Approaching Retirement?
You Have Questions. We Have a Plan.
Retirement isn’t just about having enough. It’s about knowing you have enough—and understanding exactly how your money will work for the rest of your life.
Does This Sound Like You?
- You’re within a few years of retirement—or recently retired—and the biggest question on your mind is: “How much can I spend without running out of money?”
- You have retirement accounts, Social Security, maybe a pension—but no clear picture of how all the pieces fit together or where your cash flow will actually come from.
- You have taxable accounts and are concerned about taxes.
- You are considering early retirement and would like to avoid penalties for early withdrawals.
- You know there are tax strategies you should be taking advantage of—IRA to Roth conversions, tax bracket management, Premium Tax Credit for health insurance, IRMAA planning for Medicare—but you’re not sure when to do them or how much.
- You’re paying for health insurance before Medicare and wondering how to manage that cost without triggering higher premiums later.
- Your accounts are spread across multiple custodians from different stages of your career, and nobody is coordinating them.
- You know your investment strategy needs to change. Your money needs to grow but you can’t stand to see it lose value.
- You have an estate plan that hasn’t been updated in years, or you’re not sure your beneficiary designations are still correct.
- You are told you need a trust but are still unclear why.
- Your loved one passed away leaving you in charge for the first time and need help. Fast.
- You’ve worked hard your entire career. Now you want someone to help you make sure you don’t make a mistake with the money you’ve built.
If any of this resonates, you’re exactly who we work with.
How Highland Helps You Retire with Confidence
The first years of retirement offer an incredible window of opportunity.
Balance Sheet Optimization
We first help organizing all of your accounts in a way that you can more easily understand what you own, where it is held, and how it can be accessed to support your retirement goals.
Retirement Income Planning with Guardrails
How much can you spend? Where will the cash come from? We build a year-by-year retirement income plan that answers these questions with clarity—not guesswork. Our guardrails approach adjusts as markets and life change, so you be more confident that you are on track. It is built into our investment approach.
Tax Aware Investing Strategies
A little foresight and planning can go a long way towards strategically reducing the tax burdens of investing as part of a comprehensive approach.
IRA to Roth Conversion Roadmap
Most families have built their wealth inside tax-deferred retirement accounts through employer 401k plans or Individual Retirement Accounts (IRAs). The first years of retirement offer an incredible window of opportunity. We build a multi-year IRA to Roth conversion plan that fills your low tax brackets, reduces future Required Minimum Distributions, lowers IRMAA costs, and may materially reduce lifetime taxes.
Social Security Optimization
When should you claim? Which spouse should claim first? How does timing affect your taxes, IRA to Roth conversions, Medicare premiums, and long-term income? We evaluate the decision from every angle—breakeven, longevity, tax impact, and spousal coordination—so you make the right call.
Tax Planning by a CPA
Highland’s team includes licensed CPAs who perform tax analysis directly—and in coordinate with your tax preparer. We identify opportunities like Roth conversion timing, asset location optimization, income bracket management, and tax-exempt strategies that most advisors miss.
Medicare & IRMAA Management
Medicare premiums are based on your income from two years prior. Without careful planning, a single large IRA withdrawal or capital gain can trigger thousands in additional premiums. We manage your income to minimize IRMAA surcharges while still executing your tax strategy.
Health Insurance Before Medicare
If you retire before age 65, health insurance becomes one of your largest expenses. We help you evaluate marketplace plans, understand how the Premium Tax Credit works, and structure your income to maximize the subsidy.
Estate Planning Coordination
Let’s have a long talk about your situation to better understand what your intentions are for your family when you are no longer here. We can work through your assets to better understand how things transfer. We coordinate with your estate planning attorney to help ensure your documents are aligned with your wishes. Then we help ensure beneficiary designations, account titling, deeds, and trust structures are properly updated. When life changes—a marriage, a death, a new grandchild—we prompt you to update your plan.
Investment Management
Your portfolio should reflect your retirement timeline, your income needs, and your tax situation—not a generic model. We manage your investments with a disciplined approach using diversified, low-cost portfolios. Every decision is made in the context of your overall financial plan.
Estate Administration
When a loved one passes away, you may have found yourself responsible for settling their affairs. The entire process can be confusing and time consuming. We can help with the organization and coordination.
Why Families Choose Highland
The Expert Generalist Approach
Our advisors hold the CFA, CPA, and CFP® designations—a rare combination of investment, tax, and planning expertise. This means your advisor doesn’t just manage your portfolio. They understand how your investments, taxes, retirement income, and estate plan interact—and they coordinate all of it.
Fee-Only, Independent, Fiduciary
Highland is a fee-only firm. We don’t sell products, earn commissions, or receive referral fees. Our only obligation is to you. As an independent, SEC-registered investment advisor, we are legally and ethically bound to act in your best interest.
The Professional Reimbursement Option (PRO Plan)
Highland’s PRO Plan provides a management fee credit to reimburse the cost of your independent CPA or estate planning attorney, up to a set limit. This means comprehensive tax and estate planning coordination at no additional out-of-pocket cost to you.
A Relationship, Not a 1-800 Number
You won’t speak to someone new every time you call. Highland advisors build long-term relationships with the families they serve—staying by your side through retirement, market volatility, life transitions, and the decisions that matter most.
Boutique Independence
Highland is privately owned and independent. We are not a branch office of a national firm, and we are not beholden to corporate mandates or proprietary products. Our independence means we find the right solutions for you and your family—not what corporate told us to sell.
What to Expect
Step 1: A Conversation.
We start by listening. Tell us about your situation, your concerns, and what retirement looks like to you. There is no cost and no obligation for this initial conversation.
Step 2: We Do the Math.
We gather your financial information and build a comprehensive picture of where you stand—your income sources, your accounts, your tax situation, your estate plan, and your goals.
Step 3: Your Plan.
We present a personalized financial plan that answers your questions, identifies opportunities, and gives you a clear roadmap for retirement. This includes an IRA to Roth conversion strategy, a retirement income projection, a Social Security analysis, estate plan review, and an investment strategy.
Step 4: Implementation & Ongoing Partnership.
We don’t just hand you a plan and walk away. We implement the recommendations, manage your investments, and meet with you regularly to keep your plan on track as your life and the markets evolve.
Ready to Retire with Confidence?
Schedule a conversation with Highland Investment Advisors. We’ll listen to your situation, answer your questions, and help you understand if we’re the right fit.
31 Google Reviews, 5.0 Stars
Highland Investment Advisors, LLC is a fee-only, SEC-registered investment advisor.
175 Patrick Blvd., Suite 120, Brookfield, WI 53045 | 414-755-2309
Disclaimer: All content is for information purposes only. It is not intended to provide any tax or legal advice or provide the basis for any financial decisions. Advisory services are offered by Highland Investment Advisors, LLC, an SEC-registered investment advisor.