Day 7 Transcript

Part 1:

First week’s over. Lazy Sunday. Time to reflect. One interesting question in my DMs– posed like 10 different ways this week– making me wonder if all my followers are just one dude with a lot of accounts.

The Question: If it’s so damn rewarding, why don’t more people with corporate jobs work a side hustle? My knee jerk answer is wrong– because my knee jerk answer is “most don’t have the time.” Which is a crock of shit. “Not having time” is a symptom of much larger problems… including the lack of some really important skills– without which your career has a pretty low ceiling. Three skills specifically. Maniacal focus…Ruthless prioritization… and the kind of trust in your peers that leads to sustainable delegation. But I’m a broken record on that stuff. So…

Let me make the question even harder. Why do most people get a little snooty when you suggest they try a side-hustle for themselves? The answer is that most people consider themselves good people and hustling– even the word– feels to them like a challenge to their sense of honesty and integrity. And I’m not even talking about my little tongue-in-cheek “most people only work 3 of every 8 hours… What do I want to do with the other 5?” That’s humor, not reality.

But here’s the thing: there is a shit ton of misplaced loyalty in the corporate world… even when you’re just thinking about night and weekend hustles. It makes good people feel like they’re cheating on their employer, cheating on their day job.

Which is hilarious because most corporations– we all know– the good people themselves all know– corporations are designed– intentionally– not to feel obligated to their employees. That’s not me being anti-corporate. That’s me understanding “at-will employment.” Google that if you don’t know what I’m talking about.

Legal entities don’t have heart. They don’t claim to. They don’t aspire to build character. Despite what corp comm tells you. Corporations are designed to be profit maximizing– full stop– and that’s evolved over the last 20 years to mean that they treat their relationship to employees as transactional. Which (again) isn’t me saying “down with capitalism!” Capitalism paid my mortgage. It’s me saying– to good, decent people: understand who or what you’re being loyal to. Because loyalty is like highway hypnosis for your career… for your earning potential: blink and you’re either being shown the door or you’re retiring with a lot less money than you would have had if you jumped to another company every 3 years… or if you had a side hustle. Understand who or what you’re being loyal to because it’s a choice between company and purpose; between company and financial freedom; between company and self determination… autonomy… dignity.

That guilty feeling that causes a snooty response– in genuinely good people– that’s not integrity. It’s Stockholm syndrome. That sense of loyalty would be better directed at your family, your community– your definition of purpose.

That’s also me saying that if and when your side hustle turns into something more conventionally legitimate– like a company– maybe continue to take the path less traveled and put your employees over profit maximizing.

Why? Because your side hustle is a reflection of your character. It’s an opportunity to practice virtues like courage (starting despite fear), wisdom (learning from mistakes), and justice (serving others).

Success isn’t about reaching a destination; it’s about how you travel. Balance isn’t about doing less; it’s about doing what matters most. And your unique value isn’t about standing out; it’s about standing firm in who you are.

The first week of this journey– for me at least– has been an ongoing exercise in self-discovery. Ask tough questions, confront doubts, and take a single tiny step toward something meaningful. Rinse. Repeat. That’s how you hustle smarter.

Part 2:

First week’s over. Lazy Sunday. Time to reflect, Part 2. Super quick recap for week 1… if you’re playing along. You started with questions that seemed pretty daunting: “Why am I doing this?” “What problem am I solving?” “Who am I serving?” And one week later– here you are, with answers that may still be imperfect but are undeniably yours.

This journey– like all the important ones in your life– is not about perfection; it’s about progress. If it's worth doing, it’s worth doing poorly. Every step in this journey—every little aha moment— has brought you closer to clarity; closer to having your actions match your values; closer to focusing on what truly matters to you; not your boss, not your employer; closer to seeing curiosity as your greatest asset.

It's always a good time to celebrate the small wins. Maybe you’ve defined your “why,” narrowed down your “what,” or figured out what gaps in the market get you all excited.

I don’t want to sound like Deepak Chopra but your side hustle isn’t just about building some… thing. It’s about building yourself. It’s about becoming someone who sees challenges as opportunities, someone who finds meaning in effort, someone who approaches life with both humility and ambition.

Tomorrow and all this week, we’re going to make you a master marketer. We’re going to build a website. We’re going to land you a cool domain. We’re going to teach your hustle how to fishface for Instagram, how to dance for TikTok, how to put people to sleep for LinkedIn. It’ll be fun.

That’s it for week 1. We're a whole lot closer! Work on your answers. We'll take the next small step at tomorrow's Billion Dollar Lunch Break. Shadow boss out.