Matthew Bouthillette CFP, EA, Oak Leaf Wealth Management

08/06/2026

IT DEPENDS! Not everyone needs assistance.

^This is a common answer I give when people ask if they should be working with a Financial Planner.

Many folks are extremely self-sufficient when it comes to running their financial household - and these people typically love it. While others may need or prefer to have help on this journey.

In this week's blog, I explore a few common circumstances where it may make sense (or may not) to work with a planner - in addition to listing some good questions to ask the planner you are considering working with.

How do you know you should be working with a planning team? If you decide to interview one, what do you ask? Very common questions but very different answers depending on your needs and goals. Read on to learn more!

07/30/2026

It is not hard to find thousands of articles, books, videos covering the path to building and maintaining wealth - each with varying perspectives and words of advice (both good & bad).

What always shocks me though, is the general response to the tune of

· ‘That is all it takes?’

· ‘There has to be more to it?’

· ‘You need to make substantial money to do this’

Said differently, people are often surprised at how simple it can be to build wealth over 10, 15, 20 year time frames – building and maintaining true wealth is mostly based on only a few guiding principles

The majority of the outcomes come from discipline, not making huge sums of money – now do not get me wrong, this certainly helps, but it is not the underlying driver

So, in this week's blog we will take this topic from the opposite end, and review 7 commons mistakes I notice that hold individual / families back from building and maintaining wealth:

People are often surprised at how simple it can be to build substantial wealth over 10,15, 20 year time frames – building and maintaining true wealth is mostly based on only a few guiding principles.

07/27/2026

Navigating the initial phase of retirement or a career transition can be quite daunting from a life planning perspective, let alone from a financial standpoint

With that said, this week's blog is all about what you can consider doing with your employer-sponsored retirement plan (401k) when this transition occurs - with the hope that having a guideline can reduce some level of the uncertainty associated with this type of change...

https://www.oakleafwm.com/blog/changing-jobs-what-you-can-do-with-your-retirement-plan-simplifying-hi

07/22/2026

The term ‘Financia Advisor’ seems to be used interchangeably these days – when you add the CFP® into the mix, the water can become even more murky of what an advisor actually does for their clients; or some may say what they should or should not be doing

It seems everyone has an opinion on this – whether or not you should hire an advisor, what they should cover, how they should charge, bad or good experiences, etc. it can become quite overwhelming for folks to understand what they should be looking for

In my opinion, who you work with and what they provide to you should be indicative of what you actually need at your stage of life – there is more than one way to skin a cat, so to speak

Now, I can only touch on how we operate, but, with all the
information out there - I felt compelled to put together my blog this week solely on showcasing what we do for clients, how we do it, and why we believe this works for the clients we serve

We will walk through the process we take every single client through when they enter into a financial planning engagement. The hope is to provide a better understanding of what this type of arrangement looks like, and why it is important.

07/17/2026

Ever wonder how plans to retire are put together?

I had a little bit of fun last week creating a mock scenario, where I walk through an example of how we assist clients gear up for a new life's journey - in this case, it is retirement

While these ‘plans’ never remain stagnant, the framework helps to provide guidance as they inch closer to making the transition

Furthermore, while the financials are often thought of as the central part of making the income/expenses work, I always remind clients that their assets are simply how they will ‘fund’ their plan, they are NOT the ‘plan’ as some put it, their plan is what they will be spending their time during this next phase of life

In this blog I cover questions that many folks encounter at this point , and how we go about answering them (sometimes this is overtime as life progresses!):
• When do I start taking monies out?
• How do I do that?
• Where do I take it from?
• What could my tax situation look like?
• How will I obtain health insurance if I retire earlier than age 65 (Medicare)?
• Is my estate plan in good order?

Happy Planning!

Today’s blog will take on a little different format, instead of simply discussing planning topics - we will actually be walking through a mock scenario that showcases the power and impact planning can have.

07/06/2026

Tax planning has quickly risen to become the primary concern for many prospective clients reaching out to our team

Now, it is nearly impossible to influence changes to tax brackets or rates, but we can absolutely control our tax liability through effective, proactive planning

This isn't a last-minute task reserved for December (or worse, April, when scope is even more narrow)—it's an ongoing, year-round strategy and guess what, mid-year is a PERFECT time to take a snapshot of where you have been tax-wise, and to identify opportunities available for the second half of the year

In today’s blog, I cover a few specific areas to consider for planning strategies - real planning takes time, don’t just follow the herd and make a panicked decision

Mid-year can be a great time to consider making changes financially based on what has happened thus far, financial events you are anticipating in the second half, or even to begin thinking about open enrollment in October and November.

06/30/2026

Many folks do not think of beneficiary designations as being part of their estate plan, but in my opinion, they are, in most cases, the backbone of it!

They are crucial to any legacy plan – it is vital to ensure these are accurate and up to date

Assets that do not have a beneficiary listed or rights of survivorship generally have to pass through probate (can be a slow process depending on the state). This can typically be avoided by electing beneficiaries on various accounts / assets

Remember, these elections supersede instructions in your Will for these specific assets; think retirement / investment accounts, life insurance policies, annuities, bank accounts, etc.

In today’s blog – we will cover all things beneficiaries – and underscore why it is important to check them twice 😉

When you think of an estate plan, a Will or a Trust may come to mind. However, for today I want to bring up what I believe to be one of the most underappreciated aspects of estate planning, creating and maintaining beneficiary designations

06/23/2026

No matter how you try to figure it, Roth accounts are one of the most powerful tools we have in the 'retirement savings tool box'

You contribute after-tax dollars in, tax-free growth, 100% tax-free withdrawals after 59.5 (and the Roth has been open for at least 5 years, of course 😊) – contributions can always be withdrawn tax and penalty free

In my opinion, there is mixed advice on when you should begin contributing to Roth, how much you should contribute, and how this can affect you in the longer-term -

In today’s blog we will cover exactly what Roth accounts are, when to utilize them, and the 'rules of the road', so to speak

We will also dive into Health Savings Accounts (HSAs) - an increasingly popular tool that offers a rare triple tax advantage -when used properly!

Today we will walk through the opposite of pre-tax accounts – Roth accounts (after tax) – and we will touch on Health Savings Accounts (HSA’s), which technically are triple tax advantaged if certain criteria is met.