Questions you may be asking yourself

Cashflow Planning

When answering this question, there are two main schools of thought:

  • I can earn more on my investments than my mortgage rate so I’ll pay down the mortgage slowly
  • I will sleep better at night when my mortgage is paid off

Many financial decisions such as this one are emotionally charged.  The feeling of not having a mortgage can be very liberating and that’s worth a heck of a lot.

Finding your personal “sweet spot” on this issue involves considering your preferences in tandem with other important factors such as your  overall cashflow situation and investment plan.  No one likes being beholden to a bank, but we all want to be smart with our money too.

Help me find my “sweet spot”

If you’re just starting to save and invest money for the long-term, the answer is to fund retirement first. Why? Because you can borrow against retirement savings to fund college, but you can’t borrow from college to fund retirement.

If you’ve already built up some good retirement savings, it may be worth taking a look at specialized college savings vehicles, such as 529 plans. However, before you rush to open an account, it’s good to understand all the pros and cons of different savings vehicles and consider them in light of your personal goals and preferences.

Want more guidance on this issue? Tell us about your situation…

This is the primary financial concern for millions of people. There’s a delicate balance between saving money for later and enjoying your life today. To help answer this question, people often turn to well-known modes of thought, rules of thumb, and “products” of various types which can be helpful if considered in a vacuum. Yet, for most people, these approximations rarely match up smoothly with their goals or reality.

To cut through this noise of competing soundbites, folk wisdom, and sales pitches, the first step is to get clear on the various income streams you will have in retirement, such as pensions and Social Security, and build a budget for your living expense “needs” and “wants.” From there, you can determine how much money you will need from your investments in retirement, and when. Finally, you can identify the several distinct “financial phases” you hope to travel through in your retirement and map out a gameplan that thoughtfully balances your desire to spend and enjoy on the one hand, and your concern to preserve and prolong on the other.

Help us map our our retirement gameplan.

No.
Well, probably not. When was the last time your investment advisor spoke with your CPA? When was the last time your CPA reviewed your investments to see where you can reduce taxes? This type of work rarely happens because the “siloed” model of financial services leaves you playing the quarterback. To address this, many of the wealthiest families in America form a “family office,” where all of their financial professionals operate under one roof in a collaborative atmosphere. In the real world, where the rest of us live, this type of service is hard to find, as most financial professionals, such as insurance agents, investment advisors, and accountants, provide specialized services and “stick to their knitting.”

Fortunately, there is an alternative: a professional financial quarterback who can turn your cluster of “silos” into a collaborative, proactive, well-informed team, so that you can once and for all take charge of your situation.

Tell me more about financial quarterback services.

Sometimes not knowing where your money is going causes anxiety and shame, preventing you from contacting a financial planner. Everyone has “financial baggage” and we help you feel at ease sharing your situation with us. We help you go from cloudy to clarity, leading to greater confidence in your financial decision-making. We work with you to understand:

  • How much you are earning
  • How much you are paying in tax
  • How much you are spending
  • How much you are saving

Once we get clear on the answers to these questions, we can you mobilize your resources in pursuit of your goals. We can help you make sure you are doing the best you can with what you have.

Help me figure out where my money is going.

Insurance Planning

A lot of people buy life insurance when their kids are young and a pre-mature death would leave the rest of the family in severe financial hardship. But it’s rare that the agent who sold you your insurance policy 10 or more years ago has kept in touch. By understanding your complete financial picture we can help determine if it makes sense for you to cancel your term life insurance or “cash out” from your permanent policies. In some instances, though, it may make sense to increase or extend your coverage.

Help me figure out what to do with my old life insurance policies

Like many financial planning questions, the answer depends on a number of factors including but not limited to:

  • Your family health history and longevity
  • The degree to which a long-term care need would impact your financial resources
  • Your desire to leave money to your kids

For some, the best plan is to rely on savings, assistance from family, and government aid. For others, there are an assortment of specialized insurance policies that can provide valuable protection and also incentive to go out and get care as soon as it would improve your quality of life. If you’re young enough, it may even make sense to set up a special “break glass in case of emergency” investment fund earmarked for this ultimate “long-term” objective.

Help me figure out my best planning strategy for long-term care

This is often a heart-wrenching question that lacks an easy answer. So much depends on family dynamics, including the individual financial status of multiple households and the personal values of parents, children, siblings, and other relatives. The answer begins with open, honest, and carefully-facilitated conversations, followed by thoughtful analysis and well-informed planning that considers the many different sides of this issue for everyone involved. If you find yourself worrying about your parents’ financial resources and want to unlock your potential to help in a respectful and efficient manner.

Tell us your story.

You probably have many options, including:

  • Withdrawing or “borrowing against” the cash value
  • Using the cash in the policy to purchase a different policy via a tax-deferred exchange
  • Keeping the policy unchanged, including making ongoing premium payments
  • Modifying the policy so that it is “paid-up” with no further premiums needed

Each of these options has different implications and it is important to make this decision within the context of your entire financial picture. In some situations, a new policy can be purchased that provides a much larger “death benefit” with the same or lower premiums. Other times, it makes most sense to simply cash out, be thankful that you lived this long, and either spend your hard-earned savings or reinvest it in something else.

Help me evaluate my options

In the big picture, you have four potential sources of steady monthly income in the event that you lose your ability to work due to an injury (such as a car accident) or an illness (such as cancer):

  1. Social Security: although you probably think about “retirement” before “disability” when you hear “Social Security,” the reality is if you lose the ability to do any work for at least a year, you may qualify for a monthly check from the government. That said, it may not be enough to support your current cost of living. Stay current on your benefits at www.ssa.gov.
  2. Group disability insurance: if you work for a large corporation or in the public sector, there’s a good chance your employer provides some amount of coverage. That said, make sure you know what limitations your policy has, how to qualify for benefits, and how long they would last.
  3. Individual disability insurance: although it can be pricey, this type of insurance is often the most reliable, can be customized to meet the unique needs of your household, and stays with you even if you change jobs, as long as you choose to keep it in force.
  4. Personal savings: if you have enough put away or are willing to risk “breaking the piggy bank” in case of a disability, you can always choose to “self-insure.”

Help me formulate a gameplan so I know how to stay afloat in case of a disability

Investment Planning

Many investment firms offer various types of questionnaires to this end, based on some combination of your age, time horizon, and overall appetite for risk. While these factors are certainly important, they merely scratch the surface. As a result, many investors second-guess themselves, both when the market swoons and they worry about losing too much, and when the market swells and they worry about missing the run-up.

If you really want to find out how “conservative” or “aggressive” your portfolio should be, start by defining the outcomes you want from it: how much money do you hope to get back, when, and for what purposes? Once you’ve done this, you can figure out what rate of return you need in order for your goals to be met and over what timeframe. From that starting point, you can match up the dollars you have today with a carefully-selected portfolio of investments you can live with through thick and thin, until and unless your goals change.

Sounds interesting; tell me more about this process…

It’s natural to look at your investments and judge their performance solely based on whether they have “gone up” or “gone down.” Within this paradigm, any fund that has “gone up” is “good” and any fund that has “gone down” is “bad.” Tread cautiously.

Often times an investment has gone down or up because the broader category (stocks, bonds, commodities, etc.) has gone down or up. In order to evaluate investment performance, you need to have proper expectations and then have a goal or benchmark against which to measure. This benchmark could be an index that mirrors your investment strategy or it could be something more personal, tied to the targets you need to achieve your financial goals.

In the big picture, evaluating and responding to performance is one of the most important roles your investment advisor can play. If you feel like you can’t get a straight answer, the answer is always the same, or your advisor just asks you what you want to do and then takes your order, it may be worth getting a second opinion.

I think my portfolio can use a check-up

Let’s start by stating three important facts that people often trick themselves into disbelieving:

  1. The US stock market has experienced a decline of 30% or more, on average, about once every 5-10 years as long back as anyone can remember; it will probably continue to do so.
  2. Some people can afford to ride out a severe market loss. Other people can’t. Most can afford some degree of loss, and it is possible for everyone to come up with a reasonable estimate.
  3. Nobody knows when the next “market crash” will begin, how bad it will be, or how long it will take for the market to recover. Not one person.

By focusing on these three facts, you can make an intelligent choice about how to protect your portfolio from the next crash. The first fact will give you a sense of what the “range of likely outcomes” looks like for portfolios of varying aggressiveness. The second will help you figure out how much you can afford to lose in a crash and how long you can wait out a recovery. The third fact will help you ward off all the “crystal ball jockeys” who are constantly trying to lure you into a false sense of confidence in one forecast or another.

Makes sense, but I could use some help figuring out what my stance should be

There are certain asset classes, like “large cap” stocks and government bonds, where active managers struggle to consistently beat their benchmark net of their management fees. In other areas, such as “developing market” stocks and “high yield” bonds, active managers more consistently beat their relevant passive index. To take an informed stance on this issue, start by figuring out what you already have in your portfolio:

  • In what “asset classes” are we invested, and in what proportions?
  • Are we using “active” funds or “passive” funds?
  • What are all the costs associated with the management of the portfolio?
  • What other options are available in our accounts?

From this starting point, you can begin to evaluate your portfolio on an “account-by-account, fund-by-fund” level and figure out where it might make sense to trade an index fund for an “active” fund, or vice versa.

Click here to request assistance with your portfolio x-ray

Not really understanding what your investment advisor is saying about your portfolio can be a major source of discomfort. Sometimes it’s difficult to get a straight answer or evaluate on your own what sounds on the surface to be a reasonable explanation. Most people end up just feeling like they need to trust their advisor blindly or else take their investing entirely into their own hands—both scary propositions. To help cut the tension, next time you see your investment advisor, consider asking the following simple questions and getting the answers in writing:

  • What is the purpose of each of my investment accounts?
  • What investment return are we targeting?
  • When is a reasonable timeframe to compare our actual results to our target?
  • What are the risks?

By asking these questions, you will move down the path toward becoming a more educated investor and having a more fulfilling relationship with your money.

Want us to help you start answering those questions?

Estate Planning

When you have achieved a certain degree of financial stability, it is natural to think about how your wealth might pass to your kids and grandkids. Do they have the same values and respect for money? You can help make sure they don’t squander their inheritance by:

    • Communicating and transmuting your beliefs and values about money while you are alive. We help you do this in different ways including facilitating family meetings, helping you write letters to family members, and creating legacy videos for you and your family
    • Structuring your estate plan in a manner that facilitates judicious use of inheritance.
    • Keeping reality consistent with your written wishes through appropriate asset titling and beneficiary designations.

I think my estate plan needs a check-up.

Maybe not. One of the reasons people have living trusts drafted is to avoid probate (the legal process of settling an estate). Yet, a large number of assets such as retirement accounts and life insurance policies are not “probatable” assets. We are not attorneys and don’t draft estate documents. We will educate you about various estate planning instruments, and work with your estate planning attorney to ensure that the complexity of your estate plan matches your needs.

I’d love to have a conversation about this topic without having to talk to a lawyer

Putting property into joint ownership is just one of many ways to ensure that it passes to an heir without probate if the original owner dies. However, it often introduces a host of other problems involving tax, legal liability, or government benefit issues. Although it is simple to put a property into joint ownership, there might be a much better solution for you and your family.

Help us better understand our options.

The current federal estate tax laws (2016) allow all individuals to pass a total of up to $5.45 million to whomever they choose, either during their lifetime or upon their death. Thus, a married couple with a personal net worth under $10 million may not have much to worry about. That said, many states have their own estate tax which applies at much lower levels of wealth and at rates of 10% or more. Therefore, whether you’ve built an estate worth more than $10 million or have a more modest asset base, it’s important to know where you stand, learn about your options for how to mitigate this risk (including their drawbacks), and plan accordingly.

I think it’s time to take stock of our situation and start planning.

Even if you have kept “his”, “hers” and “ours” separate, and have revised your estate documents, you may still need to do a lot of work. For example, what happens if your wife is the beneficiary of your IRA and when you pass away, she simply folds it into her own IRA, where the sole beneficiaries are her own children?

Getting into and then navigating these conversations can require a high degree of skill, patience, and sensitivity. While it may be easier to avoid having them, you will rest much easier once you’ve gained clarity on your reality, sorted through your options, and mapped out a gameplan that everyone can feel good about.

We definitely need help with this; it’s time to start planning.

Business Owner Planning

  • If this is your situation, you are vulnerable to a number of very costly and unfavorable outcomes that could result in your income declining, business losing value, and important relationships falling apart
  • The way toward a comfortable, equitable, and prosperous business relationship involves a series of structured conversations in which these potential “bad outcomes” are played out to their logical conclusion, opportunities to address them in advance are weighed and considered, and ultimately, a formal agreement comes together in which all owners of the company decide how everyone should be treated and where the money will come from if it is needed in a time of stress.

I think it’s time to start the conversation. Can you give me some pointers?


There may be opportunities and tax advantages to purchase insurance such as life, health, disability, and long-term care through your business. The first step, though, is to determine what types of insurance make sense for your situation. Given that it’s also important to understand the tax complexion of these purchases, it’s important to have your accountant or financial officer involved in the process, in addition to a good benefits consultant. Oftentimes, what we find is that business owners purchase insurance at different times, through different brokers, and lack a reliable process for reviewing what they have, making sure it’s as appropriate and efficient as possible, and getting the necessary input from other key members of their financial team.

I think my business insurance portfolio could use a holistic review

Most business owners default to a 401(k), but there are other plans that may fit your needs better and some advanced plans which allow you to shelter more money from taxes.

If you currently have a 401(k), when was the last time you reviewed:

  • How well the plan is meeting your objectives?
  • Whether you can reduce your fees?
  • The educational programs your investment advisors provide to your employees?

Let’s talk more about retirement plans.

Many family-owned businesses struggle mightily with succession planning. This is especially true when there is an “heir apparent” and other children who have either chosen a different path with their lives or who also work in the business but in non-executive roles. While the “path of least resistance” is to do nothing, it often guarantees a disaster when crisis finally hits. The best approach is to start planning now, knowing that if you do it right, it will have however much flexibility you want for change down the road. To do this well, you will need a team of advisors, including an attorney, accountant, financial planner, and possibly others. The leader of the team should be someone who has a process that begins with a thorough exploration of your personal values, goals, and vision for your family, your business, and your own life. Given that most attorneys and accountants focus on their technical expertise, you are most likely to find the right team leader in a financial planning firm with a strong business succession process.

Can I tell you about my business and see what you think?

Philanthropic Planning

When thinking about giving to charity, you can give material assets (such as clothing and electronics) or you can give financial assets (such as cash, stocks, and mutual funds). Depending on what you have and what your overall financial situation looks like, one type of asset may be more beneficial for you to give than another. Due to registered charities’ tax-exempt status, “a dollar is a dollar is a dollar” to them. By knowing which of your assets are worth “100 cents on the dollar” to you and which may only be worth “80 or 90 cents,” you can stretch your charity budget farther, make a bigger difference in the world, and leave a more impactful legacy for your heirs. If you’re looking to make a particularly large philanthropic impact through significant gifts, either during your lifetime or after your death, the difference between your best and worst options can be literally hundreds of thousands or even millions of dollars that can go to charity and your family instead of tax.

Help me learn more about charitable giving.

A lot of charitable giving is done reactively, in response to an Ice Bucket challenge, or a friend’s request to support a walk for their charity. A Giving Plan identifies specific organizations you support and how much you intend on giving in certain years. Creating a giving plan can be an extremely valuable tool for you and your family.

Help us get a head start on our family Giving Plan.