👋Hello, my friend — Quick one for you before I head out on my Griswold-style summer roadtrip with the fam. This article is about a small thing I practice in my own career that’s become a key tenant — and also an area where I see A LOT of people fall down. Hope it’s helpful to you or someone you know.
Let’s do it!
Enough with the problems, bring me solutions
A few nights ago, I was out to dinner with a group of buddies — a very successful group as it happens — C-suite execs, top investors, business owners, newsletter writers (well, only one of the latter)… but a group that has generally done quite well for themselves in the world of business.
Anyhow, at some point, the conversation turned to careers — challenges we’re facing, opportunities that are arising (AI!), and things we’re seeing in the people we manage— and even in our own kids as they approach workforce age.
I threw out a simple idea that, as soon as I said it, got an immediate flood of agreement:
One of the biggest and most consistent mistakes I see from people — especially earlier in their careers — is always bringing their boss problems, never bringing them solutions.
Everyone had examples. Everyone had stories. It struck a chord.
So I thought it was worth putting in front of you, too — especially as we head into the back part of the year, when a lot of people are thinking about performance reviews, promotions, and what it takes to stand out.
Here’s the thing:
Most people think they’re doing a good job if they can spot the problem and flag it.
They’re not wrong — that’s step one.
But it’s only step one.
Don’t Drop the Problem and Walk Away
A typical one-on-one with a manager might go like this:
“This project is off track. What should I do?”
“This person is being difficult. What should I do?”
“This deadline is impossible. What should I do?”
You’re showing up with the problem — and then immediately pushing the mental load onto your boss. Now your manager — who probably has 100 other things on their plate — needs to stop, context switch, and solve it for you.
This is how most people operate.
It’s also a great way to stall your career out.
The Better Move: Come With Solutions
Instead, try this:
Before your one-on-one, take 10 minutes and do the following:
Define the problem clearly.
Brainstorm 2–3 potential solutions.
Pick one that you think is best.
Present all of that — cleanly and concisely — to your manager.
Let’s say your project is off track. You might say:
“We’re not going to hit the deadline. I’ve thought through three options:
We push the timeline back and reset expectations with stakeholders.
We reassess whether the project is essential right now.
We change up the team or the approach to get it back on track.
Of the three, I think option 3 gives us the best chance to succeed. Here's why…”
Now you’re doing real work. You’re thinking. You’re owning the problem. And you’re relieving your boss of a big mental burden.
It also gives your boss a clear, simple decision path:
Do they agree there’s a problem?
Do they agree with your proposed solution set?
Do they agree with your recommendation?
You’ve made their job easier.
And you’ve just shown them how you think.
This Is How You Earn Autonomy
Some people might push back:
“My boss makes more money — shouldn’t they be the one solving the hard problems?”
Maybe. But that’s a limiting mindset.
The best leaders I know want to work with people who can take ownership, make decisions, and run with things. They don’t want to micromanage. They want to trust their team.
When you show them that you’ve already thought through the issue, explored multiple paths, and are willing to recommend a way forward — you earn that trust. And you earn more autonomy.
Done well, this becomes a flywheel:
You bring solutions → You gain trust → You get more ownership → You grow faster.
And here’s a little secret:
A great boss will sometimes let you run with a solution they wouldn’t have chosen themselves — because they want you to learn, develop, and lead. That’s how the best managers operate.
This Works at Every Level
It doesn’t matter if you’re straight out of college or reporting directly to the CEO — this mindset scales.
It’s a small tweak. But it’s one that I’ve seen repeatedly separate high-performers from everyone else.
And like I mentioned, when I brought it up with my friends — many of whom have seen and done a lot in their careers — it landed immediately. Everyone had examples. Everyone had stories. Everyone wished more people would do this.
So I’m passing it on to you.
Use it. Share it. Teach it to your team. Teach it to your kids. It’ll serve them (and you) well.
That’s it for this week, but before you go…
Content Diet
For all my health & fitness nerds…
Podcast: The Tim Ferriss Show — Dr. Rhonda Patrick: Protocols for Fasting, Fat Loss, Reversing Aging, and Battling Disease
I’m a big fan of both Tim Ferriss and Dr. Rhonda Patrick — they’ve taught me a ton over the years. This recent episode was a standout.
What I loved:
They dive into what they’re recommending and trying for their aging parents — from exercise regimens to specific supplements. Super practical and personal.
Rhonda breaks down everything from creatine to fish oil to magnesium and vitamin D, with specifics on doses and rationale.
Great segment on VO₂ max and its importance as a longevity marker.
My own takeaways:
I’m probably getting back on creatine — I’ve been off it for a while.
Going to reintroduce more HIIT cardio. I’ve been strength-focused lately and need to re-balance.
Highly recommend giving this episode a listen. Tons of actionable wisdom.
For all of my AI nerds…
Podcast: a16z Podcast - Balaji Srinivasan: How AI will Change Politics and Money
Balaji is one of the most prolific thinkers/speakers/writers on all things tech/AI/crypto… But please, let me warn you: this conversation was SUPER NERDY… I mean, like, I wasn’t sure I wanted to recommend it because it’s so damn technical and in the weeds on all things AI. Listen, I only probably picked up 60% of what they were saying but I do think there’s something to be said for listening to smart people converse on a super technical topic even if you’re not digesting all of it. That’s what I’m telling myself anyhow.
For all my finance nerds…
Podcast: Invest Like the Best — Alan Waxman — Building Sixth Street
Patrick O’Shaughnessy and the team at Colossus don’t tend to miss much when it comes to quality content, and they didn’t miss here either. I enjoyed this conversation with Waxman, who “grew up” professionally in the special situations group at Goldman Sachs — a group that the Wall Street Journal once called “the Navy Seals of Wall Street.”… anyhow lots of insight into how a great investor thinks — with a lot of focus on creativity and culture.
That’s it for today!
Make sure you wave if you see me and the rest of the Griswolds driving our station wagon through North Carolina, Virginia, DC, Pennsylvania, New York, New Jersey, Connecticut, Massachusetts, Rhode Island and back again! We’ll see if they let me write a newsletter along the way… #WallyWorldorBust
Enjoy the rest of the summer!
Greg