Sometimes life’s big milestones arrive in a neat, straight line. And sometimes that’s just not what happens—or what we want to happen. How do we plan for a swoopy life?
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Sometimes life’s big milestones arrive in a neat, straight line. And sometimes that’s just not what happens—or what we want to happen. How do we plan for a swoopy life?
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by Mark Leibman, President
With serious planning and determination, many of us are gearing up for the next round of New Year’s resolutions. The change in the year will be the time we finally lose weight, or drink less, or exercise more, or wake up at 4 a.m. like those social media productivity thought-leading rockstars do!
As for me, I will not have a New Year’s resolution. I won’t be hustling to be the oldest participant in the hardest 5k in the state in 2026. I will not be striving to achieve or maintain a specific weight. I will not be avoiding or including certain foods in my diet. No resolutions. Not one.
Many of you have heard me say that I’m planning to work to age 92. Will any New Year’s resolution make that happen? There’s nothing magical about December 31 (except perhaps some fireworks at midnight!). I don’t measure my health by a calendar.
Instead, I measure my efforts every single day.
When you really think about it, doesn’t wealth work the same way? Even though we measure markets on an annual basis, that’s really just a long-held standard for consistency. You may have heard that in 2025, the stock market (as measured by the S&P 500) was up 12% for the year, January to December. But we have the tools to calculate the return for whatever 365 consecutive days you’re interested in. We can look at the results birthday to birthday, or any other range we’d like.
The process of becoming financially independent—of gaining the option to live on your wealth instead of your labor—uses essentially the same process as my health goals. Steady decisions, over time.
And we’re here to help anybody navigate the process. We try to offer guidance in your journey through the economic ups and downs, the noise of market pundits both on business channels and at the café. To focus on your financial health overall, instead of some calendar-year resolution.
Just like my health goals don’t change when I buy a new calendar, my wealth goals don’t need to either.
Clients, don’t think we are against all New Year’s resolutions. There’s actually one I highly recommend: in 2026, help someone learn what’s going on here at 228 Main in beautiful downtown Louisville. I know I’ll try to stick to that one too.
Thank you all, for everything.
Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly.
All investing involves risk including loss of principal. No strategy assures success or protects against loss.
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Play the audio version of this post below:


by Mark Leibman, President
With serious planning and determination, many of us are gearing up for the next round of New Year’s resolutions. The change in the year will be the time we finally lose weight, or drink less, or exercise more, or wake up at 4 a.m. like those social media productivity thought-leading rockstars do!
As for me, I will not have a New Year’s resolution. I won’t be hustling to be the oldest participant in the hardest 5k in the state in 2026. I will not be striving to achieve or maintain a specific weight. I will not be avoiding or including certain foods in my diet. No resolutions. Not one.
Many of you have heard me say that I’m planning to work to age 92. Will any New Year’s resolution make that happen? There’s nothing magical about December 31 (except perhaps some fireworks at midnight!). I don’t measure my health by a calendar.
Instead, I measure my efforts every single day.
When you really think about it, doesn’t wealth work the same way? Even though we measure markets on an annual basis, that’s really just a long-held standard for consistency. You may have heard that in 2025, the stock market (as measured by the S&P 500) was up 12% for the year, January to December. But we have the tools to calculate the return for whatever 365 consecutive days you’re interested in. We can look at the results birthday to birthday, or any other range we’d like.
The process of becoming financially independent—of gaining the option to live on your wealth instead of your labor—uses essentially the same process as my health goals. Steady decisions, over time.
And we’re here to help anybody navigate the process. We try to offer guidance in your journey through the economic ups and downs, the noise of market pundits both on business channels and at the café. To focus on your financial health overall, instead of some calendar-year resolution.
Just like my health goals don’t change when I buy a new calendar, my wealth goals don’t need to either.
Clients, don’t think we are against all New Year’s resolutions. There’s actually one I highly recommend: in 2026, help someone learn what’s going on here at 228 Main in beautiful downtown Louisville. I know I’ll try to stick to that one too.
Thank you all, for everything.
Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly.
All investing involves risk including loss of principal. No strategy assures success or protects against loss.
Want content like this in your inbox each week? Leave your email here.
Play the audio version of this post below:

Every once in a while, the schedule gets really and truly full. We might have places to be throughout the day, for many days in a row. Weeks might go on like this, in an exciting blur.
It’s not a bad problem to have, but sometimes, it can feel like we’re being pulled in more than one direction.
Some of you may experience this sensation too, as you also wear multiple hats in life. You may have commitments as a parent, an employee or an owner, a teacher, a partner, a community member, and more.
Here’s an idea that might provide some relief: we may have many hats, but we only wear one hat at a time. It’s okay to allow ourselves to focus on one at a time, even if we must switch hats often.
The same general principle is true about our financial goals: it may seem prudent to save for retirement, and a house, and a child’s education, and all the other things one may want in a lifetime… but the secret is that you don’t pay for these things on the same day, or week, or month, probably.
Having many hats doesn’t mean we can’t focus—and strategize. Time is finite, of course. But we take things one hat at a time.
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Clients, it’s Caitie here. I’m so thrilled to introduce you to our newest teammate, Allison Bauers! In a small business, we tend to wear many hats, so this week, we’re chatting about how our roles and duties will change in the coming months.
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It’s one of our core principles for a reason: “avoid the stampede.” We live in uncertain times, and it is understandable to get spooked by the day’s headlines. But we do not believe that safety is found following the herd.
Omaha is famous for its stockyards and slaughterhouses; we know that when the cattle are all getting steered together, it rarely ends well for the cattle.
Consider some lessons from history in this classic message.
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For many people we know, money represents work. It’s the sweat and the time and everything else that goes into one’s livelihood.
It may have started decades ago, perhaps with a job for a local farmer, walking beans or baling hay. (Does that reference date us?) It’s all the jobs that followed, too. No matter where those paychecks came from, the work behind them can become a source of pride—one that can also fund our retirement years.
We’re fortunate to know many people who end their careers with resources beyond their needs. It’s a nice problem to have: what happens when the excess outlives us? What’s the next “life” for what you’ve earned and accumulated?
We’ve been hearing from some of you about these big financial legacy questions, and there are many possible answers. In no particular order, here are a few ideas that you have been sharing with us.
Spend it on shared memories. For many, the pace of retirement includes more travel and experiences that weren’t possible during the working years. And while you’re at it, you might think about including those closest to you. Some might take their children or grandchildren with them on the big adventures. If you don’t want to leave behind wealth well beyond your beneficiaries’ needs, spend well now, with them: create the memories while you have the opportunity to do so. Bonus? They have another shared memory to enjoy, long after the experience is over.
Consider making gifts where they would make a difference now. There’s no rule saying you have to wait until you’re gone to get the excess to your beneficiaries. An inheritance can be life-changing, but who’s to say that a well-timed gift couldn’t make a big impact? It could be that splashing around a little cash now might make more difference in the long run. Maybe a loved is working toward a down payment on their first house, or some seed funding for their business expansion, or some other worthwhile project that you’d like to support. Why not now?
Direct it to the causes you care about. You can turn some of your charitable intentions into plans now, too. Your legacy planning may already involve leaving behind some assets to charity, and there are other strategies that might fit your goals. For example, a Donor Advised Fund (DAF) can be set up to benefit organizations of your choice after you’re gone, but it can also be left to a successor: a person you trust to direct charitable distributions of your gifts. They could carry on the work you start now.
Making these kinds of choices truly is a great problem to have. Generational wealth is a powerful tool and privilege. It also highlights the tensions we feel around money: what is the utility of money in our lives—and beyond? We don’t have to know all the answers, but there might be a chance to unlock some exciting opportunities for the generations ahead, if only we get a little more intentional or organized now.
Clients, may your wealth bring you only the best of dilemmas. We’ll be here to try to help you along your way.
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