Day 14 Transcript
I was going to talk about how every moment spent naked in public will teach you more than a lifetime spent wearing your work armour. But I can’t stop thinking about yesterday’s rant about networking and how hard it is.
Starting a side hustle— building any business, really—is like signing up for a marathon where the finish line keeps moving farther and farther into the distance. Most people don’t even make it to the starting line, not because they lack ideas, but because their day job is a really comfortable bed. Why run when your legs are going to ache, your lungs are going to give out, your heart’s going to just up and explode.
Most people don’t make it to the starting line, because they don’t think they have a chance at winning. Because they define winning as finishing the race… when any good suburban Mom will tell you that the real definition of winning is just participating. Giving it your all.
Most people don’t make it to the starting line because they’re afraid of the discomfort that comes with putting themselves out there. And let’s be honest: it is uncomfortable. If you want to do anything that will make a difference in the world, you’ll face awkward conversations, dead-end emails, moment after moment after moment where you feel like the world’s biggest amateur.
As I said yesterday, discomfort is the price of admission for success. I said it in the context of networking but networking is really a metaphor for building a business, for building relationships, for building a legacy. And all that… requires showing up– where your clients are– it requires introducing yourself to strangers, making small talk, pitching your idea without sounding desperate; it requires asking complete strangers to trust you; it requires asking them for money. Discomfort, discomfort, discomfort. Every handshake, every follow-up email, every awkward conversation is discomfort. Hell, the persistence to continue is itself discomfort.
Have I sold you on marathoning yet?
Yeah well, here’s the thing I’ve learned after doing all of this—the networking, the persistence, the rejection, the long hours—it turns out that what looks hard from the outside is… actually hard… and deeply, deeply rewarding once you’re in it. The discipline of running—of building something from scratch—is meaningful in and of itself. And it’s never about reaching some imaginary finish line or hitting some arbitrary milestone; it’s about finding joy in the process.
That’s why even failed entrepreneurs run multiple marathons. It’s not because they’re gluttons for punishment but because running itself is purposeful and enjoyable. Every conversation teaches you something new. Every rejection makes you sharper. Every small win feels like a massive triumph because you earned it. You got out of that comfortable bed.
Winning isn’t crossing some distant finish line—it’s being brave enough to show up.
That’s why you do better at your day job when you have a side hustle. Once you start exercising the muscles your side hustle needs, you bring that game to everything you do… because you’re a different you now.
So if you’re hesitating to start your side hustle because it feels overwhelming or scary—keep reminding yourself that yes it is scary and that’s ok because you’re brave.
The race may be long and unpredictable, but running it? That’s where all the answers live.
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So, quick retro: You’ve spent the last two weeks defining your why, mapping your brand, and building your digital home. You’ve validated your idea, set up your legal and financial foundations, and maybe even started to see your hustle take shape. But here’s the thing: none of that matters if you can’t sell. The difference between a hobby and a business isn’t just strategy or branding—it’s whether you can turn your lunch break into actual revenue. That’s why we’re shifting gears in Week 3.
Starting tomorrow, we’re going all-in on sales. Not the sleazy, used-car-lot kind, but the kind that solves real problems and builds real relationships. You’ll learn how to spot buying signals, craft a pitch that lands, handle objections with confidence, and close deals without feeling pushy. You’ll build systems to track leads, automate follow-ups, and delegate tasks so you’re not the bottleneck in your own business. And you’ll do it all in the same bite-sized, lunch-break chunks that got you this far—because sales isn’t a talent, it’s a skill. And like any skill, it gets better with practice.
If you’re like me– an introvert who thoroughly enjoys building and strategizing… you might be asking “Why start now?” Because sales is the heartbeat of every successful side hustle. If you wait too long to learn how to sell, you risk building something beautiful that nobody buys… you risk strategizing in a way that’s disconnected from reality.
Look– I’ve beat myself up a lot about whether to include a whole week on sales. Because I hate selling. But this is less about me and more about you– and the best possible use of your first month hustling. By front-loading sales, my hope is to give you the best shot at turning your hustle into something that actually pays—and my original week 3– getting you ready to scale, automate, and build partnerships can wait another week. So get ready. Week 3 is where you stop thinking about selling and start making it happen—for real– one lunch break at a time. See you tomorrow.