Money Monday Blog

I recently had a conversation with a business mentor that shifted my perspective on delegation. He shared a simple framework that highlights the stages of delegation—and the personal growth that comes with each.

1. Delegating What You’re Bad at and Don’t Enjoy

This is the easiest place to start. If a task drains your energy and you’re not skilled at it, it’s a prime candidate for delegation. Letting go of these responsibilities frees up your time and ensures that someone more capable can handle them effectively.

2. Delegating What You’re Good at but Don’t Enjoy

This stage is trickier. It’s tempting to hold onto tasks simply because we’re competent at them. But if they don’t bring you joy or align with your strengths, they’ll eventually sap your energy. Passing these responsibilities to someone who thrives on them benefits both parties.

3. Delegating What You Love and Are Good at

This might feel counterintuitive. Why give up tasks that you enjoy and excel at? Because true leadership often requires us to focus on the highest and best use of our time. Delegating even these tasks allows you to operate at a strategic level, where your influence can have the greatest impact.

4. Delegating for Others’ Development

This is the ultimate stage of delegation—and the most rewarding. These are tasks you’d prefer to keep because you enjoy them or they’re integral to your identity as a leader. But delegating them isn’t about you; it’s about building the next generation of talent. Handing over these responsibilities empowers your team to grow, step into leadership roles, and carry your organization forward.

Delegation isn’t just about handing off tasks—it’s about intentional growth, both for yourself and your team. Each stage requires trust and a willingness to let go, but the rewards are exponential: more time, greater focus, and a stronger, more capable team.

Where are you in these stages? And what’s your next step toward building a legacy of empowered leaders?

As a financial advisor and business owner, I’ve learned that success isn’t just about the decisions we make—it’s about refusing to stay stuck when circumstances aren’t ideal. The quote, “What you aren’t changing, you are choosing,” is a powerful reminder that inaction is still a choice.

This quote resonates in a new way lately as I have a pile of personal and professional things I’d like to change. Simply reminding myself that I have a choice is ironically obvious and encouraging all at the same time. Life’s daily grind has a way of luring us to sleep. Times of reflection can help wake us up to the decisions right in front of us.

It’s tempting to feel like a victim when life throws curveballs, but that mindset doesn’t serve us. Playing the victim strips away our power. Instead, we need to embrace responsibility and choose action over inertia.

Change isn’t easy. It demands courage, discomfort, and energy—but it’s also the pathway to growth. Every day we can ask ourselves: Am I okay with things staying this way? If not, it’s time to act.

As leaders, we owe it to our clients, teams, and ourselves to make deliberate choices that align with the future we envision. The hardest part is often the first step, but the reward? A life and business that reflect intention and purpose.

Choose growth. Choose action. But most importantly, choose to change the things holding you back!

As financial advisors, we often see a frustrating reality: the same dollar is taxed not once, but up to four times throughout your life (credit to Chris Scearbo for the thinking below). Understanding this can help you make better decisions and plan for a more efficient financial future.

When You Earn It

Whether through wages, bonuses, or business profits, taxes like income tax, payroll tax, and self-employment tax immediately take a slice of your hard work. For many, this is the first big hit.

As You Grow It

Investments are a powerful tool for wealth building, but Uncle Sam has his eye on the prize. Dividends, interest, and mutual fund distributions.

When You Spend It

After already paying the first two taxes, many investors will need capital for a financial goal in the future. At this point, selling portfolio positions creates a capital gain tax.

When You Pass It On

Lastly, estate and inheritance taxes may come into play when transferring wealth to the next generation. Even after a lifetime of paying taxes, this final toll can diminish the legacy you hoped to leave.

The good news? There are strategies to minimize taxes at each stage—whether through thoughtful income planning, tax-efficient investing, charitable giving, or proper estate structuring. The key is to take a proactive, holistic approach to your finances, ensuring more of your hard-earned money stays where it belongs: with you and your family.

Paying less tax means you can Plan wisely, live fully, and pass on a legacy worth remembering.

My family had the opportunity to go to Europe last summer. My son and I woke up early one morning to take the tube out to Richmond. Visiting Ted's pub and apartment and bumping into other fans was so much fun.

The enthusiasm for this show is a reminder that we are all in desperate need of optimistic and encouraging voices. See below for my Top Ten Ted Quotes (spanning all seasons and in no particular order):

1. "Taking on a challenge is a lot like riding a horse. If you're comfortable while you're doing it, you're probably doing it wrong."

2. "I think you might be so sure that you're one in a million that sometimes you forget that out there, you're just one of 11."

3. "Be curious, not judgmental."

4. "I promise you, there is something worse out there than being sad, and that is being alone and being sad. Ain't no one in this room is alone."

5. "Life is like riding a bicycle. To keep your balance, you must keep moving."

6. "The happiest animal on earth is the goldfish. Do you know why? Got a 10-second memory. Be a goldfish."

7. "Doing the right thing is never the wrong thing."

8. "You say impossible, but all I hear is I'm possible."

9. "I hope that either all of us, or none of us, are judged by the actions of our weakest moments, but rather the

strength we show when and if we'e ever given a second chance."

10. "Believe."

I’ve read several versions of the parable below. I did a little homework to find its creator… turns out it was a German writer named Heinrich Böll, and was penned in 1963.

I re-read this anytime my life has gotten too complicated. It’s a reminder that many of us miss out on life’s simple pleasures in the pursuit of more. I hope it speaks to you today, as it has always spoken to me.

The Parable of the Banker and the Fisherman

The American investment banker was at the pier of a small coastal European village when a small boat with just one fisherman docked. Inside the small boat were several large-fin tuna. The banker complimented the fisherman on the quality of his fish and asked how long it took to catch them.

The fisherman replied, “Only a little while.”

The banker then asked why he didn’t stay out longer and catch more fish.

The fisherman said he had enough to support his family’s immediate needs.

The banker then asked, “But what do you do with the rest of your time?”

The fisherman said, “I sleep late, fish a little, play with my children, relax with my wife, stroll into the village each evening where I sip wine and play guitar with my friends. I have a full and busy life.”

The banker scoffed. “I am a Harvard MBA and could help you. You should spend more time fishing and with the proceeds, buy a bigger boat, and with the proceeds from the bigger boat, you could buy several boats.

Eventually, you would have a fleet of fishing boats. Instead of selling your catch to a middleman, you would sell directly to the processor, eventually opening your own cannery. You would control the product, processing, and distribution. You would need to leave this small coastal fishing village and move to a larger city where you will run your expanding enterprise.”

The fisherman asked, “But how long will this take?” To which the banker replied, “Fifteen to twenty years.” “But what then?”

The banker laughed and said that’s the best part. “When the time is right, you would announce an IPO and sell your company stock to the public and become very rich; you would make millions.”

“Millions?” asked the fisherman. “Then what?”

The banker said, “Then you would retire. Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, relax with your wife, stroll to the village in the evening, sip wine, and play guitar with your friends!”

Last year, I was at an MLS game with my daughter (a winning night for FC Cincinnati). A friend approached with a big smile and said he wanted to do something nice for me. I had given him some personal advice that helped him significantly, and he wanted to return the favor. He knew my son (who wasn’t with me then), and I liked cars. He promised to lend us one of his exotic cars for a few weeks to enjoy. I was excited for my son but didn’t bring it up to him; the promise was made after my buddy had likely had many cocktails, and I didn’t know if he’d remember.

Turns out I was wrong. Sure enough, when I woke up the next day, a bright red Lamborghini Huracan sat in our driveway.

Here’s what I learned from my time with my very own supercar:

The most fun part of having it was getting to share it. My son and I had some epic rides, and it was fun picking my buddies up for rides. Wealth’s main utility is the ability to share it.

By my 10th time getting behind the wheel, I didn’t always remember I was driving a Lamborghini. Cars on the highway would roll down their window to take a photo, and I would wonder what they were photographing until I remembered I was behind the wheel of a Lamborghini. Even the ultimate luxury (a $300k sports car) faded into feeling like just a mode of transportation once I was used to it. Our brains adjust quickly to our new normal, and in our quest for more, we often don’t appreciate the new toys and luxuries as much as we expect.

The car was a blast to drive, but there were inconveniences that I didn’t expect. It sat so low that there were buttons to raise and lower it to avoid it dragging as I pulled into the driveway. It had several other little quirks that were no big deal but were trade-offs that came with the precision of being able to go 0-60 in 2.5 seconds. I think this is a pretty good metaphor. Everything in life has trade-offs. The car most likely to go the fastest in a straight line will unlikely have the versatility required to be a daily driver. The same can be said for investments.

A diversified portfolio complement more complicated asset classes like private equity. If I ever owned a Lamborghini, I’d also want a Ford F-150 (or similar truck or SUV) that is super practical. The truck in the garage makes owning the supercar more practical, similar to how safer investments give you the liquidity and peace of mind to swing for the fences on other investments.

Before we dive in, let's revisit the volatility of the last three years. It has been a whirlwind for most investors in every asset class. Below is a quick recap:

• 2020 - The COVID crash was history's fastest bear market recovery. Most indexes fell by more than 30% in 30 days and then recovered to new highs within six months.

• 2021 - New market highs were created repeatedly throughout the year in most indexes, especially technology. Many equity indexes saw positive returns between 20% and 30%, fueled (in part) by easy money policy. In addition, residential real estate skyrocketed.

• 2022 -The euphoria ended as inflation spiked, leading to a change in fed policy. Almost every asset class and sector (including bonds) fell 10-30%.

• 2023-2024 - As of the writing of this article, markets are near all-time highs.

As a financial advisor, I'm often at the center of conversations about the right time to sell assets. This question gets more frequent during times when the markets trade over huge ranges, hence my reason for mentioning the volatility above. A question I get all the time goes something like, "I know we need to sell X (insert real estate, stock, closely held business, etc.); how long will it be before it gets back to Y (insert whatever was the absolute market high)." I sincerely empathize with this question because we can all get caught in the trap of feeling FOMO when we don't sell something at its absolute peak. Our rational self knows this isn't usually possible, but the feeling we missed an opportunity is real, and that feeling should be explored.

My friend James has a saying that I love. He says, "Our old ceiling becomes our new floor." This has so much application to wealth and investing. Maybe it's that we put our house on the market a month too late, got busy on the day we planned to sell that stock, or had too much of our self-worth tied to a certain net worth number that has now fallen. Regardless of the circumstance, we can get stuck thinking we can't take action or, worse yet, can't experience happiness until things return to their previous high. This mental anchoring can feel like a prison. Here's why: there is a chance that it won't return in the near term, or conversely, it might rebound, and then you could fear it might hit a new high and you will miss it (if you sold).

Either way, it is paralyzing.

So, now that we've clearly identified the problem, what's the solution? Here are the steps we recommend for our clients:

1. Give yourself grace and understand the role emotion can play. We all want to think of ourselves as logical versus emotional investors, but emotion always plays a role. It's essential to realize it and limit its impact.
2. Set price targets ahead of time. Again, this isn't important if your investments are only in a diversified index or mutual funds, but it is important if you have something you need to sell. We typically recommend limiting any one individual stock to a maximum of 5% of a client's portfolio. If an investment has grown well beyond that range, it may be time for a trim due to the excess risk from a lack of diversification. Setting price targets ahead of time eliminates the emotion on the day the investment reaches that target because the decision was made ahead of time. (Note: The 5% individual stock max will not be practical for those executives who get paid a large portion of their compensation in stock, but we believe it is good guidance for everyone else.)
3. Think in ranges rather than exact numbers. If you didn't set a price target on a specific position ahead of time, thinking in ranges for assets that have grown may be helpful. Here are a few examples. If a stock has traded within a certain degree over the last 24 months, consider targeting that range's upper half or quartile for an exit. Also, regarding retirement, advertisements on TV have convinced us we all have an exact number we need to get to for retirement. If we fall below that number, financial security is lost. Your advisor can help you determine what range you need to be in, but please don't anchor to an exact number for your own sanity.
4. Don't let the tax tail wag the dog. Tax mitigation is very important, but no one ever went broke paying taxes.
5. Be clear about your goals. For most investors, the exact price of an investment is less important than their ability to meet their financial goals. Make sure you are in touch with what the money is truly intended for. If you have already achieved financial security, you might not need the emotional turmoil and stress of trying to perfectly time every investment transaction (which isn't possible anyway).

We hope today's article allows you a little extra freedom and joy as you consider your financial situation. Money should be considered fuel to help us live the life we want rather than a measurement unto itself. Living well is about perspective and ditching the notion that we can get everything perfect.

I’ve found that I don’t always have 100% clarity on what I want for my life, family, business, etc. I often find more clarity in what I don’t want, the things that would cause regret. Sometimes having clarity on what we don’t want is a good starting point to figure out how to point our lives in the direction of what we do want.

I learn a lot from talking to my older clients about their life. Not only what they got right but what they got wrong as well.

A few years back, I read an article by Bronnie Ware that was a perfect summary of regrets I’ve heard my clients mention. Ware was an Australian nurse who spent several years working in palliative care, supporting patients in the final weeks and months of their lives. During her time in this role, she noticed that many of her patients expressed common regrets and began to document these in a blog. This eventually led to her book, "The Top Five Regrets of the Dying," which has become a best-seller and has inspired many people to reflect on their lives and priorities.

In the book, Ware shares the top five regrets that she heard from her patients:

1. "I wish I'd had the courage to live a life true to myself, not the life others expected it being.”

Many people regret not pursuing their own dreams and passions, instead living a life dictated by others' expectations or societal pressures. Ware emphasizes the importance of being true to oneself and pursuing what truly brings joy and fulfillment.

2. "I wish I hadn't worked so hard."

Many of Ware's patients regretted spending too much time and energy on work at the expense of their personal lives and relationships. She encourages readers to prioritize their relationships and make time for the things that truly matter.

3. "I wish I'd had the courage to express my feelings."

Many people regret not expressing their feelings more openly and honestly, whether it be telling someone they love them or speaking up when they feel wronged. Ware encourages readers to be more vulnerable and authentic in their relationships.

4. "I wish I had stayed in touch with my friends."

Many of Ware's patients expressed regret over losing touch with friends over the years, and not making enough effort to maintain those relationships. She encourages readers to prioritize their friendships and invest time and energy into maintaining those connections.

5. "I wish that I had let myself be happier."

Many people regret not allowing themselves to experience more joy and happiness in life, often due to fears or beliefs holding them back. Ware encourages readers to let go of limiting beliefs and embrace happiness and joy in their lives.

Overall, Ware’s observations are a powerful reminder of the importance of living a life that is true to oneself, prioritizing relationships and connection, and pursuing joy and fulfillment. Ware's insights and reflections offer a valuable perspective on life and death and should inspire us to think about living in a way to minimize regrets… hopefully opening a pathway to a life of fulfillment.

As financial advisors, we often forget that our clients have a money story that pre-dates our relationship. For many clients, that money story was great, but for others, it was painful, even if they are successful now. We may be the only one who knows their story, a great responsibility we must take seriously.

As a new advisor, I was so focused on saying the right thing that I typically missed the opportunity to see that this was just another human sitting in front of me with a history of money triumphs and mistakes (just like me). They were probably nervous about being judged and hoped my plan would help them. Simply remembering this would have made me a better advisor.

The other day, one of our clients (and also a personal friend) talked about feeling uneasy before the meeting. He and his wife have a complicated money story, and they had to declare bankruptcy during the financial crisis. He now has a thriving business and great marriage, but the wounds remain.

Conversations about money often cause a fight between him and his wife.

The interesting thing about shame is that it can cause us to avoid the topic entirely, worsening the situation and creating a constant negative feedback loop. Shame can also cause us to make things too complicated rather than understanding the solution can often be simple once we remove the emotion of our past.

I had the opportunity to talk to my friend a few minutes before his meeting (One of my partners is his advisor and was going to run the meeting). I told my friend three things going into the meeting:

1. Shame can cause us to avoid or overcomplicate our situation, and that is totally normal. Now that you know that, don’t overcomplicate your planning.
2. What you need to do is really simple, pick a percentage of your income that you will save. You don’t need a bunch of budgeting exercises or complicated strategies. Just start today and have it automatically come out of your checking account (5-20% is a good start).
3. You will have a great meeting today; you are better off starting small than not starting at all. You are totally in control of your future. You got this.

Sometimes my job is simply to have enough empathy to understand where someone is coming from and give them hope for the future. In life… lending confidence and encouragement to others is almost always a good start.

I often get asked by clients about my financial plan. I believe each person’s goals should inform their personal financial plan, but I think this question is usually asked because there is a natural curiosity… What does a financial advisor do with their own money, and do they follow the advice that they give to others?

Below, I will outline our family's plan. In many ways, this is irrelevant, but I've always found it interesting to see what financial professionals (who are in the business of giving advice) do with their own money. The percentages below are rounded to make the math easy, but I looked back at what we did so that you can see where the money actually "went." We all tend to tell each other what we intended to do; I was curious to look back at what we did. I believe it is best to break your income into percentages. It is much easier to think and plan in percentages than dollars:

A summary of what I Intended to do is below:

• 15% charitable giving
• 20% savings
• 30% tax
• 15% fixed expense
• 10% discretionary
• 5% travel

I'll zoom into three categories: charitable giving, saving, and I'll combine discretionary and travel (fixed expenses and taxes are self-explanatory).

Charitable giving 15%

• 10% of income went directly to our church (an old- school tithing principle that I believe in)
• 5% went to our Donor Advised Fund, which serves as the catch-all for all of our other giving, and having this in an account makes it easy to talk about what we want to do with the money as a family.

Savings 27%

In all honesty, I tried to save 30%, but I ended up almost at precisely 27%. The savings below is automated, and I put the strategies below:

• 401k
• 529 Plans
• Brokerage Account (Direct Indexing)
• Permanent Life Insurance

Discretionary/Travel 18%:

This category is essential as it is the primary category that impacts family relations. I'm not recommending this for everyone, but here is how my wife and I allocate this category. Everything we have is a joint account except two accounts in this category.

• 5% went to Lindsey's discretionary/variable account
• 5% went to Ben's discretionary/variable account
• 5% went to joint travel/experience account

We spent an extra 3% in this category, so the numbers don't add up. I had to add 3% to the travel account after an entertaining year😀😀.

One quick note for our plan and marriage: Every goal is agreed to, and the two accounts that aren't joint are transparent. They show up in the online login. Both of us wanted a little autonomy in how we handled daily discretionary expenses. Lindsey tends to pay for groceries and costs for the kids, and I tend to pay for dinners out and entertainment.

What's your plan? Would you feel comfortable showing it?