Our Approach

We will help you align your time and money with what you value most.

Initial Retirement Planning Process

  • 1. How Much Can I Spend?

    First, we’ll get an idea of what you might be able to spend in retirement given your resources and obligations.

    You spent your working life more or less knowing what you could safely spend based on what you earned. That paradigm shifts in retirement, and it’s our job to help you navigate it.

  • 2. Explore Options

    Next, we’ll explore some options for special goals, contingency planning, and tax optimization.

    Maybe you are considering a big move, a large purchase, a second-act career, or a long bucket list. We’ll look at the impact on your spending capacity and tax strategies to fund your goals efficiently.

  • 3. Implement Your Plan

    Together, we’ll pick an initial plan and start implementing the action items in order of urgency.

    We will help you shoulder the burden of implementing your plan and tracking the details so that you have the confidence and freedom to live your life.

  • 4. Monitor the Plan & Adjust as Needed

    We will monitor the plan to keep your financial life on track. We will let you know when a change is needed or looks likely. and we will adapt to new challenges and opportunities as life unfolds.

    We typically meet with clients 2-3 times per year, but we’re always on call and we will proactively reach out to you when there’s a need or opportunity.

We avoid lengthy binders with complex spreadsheets and charts

These “door-stop” plans give a false impression of precision and gravitas (and most people never read them). A financial plan has a short shelf life anyway because your life and the world are constantly changing. We believe planning is an ongoing process, not a binder. You need a plan that’s distilled down to the essentials and empowers you—without overwhelming you. Let us track the details and crunch the numbers so that you can focus on the big picture.

Our Investment Approach

We take a disciplined and long-term approach to investing. We aim to minimize unnecessary or hidden fees that can eat into returns over time, and manage for tax efficiency without sacrificing returns. Together we’ll create an investment allocation that is diversified across asset classes and aligns with your goals and risk tolerance.

We are not “stock pickers” or “yield chasers.” Achieving above-market returns over the long term is exceedingly difficult (some would say impossible). We believe you will have the best chance of reaching your investment objectives by sticking to a good plan, avoiding common pitfalls, and managing emotional biases.

Want to learn more about our approach?

Check out this FREE GUIDE

Whether you're looking to retire at 35, 65, or never, beware of these 10 common myths that can keep you from reaching your goal (or keep you from being happy once you get there).

  • Too many advisors don’t spend the time it takes to learn what it costs to be you, but cash flow analysis forms the backbone of any thorough financial plan. It’s critical to understanding your current financial situation and making meaningful projections. This is true whether you’re facing a major life transition or just need help answering the question, “Can we afford this?”

  • We start by asking the question, what does retirement mean to you? Do you plan to work until you’re 65 and then clock out and hit the golf course every day, or are you considering another road? With changes in generational attitudes toward work and retirement, more and more individuals are looking to make work optional, have multiple mini-retirements, start a business, or embark on a passion project. Maybe you’ve seen your parents struggle to find meaning or purpose after retiring, or you have seen an unexpected illness cut short someone’s dream retirement. You want to enjoy yourself now and still make sure you’ve got your bases covered, especially as life expectancies continue to rise. Retirement planning includes detailed modeling, scenario analysis, and savings and distribution strategies to maximize your after-tax net wealth and make sure you don’t outlive your savings.

  • Whether you want us to manage your investments or you’d just like a second opinion, our holistic approach to financial planning makes us ideally situated to make ongoing investment recommendations that are tailored to your unique situation and goals. We believe in taking a disciplined and long-term approach to investing; we strive to generate superior risk-adjusted returns through customized allocations, diversification across sectors and asset classes, low turnover, tax-efficient asset location, low fees, and by managing emotional biases. Having a solid investment plan will not only give you the confidence that you’re well positioned for the future, but it will also serve as a check against costly impulses to sell when markets are weak or speculate on the latest market fads.

  • Debt can be a tool for reaching your goals or an albatross around your neck. Whether you have mortgage debt, or student loans, or you’re embarrassed about carrying a credit card balance, we’ll create a plan to pay it down in a way that is optimal for you. How you manage debt is just as important as how you invest your savings and it can be just as fraught with emotional as well as technical considerations.

  • Because we don’t sell insurance or receive any commissions, Oakleigh can offer objective advice to be sure you have the coverages you need, and nothing you don’t. We will consult on health insurance, Medicare options, life insurance, property and casualty insurance, disability income insurance, long-term-care policies, and other insurance products such as annuities. We can make referrals to reputable insurance products and agents to assist in implementing your plan.

  • We’ll review your recent tax returns to be sure that you’re taking advantage of every savings opportunity available to you. However, the real value in working with us for tax planning is our ability to project your future income and tax liabilities to create a tax strategy that gives you the greatest net-after-tax results. While we don’t prepare taxes, our unique perspective as holistic financial planners and investment managers gives us the foresight and tools to organize and implement longer-term tax strategies.

  • Education can be one of the biggest expenses outside of homeownership for most families, but also one of the greatest gifts a parent or grandparent can give to a child. We’ll come up with a plan that aligns with your values and your budget while taking advantage of the myriad of education funding options out there.

  • Owning or managing a small or large business creates some exciting opportunities to benefit from holistic financial planning. If you’re thinking about starting a business, we can help review your business plan and assess how it will impact your family’s finances. If you already own a business, we’ll review your financial statements and outlook. We can help you manage the interplay of your personal and business finances, consult on retirement plans and other benefits options to maximize owner tax savings, help you manage around variable income, and plan for growth and transitions.

  • Estate planning can be an uncomfortable subject for many families, and so often we just avoid it, even when many of us have seen the sad consequences of the lack of a plan. Navigating these important conversations requires the sensitivity and skill of a good counselor as well as financial expertise. End of life and estate planning are important parts of our holistic offering for any age client. We’ll review your wills, powers of attorney, advance directives, and beneficiary designations to be sure that your wishes will be carried out and the people you love will be cared for.

  • Like it or not, money touches so many areas of our lives, and it is often a central concern in any major life event. Having a clear picture of your values and goals along with your financial constraints can help to reduce anxiety and refocus on what matters most. Whether you’re facing a career change, divorce, loss of a loved one, a major windfall, or a devastating setback, we’re here for you, no matter what comes your way.

Practice Areas