I Can't Afford This. I'm Doing It Anyway

Sometimes the work that matters most doesn't pay a dime.

We’d go to the field almost every Sunday. Just the two of us. Rain or shine. A bag of about 40 frisbees.

My daughter would pick up a disc, back up a few feet, and launch it as far as she could.

Ultimate frisbee has this thing called a Pull. Think of it like a kickoff in football. Each team has seven players on the field, and one person on the defensive line throws the disc to the other team. They throw it as deep and as high as they can so their teammates can sprint down the field and pin the opposition before they can get moving.

In high school, my girl played with some of the best pullers in the country. She was on a mixed team and a couple of the boys had turned this into an art form. She knew this could be a superpower for her. She’s strong, focused, has amazing technique. And she knew that with enough work, she could be the kind of player who changes a game with a single throw.

So each weekend we’d trot out to a field or a park or the street and she would practice. And it paid off. She now plays for the UW team and anchors their D line. She pins opposing teams deep while her teammates race down to cover. Time and time again, her throws have forced panicked, rushed decisions and turnovers that led to easy scores.

And when I see that happen, I think about those afternoons. Fielding discs, chasing plastic, refilling the bag so she could keep throwing.

There is real power in getting your reps in. In stacking enough attempts that you start to learn what works, what doesn’t, and what happens when you try something a little different. Reps give you room to experiment. To fail small. To adjust. And eventually, to be ready when the moment actually shows up.

So this week, let’s talk about reps, why the best way to get better is to get busy, and how to start stacking the experience that prepares you for the moments that matter.

Go Find Your At-Bats

For the last several months, I’ve been working with a startup out of Colorado. Great guys doing really cool work. I believe in what they’re building and I think their product is going to matter.

We meet every week. During the week I put in a few hours of work. Anything from helping with mission and purpose statements, to testing and QA, to go-to-market strategy, to tech stack conversations. And on and on. It’s been a lot of work.

And I have made all of zero dollars doing it.

Which is honestly insane. I lost my job a few months ago. I need the money. I’ve burned through my emergency fund. I’ve been somewhat living off credit cards. Volunteering my time is not exactly what a financial advisor would recommend right now.

But it has been one of the best investments I’ve made in a long time.

These guys love me. And since I’m unpaid, anything I do, like anything at all, adds value. They are genuinely grateful for my perspective and my input. And they’ve become something of a professional sandbox for me. I’ve tried out different frameworks and approaches with them. Some land. Some not so much. But it doesn’t really matter because we get the gift of figuring it all out as we go.

And how great is that? We don’t have to have it all figured out. I’ve been able to create this safe little world where I can learn and contribute and everybody wins. So say yes to things that might not make sense on paper. Pro bono work. Side projects. Favors for people you believe in. And treat every single one like it counts.

Reps Compound

Consider this story from the book Art & Fear. A ceramics teacher splits his class in two. One half will be graded on quantity. He’ll bring in a scale on the last day, weigh their pots, and dole out grades by the pound. The other half will be graded on quality. They only have to make one pot all semester, but it has to be a great one.

Spoilers: the quantity group produced the best work. The quality group sat around theorizing about what the perfect pot should look like, and the quantity group was heads down making pots. Tons of them. Bad ones, lopsided ones, then eventually slightly better ones, then good ones, then a few great ones. Every pot taught them something the next one got to use.

That’s the great thing about putting in the work. Each attempt teaches you something that makes the next one more valuable. The lessons stack on top of each other and the curve gets steeper, not flatter.

Which is why lately I keep saying to anyone who will listen, go stack those reps! Cause the free hours I’m putting into the Colorado startup aren’t just helping them. They’re sharpening instincts I’m bringing into paid client work. A go-to-market conversation I had with them last month gave me a framework I used with a client a couple weeks later. A messaging exercise we ran together showed up in advice I gave a different founder over Zoom. And it’s not like this was planned out. I don’t have some master roadmap here, I am building the plane in the air. But it works out and just kinda happens because the work was live and my brain was paying attention.

And these skills don’t just stay in their lane. Something you practice in one corner of your life shows up in a totally different corner a while later. The patience you build coaching your kid bleeds into how you handle a difficult colleague. The writing you put in on a personal project (like say a weekly newsletter) makes your project emails more concise and interesting. The hard conversation you had with your kid might prepare you for the one you’ll need to have with a client.

Make Your Reps Count

So this is all well and good, but how do you actually do this? There’s a difference between mindlessly repeating something and stacking the kind of practice that actually builds you. John Zeratsky, who helped invent the design sprint at Google Ventures, breaks it down into three things every real rep needs.

1. A clear goal. You have to know what you’re trying to do. Not in a corporate-OKR (god I hate those) kind of way. Just enough that you can tell whether the attempt worked. My daughter’s goal on those Sunday afternoons wasn’t “be good at frisbee.” It was “throw this disc 60 yards and have it hang in the air long enough for my teammates to get downfield.” Specific. Measurable. Honest.

2. Feedback as you go. You need to know what happened. Did the disc fly the way you wanted? Did the client respond to the new framing? Did the workshop make sense to the room? Without feedback, you’re not stacking reps. You’re just stacking guesses. Sometimes feedback comes from another person. Sometimes it comes from your own honest self-assessment. Either way, you want the truth (even if you can’t handle the truth) so make sure you make it happen.

3. Another try, right away. I know, this might feel exhausting. But a rep without a follow-up isn’t really a rep. It’s an experiment with no second trial. You learned something, but if you don’t get to use that lesson on the next attempt, the learning dissipates. The reason my daughter got better is that she didn’t throw one disc and go home. She threw the next one. And the next one. And the next forty. Her arm was often very sore the next day.

Put those three things together and the practice starts to do its real work. Without them, you can put in years and barely move. With them, six months can make you almost unrecognizable to your past self.

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Oh and yeah, I write this other newsletter every dang day about AI. Check it out:

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Conclusion

I spent last weekend in Portland watching my daughter and her team compete. And almost every time she held the disc and let it fly, I thought about those weekends at the park. Literally hundreds of hours and thousands of throws.

It’s easy to wonder if the work is worth the effort.

Trust me, it is.

A few months into working with that Colorado startup I mentioned earlier, the founders introduced me to someone in their network. That introduction turned into my biggest client of the year. I didn’t take the unpaid gig because I was playing some long game. I took it because I believed in what they were building and I wanted the reps. The referral was a nice little bonus on top of it all. Or, perhaps that was just part of the plan. To do good work, to learn, to grow, to impress, and then jump on an opportunity when it arises.

That’s kinda how it works. You don’t stack reps for a specific payoff. You stack them because the work is the point. And then one day, when the moment actually shows up, you realize you’ve been getting ready for it all along.

So go stack yours. One day you’ll be standing on your own sideline, watching something you quietly built years ago do exactly what you hoped it would.

Ever Forward,
— Derek (aka Chief Rabbit)

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P.S. A quick ask before you go.

A member of our Seattle community, Anna Le, has been missing since Sunday, April 5. She’s 21 years old, 5’6”, about 160 lbs, with dark brown eyes and hair. She was last seen in the Brighton neighborhood of Seattle wearing a black t-shirt, dark denim jeans, and white and blue Nikes. She was driving a silver 2010 Toyota Highlander, license plate ACE8577.

Her family and friends haven’t been able to reach her. If you have any information about where she might be, please call or text her family at 206-225-9367 or 206-778-6227.

If you live in the Seattle area, please share this. A post, a repost, a text to a friend. You never know whose eyes might land on the right detail at the right moment. Thank you.

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