I Wrote a Letter to My Past Self — Here’s What I Wish I Knew Before Becoming an Entrepreneur

Timelines lie. That's the blunt truth at the heart of Jake Karls' letter to his younger self, and it's a truth every founder eventually collides with. The entrepreneur behind Mid-Day Squares doesn't offer growth hacks or funding tips here — he offers something rarer: an honest map of the emotional terrain no pitch deck ever shows.

What strikes me most is his framing of the "invisible middle" — those long stretches where nothing is technically broken, but nothing feels like it's working either. I see this constantly with founders preparing to pitch investors. They mistake a quiet plateau for failure, when in reality trust is being built, relationships are forming, and skills are sharpening below the surface. Karls is right to call this disorienting. It's also, in my experience, exactly when founders are most tempted to make a rash pivot or walk away entirely.

His point about tolerance rather than pure skill being the real differentiator is one I'd underline twice. Investors aren't just betting on an idea; they're betting on a founder's capacity to sit in uncertainty without flinching. That steadiness — not the flashy milestone update — is often what separates the entrepreneurs who make it to a second or third raise from those who burn out after the first setback.

The practical advice near the end is simple but sound: focus on direction over speed, watch for small signals, resist unnecessary pivots, and stay grounded in real feedback rather than assumptions. None of this is revolutionary, but the reminder is timely. So many founders equate slow with wrong. Karls makes a compelling case that slow is often just... early.

If you're in the thick of building something and it doesn't yet feel like it's working, this piece is worth the five minutes. Go read the full letter on Entrepreneur.com.