Matthew Bouthillette CFP, EA, Oak Leaf Wealth Management

Matthew Bouthillette CFP, EA, Oak Leaf Wealth Management Matt is a CFP® and Director of Tax Planning at Oak Leaf Wealth Management.

He works with individuals and families to implement specialized financial strategies with the goal of inching closer to their desired ‘next phase’ of life.

Are you taking a proactive approach to your wealth, or are you just reacting to tax season?Tax planning has always been ...
12/29/2025

Are you taking a proactive approach to your wealth, or are you just reacting to tax season?

Tax planning has always been a pillar of sophisticated wealth management, but lately, it’s become a hot topic—and for good reason.

However, there is no "magic bullet" in this arena. Context is everything, and a strategy that works for one family might not be right for yours, and nor should it be!

We believe in transparency and education tailored to your specific circumstances. That’s why we’ve launched our YouTube channel!
We’re hoping to share snippets of how we work to educate and assist clients on their individual journeys

Please join us in viewing, we’d love to hear from you:

06/27/2025

ROTH CONVERSIONS

This is a great opportunity for tax efficiency, however, it is not a one size fits all strategy:

You should consider ROTH conversions during years of:
• Lower income – i.e. sabbatical or in between jobs
• Early on in retirement or prior to Required Minimum Distributions = anticipation of being in a higher tax bracket down the road
- Performing ROTH conversions early on to reduce your RMD level, while withdrawing these pre-tax dollars at a lower tax bracket
• Prior to turning on Social Security Benefits

Situations to watch out for:
• If you convert while you are still working, understand that the amount you convert will be tacked onto your overall income
- This could lead you to bump up into a higher marginal tax bracket
• If you perform conversions while collecting Social Security, benefits you will likely increase the taxable amount of your benefits – this can be avoided with proper planning
• ***IMPORANT - If you are under age 59.5 and plan to perform a conversion, do not have taxes withheld as part of the conversion. If you do, the amount withheld for taxes will fall under the early distribution rules, and could be subjected to a 10% penalty

For example, if you convert $100k and have $20k withheld for taxes, not only will you only convert $80k, but you will pay an extra $2,000 (10% penalty tax) on the amount withheld. Therefore, if you are performing a conversion under 59.5, be sure to not withhold any taxes on the conversion and pay the taxes out of cash!!!

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/26/2025

Balance Sheet exercise: assets – liabilities = net worth

While this can be / seems like an elementary exercise, I’ve found that having a good understanding of your balance sheet can uncover inefficiencies and opportunities for improvement:

• Consolidating investment accounts from previous employers & institutions to align with new asset allocation – plus easier record keeping
• Identifying opportunities to consolidate debt / liabilities for lower interest rates & better terms
• Asset location / tax treatment of assets (not enough assets in the tax-free & taxable buckets)
• Liquidity – not enough or too much (high cash level or too much in retirement accounts: cannot touch until age 59.5)
• Concentration Risk – i.e. company stock / business makes up a large portion of net worth
• Use net worth figure to understand if there is a risk of estate / inheritance tax now or down the road (based on primary residence state or applicable federal level)
• Identifying assets for gifting / charitable strategies

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/25/2025

Balance is key in almost all aspects of life - but especially within your finances

There is no 'one size fits all strategy' for savings, investing, spending, etc. - for some folks, having a budget to follow can drive them crazy, and actually create worst habits of preventing enjoyment today by worrying too much about the future

In my experience, clients who derive the most enjoyment from their money today have balance around spending, investing, etc. - sure they worked hard to build up some level of assets to have this choice and flexibility -

But through it all they focused on spending on what THEY value, not what will make them look 'wealthy' or make them feel good for a day or so - sometimes we do not realize how easily we spike the credit card to buy something we simply do not need

Diving into what you truly value and want out of life can often be the key to financial peace - both in numbers and mindset

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/24/2025

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

To recap - beneficiary designations are the person(s) you elect to receive a specific asset(s) upon your passing. Usually, a spouse is listed as a primary beneficiary (first), if this spouse is deceased at the time of the account owners passing, the contingent beneficiaries will kick in (second in line) – this could be children, relatives, friends, etc.

o This election is called a ‘Transfer on Death Registration’ (TOD) for a taxable investment account (non-retirement)
o For bank accounts, this is commonly called a ‘Payable on Death Registration’ (POD)

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, etc.

Recently, I came across two separate situations where the ex-spouse was listed as a beneficiary on life insurance and a 401k plan – as you can imagine, this is not the intended beneficiary – I helped these folks update the election ASAP

You work your butt off to build up these assets, it is more than worth it to protect them and ensure they pass on to the correct person(s)!!

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/23/2025

In my experience working with clients, I believe they key to operating an efficient financial household is to have a good handle on your cash flow - whether your household earns $150k/year or $750k/year

It is important to at least have an idea of the following figures (ballpark): inflows / outflows
-Monthly income (net) / living expenses
-Contributions to retirement accounts
-Amounts being paid towards federal / state income taxes, property taxes
-If you have a surplus each month - where is it going?

Too often I encounter folks who objectively make a healthy household income, but do not have liquid funds available to cover simple household / car expenses, additional taxes owed, etc.

Not having a good gauge in this area could lead to illiquidity problems and put you in a position to take on unnecessary consumer debt, dip into your retirement savings early (could be subject to taxes and penalties, not have the ability to take advantage of investment opportunities, or have the cash for a down payment on that lake house you have been eagerly waiting to come on the market...

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/20/2025

A few clients I have would not be able to make the retirement decision pre age 59.5 as easily if they did not plan ahead and healthy fund a taxable brokerage account

While the pros and cons are becoming more visible (which is a great thing!!!) I do find that they are still highly underutilized

When used properly they can provide choice & flexibility from an investment, tax, and liquidity perspective:

• No contribution limits
• No early withdrawal penalty to access funds
• Assets held longer than 1 year then sold are subject to capital gains rates (15% for most people at the federal level - plus state and NIIT if over the limits) – could do some planning to pay 0% on the federal level
- Assets held less than 1 year then sold are subject to income tax rates
• Potential opportunities for tax loss harvesting (can utilize up to -$3,000 of loss per year to offset ordinary income)
- You can borrow against the account balance to purchase real estate, facilitate home improvements, provide liquidity without selling assets in the account and paying capital gains taxes

All investing involves risk, including the possible loss of principal. There is no assurance that any investment strategy will be successful.

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/19/2025

Retiring with purpose is often the goal, yet few consider what they are retiring 'to'

I have had a few clients this year who were given the 'early retirement option' by the Federal Government - all 4 clients are more than capable from a financial standpoint to retire - even if bills were passed that affected healthcare coverage and pension amounts

However, only 1 is truly ready mentally to retire - the remaining 3 clients are simply not there yet, and they may never be ready - the one client already has plans to do some small consulting gigs and pick up a part-time shift at the golf course

I have had several conversations with these 3 clients, and they all concluded they are not ready to give up their work - they have quite a bit of purpose and passion for their current projects

Additionally, they all at some level recognized that they would not know what to do with themselves if they did not work - 'I have enough assets to sleep well at night but I am not sure I would have enough purpose to get out of bed in the morning'

Answering the question of purpose is just as important as confirming you can retire from a financial standpoint

For a comprehensive review of your personal situation, always consult your legal advisor. Neither Cetera Advisor Networks LLC, nor any of its representatives may give legal advice.

06/18/2025

Perspective can be just what you need, especially when you feel as if you have not made any progress

New planning clients - 50 years old, solid household income, 3 children - all out of college with stable jobs, apartments, soon to be spouses....

Both clients felt they are very behind on retirement savings, they are scared they will not have enough funds to help their children pay for weddings, down payment on first home, 'I will be working until I am 90 years old'

I stepped back and highlighted that they have:

-Paid off their mortgage 5 years ago
-Put all three kids through college wouldn't incurring any debt
-They are free from any consumer debt; car loans, credit card debt, student loans, etc.
- They have 10-12 years to gradually increase retirement savings (goal is ages 60-62 to retire)

These clients have accomplished a great deal to date - despite all this they still have $250k saved in retirement accounts

They have done the parent duty of giving their children a wonderful life, but now the focus needs to shift to themselves - to ensure they will be OK in the longer-term. As a parent, this can be very difficult to let go....

Fast forward a few meetings later, we confirmed that by increasing what they are already contributing to 401ks by 5%, and systematically savings for bigger ticket items - they are on great pace to retire when they desire

Simple tweaks and a bit of perspective can sometimes make all the difference!

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/17/2025

Clients recently purchased a second rental property out of state - this is a place they love to travel to and plan to eventually move to:

All was going well for 2 months after closing - then a few bumps in the road:
- The town was sending them letters concerning approval to rent the property; they are not able to rent the property until this approval process is complete
-$10,000 plumbing issue
- Current daycare for their children abruptly closes - the new one they found is $1,500/month more

With this in mind, during our recent call I suggested they both reduce 401k contributions by 5% each, and cut down their contribution to their taxable account from $3k/month to $1k/month until this irons out

These adjustments will allow them to stay afloat and feel more secure, without sacrificing their longer-term plans

They were relieved when I suggested these changes, as they did not know how they would weather this storm - true planning centers around adapting efficiently to changes as life evolves

If you just base your decisions on 100 page financial plan output, you may be causing more stress than necessary

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/16/2025

Communication and mutual respect matters - ESPECIALLY amongst professionals in your circle

Recently connected with a CPA over coffee to discuss a client referral I sent over - this was the first time I worked one on one with this specific CPA, as it was a new relationship

I came prepared with the tax letter I provided the clients to assist them with doc gathering for 2024 taxes, tax projections we worked off for 2024 and now 2025, which are updated through the year to make informed decisions concerning estimated payments, withholding amounts from W2s (including documentation on AMT implications from ISOs in 2024 and for 2025 plans), documentation of the back-door ROTHS we completed for both spouses in 2024 and plan to for 2025

I provide this service to assist both the client and their CPA

The next 90 minutes was spent discussing how this type of planning and relationship management between the client and professionals is extremely vital to even come close to a positive outcome for the client - we agreed this was been very much lacking in other relationships we have had with professionals

There are many great advisors out there doing impactful tax planning, but we still have many more to go

For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Neither Cetera Advisor Networks LLC nor any of its representatives may give tax or legal advice.

06/13/2025

Designing a proper estate plan is a crucial piece of one's financial puzzle...

Often times folks will mention that they do not need to plan here because their 'asset level is too small', their 'situation is fairly simple' or because 'taking action is very expensive'.

When in reality, the cost of not doing anything can far outweigh the upfront cost to execute these documents if something were to transpire.

In addition, some of the planning in this area can actually protects a family's assets while they are living, versus being perceived as only useful if someone passes away.

For a comprehensive review of your personal situation, always consult your legal advisor. Neither Cetera Advisor Networks LLC, nor any of its representatives may give legal advice.

Address

598 Great Road
North Smithfield, RI
02896

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