, the sense that you’re always behind.
You pick one small, non-negotiable habit. Maybe it’s a real lunch break (now that you’re running out of my awful content)... so pick a habit and lose all the screens you might rely on during that habit. Like for lunch, just food and a walk.
Or… set a hard stop for work. If you have a 9-5, it doesn’t have to be 5. Maybe it’s 7… or 8… or 9. Notice how I’m not being judgy. Because if it's worth doing, it’s worth doing poorly.
What else? Maybe do a daily check-in with someone who’s genetically wired to call you on your bullshit. The kind of ass that’s really good at helping you set a boundary and treat it like a client meeting: immovable, important, not up for debate… that kind of thing.
What else? If you’re a complete nerd like me… maybe you build your own founder-flounder dashboard…. 1) Because it rhymes. And 2) because it lets you track your energy the way you track the stuff you think is cool: your engagement metrics, your CAC (Customer Acquisition Cost), your LTV (Customer Lifetime Value). The stuff we talked about way back on Day 4 when we were writing our business plan. The KPIs in the dashboard would be stuff like: Did you sleep? Did you exercise? Are you eating healthy? Are you connecting with a special disagreeable someone who loves you and actually gets it?
Self-care is super important– first because everyone deserves it (even if your Dad thinks it sounds wussy) and second (for you alpha nutjobs) if you’re running on empty, your business will too.
Burnout– is super common, totally natural, and a sign from God that you need to work on superskill #3– delegation. Not in the way you think. Not… like delegate all the stressful stuff to your team. What I mean is that everything you’ve learned about the delegation of tasks…. Apply that to emotional labor. That means you need to: find a peer, a coach, a therapist, a friend who can help you process the hard stuff. You get exactly zero points for suffering in silence.
The founders who seem to tap into seemingly bottomless wells of energy…. They’re the ones to build support systems for their emotional tasks as deliberately as they build automation for their repetitive tasks… as deliberately as they build their product.
Ok. I’ll play the role today. Here’s an exercise. Tonight, write down three things that drained you today and three things that filled you up. Super simple. Tomorrow, do one more of the latter and one less of the former. That’s it. Small wins, every day. Over time, those micro-habits will compound into resilience… into that bottomless well of energy.
That’s how you hustle… not smarter… wiser.
Part 3: Recognize that the Alamo is not that Special: The 28-Day Case Study
This is Day 34, 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.
Two words: self-care. Three words: working on it.
I did the exercise today. I asked myself “Where I’m running on empty, and what’s it really costing me. My answer– after five weeks of constant content creation– was… well. And it cost me time with my boys. That’s why I drop content like shows on Netflix… once a year in chunks. So the rest of the year, I can reduce the cost to these guys.
And question 2 was: What’s one boundary you could set this week to protect yourself for the long haul?
Don’t eat alone.
The larger message here is that I’m just like everyone else. I too have burned out in the past and unless I’m diligent– unless I focus and prioritize my physical and emotional life– I risk burning out again.
And that’s ok.
Join me tomorrow for the dramatic series finale. Whisper: “No drama.”
Prompt #1 - Self-Care
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Prompt #1 - Self-Care ○
Welcome to Bonus Week, Day 34 of Lunch Break Millionaire! Today, we’re tackling a topic most founders ignore until it’s almost too late: **self-care as a business skill**. You’ll learn how to recognize burnout, set boundaries, and operationalize your own well-being—so you don’t become the bottleneck in your business.
You’ll be guided by Ivy League faculty whose research is foundational in resilience, emotional intelligence, and founder well-being:
- **Professor Shawn Achor, Harvard:** Expert in positive psychology and sustainable performance.
- **Professor Laurie Santos, Yale:** Authority on the science of happiness and habit formation.
- **Professor Stewart Friedman, Wharton:** Specialist in work-life integration and boundary-setting.
**What Today’s Coaching Will Help You With:**
You’ll take an honest inventory of where you’re running on empty, identify the hidden costs of over-engagement, and design a simple, sustainable self-care habit that protects your energy for the long haul.
### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **Where are you running on empty, and what’s it really costing you?**
- Be specific: Is it sleep, emotional bandwidth, relationships, focus, or something else?
2. **What’s one boundary you could set this week to protect yourself for the long haul?**
- Think about a small, non-negotiable habit, a time block, or a support system you could put in place.
### Step 2: MBA Skill – Operationalizing Self-Care
Today’s MBA lesson is about treating self-care as a *founder’s operational system*:
- **Recognize the Warning Signs:** Fatigue, irritability, brain fog, and feeling disconnected are signals—not weaknesses.
- **Set Micro-Boundaries:** Start with one small, non-negotiable habit (e.g., a real lunch break without screens, a hard stop for work, or a daily check-in with a trusted friend).
- **Track Your Energy Like a KPI:** Build a simple dashboard for your well-being—track sleep, exercise, nutrition, and emotional check-ins as seriously as you track business metrics.
- **Delegate Emotional Labor:** Just as you delegate tasks, build a support system (peer, coach, therapist) to help you process stress and setbacks.
### Step 3: Coaching & Action Plan
After you reply, I will use the research and frameworks of Professors Achor, Santos, and Friedman to:
- Help you analyze your current self-care gaps and their business impact.
- Guide you in designing a realistic, founder-friendly self-care habit or boundary.
- Suggest ways to measure your progress and reinforce your new habit.
- Offer real-world examples of founders who operationalized self-care to fuel long-term success.
**How to use this prompt:**
- Respond with your answers to the reflection questions above.
- I’ll help you refine your self-care plan, offer encouragement, and suggest next steps for making it stick.
Secret Dessert Course
One of the hardest parts of self-care as a skill is learning how to ask for help. The prompt below will coach you on overcoming common barriers to help. We can all use a hand building a support system that sustains our hustle without burning us out.
Just copy and paste the following prompt into your favorite AI assistant to enjoy Day 34’s dessert.
Prompt #2 - Transform Feedback into Features
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Prompt #2 - Transform Feedback into Features ○
We’re here to coach you on overcoming common barriers to help-seeking, crafting effective requests, and building a support system that sustains your hustle without burning you out.
You’ll be guided by Ivy League experts in organizational behavior, psychology, and leadership:
- **Professor Francesca Gino, Harvard Business School:** Expert in decision-making and overcoming self-sabotage.
- **Professor Adam Grant, Wharton School:** Authority on generosity, reciprocity, and effective collaboration.
- **Professor Laura Huang, Harvard Business School:** Specialist in founder mindset and building resilience through social support.
**Why This Matters:**
Founders who ask for help early and often avoid the trap of self-erasure and burnout. Even imperfect help-seeking builds trust, reduces isolation, and leads to better decisions and outcomes.
### Step 1: Reflection Questions
Please answer these in a few sentences each:
1. **When was the last time you asked for help with your hustle or work?**
- How did it go? What made it easy or hard?
2. **What fears or beliefs hold you back from asking for help?**
- (e.g., fear of burdening others, appearing weak, not knowing what to ask for)
3. **Who in your network could you realistically ask for help this week?**
- Think peers, mentors, friends, or professionals.
4. **What’s one small, specific request you could make to someone this week—even if it feels awkward or imperfect?**
### Step 2: MBA Skill – Effective Help-Seeking & Social Capital
Today’s MBA lesson is about transforming help-seeking from a vulnerability into a strategic skill:
- **Normalize Imperfect Help-Seeking:** Asking poorly is better than not asking at all. Each attempt builds confidence and clarity.
- **Be Specific:** Clear, focused requests increase the likelihood of getting meaningful support.
- **Build Social Capital:** Help is a two-way street. Offering value and gratitude strengthens relationships.
- **Overcome Psychological Barriers:** Recognize and challenge beliefs that “I must do it all” or “I’m alone in this.”
- **Leverage Diverse Supports:** Emotional, practical, and informational help all matter—build a varied network.
### Step 3: Coaching & Action Plan
After you reply, I will use the research and writings of Professors Gino, Grant, and Huang to:
- Help you identify your biggest barriers to asking for help and how to overcome them.
- Guide you in drafting a clear, actionable help request tailored to your network.
- Suggest ways to nurture reciprocal relationships that sustain long-term founder resilience.
- Share examples of founders who successfully built support systems by embracing imperfect help-seeking.
**How to use this prompt:**
- Respond with your answers to the reflection questions above.
- I’ll help you craft your first imperfect help request and suggest next steps.