One Idea Pays Rent The Other Starts A Revolution

Picture a meeting room. The air is recycled ambition. Someone is guarding a spreadsheet like it is a newborn. Everyone is hungry, but nobody wants to admit it, so they snack on caution.

You walk in with two ideas.

The first idea is the one with clean shoes. It is polite. It has done this before. It can be explained in one breath without anyone reaching for legal. It is the idea that will work because it already worked, at least enough to keep the lights on.

We email the customer a demo video.
Simple. Stable. Trackable. Nobody faints.

And then you bring the second idea.

The second idea is not wearing clean shoes. It is barefoot and a little bit smug. It is the idea that has no process, no approval path, no neatly laminated playbook. It will require effort, alignment, and possibly the kind of realignment that makes calendars whimper.

We turn it on for them so they can mess with it using their own data.

Now the room wakes up.

Because everyone in there knows a secret they rarely say out loud: the safest idea is usually designed to be survivable, not unstoppable. The safe idea optimizes the current machine. The wild idea asks if the machine is even pointed at the right mountain.

This is the easiest way to elevate your work: show you can execute, and show you can imagine.

The first idea earns trust. The second idea earns outcomes.

Bring both, every time. One to prove you are credible. One to prove you are alive.

Stay Positive & You’re In The Ideas Business, Aren’t You? (Aren’t We All?)

Unlocking Potential #19: Q&A With Mitch DeWitt

Unlocking Potential is back—this time with a Financial Week spotlight. I’m always interested in the people who can talk about money without turning it into either a spreadsheet sermon or a Reddit roulette wheel. Mitch DeWitt (CFP®, MBA) does exactly that: practical, calm, and a little rebellious in the best way.

Q: What’s a “financial truth” you wish more high-achieving people would accept sooner—because it would save them years of stress (or years of overconfidence)?

Stockpiling a bunch of money aimlessly is overrated. Figure out what matters to you and use your resources intentionally.

Q: What’s one belief about investing or planning you held early in your career that you’ve changed your mind about—and what experience changed it?

There isn’t always a “right” answer. As an engineer by education, I used to want a precise formula to achieve financial success; that simply doesn’t exist. Finances and financial planning are an art form. I didn’t have an “aha” moment to realize this—rather, it came from many years of experience.

Q: If you could give someone one constraint to follow for the next 30 days that would improve their finances fast (a rule, a ritual, a boundary), what would it be?

Find something to automate in your financial life. It could be a monthly transfer to your high-yield savings account, a regular contribution to your brokerage account, or increasing your employer retirement plan contributions. Sometimes people just need a little nudge—just do it and don’t overthink it.

Q: Beverage check (personal curiosity: since I own Garth’s Brew Bar on Monroe Street…gotta ask!): what’s your go-to drink when you’re celebrating a win—or decompressing after a long week?

I would consider myself a seasonal drinker. In the hot summer months I enjoy wheat beers (Weihenstephaner Hefe Weissbier). During the fall I enjoy a strong ABV, hoppy IPA (or double IPA!). However, when it comes to celebrating a win, I gravitate towards a dram of an Islay-style scotch.

Q: How can people find you?

Mitch DeWitt

Stay Positive & Cheers

Fulfillment Meter

The thing we actually crave is the feeling of fulfillment. Not happiness. Not productivity. Fulfillment. It’s the quiet aftertaste that shows up when you did something that felt true, even if it was small, even if nobody clapped.

So how do you measure it?

Try this: would you willingly live today again?

Not in a nostalgic highlight reel way. In the full, unedited, include the emails and the weird snack choices way.

We resist asking because it is inconvenient. Because it turns the day from a blur into a verdict. Because if we admit we spent eight hours polishing a doorknob that opens to a broom closet, we might have to stop. And stopping is terrifying to any system that profits from your busy face.

Tonight, take ten seconds. Ask the question. If the answer stings, good. That is your compass remembering it has a job.

Stay Positive & More Days Feeling Fulfilled > Not

Can You Make This Better?

Making something better is not a gift from the gods. It is a decision you make while your coffee is still thinking about becoming coffee.

You can ask someone: “How would you improve this?” Instantly you hand them a clean little chance to matter. People love that. It is emotional tip money. I have never met a human who could not make something better when invited. Even the cranky ones perk up, because critique is just love wearing work boots.

You can ask yourself. Not in a dramatic journal way. In a quick, sharp way. “What is the fastest improvement?” Your brain is a raccoon. Give it a shiny prompt and it will come back with a stolen diamond in under a minute. Instant gratification, plus momentum, plus a tiny hit of competence.

And AI? Come on. This should be a default motion like blinking or checking the fridge again. Twenty seconds to paste, upload, or screenshot. Five words: “Make this clearer and tighter.” That is not “extra.” That is the final funnel. That is respect for the work.

The main excuse is time. Which is adorable, because asking the question is often the fastest part of the whole project. “I do not have time to improve it” is usually code for “I do not want to look at it again.”

Anything short of passing it through the last funnel is slop. And we did not wake up today to serve slop.

Stay Positive & Serve Better

Stock Market Squirrels

I once watched a squirrel bury an acorn like it was hiding state secrets. No spreadsheet. No podcast. No “hot tip” from a cousin who swears he knows a guy. Just a twitchy little mammal making a humble deposit into the future.

That is investing, before we decorate it with jargon and anxiety.

The first life lesson is that time is the only employee who never calls in sick. Compounding is not magic, it is repetition with a cape. Small, boring contributions done consistently turn into something that feels unfair to anyone who insisted on fireworks. The market rewards the patient the same way a garden rewards the person who keeps showing up with water instead of opinions.

The second lesson is that feelings are terrible financial advisors. The market is basically a mood ring worn by millions of nervous humans, and it changes color for reasons ranging from “real” to “what on earth are we doing.” If you can learn to watch numbers jump without letting your inner toddler grab the steering wheel, you start to build a superpower that works everywhere. Meetings. Marriages. Mondays.

The third lesson is humility. You are not the main character in the universe’s portfolio. You can be right and still be early. You can be careful and still get surprised. Diversification is not fear, it is respect for how weird life is.

And perhaps the best lesson, the one George Carlin would grin at, is this: most people want certainty, but certainty is a sales pitch. Investing teaches you to make peace with uncertainty, then place your bets anyway, calmly, like that squirrel. Not because you are sure, but because you are serious about your future self eating in winter.

Stay Positive & Grab Your Acorn

Swinging The Conversational Door Open

Most conversations fail for the same reason most diets fail. We start with punishment instead of appetite.

Conversational regard is the opposite move. It is the small courtesy that says, I see you, and I came here to build, not to win.

Power one is naming the person before naming the topic. Not flattery. Calibration. “I wanted to throw an idea at you because you like to push the status quo.” Now the idea has a runway. You did not just toss a thought grenade into their day. You handed them a role they already enjoy playing. Humans will often live up to the best version of themselves you speak out loud.

Power two is checking visibility. “How was my response to that?” or the post meeting classic, “Is there anything I could have done better in there?” This is sneaky magic. If they say you did great, they get the satisfaction of endorsing competence. If they offer feedback, you get a sharper next rep. Either way, they feel included, and you get upgraded.

Power three is the simplest and the rarest: permission to be honest. “If I am missing something, tell me.” People relax when they are not being recruited into pretending.

Treat regard like a revolving door of habit, not a tactic. The conversation gets warmer, the truth shows up faster, and everybody leaves with a little more dignity than when they entered.

Stay Positive & Can I Get The Door For You?

The Friend That Calls You On Your Stuff

Most of us don’t need more motivation. We need a mirror that doesn’t flinch.

AI can be that mirror, if you stop using it like a vending machine and start using it like a coach with a clipboard and a slightly raised eyebrow.

Try this: hit record on your phone for a normal day. Upload the audio and ask your AI to count how many times you said “hurry up” or “we’re late” or “just do it.” Then ask for three replacement phrases that keep the urgency without sounding like you’re running a tiny airport with no joy. You’ll learn what kind of weather your words create.

Next: tattoo your tools with rules. In your project instructions, add: “Always include one wild idea that challenges the status quo.” Or: “If you give me a plan, also give me the smallest rebellious first step.” Suddenly your AI stops being a polite intern and starts being a spark plug.

Two weirder ones:

  1. The “future eulogy” prompt: paste your calendar for the week and ask, “What would Future Me thank me for, and what would he roast me for?” Brutal. Useful.
  2. The “friction map”: after a workday, dump your Slack, notes, and to do list in and ask, “Where did energy leak, and what is one system change that stops the leak?”

AI won’t fix your life. But it can absolutely catch you in the act.

Stay Positive & Phone An AI