At Hill Investment Group, we often say that real financial planning isn’t about being exactly right today—it’s about being less wrong tomorrow.

That may sound strange coming from a team grounded in evidence, logic, and long-term thinking. But we also know life doesn’t follow a straight line. That’s why we believe the most valuable part of financial planning isn’t the plan itself—it’s the process of ongoing planning.

Carl Richards, a friend and fellow long-term thinker, offers a great analogy we love to share:

Airline pilots prepare a flight plan before every trip. Yet when asked how often the flight goes exactly according to that plan, the answer is: rarely.

Course corrections are built into the process because the unexpected is expected. Weather changes. Winds shift. But the destination remains the same—and they keep adjusting until they land safely.

The same principle applies to your financial life. We build your plan using the best data available—making thoughtful assumptions about returns, taxes, inflation, goals, and more. But the moment the plan is complete, we know one thing for sure: it will be wrong. We just don’t know how yet.

That’s not a flaw. It’s reality.

Real planning is what happens next. It’s the process of revisiting, refining, and adjusting—so you can stay on track, even when the world around you changes.

That’s why our team is here: not just to build your plan, but to keep you flying steady all the way to your destination.

Take the Long View.

As you may recall from last month, we asked for nominations for the Rick Hill Award — our way of recognizing someone on our team who truly embodies service, integrity, and leadership. This award is named after our co-founder, Rick Hill, whose influence continues to shape our culture.

We’re excited to share that Nick Ashby is this year’s winner! Nick’s dedication to our clients and team, willingness to step up whenever needed, and steady, thoughtful approach to challenges make him a standout. He makes our firm better every day, and we’re lucky to have him.

We also want to give a big shoutout to Nell Schiffer and Katie Ackerman, who earned honorable mentions this year. Nell’s leadership and commitment to client service are second to none, and Katie’s attention to detail and operational excellence keep us all moving forward. They both make a huge impact, and we’re grateful for them.

Please join us in congratulating Nick, Nell, and Katie! Their contributions remind us why we take the long view.

At Hill Investment Group, we’ve found that when a few clients ask similar questions, many more likely share the same curiosity. To better serve you, we’ll periodically feature this “Hey Hill” segment in our newsletter, addressing common client questions and explaining our perspective. To submit questions for future newsletters, email us at service@hillinvestmentgroup.com.

Hey Hill, should my Social Security income change how I invest?

Many investors underestimate how significantly Social Security can impact their financial plans. Rather than viewing it merely as a government benefit, think of Social Security as what it truly is—a guaranteed, inflation-adjusted income stream, similar to a bond within your portfolio.

This means your actual fixed-income allocation may be higher than you’ve realized. As a result, incorporating Social Security into your planning can allow you to take on more investment risk than initially assumed, potentially enhancing your portfolio’s long-term growth.

Clients often ask us:
– Should I reduce my stock exposure as I near retirement?
– How much investment risk is appropriate?
– How should I factor Social Security into my overall investment strategy?

Reframing Social Security as a reliable income source can help you feel more confident maintaining a higher equity allocation, improving your portfolio’s potential for growth over time.

Want to discuss how this concept applies specifically to you?

We’re here to help. Reach out at service@hillinvestmentgroup.com.