November 2025
One of Shakespeare’s most commonly (mis)quoted lines?
A rose by any other name would smell as sweet.
And this month, I’ve been reflecting on that as it relates to purpose. There are a thousand other names for purpose, all with their own subtleties and nuance. And many of these variations on purpose can be even more impactful, in the right setting.
The business of alignment
If you’ve been following me for a while, you know that entrepreneurship shaped most facets of my life—my father was an entrepreneur, I’m an entrepreneur, I run a business with two wonderful partners, and we serve a host of amazing business owners and retirees.
And a big part of success, particularly for any business with multiple owners? Alignment.
It’s something I explored in this month’s podcast with my business partner Bill Mulvahill. Bill ran a business on his own before joining forces with Trailhead, and we talked a lot about what makes a successful partnership—both in our experience working together and what we’ve seen work for other companies. (As well as a few things that we’ve seen fail.)
And the big takeaway? You need alignment.
So, what does that mean?
It’s a little bit about purpose—having common goals and values. But it can also be about process. And how you approach this alignment can be critical to long-term success. Watch the full podcast to hear the ins and outs.
Aligning your purpose
As soon as we finished taping, I realized that alignment extends far beyond entrepreneurship. For instance, when we hold annual meetings to discuss charitable giving or the legacy retirees want to leave… really, what we’re doing is aligning your finances to your purpose.
Purpose is only part of the equation. The ongoing work is to make sure your life, and your finances, are aligned to that purpose. That means constantly reevaluating:
- What is your purpose, and is it still what you put on paper a year ago?
- Are you living your life in a way that aligns with that purpose?
- Does your life align with your finances? (This is another big one.)
- Do your finances align with your purpose?
It all starts with purpose, but alignment takes the purpose off the page. I put together some thoughts on aligning your money to your goals.
Aligning your portfolio
We’ve seen countless headlines so far this year about volatility. Here’s a roundup from the last month alone:
Everything is doom, gloom, and panic… or utter delight. Of course, there’s good reason to be wary—we’ve seen cracks in basic economic principles, from free trade to functioning government. And yet, there’s also reason to celebrate. The market keeps rebounding.
The seeming disconnect could drive you insane if you let it.
Which is why purpose and alignment are critical right now, and likely to be even more so in 2026. Everyone from regular folks to professional traders expects that volatility to continue.
And yet, it’s hard to tune out the noise. Even when you’re working with an advisor. Even when you have a plan.
And so this is when you want to look at your portfolio and your purpose. Are they aligned?
Remember, you’re not investing to outperform or even match the S&P 500. You’re investing for a goal, or a series of goals, and your portfolio hopefully reflects that. Those are the discussions you want to be having, now more than ever.
Creative alignment
When I started these monthly musings, I wanted to dedicate a section of it to creative pursuits. After all, creativity makes me a better business owner and a better financial advisor. I find this to be the case for most people.
You might not be into art, or into music, but most of us want to create something in this world. That might be a home and life for your family. It might be a business, a mark, a lasting impression. But we’re inclined to build.
And so I’m thrilled to share two things.
First: My band’s full album is out now! It’s been a labor of love and I’m so glad you’ve enjoyed the music. In some ways, creating it has been more fun than releasing it, since the creative process is what I love.
Second, I’m going to be more intentional about creativity on purpose. to look at all the different types of creativity at play in the world today. I don’t think we should have to pigeon hole creativity. In fact, that’s the opposite of what creativity asks us to do!
