What's heavy and what's hopeful
Sep 19, 2026I've been sad lately.

Not about my own life, which is genuinely full and good. Sad about the people around me. Someone close to me is walking through a brutal stretch. A kid my family loves is watching their parents split up. And a handful of business owners I care about are hitting wall after wall after wall, the kind of season where you start to wonder if you're doing something wrong.
I'm wired to see the glass half full. I always have been. Most days it feels like a gift. But lately it's run straight into how much hard stuff the people I love are carrying, and honestly, I don't quite know what to do with that except sit in it and not look away.
So I'm not going to pretend everything's shiny this week. Which, it turns out, is kind of the whole point.
Some friends of ours taught us a little practice years ago. When we're together, we go around and each share two things: what's heavy, and what's hopeful.
That's it. Not "how are you," which everyone answers with "good, busy," and not a status update. Just, what's weighing on you right now, and where are you finding hope. It sounds small. It has completely changed how we're with each other.
Because here's what it does. It gives you permission to be honest about the hard thing without turning the whole night into a therapy session. And it makes room for hope without forcing anyone to fake it. You get to hold both at once, which is usually closer to the truth of where any of us actually are.
I've come to believe that showing up like that, openly, a little vulnerably, is the fastest way to build real trust with anyone. It's certainly faster than pretending you've got it all together.
Which brings me to a parking lot a few weeks ago.
I pulled in for a networking meeting at the same time as a guy I really admire. He's sharp, great personality, genuinely good instincts for business. We both got out of our cars, and I stepped over to give him a hug and say hey.
And before "hello," before anything, the first words out of his mouth were, "How's business?"

It landed a little heavy on me, if I'm honest. Not because he did anything wrong, it's just the water we all swim in. But it made me a little sad to think that's what he assumed I'd want to lead with. That business is the thing I care about most when I see someone I like.
I gave him a gentle hard time about it right there in the lot, and we ended up having a real conversation about it later. And what I told him is this. For as long as I can remember, I've cared more about knowing people than about getting people to know me and hire me. I know that's probably terrible advice if you're hungry and need the work. But my favorite projects, my favorite stories, my favorite relationships have all come from the same place: two people being honest about what's heavy and what's hopeful, and building something real from there.
That honesty, by the way, is the same reason we just built a dumb little tool I'm weirdly proud of.
People have asked me approximately one million times, "How much does video cost?" And it's the wrong question. So we made a calculator to help people get to the right one, which is "what's this actually worth to my business?" If you've ever wondered, it lives at value.tellstudios.com. That's me refusing the transactional question in calculator form, which feels very on brand for this particular letter.
Anyway. Here's what I keep coming back to.
I don't want to spend my life, or my business, performing a version of myself who has it all figured out. I'd rather be someone people can be honest around. Someone whose being in the room makes it a little safer to admit the hard thing. Because our stories aren't finished. The heavy stretch isn't the ending. And the fastest way I know to remind someone of that is to stop pretending my own life is all hopeful and none heavy.
So my hope for you this week is simple. Be yourself. Drop the front you think a business meeting requires. Surround yourself with people who actually have your back, and if the people around you don't, that might be the real thing worth changing.
And here's what I'd genuinely love. Hit reply and tell me one of each from your world right now. What's heavy, and what's hopeful. I read every single one, and I'll hold whatever you send with care.
Onward, my friend,
Ryan
P.S. If "what's heavy and what's hopeful" is new to you, steal it. Try it at your next dinner, with your team, with your family. Ask the two questions and then actually listen to the answers. It's the closest thing to a life hack I've got, and it isn't a hack at all.