What if everything you've learned about SMART goals is actually making you dumber?
Ninety-two percent of people abandon their New Year's resolutions by February—and it's not because they lack willpower. It's because traditional goal-setting frameworks were never designed for the chaotic reality of entrepreneurship. In this episode, we sit down with Leanne Linsky, a stand-up comedian turned tech entrepreneur who built Plausible, a live online comedy club platform. Discover why breaking goals into bite-sized pieces isn't enough, how to avoid the vanity metrics trap that's killing your momentum, and why building failure into your goals might be the secret to sustainable success. This conversation will completely shift how you think about progress, accountability, and what it really means to achieve something meaningful.
Most founders fall into the same trap: they set goals that look perfect on paper but crumble under the pressure of real entrepreneurship. The problem isn't that we're not ambitious enough—it's that we're focusing on the wrong metrics entirely.
Take social media followers, for instance. You can craft a SMART goal around hitting 100,000 Instagram followers by year-end. It's specific, measurable, achievable, relevant, and time-bound. But it's also completely useless if those followers never buy anything. Leanne puts it perfectly: "You can't just post once and expect all your shows to be sold out. You've got to be the Bed, Bath & Beyond coupon—sending it out on a regular basis."
The real shift happens when you stop chasing vanity metrics and start asking one simple question each day: "What's the one thing that will move me closest to my goal today?" This isn't about productivity hacks or time management tricks. It's about fundamentally changing how you think about progress.
Breaking goals down matters, but not in the way you think. Instead of just making smaller tasks, you need to work backward from who you need to become. Want to write a book? Don't just schedule writing time. Study what authors actually do daily. How do they structure their time? What habits do they maintain? Then build those characteristics into your routine.
The most successful founders treat entrepreneurship like a game where failure is just good information. Every rejection, every failed experiment, every pivot teaches you something valuable about your market, your product, or yourself. The goal isn't to avoid failure—it's to fail faster and learn more efficiently.
Here's what changes everything: accepting that your goals will shift, and that's not a bug in the system—it's a feature. The founders who thrive are the ones who stay aligned with their core values while remaining fluid about tactics. Your strategy might change, your timeline might shift, but your fundamental mission stays constant.
Success isn't about hitting every goal exactly as planned. It's about building a system that keeps you moving forward, celebrating the small wins along the way, and staying curious about what each outcome teaches you. The real winners aren't the ones who never fail—they're the ones who fail, learn, and adjust faster than everyone else.
Watch the Full Episode on The Goal Setting Trap That's Killing Your Momentum with expert Leanne Linsky below:
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