September 2025
Last month, as I was sitting down to write my monthly musings, I was thinking that I wanted to bring more positivity to the conversation. There’s so much division in the country, and the headlines—whether they’re economic, social, or political—feel increasingly alarmist.
But then something happened that made positivity difficult. And I sense there’s a lesson in that, too. One that ties back to purpose.
Back to basics
As many of you know, I’m based in Minneapolis. What you may not know, however, is that I used to live just around the corner from Annunciation Catholic Church—where a deadly mass shooting took place three weeks ago. My oldest child spent countless afternoons playing in the Annunciation playground.
Minneapolis is no stranger to this particular type of 21st century American tragedy. From George Floyd to the assassination of Melissa and Mark Hortman, we’ve kept going, one foot in front of the other.
This shooting felt different, at least for me. It felt like a near miss, a lucky break, a wake up call. I was, and still am, very much demoralized.
But I’m doing my darndest to try to practice what I preach: I’m falling back on purpose.
At the end of the day: What do I value? Am I doing everything I can to protect and support those things? And if I’m not, what changes do I need to make?
I won’t go so far as to say purpose provides optimism. But it can provide a path forward. And I’d argue that at times like these, moving with intention is the best we can ask for.
Not sure how to go about defining your purpose? Here’s what my family put in our mission statement.
Purpose in your portfolio
Originally, I was going to suggest ignoring the headlines as they relate to your investment portfolio. Every time we’ve seen the market fall this year, it has rebounded almost as quickly, often to new records. Major policy shifts are announced and then clawed back.
Suffice to say, if you hyper-focus on the details of the day-to-day, you’ll come away thinking things are far worse than if you simply check in once every few weeks.
I’m not saying ignorance is bliss, or even suggesting that you disengage. I’m simply suggesting you engage on purpose.
Remember: You’re not trying to beat the S&P 500 or make money for the sake of it. You have an investment portfolio to serve a purpose—retirement, providing for your family, a specific goal.
Ask yourself: If the market is up or down today, does that impact my life right now? Chances are, the answer is no. Next, ask: Do big market moves impact my purpose? Will this jeopardize my goals?
These are the types of questions I ask my clients. What are we trying to protect? What are we trying to grow? And, of course, why?
My team and I at Trailhead Planners can run projections to help you understand how different scenarios might impact your goals. Think of it as blinders that help you focus, rather than a blindfold.
The gap and the gain
The final question I’ve been asking this month is simple: Why is it so hard for us to stay focused and optimistic?
I fully believe in the advice I’ve shared so far in this newsletter. When things get hard, we go back to basics. When investments feel uncertain, we reconnect to purpose.
But to be totally frank: Sometimes it feels like purpose isn’t enough. And that’s because of expectations. Let me explain.
We tend to have a vision in our head of what our life should look like: My house should be clean; my bank account should have $___; my government should do ___. More often than not, there’s a gap between these expectations and reality. That gap almost always creates a negative perception of things.
That gap gets in the way of our purpose. It keeps our focus on what we lack (the gap), instead of what we have (the gain), and what we’re working toward.
If you’re having a hard time reconnecting with what’s important, I suggest getting out of the gap. Take a moment and look around—ground yourself in the present. Reflect on how far you’ve come. And detach from your previous expectations.
Read more about how you can shift your perspective to mind the gap.
Remember: Life is beautiful
When times are hard, art, music, and beauty become more important than ever. This isn’t about escapism, it’s a real psychological phenomenon. Our brains are happier when exposed to beautiful scenery.
For me, making music helps me process the world around me, and gives me a creative outlet. My band, Stone Arch Rivals, was deeply and personally impacted by last month’s shooting, but, after much conversation and dialogue, we still took the stage for a show that weekend. There was joy, sadness, more than a few tears, and it all came out in the music.
So my wish for you this month is that you find something beautiful, creative, and healing to enjoy. Remind yourself of all the beautiful things in this world.
And if you need a song to get you started, here’s our latest single: Sitting on the East Side.
