This might not work
The upside of taking more risk
👋Hello, my friend. This week I’ve been thinking a lot about priorities — how we choose what gets our time and energy — and if I’m being bold enough in the projects I’m choosing, both personally and professionally. I think there’s upside — possibly a lot of it — by taking a bit more risk.
Let’s get into — but before we do…
💪Intentional Wisdom x Peloton
Shout out to SilvadeneQueen for winning this week’s Intentional Wisdom Peloton “How much can you work out?” challenge. Well done with over 10 hours of workout time!
This week’s challenge: 3 strength workouts. Let’s see who can get it done.
Reminder: You can join that community for free here.
Parallel Tracks
Like many of you, I’ve lived for years with parallel tracks: the work that sustains me today and the projects that excite me for tomorrow.
I sometimes catch myself thinking: If I could just go all-in on one thing, I could be the best in the world at it. But I’ve also learned that the reality of today doesn’t have to hold me back from moving toward that vision.
The key is finding small, incremental steps that start shaping your world closer to the one you imagine.
Shaping the Work You Do
One thing I’ve noticed: the world is more malleable than we often give it credit for.
Even in my day job, over 13 years, I’ve morphed my role from something that once had me elbows-deep in Excel spreadsheets (not my superpower) into work that matches my unique skills and interests. Things like podcasting, creating content, experimenting with new formats.
That didn’t happen overnight. It was a slow process of shaping the role — nudging it bit by bit — until it better fit the things I’m actually good at and enjoy.
That same principle applies outside of work. If there’s something you want to be doing, you don’t always need a giant leap. You can start tinkering your way toward it.
Systems Over Willpower
Here’s what helps: systems.
I don’t protect mornings for high-energy tasks the way some productivity experts suggest. I’d love to, but that’s not my reality today with work, kids, etc.
What I protect is time to think — often on a walk outside or on the treadmill.
That thinking time has become a kind of system for me. It gives me space to process ideas, make connections, and sometimes come back with the seed of something worth testing.
If you’ve been reading this newsletter for a while, you’ll also know that I schedule out my weeks hour by hour. Workouts. Side projects. Even walks with my wife. All in the calendar by Sunday afternoon.
Overkill? Maybe. But I’ve learned that if you leave it up to chance, the urgent will always crowd out the important.
Tiny Experiments
Which brings me to tiny experiments.
I love tinkering with new approaches — in my health (intermittent fasting, keto, new routines), in the content I make, in how I structure my time.
Most experiments don’t change my life overnight. But they do compound. They build momentum, confidence, and clarity about what works and what doesn’t.
That’s how progress really happens.
Rethinking Risk
The throughline in all of this is risk.
We’re taught to treat risk as dangerous. But careers — like portfolios — reward those who take smart, calculated bets.
The best investors aren’t paid to sit in Treasury bills. They’re paid to find asymmetric opportunities — risks that might not work but could pay off massively.
So why should our careers be any different?
The truth is: avoiding risk is itself risky. It keeps you stuck. It prevents the upside.
One Conversation a Week
One way I’m starting to put this into practice: committing to one conversation a week that scares me.
Not terrifying. Just enough to feel a little over my skis.
It could mean reaching out to someone I admire in my industry. Or asking for a conversation with someone a few steps ahead. Or pitching an idea that feels like a stretch.
Here’s what I’ve realized: no matter how senior you are, there are always people further along. People who look like they have it all figured out. But more often than not, they’ve been in your shoes. And many are surprisingly willing to help.
The barrier isn’t them. It’s usually our own lack of ambition — or courage.
This Might Not Work
Seth Godin has a phrase I love: “This might not work.”
It’s a reminder that if something definitely will work, it’s probably too safe.
And let’s be honest: the status quo is boring. At its worst, it’s soul-destroying.
We need change. Positive momentum. Little bets that push us forward.
Because that’s what makes work rewarding — not just grinding it out day after day, but pushing the boat out, testing limits, and surprising yourself with what’s possible.
Final Thought
I can’t always go all-in on one thing. Most of us can’t. But I can take incremental steps, run small experiments, and keep shaping my world closer to the one I want.
That means protecting time to think. It means being more deliberate about the risks I take. And starting now, it means at least one conversation a week that stretches me.
It might not work.
But it might just change everything.
That’s it for this week but before you go…
Content Diet
Tim Ferriss x Seth Godin — This is Strategy
These two are both total pro’s in every way so I’d listen to them talk about anything but in this case they were talking about Godin’s new book This is Strategy. It’s all about the ways to create an actual strategy (for a business or any pursuit) as opposed to getting bogged down in the tactics. By the way, I recently started sorting podcasts by “Most Snipped” in the Snipd app (remember I had their CEO on my pod?) and it’s an awesome way to surface the podcast episodes that have resonated most with people. This was one of those conversations.
Michael Sidgmore on The Compound & Friends
For all of my finance nerds, I’m finding some inspiration in what Michael Sidgmore is doing with his podcast and newsletter Alt Goes Mainstream. He joined The Compound & Friends who I’m also drawing inspiration from currently, for a great conversation on the wealth management space and how alts managers are approaching it. I think a lot about this kind of stuff in my day job, so I really enjoyed this one.
That’s it for today — as always, thanks for reading!
Greg