Tax season comes with a lot of moving parts. A missing form, incomplete data, or a late reaction can cost you time and money. Our goal is simple: carry some of that load so you don’t have to.

At Hill Investment Group, we think about taxes all year, because after-tax outcomes matter. Taking the Long View means managing what you keep, not only what you earn.

What we do year-round

Tax awareness is built into the daily work behind your portfolio. 

We place tax-heavy investments in the right accounts to reduce avoidable drag. 

When the opportunity exists, we harvest losses to offset gains while keeping your strategy intact. 

We lean on ETFs where appropriate, which tend to avoid the surprise capital gain distributions that show up in many mutual funds. 

When cash flow, withdrawals, or charitable giving are part of your picture, we help coordinate the timing and structure so everything stays aligned with your plan.

What we do during tax season

Tax season should feel orderly. For clients where we manage the full relationship, we coordinate directly with your tax preparer, track form releases and revisions, and prepare a clean packet with the core reports your CPA needs. 

No hunting through portals, no guessing which forms matter.

For clients earlier in their journey with us, many of these same principles are at work in how we manage your portfolio, and we’re always happy to point you in the right direction.

The goal, as always, is to make this easier for you.

What you still need to handle yourself

Some items live outside Hill, like W-2’s,  old employer retirement plans, accounts held elsewhere, K-1s, and certain custodian forms.

Easy to miss items

• IRA Form 5498: Useful for keeping contribution and cost basis records accurate over time.
• HSA Form 1099-SA: Required if you took money out of an HSA.
• Qualified charitable distributions: Your 1099-R will not label a QCD for your CPA. However, if we facilitated it, we would help send a list to your CPA.

If you want to talk through tax planning as part of your broader plan, reach out to us at service@hillinvestmentgroup.com.

We are pleased to formally introduce Sarah Larsen, our Executive Operations Lead at HIG.

Many of you may have already interacted with Sarah. Over the past year, she has supported our team in a part time capacity and has recently joined us full time as the operational and organizational backbone of the firm.

Sarah’s work spans executive support, people operations, finance, and firm administration. Her role is designed to help our leadership and advisory team stay focused on what matters most: serving you well, thoughtfully, and consistently.

As part of our recent expansion of service hours, you may hear Sarah’s voice if you call later in the day. Her presence helps ensure that when you reach out to Hill, there is a steady, capable person on the other end who knows our team and how we work.

Sarah brings more than eight years of experience running her own administrative support business, following an earlier chapter in advertising. While she enjoyed building and leading her own firm, she was drawn to HIG’s culture, values, and people. When I approached her about stepping into a full time role, it felt like a natural fit and the right place for her to do her best work.

Known for her curiosity and can-do mindset, Sarah is a lifelong learner who is not afraid to jump in, figure things out, and move important work forward. Her focus on building strong support systems helps our leadership and advisory teams operate at their best so we can continue delivering thoughtful guidance and strong long-term outcomes for the families we serve.

Based in Seattle, Sarah lives with her husband Patrick, their two children Luke and Piper, and their dog Rosie, a Cavapoo. A California native, she has fully embraced life in the Pacific Northwest, rain included.

We are grateful to have her on the team and excited for the ways her work strengthens the Hill experience for our clients.

Recently, we hosted a review meeting with a longtime client. He leaned back in his chair and asked a question I could tell had been on the tip of his tongue all meeting, “Is Social Security going to be there for us when we can take it?” His voice was half-joking, but his eyes told me this was a question he’d been pondering for a while.

A few weeks later, in a meeting with a much younger client, a similar question came up as we reviewed her Longview Analysis. “We should probably assume we won’t get any Social Security,” she stated. “I keep hearing it will be gone by the time my generation retires.”

Social Security is one of the default income streams we have built into our planning, but there are plenty of headlines warning that it is “running out of money”. So are we crazy to plan assuming that it will be around?

The short answer is no. And part of taking the Long View is remembering that headlines are designed to grab your attention, not necessarily to give you the full story. When we step back and look at the complete picture, Social Security is often far more durable than the news cycle suggests.

Much of the anxiety around Social Security comes from the annual reports released by the Federal Old-Age and Survivors Insurance (OASI) and Federal Disability Insurance (DI) programs projecting their Trust Funds to be depleted by 2035. These Trust Funds are simply reserves built up during years when Social Security collected more in payroll taxes than it paid out.

As Baby Boomers retire and live longer, benefit payments now exceed annual contributions, which means the reserves are being drawn down. But what the headlines often leave out is that the Trust Funds are not the system itself. Even if the reserves are depleted, workers will still be paying payroll taxes every paycheck, and those ongoing taxes are currently projected by the Social Security trustees to continue funding roughly 80% of benefits.

The problem Social Security faces is primarily a math problem, not an existential one. And the math problem has multiple straightforward fixes that have been discussed for years, including:

• Increasing the Social Security payroll tax rate modestly
• Subject all wages to Social Security payroll tax (remove the current cap)
• Reduce current and future benefits
• Reduce only the future beneficiary’s benefits
• Raise Full Retirement Age
• Slow benefit growth for top earners
• Change the way cost-of-living adjustments are made
• Some combination of two or more of these measures

Many policy experts expect that lawmakers will need to make adjustments over time, although it is uncertain which combination of tools they will choose. Social Security is a significant program that is relied upon by many Americans. More than 70 million Americans receive benefits today, and nearly every worker contributes with the expectation that those benefits will be there when they retire.

It remains one of the most consistently popular programs in the country and has been the backbone of American retirement for generations. That level of reliance and public support is one reason many policymakers focus on keeping it solvent.

At Hill, we plan based on data and evidence, not speculation. For clients nearing retirement, we typically model full benefits under current law. For younger clients, we still model full benefits, but we review scenarios that assume reductions so your long-term plan stays durable regardless of what policymakers decide. These scenarios are planning tools and do not represent predictions about future legislation. What we do not do is assume Social Security will disappear. The evidence available today does not point in that direction, and the popularity of the program makes that outcome appear extremely unlikely, although future changes to the program are always possible.

Of course, if you’d like us to assume a “doomsday” scenario where no Social Security” system exists, we’d be happy to model it for you. But for many clients who’ve been consistent savers over the years, they will learn that they will still be fine without the additional income from Social Security.

While it is true that Social Security is under strain, it is not collapsing. The headlines sound alarming because uncertainty sells, but the reality is far more stable and manageable.

If you have been feeling uneasy about what this all means for your plan, let’s talk. We want you to understand the system, understand your plan, and feel confident about the path ahead.