Ideas from Matt

Most of us have been on both sides of this moment: someone asks for something, and neither person has a clear picture of what "done" looks like.

The requestor wants a quick, directional answer. The person doing the work assumes they need to deliver something polished and thorough. And so begins the quiet spiral of mismatched expectations, where someone over-invests in something that didn't need to be perfect, while the person waiting wonders why it's taking so long.

Here's a simple question that cuts through all of that: "Would you rather have it at 75% tomorrow, or 95% next week?"

This framing works because it makes the tradeoff between speed and quality explicit rather than leaving it buried in assumptions.

Why this question works:

• It clarifies what "done" actually means. Many requests don't require a finished product. They need a rough draft, a directional answer, something to react to. When someone chooses 75% tomorrow, they're telling you that speed matters more than polish.
• It makes the cost of quality visible. Most people underestimate the effort required to go from "pretty good" to "really good." That last 20% of quality often takes 80% of the effort. This question surfaces that tradeoff before anyone gets frustrated.
• It reveals the real purpose of the work. A request for 95% signals the deliverable is going somewhere important. A request for 75% means it's probably an input into a bigger conversation. Knowing the destination changes how you approach the journey.

The hidden benefit? This question gives the requestor permission to ask for less.

In most professional cultures, there's an unspoken expectation that everything should be excellent. But excellence takes time, and not everything deserves the same investment. When you offer 75% as a legitimate option, you're making it safe for someone to say, "Actually, I just need something to react to."

That's a gift to both sides. The person doing the work gets realistic expectations. The person asking gets what they need faster.

Try it this week: The next time someone asks you for something, offer the tradeoff explicitly. You might be surprised how often people choose 75% tomorrow.

The best professionals don't just deliver great work. They ask the right questions before they start.

Last Updated: February 2025

I'm not retiring. But I'm starting to practice.

Beginning this January, I'm taking two random days off each month. Not vacation. Not sick days. Retirement days.

Here's why.

Last year, my daughter graduated from college and is now working full-time. My parents are both struggling with their health. My mom has emerging dementia, and I watch her lose the capacity to do things I know she wishes she'd done when she was healthier. That's clarifying in a way I didn't expect.

I also had surgery for a detached retina on New Year's Eve. It's fine now, but there's nothing like a health scare to remind you that physical capability has an expiration date. The things I want to do in retirement require a body that cooperates. Waiting until 65 to discover what I love means discovering it with less capacity to pursue it.

So I'm not waiting.

Two days a month is roughly 10% of my working time. I'm not sure what I'll do with those days yet. Maybe golf one day and a museum by myself on another. Maybe a long walk or a few hours solo in a coffee shop with a book that has nothing to do with work.

The honest truth is I've never been retired before, and I don't know anyone who does it particularly well. So I'm hoping to learn now, while I still have the energy and curiosity to figure it out.

If this works, maybe I'm 20% retired next year. Then 30%. A glide path instead of a cliff.

The guilt is real, by the way. I've worked hard my entire adult life. Taking a random Tuesday off to wander feels indulgent in a way that's hard to shake. But I think the guilt is misplaced. I've watched too many people sprint to a finish line only to arrive too exhausted or too sick to enjoy what they'd been running toward.

I'd rather practice now.

My team knows this is coming. I'm telling them — and now you — because making it public makes it real. This isn't me checking out. It's me checking in on a version of my life I've never explored while I still have the chance to shape it.

Two days a month. Let's see what I learn.

'The Fortune Teller and the Four-Year-Old' is a distinctive yet simple activity, offering a refreshing departure from traditional icebreaker exercises. It’s designed to create immediate connections between individuals who may not be well-acquainted.

Here’s how it unfolds:

• Start by dividing the attendees into pairs. One participant in each pair assumes the intriguing role of the 'Fortune Teller', while the other adopts the curiosity of a 'Four-Year-Old'.
• The Four-Year-Old's mission is to ask the Fortune Teller questions about their imagined future, such as "What will I be when I grow up?" or "Whom will I marry?"
• Instead of providing fictitious predictions, the Fortune Teller responds with stories taken from their own history. For instance, in answering "What will I be when I grow up?" the Fortune Teller might share, "You’ll grow up to be an accountant in a bustling firm in Chicago." This response, disguised as a prediction, is a sharing of the Fortune Teller's own life lessons and experiences.
• To delve deeper, the Four-Year-Old is then encouraged to ask further questions about the Fortune Teller's narrative, adding depth to the conversation before moving on to their next query.
• After dedicating about 15-30 minutes to this engaging exercise, the pairs switch roles, allowing everyone to gain insights from both perspectives.

This seemingly simple exercise is a minimal time investment that yields substantial dividends, including stronger team bonds, improved communication, and a heightened sense of empathy among team members.

Moreover, it encourages participants to reflect upon their own life journeys, fostering greater self-awareness and understanding toward others.

So the next time you find yourself in a gathering with individuals you're keen to connect with on a deeper level, try out this fortune-telling exercise. It could be the key to establishing faster, more effective connections and meetings.