Ep 273: The Mid-Year Money Checkup: 9 Things to Check Before the Year Slips Away
The Mid-Year Money Checkup: 9 Things to Check Before the Year Slips Away
You change your oil every 5,000 miles or so. Nobody waits for the engine to seize up on the highway to think about it. Your finances deserve the same treatment — and we're right at the halfway point of the year, which is exactly the moment to pop the hood before a bunch of December deadlines sneak up on you.
This episode is nine things, no long story, no single deep dive. Some apply if you're a business owner, some don't — but almost everyone listening will hear at least three or four that apply directly to them.
"A fifteen-minute check-in in July is a lot cheaper, financially and emotionally, than the same conversation happening in a panic in December."
The 9-Item Checklist
- 1. The Roth Conversion Window — a lower-income or down-market year can make this the best conversion opportunity you'll get.
- 2. Charitable Giving Strategy — bunch giving or fund a donor-advised fund now, not in the last week of December.
- 3. Retirement Contribution Pace Check — are you actually on track to max out by December 31st?
- 4. Buy-Sell Agreement & Valuation Freshness Check — business owners: does that document still reflect reality?
- 5. The Mid-Year P&L Sit-Down — with your CFO, CPA, advisor, or just yourself and a cup of coffee.
- 6. The Zombie Subscription Audit — find the charges you forgot you were paying for.
- 7. Portfolio Drift Check — your allocation has probably wandered from target, even if you never touched it.
- 8. The Net Worth Snapshot — recalculate it and compare to January. Fifteen minutes, real data instead of a vibe.
- 9. Did Anything Big Happen This Year? — marriage, divorce, a new kid, a home purchase, a sale. Any of these should trigger a full plan review, not just a line-item update.
Episode Timestamps
- 00:00 — Cold open: the oil change analogy
- 02:15 — 1. The Roth Conversion Window
- 04:15 — 2. Charitable Giving Strategy
- 06:15 — 3. Retirement Contribution Pace Check
- 08:15 — 4. Buy-Sell Agreement & Valuation Freshness Check
- 10:15 — 5. The Mid-Year P&L Sit-Down
- 14:00 — 6. The Zombie Subscription Audit
- 16:00 — 7. Portfolio Drift Check
- 18:00 — 8. The Net Worth Snapshot
- 20:00 — 9. Did Anything Big Happen This Year?
- 22:30 — Close: pick two, put a date on the calendar
Got a question raised by this list? Book a free 20-minute Vision Call: weeklywealthpodcast.com/vision
Know someone who needs this list more than you do? Send them the episode — it's more useful than another group text about the weather.
Resources Mentioned
- Sellability Score — for business owners revisiting their buy-sell agreement or valuation
- Book a Vision Call
00:00 - Untitled
00:09 - Mid-Year Money Checkup
04:08 - Charitable Giving Strategies: Planning Ahead for the New Year
10:12 - Transitioning from Revenue Driver to Business Architect
10:40 - Understanding Subscription Audits
17:41 - The Importance of Annual Reviews
Well, hey everybody, here we are in July of 2026 and today we're going to talk about some mid year money checkup items that you need to be thinking about.
Speaker ANine things to check on before your year slips away.
Speaker ANow, these will apply to business owners.
Speaker AThey will apply to the mass affluent, they will apply to the high net worth, and they will apply to just the average Joe.
Speaker AMost of them are pretty applicable to all of us.
Speaker AAll right, everybody, let's get going.
Speaker AI hope that you enjoy this episode.
Speaker AAnd here we go.
Speaker AWelcome to the weekly wealth podcast.
Speaker AI am certified financial planner David Chudick.
Speaker AThis podcast and my wealth management practice are both designed to help the mass affluent to live better lives by how they handle their money.
Speaker AWe talk about financial strategies, prosperous mindsets, and simply how to build true wealth.
Speaker ASo come on and let's enjoy this journey together.
Speaker ALet's get this episode started.
Speaker ASo you change your oil every 5,000 miles or so, right?
Speaker AI mean, nobody waits until the engine seizes up on the highway to think about it.
Speaker AYou just do it on a schedule because waiting for a problem to announce itself is a bad strategy for anything that's expensive.
Speaker AYour finances need the same thing.
Speaker AAnd we're right.
Speaker ALittle bit past halfway mark of the year, which means this is exactly the moment to pop the hood before December sneaks up on you with a bunch of deadlines that you didn't see coming.
Speaker ASo today, no long story, no deep dive on any one topic.
Speaker AI've got nine things I want you to check on before the year gets away from you.
Speaker ASome of these apply if you're a business owner.
Speaker ASome apply if you're not.
Speaker AAlmost all of you are going to hear at least three or four that apply directly to you.
Speaker ASo let's get to it.
Speaker ABut before we get going, help us out.
Speaker AMake sure to follow the show on the platform that you're listening to.
Speaker AIt's a real simple ask and it helps you to get notified when all new episodes come out.
Speaker AAnd also follow us on Facebook, follow us on Instagram, and follow our channel.
Speaker AOkay, so I'm going to talk about nine things this episode, so you better listen quickly.
Speaker AWe have a lot to cover.
Speaker AThe first one is the Roth conversion window.
Speaker ASo if your income dipped this year or if the market pulled back and your account balance is lower than it was, maybe in January, this might genuinely be the best year you'll get for a Roth conversion.
Speaker AYou're converting at a lower balance and potentially a lower tax bracket.
Speaker ABoth work in your favor.
Speaker AThis window doesn't say Open forever.
Speaker AAnd it's not a go get it in November decision because the math depends on where your income actually lands for the year.
Speaker ASo let's review a little bit about how Roth conversions work with your pre tax accounts.
Speaker ASo your pre tax accounts, you are putting money in your accounts and you are getting a tax break on the way in.
Speaker AAnd then when you pull money out of the accounts during retirement, you're paying taxes on the way out.
Speaker ANow many people find that it is desirable to take some of their pre tax money and convert it to a Roth.
Speaker ANow doing that creates a taxable event.
Speaker ASo if I have a $500,000 pre tax IRA and if I convert 50,000 of it to a Roth IRA, that will create some tax on $50,000 of income.
Speaker ANow let's say I'm a business owner and let's say that my income is down this year and I'll be in a lower tax bracket.
Speaker AWell, that's why this year might be the best year to work on some Roth conversions, because I'll pay a lower percentage of that phantom income this year to the IRS because my income was down.
Speaker AThe other thing that could happen is your IRA could be down in value.
Speaker AAnd that's a great time to consider Roth conversions because you are converting more or the same amount of shares as you normally would.
Speaker ABut when that pops back up and the market recovers, you will have a higher account balance in the new Roth that again will come out tax free and not affect your irmaa.
Speaker ANow if you don't know what IRMAA is, go back and listen to our episode that we did about it last year.
Speaker ABut it has to do with your Medicare premiums.
Speaker ANumber two is your charitable giving strategy.
Speaker ASo if you give to charity every year anyway, and I know a lot of you do, stop writing that check in the last week of December out of habit.
Speaker ALook at bunching a few years of giving into one year or funding a donor advised fund now while you actually have time to think through it instead of doing it in a panic between Christmas shopping and New Year's.
Speaker ARemember, if you make a contribution to a non profit organization that has to be done by midnight of December 31st or else it doesn't count for this year.
Speaker ASo don't let it sleep up on you.
Speaker AAnd be purposeful with your giving.
Speaker ARight?
Speaker ADon't just give because you want to get a quote, write off.
Speaker AGive the right amount for you.
Speaker AGive some thought into what really is in your heart as far as how generous you should be based on your current, your current desires and your current financial situation.
Speaker ASo take a little bit of time, slow down, ask yourself, ask your partners, ask your financial advisors, ask your family members, what should our giving strategy be for this year?
Speaker AWhat does my financial reality allow me to do?
Speaker ASo number three, what about a retirement contribution pace check?
Speaker ASo do some quick math.
Speaker ATake what you've actually Contributed to your 401k, to your SEP IRA, to your solo 401k so far this year and check if you're actually on pace to hit the max, if you need to hit the max, and if you can afford to, or if you are close to it.
Speaker AThis has to be done by December 31st.
Speaker AIf you're behind, you've still got almost six months to adjust the number coming out of every paycheck.
Speaker AIf you wait until October to notice, you've got two or three months to fill a six month gap.
Speaker AAnd that's a much harder math problem that will create much smaller paychecks for you between then and the end of the year.
Speaker ASo if you have a financial advisor, this might be a great phone call or great appointment topic and that's to make sure that you are contributing the correct amount of money to your retirement plans this year.
Speaker ANow you know I love the business owners and we always have to have some content and advice for the business owners.
Speaker ASo let's talk about your buy sell agreement and your valuation freshness check as number four.
Speaker ASo if you have a buy sell agreement, when's the last time you actually looked at it?
Speaker ANot just to confirm that it exists, but read it.
Speaker AA lot of these were written years ago with a valuation formula or fixed number that has no nothing to do with what the business is actually worth today.
Speaker ASo here's the deal with buy sell agreements.
Speaker ALet's say you have a business partner.
Speaker ALet's say your business partner passed away tomorrow.
Speaker AMore than likely you are now a business partner with that partner's spouse or heirs.
Speaker ANow again, more than likely you didn't choose to be business partners with their spouse and you probably don't want to be business partner with their spouse and their spouse may not want to be a business partner with with you.
Speaker ASo what business owners typically do is they have an attorney drop an agreement that in really basic terms say if you die, I'll buy your heirs out and own 100% of the company.
Speaker AAnd if I die, you will be obligated to buy my heirs out and you will own 100% of the company.
Speaker ANow that's easy to do if your cash flow is very high.
Speaker ABut oftentimes for companies that have valuations of millions and millions and millions of dollars, when one partner dies, the other partner doesn't have the ca to buy the heirs out.
Speaker ASo at that point, there are two things that you can do.
Speaker AYou can borrow money or maybe you would have taken out a life insurance policy on your business partner.
Speaker ASo for a lot of business owners, the answer is, yeah, like I have not looked at my buy sell agreement.
Speaker AI'm not sure how relevant it is.
Speaker ABut make sure that we're doing this not in a crisis or in the middle of a real life event.
Speaker ANow, if you want an estimate of what your business might sell for now, this is not a certified appraisal, but take the sellability score.
Speaker AIt'll give you a range of values.
Speaker ASo go to www.weeklywealthpodcast.com sellabilityscore.
Speaker AThat's www.weeklywealthpodcast.com SellabilityScore.
Speaker AIt may take you 10 or 12 minutes.
Speaker AYou'll answer some questions.
Speaker AIt'll help you to understand what parts of your business can become more valuable if you nail down some of the eight drivers of value.
Speaker AAnd it'll also give you a range of values that your business might sell for.
Speaker AThis is a really good starting point and a really good way to have that conversation.
Speaker AThen of course, if the buy sell agreement itself needs any updating, that's where your attorney gets involved and that's where they can help you make sure that you are on point legally.
Speaker ANow, what about a mid year profit and loss sit down?
Speaker ASo if you sit down with your profit and loss statement and hopefully you have one of them, hopefully you're working with a bookkeeper or a CFO or fractional CFO inside of a program like QuickBooks or anything like that.
Speaker AThere are many of them, but it doesn't matter who's across the table from you.
Speaker AIt could be your cfo, it could be a fractional cfo, your financial advisor, your cfo, or honestly, just yourself and a cup of coffee, or yourself and a spouse or a business partner.
Speaker ABut what matters is that you actually look at where the business is tracking against where you would where you assumed it would be in January.
Speaker AHalf the value here isn't even in the analysis.
Speaker AIt's in the discipline of doing it on purpose on the date you picked instead of finding out in February how the year actually went.
Speaker AOkay, so we have to know the numbers.
Speaker AThis is no fun.
Speaker AAnd this is why I am a huge proponent of working with professionals.
Speaker ABecause if you have your CFP or if you have your CPA or fractional CFO working with you, pulling these reports and almost forcing you to look at them, then it makes you make the decisions that we all know that we need to make.
Speaker BDid you know almost half of all business owners will hit the same stumbling block?
Speaker BThey become the primary revenue driver for their company.
Speaker BThe Rainmaker.
Speaker BAvoid the downhill trap of becoming the Rainmaker and make the transition to architect of your business.
Speaker BDownload the free ebook the Rainmaker's dilemma by visiting www.weeklywealthpodcast.com on rainmaker.
Speaker BAgain, that is www.weeklywealthpodcast.com rainmaker.
Speaker AAlright, so number six is one that I am not really good at and that's the subscription audit.
Speaker ASo if you pull up your bank statements, your credit card statements and actually read through every recurring charge, so don't skim through it, just read through it.
Speaker AAnd this is if you're a business owner, it applies to your business account and if you're a.
Speaker AAnd on the personal side, it applies to your personal expenses also.
Speaker ASo do you remember when maybe that series came out that you saw on social media, that is on one of the streaming services and you signed up for that streaming service for a free seven day trial and you said, yes, I will go in and I will cancel it before the seven days is up.
Speaker AAnd of course you're busy, I'm busy, we're all busy.
Speaker AWe never unsubscribe to those streaming services, right?
Speaker ASo if you have two or three or four of them coming out of your credit card every month for $10, $20, $30, that's real money.
Speaker AThat adds up.
Speaker ANow what about the app trial?
Speaker AThat quietly became a real charge eight months ago.
Speaker A$10 A month, $20 a month, those kind of things add up.
Speaker AAgain, the gym membership, you haven't been there since March.
Speaker AWell, maybe either start going to the gym and getting your money's worth or cancel the gym membership.
Speaker ANow some of these are not going to change your retirement date.
Speaker ABut I always make a joke that I'm the one who talks about this stuff all the time, right?
Speaker ABut I screw this stuff up a lot.
Speaker AI had one of those car wash subscriptions in a car wash in my town and it was, I don't know, $20 a month, no big deal, right?
Speaker AWell then a car wash opened right by my office and I said this is going to be more convenient and I can actually support the local economy if I get a subscription to this car wash.
Speaker ASo the New one was actually, I think $5 less per month.
Speaker AAnd I told myself I would cancel the old one, but two months, five months, six months, I don't know, maybe it was a year that I had two car wash subscriptions.
Speaker ASo again, it's not a difference between being able to afford groceries or not.
Speaker ABut why let money just leave your life with just carelessly see what you can find that's recurring that you're not using.
Speaker AAlso, on the business side, I bet if you're a business owner, I bet there's some software that you're not using anymore.
Speaker AI bet maybe there's an advertising program that's not yielding results.
Speaker ASo the subscription audit, it'll take you a few minutes.
Speaker AMake a game out of it and see how much money you can find that you've been spending each month that's not yielding results or that you're not using at all.
Speaker AAll right.
Speaker ANumber seven is the portfolio drift check.
Speaker ASo most of us, if we're not working with a financial advisor who's managing our money, we need to look at our investment portfolios.
Speaker ASo if you intended to have a 70, 30 split of stocks versus bonds in January, maybe at this point in the year, you have an 8020 split, or maybe a 6040 split, or maybe a 5050 split.
Speaker AAnd that's without ever even making a single trade because one of your asset classes may have done significantly better than you expected and better than the other asset class.
Speaker ASo that's drift, and it's worth checking out before it turns into a real risk level event that you didn't actually choose.
Speaker ASo look at your portfolio, look at your different accounts, make sure that you still own the same percentage of the holdings that you want to own.
Speaker AAnd if not, you got to take the time.
Speaker AAgain, if you're not working with a financial advisor who's helping you with this, if you're doing it on your own, you have to go in and rebalance.
Speaker ARemember, one of the simple principles of investing is buy low, sell high.
Speaker ASo if we started off with a 70% stock, 30% bond allocation, and if maybe six months into the year, you now have 80% of your money in stocks, 20% in bonds, let's buy low, sell high.
Speaker ARight.
Speaker ASo if we sell off some of the stocks, we're selling high and we are realizing some profit, and then we're going to buy some of the bonds, that in theory would be at a low.
Speaker ASo that's a really overly simplified explanation, but we need to make sure that our allocations make sense and they don't drift.
Speaker ANow, what about a net worth snapshot?
Speaker AIf you calculate your net worth now, today, and you put it next to the number from January, so that's assets minus liabilities.
Speaker AMost people have a vague sense of whether things, you know, are they going fine.
Speaker ABut very few people can actually tell you the number in either direction.
Speaker ANow this takes 15 minutes.
Speaker AOr if you're a client of mine, you would just log into your portal and you would know.
Speaker ABut actual data is important to have instead of a vibe.
Speaker AAll right, so is your net worth increasing or have you gradually drifted into debt?
Speaker AIs your net worth increasing because your investments have done well, but you're not necessarily contributing as much as you need to?
Speaker AOr is your net worth increasing because you're contributing a lot and your investments have not done well?
Speaker AOr, or some combination of both?
Speaker AOkay, so it's great to have the data and know what your net worth is.
Speaker AAnd we're early enough in the year to where we can still do some things about it if it's not where you want it to be.
Speaker AAll right, and here's number nine.
Speaker ADid anything big happen this year?
Speaker ASo this is like an all in one catch up.
Speaker ADid you get married, divorced, have a kid, get an inheritance, buy a house, start a business, sell a business, have health issues, get a big promotion, lose a job?
Speaker ANow those are not just emotional milestones, those are triggers to actually revisit the whole plan, not just one line item.
Speaker ASo a new spouse might mean new beneficiaries, new kid might mean new life insurance, or at least revisiting how much and what type of life insurance you have.
Speaker AMaybe you bought a new house and you, your umbrella insurance policy should be added into the conversation.
Speaker AMaybe, just maybe, you had a health issue and you are a business owner and now you're starting to think about your exit strategy.
Speaker ALike what would happen if you didn't wake up.
Speaker ASo these are all things that we need to look at.
Speaker ASo if you're not at any of these, that's not a get to it eventually.
Speaker AThat's like, do it this year.
Speaker AAnd in an ideal world, it's due with your financial advisor.
Speaker AAnd you can Certainly email me davidarallelfinancial.com if you'd like to discuss it.
Speaker AOr it's think about these things at a point very soon.
Speaker ALife doesn't wait for your annual review to happen for you.
Speaker AIf something big happened this year, then your plan needs to know about it now, not in December.
Speaker ASo did you have anything big happen to you this year, either positively or negatively.
Speaker ALet me know.
Speaker AGo to www.weeklywealthpodcast.com, click on the microphone icon and leave me a voicemail.
Speaker AAll right, so those are nine things.
Speaker ANine things, maybe three or four or five apply to you.
Speaker AYou don't have to deal with all of them this week, but pick two right now before you move on to the next podcast in your queue and put a date on your calendar to actually do them.
Speaker ANot assumed date, like an actual date, or set an appointment with one of your advisors to deal with it with them.
Speaker AThat's really the whole message of this show.
Speaker AHow we handle our money should positively impact our lives and the lives of those around us.
Speaker AAnd a 15 minute check in in July is a lot cheaper, financially and emotionally than the same conversation happening in a panic in December.
Speaker AOr worse, not happening at all.
Speaker ASo if any of these nine topics raised a question you'd rather just hand off, go to www.weeklywealthpodcast.com Vision let's knock it out together.
Speaker AThese are important and what one of my favorite authors, Jim Rohn, said.
Speaker AHe always said what's easy to do is also easy not to do.
Speaker ASo some of these things things are easy to deal with, they're easy to address, they're easy to fix, they're easy to handle, whatever modifications need to be done.
Speaker ABut you're busy, I'm busy, we're all busy, and it's tough to get to them without a little bit of accountability.
Speaker AAll right everybody, that is going to wrap up the show.
Speaker AAnd until next episode, I wish everybody a blessed week.
Speaker AThanks everybody.
Speaker BThe information presented on this podcast is for general educational purposes only and does not constitute financial investment, legal or tax advice.
Speaker BParallel Financial is registered with the U.S. securities and Exchange Commission as a registered investment advisor.
Speaker BRegistration does not imply a certain level of skill or training, nor does it constitute an endorsement by the sec.
Speaker BAll investing involves risk, including the potential loss of principal.
Speaker BPlease consult a qualified financial professional before making any financial decisions.
Speaker AAnd here is your bonus content for this episode.
Speaker ASo you'll remember we did an episode about the Freedom Point and that's the point where maybe your business is worth enough money to where it can fund a big old bucket of money that can give you a very good chance of living the ideal life financially for the rest of your life.
Speaker ASo it might make makes sense to de risk and start thinking about exiting your business.
Speaker ASo if the Freedom Score is something that you would like to know what your number is, go to www.weeklywealthpodcast.com freedomscore that's www.weeklywealthpodcast.com takes just a few minutes.
Speaker AIt gives great information and it can help you to guide your decisions using facts, not emotions.
Speaker AAll right, that'll really do it this time.
Speaker AHave a great week and let's catch up.
Speaker ANext episode.