Mid-Year Money Check-In

With summer now in full swing, I’ve been catching up with several people who’ve recently helped their kids or grandkids cross the finish line of another school year. As always, the final stretch brings the infamous Finals Week: a whirlwind of all-nighters, caffeine overload, and last-minute cramming.

But while Finals Week tends to steal the spotlight, mid-terms also stir up anxiety. Serving as a checkpoint, they encourage students to stay engaged and on track throughout the semester rather than saving all the stress for the end.

Personally, I found midterms to be valuable. They kept me accountable, required me to study throughout the semester, and provided me with a clear sense of which topics needed more attention.

Now that we’re nearing the mid-point of 2025, it’s a great time to apply that same mindset to our finances. Below, you’ll find seven questions to ask yourself. Print it out, use it as a checklist, and I hope you will “ace” your financial mid-term.

7 Questions to Ask Yourself

1. How much cash do I hold?

Many of our clients have excess cash flow due to high earnings, without an automated system, cash often builds up without a purpose.

This does not just apply to individuals. Businesses frequently hold large cash balances that sit idle. If your goal is to keep the funds liquid without volatility, there are great solutions that offer:

  • FDIC insurance (if desired)
  • Competitive rates around 4%
  • Same-day transfers

Once you’ve optimized your emergency reserves, consider investing the excess cash in growth-oriented securities (if this aligns with your goals).

2. When was the last time I reviewed my property & casualty insurance?

I recently spoke with a friend who was surprised to find herself paying a substantial amount out-of-pocket for a claim on her rental property – something she assumed would be fully covered.

It’s a tough reminder of how important it’s to periodically review your property and casualty insurance. A quick review helps to:

  • Ensure you’re adequately protected against catastrophic events
  • Avoid overpaying for unnecessary or excessive coverage

Property & casualty insurance typically includes auto, home, and umbrella policies. Business owners and/or rental property owners should pay special attention to make sure their coverage aligns well with their goals. Typically, sharing the declaration pages of your insurance policies helps a professional to complete a thorough review.

3. Am I on track to maximize retirement contributions?

For those who are employed, maximizing retirement contributions is generally considered a best practice. For 2025, the contribution limits for workplace retirement plans like 401(k), 403(b), and 457 accounts are:

  • $23,500 standard contribution limit
  • An additional $7,500 “catch-up” contribution if you’re age 50 or older by year-end
  • New for 2025: If you’re between the ages of 60 and 63, the catch-up limit increases to $11,250, provided your plan allows it

Additionally, investors may be able to defer up to $7,000 (plus a $1,000 “catch-up” contribution if age 50 or older) to a Roth IRA or Traditional IRA. Eligibility depends on your income and whether you’re covered by a workplace retirement plan.

Other tax-advantaged options include:

  • Health Savings Accounts, if you’re enrolled in a High-Deductible Health Plan
  • Retirement plans for business owners, which often allow for significantly higher contribution limits

The rules are complex and change annually, so consult your advisor to help navigate the world of retirement contributions.

4. If I’m giving to charity, am I only giving cash?

While many charities receive the bulk of their donations in December, now is a great time to plan your giving before the year-end rush. Most people default to giving cash, whether by check or bank transfer, but there are often more tax-efficient ways to give.

One powerful tool to consider is a Donor-Advised Fund (DAF). These offer several advantages…

  • Seamless donation of appreciated securities without triggering capital gains taxes
  • “Bunch” multiple years of giving into one to maximize your deductions
  • Contributions can grow tax-free until you are ready to grant
  • One tax receipt instead of many

If you are over age 70.5, you may also consider a Qualified Charitable Distribution (QCD), which involves making a direct transfer of money from your IRA to a qualified charity. This can potentially satisfy your Required Minimum Distribution while reducing your taxable income.

Both DAFs and QCDs are tools to consider if you are charitable.

5. Do I have any large expenses upcoming?

With the stock market (as measured by the S&P 500) now back in positive territory for the year, it’s wise to set aside cash for upcoming expenses – whether it’s a new car, a home renovation, or vacation.

By earmarking funds in advance for short-term needs, you give your longer-term investments the freedom to stay focused on growth without the pressure of sudden withdrawals.

6. Are all my monthly subscriptions necessary?

In today’s world of auto-renewing subscriptions and one-click Amazon purchases, it’s easier than ever to spend without noticing. The convenience is nice – we no longer need to pull out our checkbook, and we rarely need to check our bank statement. The downside is that it leads to mindless spending due to the lack of awareness and intentionality.

The summer is a great time to take an inventory of monthly subscriptions (streaming services, apps, memberships) and ask yourself: Am I actually using this?

7. Do Alternatives and/or Private investments belong in my portfolio?

In 1996, there were over 8,000 publicly listed companies. In 2024, that number has dropped to around 4,000. Meanwhile, of businesses generating more than $100m in annual revenue, 87% remain private, with only 13% publicly listed (source: Blackstone).

As private companies now represent a larger share of the economy, the financial industry has evolved. There is now a range of products, known as Alternatives Investments, that provide access to these private markets.

Alternatives may include:

  • Private Real Estate
  • Private Credit
  • Private Equity
  • Hedge Funds

These investments are typically illiquid, meaning your money may be tied up for a period, and they carry risk, just like any investment. After all, There’s No Free Lunch.

Note: Alternative Investments typically require the investor to be either a(n):

– Accredited Investor (earned income exceeding $200,000 (or $300,000 with a spouse) for the past two years and reasonably expect the same for the current year, or if they have a net worth of over $1 million, excluding their primary residence.

– Qualified Purchaser (own at least $5 million in investments excluding primary residence and business property.

However, with careful due diligence, we believe Alternatives can complement a Dividend Growth portfolio and thus play a valuable role in portfolio construction.

If you’re interested in learning more about our approach, we’d be happy to share David Bahnsen’s white paper, Why and How We Use Alternatives. Just email us at to request a copy.

How’d Those Mid-Terms Go?

Now that you’ve reflected on the questions above, we hope this “mid-term exam” will help you as you head into the second half of 2025.

If any action items surfaced as you read this article, we’d love to hear how we can help. Reach out to your advisor or contact us directly at . We’d love to support you.

With Independence Day around the corner, we will take a one-week break and will return with our next Thoughts on Money the week of July 7th. Enjoy your holiday, and God Bless America!

Blaine Carver
Private Wealth Advisor

Trevor Cummings
PWA Group Director, Partner

The Bahnsen Group is registered with Hightower Advisors, LLC, an SEC registered investment adviser. Registration as an investment adviser does not imply a certain level of skill or training. Securities are offered through Hightower Securities, LLC, member FINRA and SIPC. Advisory services are offered through Hightower Advisors, LLC.

This is not an offer to buy or sell securities. No investment process is free of risk, and there is no guarantee that the investment process or the investment opportunities referenced herein will be profitable. Past performance is not indicative of current or future performance and is not a guarantee. The investment opportunities referenced herein may not be suitable for all investors.

All data and information reference herein are from sources believed to be reliable. Any opinions, news, research, analyses, prices, or other information contained in this research is provided as general market commentary, it does not constitute investment advice. The team and HighTower shall not in any way be liable for claims, and make no expressed or implied representations or warranties as to the accuracy or completeness of the data and other information, or for statements or errors contained in or omissions from the obtained data and information referenced herein. The data and information are provided as of the date referenced. Such data and information are subject to change without notice.

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Hightower Advisors do not provide tax or legal advice. This material was not intended or written to be used or presented to any entity as tax advice or tax information. Tax laws vary based on the client’s individual circumstances and can change at any time without notice. Clients are urged to consult their tax or legal advisor for related questions.

This document was created for informational purposes only; the opinions expressed are solely those of the team and do not represent those of HighTower Advisors, LLC, or any of its affiliates.

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About the Authors

Trevor Cummings

Private Wealth Advisor, Partner

Trevor is a Partner and Director of our Private Wealth Advisor Group.

As the author of TOM [Thoughts On Money], Trevor endeavors to write and speak about financial concepts and principles in a kind of “straight” talk demeanor and posture.

He received his Bachelor’s degree in Organizational Leadership from Biola University and his MBA from California State University, Fullerton.

Blaine Carver, CFP®, CKA®

Private Wealth Advisor

Desiring to be a financial advisor since high school, Blaine has continued this passion by stewarding client capital for over a decade. A patient educator, he enjoys aligning clients’ financial resources with their values, particularly through creative charitable gifting strategies.

Blaine holds a Bachelor of Business Administration in Finance from Seattle Pacific University, where he also led the soccer team as captain.

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