Chad Willardson Interview – How to Retire Well

Today’s video is an interview with Chad Willardson, president and founder of Pacific Capital in California. Chad is a certified financial fiduciary and a chartered retirement planning counselor. He has a lot of experience helping people live their ideal retirement and retire well.

Some of the topics we discuss are the differences between retirees who have retired well and those who struggle. Chad also shares a little bit on retirees that have continually grown their purpose and their significance in retirement. Lastly, he shares how to pass values onto your kids and grandkids because as important as the money part is, wisdom is even more important.

Differences Between Being Successful in Retirement and Struggling

Those who are successful focus on the cashflow and that’s their main focus. I think those who are unsuccessful often focus on a lump sum number. They hyperfocus on some arbitrary value of assets and they feel that once they hit that number that they can retire. Those who are really successful are looking at the cash flow planning, their budgeting, income from investments, passive income, real estate income, and they have a handle on what they’re going to spend and what they can earn.

One other trait of the unsuccessful is that they get caught up with whatever is happening in the news, and will shift their investment strategy based on the scary headlines. Sometimes that can cause a very permanent outcome in what they do with their money, which then leads to a much lower cash flow, which then causes a real harm to their lifestyle spending opportunities.

Ignoring the Talking Heads

When it comes to the talking heads on your tv, try to focus on what’s within your control – your spending and spending commitments, memberships, subscriptions, etc. It can be scary to go off the payroll in a sense and become retirees and just live off your assets or your passive income. That’s a big jump.

You’re used to getting a paycheck and going to work, and now you’re constantly asking yourself, do I have enough? That’s the question that will perpetually be in your mind causing anxiety and stress until you’ve gone through some very thorough planning to test that. Look at the cash flow, look at your expenses, look at your taxes. How much income can you rely on?

We certainly don’t discount the big concerns: inflation, interest rates changing, housing market, the depression or recession that may be looming in the background. These are real concerns, but they’re outside of your control. As you’re looking at your retirement plan, you’ve got to focus on things that you can make changes in.

Sense of Purpose In Retirement

You’ve got to retire to something, not just retire from something. As you retire, you need to have a game plan of what you’re going to do. Write out a list of things you’re excited about, new hobbies you’re going to pick up on. Do not just cut the cord and jump. Retirement could be a third of your life. Can you imagine just aimlessly waiting to die for 20 to 30 years? It just doesn’t make sense. Use your wisdom in your experience to do something creative and good. There’s a lot that could be done beyond your full-time career when that’s up.

Creating a Legacy Plan

There’s a lot to be passed on and inherited beyond financial assets. People really do care about passing on a legacy of values and principles, and stories. To be successful and to have an abundant mindset is to be generous and to not believe that money is scarce and that opportunity is a zero-sum game. If you’ve got an abundance mindset and you’re generous, why not teach that to the next generation?

Whether that’s starting a charitable foundation, asking your kids and grandkids, “What causes do we care about as a family? What can we give money to? More importantly, what can we give time and service to?” Think about ways of creating a legacy plan for your family in retirement. What could I do and utilize my abundance of time and money and resources to really leave a lasting impact on the next generation?

Is Retirement Ever the Wrong Choice?

Is not retiring, even if someone has the financial means to and the ability to, ever a good option? You can certainly set up your business in a way that allows you to focus on the few activities that really give you energy.

If you have that fortunate opportunity to be a successful entrepreneur and create your lifestyle and schedule, there’s a way to stay engaged without selling your company or stepping down.

Information Overload

Beware of information overload. Just like with fad diets, there are a lot of fad retirements. There are a lot of myths out there. Be aware of making significant financial decisions without good counsel. There’s a lot of value in getting multiple opinions before you make any big decisions.

Disclaimer: Since we don’t know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Streamline Financial Services, LLC or its members cannot be held liable for any use or misuse of this content.

Affiliate Disclaimer: This post may include affiliate links where we may earn a payment when you click on the links at no additional cost to you. 

Disclosures: Securities offered through LaSalle St. Securities LLC (LSS), member FINRA/SIPC. Advisory services offered through LaSalle St. Investment Advisors LLC (LSIA), a Registered Investment Advisor. Streamline Financial Services is not affiliated with LSS or LSIA. LSS is affiliated with LSIA.

5 Tax Efficient Wealth Transfer Strategies

Reduce the Future Tax Burden of Your Family

​​This video will give you five things to do to take over more control over how much tax you pay to the government. But there’s a little bit of time left before the benefits of the Tax Cuts and Jobs Act goes back to previous levels. We’re not certain how this 2025 sunset will impact family estate planning, but many people are taking advantage of some of the preferential treatments now. You don’t need to have a lot of money to benefit from some of these strategies. 

There are a few benefits of the Tax Cuts and Jobs Act that are going to be scheduled to revert back to the 2017 levels. Things like… 

  • the high lifetime gift, 
  • the estate tax,
  • generation-skipping tax exemptions 

Remember, your money can really only go to three places. It’s either going to go to your family, causes you care about, or Uncle Sam. Most of our clients usually prefer two out of the three of those. Yes, paying taxes is fine and we’ll pay the fair share but we don’t necessarily have to tip Uncle Sam. 

#1: Annual and Lifetime Exclusion Gifts

The first strategy to know about is the annual and lifetime exclusion gifts. If helping your children is important to you – this strategy can be useful whether you have a little or a lot of money. In 2022, the annual gift tax exclusion amount is $16,000 per beneficiary. So if you’re married, you can give $32,000 to your kids or really any beneficiary without having to file a gift tax return. But if you do go over, then it’s recommended that you do file one. So it’s recommended that you stay under $32,000.

If reducing your future estate tax is important to you, the IRS said that taking advantage of the annual exemption amount now is not going to be negatively impacted after the 2025 sunset when the Tax Cuts and Jobs Act levels are expected to go back down. So it seems like gifts made under the current exclusion amount should not be subject to future estate taxes (which is good). 

#2: Education Funding

The next tax-efficient wealth transfer strategy is education funding. The IRS allows anyone to pay educational expenses as long as it goes directly to the institution, essentially removing assets from your estate without a tax impact. Some institutions allow you to prepay multiple years at once of the education expenses. 

Another education funding vehicle is a 529 – an education savings plan which you could contribute up to the annual gift tax amount per year. Some of those 529s even allow you to take a tax deduction on your estate taxes. Each state is a little bit different when it comes to that, there are different sets of rules, so just be sure to talk to your tax person or financial professional before doing that.

#3 Paying for Medical Expenses

The third strategy is similar to education funding and that’s just paying for medical expenses. If you pay directly to the medical provider and if the expenses are not covered by insurance, it has the same impact as paying education expenses, but just for medical. 

#4 Charitable Giving

Now, the next strategy that can be useful is if there are certain things happening in the world that break your heart. If you have a desire to help people in need, you can save money on taxes through charitable planning.

Charitable giving is especially beneficial if you have:

  • investments that have appreciated and gone up in value over time, 
  • real estate 
  • business interest

Many people are using donor-advised funds that allow you to give a portion of something that’s illiquid to a donor-advised fund. 

So let’s say you had 5% of a building that had appreciated value. You could essentially give 5% of that building (which is then sold and then converted into whatever investments you want). The day that you give the gift should give you the tax deduction or tax benefit that same year.

The same thing can happen with business interest. If you carve out a piece of the business that you choose and gift it, you can get that tax benefit. When that tax deduction and that appreciated asset (or piece of an appreciated asset) is gifted and sold within the donor-advised fund, that doesn’t cause a capital gain for you. 

This is one way to not pay capital gains tax on part of your appreciated assets, but it’s a great way to fund your giving expenses in the future or what will be your giving expenses. Plus, you can do it now without impacting your cash flow. However, there are all sorts of rules around this. Again, this is a high-level, big picture view but it’s example of how other people are benefitting from this strategy. 

A donor advised fund is like a charitable bank account where you get to control the outflows and where it goes, but you really don’t include this in your estate (your total estate). It’s technically out of your estate. So you get to control it and where it goes. You can either set it up on one-time payments or you can set it up on monthly recurring to charities that you care about.

Speak with your financial professional about specifics before implementing something like this. If you’re interested in learning more about what’s possible with your giving, click on the Charitable Planning Strategy session. It’s not a call to work together as we do with most of our clients, it’s strictly just to talk about your giving strategy and then to help you develop one if you don’t have one. 

#5 Trusts

The next strategy is to think about various types of trusts that you have available to you right now. These trusts are sometimes used if you don’t want to give assets directly to beneficiaries at this present moment, but maybe at a later date.

Some trusts allow you to control the assets until the beneficiary reaches a certain age or requirement. One is called a Crummey Trust that allows the guarantor to determine really how long the assets should remain in the trust, which gives some control over which beneficiaries or when beneficiaries can take full ownership. 

There are also Charitable Trusts that essentially allow a charitable gift into a trust and allows you to receive an income while you’re still alive. Then, when you pass away the remainder goes to the charity. This is another way people are sometimes using charitable planning when related to estate taxes and estate planning. 

Overall, these five strategies give you some idea of how you might be able to lower future estate tax liability for you and your family. 

INVEST IN KIDS ILLINOIS: Step-By-Step Walkthrough

Today I’m going to be talking about how to qualify and to actually get the credit for the Invest In Kids Act program.

I’m going to walk you through what to do step by step:

  1. Request a letter ID with Illinois;
  2. Activate your account;
  3. Reserve the Invest In Kids credit; and finally,
  4. Make the donation.

If you’re not familiar with the Invest In Kids program, click to see my previous video on what the program is and some of the benefits, then come back here to see how to take the steps to make it happen for you this year.

STEP ONE: Request a letter ID with Illinois

If you don’t already have an account at

  • Click on the “Individuals” tab at the top
  • “Request letter ID” from under the Miscellaneous heading
  • Enter your social security number and ONE of the following:
    • Your most recent, adjusted gross income (you can find this on last year’s tax return)
    • Your driver’s license number
    • Your Illinois state ID number
  • Click “Submit”

In 7-10 days, you’ll get your letter ID in the mail. Once you get that, you can go to step two.

STEP TWO: Activate Your Account

After you receive your letter ID, it’s time to activate your account on

  • Look for the section titled: Login to MyTax Illinois, and click “Sign Up Now”
  • Enter your social security number
  • Click “yes” to activate your MyTax Illinois account
  • Enter the letter ID you received in the mail
  • Enter EITHER:
    • Your individual Illinois PIN (there will be a link on the page where you can look it up), or
    • Your most recent, adjusted gross income (you can find this on last year’s tax return)
  • Fill in your name and email
  • Pick a username and password and fill in the reminder for that information
  • Click “Submit” at the top of that screen, then “OK” on the next screen

You will receive an email confirmation that your account was activated.

STEP THREE: Reserve Your Credit

There are different Scholarship Granting Organizations (SGOs) and you should be able to use any of them for each school, but some schools have preferences on who they’re using. So to be safe, and because you’re giving money, I would recommend confirming with the school on which SGO they prefer. In this example, I’m going to use the Bright Promise Fund.

  • Enter your username and password on the login screen, click “Log In”
  • Under Account Type, select “Individual”
  • Under I Want To … , select “Contribute to Invest In Kids”
  • Read the overview of the program and click to acknowledge
  • Choose your region (if you don’t know it, you can either ask the school or look it up)
  • Choose the Bright Promise Fund (or your preferred SGO)
  • Put in whatever amount you’re choosing to donate
  • Confirm and authorize the amount to give
  • Enter your email
  • Click “Submit”

On the next screen, you will receive a confirmation. Print and save this confirmation to get credit when you give the actual gift in the next step.

STEP FOUR: Make the Donation

Again, for this example, I am using Bright Promise Fund. Your preferred SGO may be slightly different.

  • Navigate to
  • Click “Donate Online”
  • Next to SGO ILL Tax Credit Donation, click “Here’s How”
  • Read and confirm that you have done the three required steps shown on the screen
  • Write a check in the amount you determined in step three
  • Mail the check to the provided address, along with your contribution certificate

Rather than just use USPS, I actually did FedEx, just so I could track it to make sure that it arrived. And if you want to really be sure that they’ve received it and they get it counted for the correct year, call them up and make sure they’ve received it.

One more thing to mention, you’ll want to write on the check the name of the school to designate the gift to them, and then also write it on the actual certificate that you print out and include with the check.

And there’s actually one step more. Once you’ve sent the check and the certificate to the SGO and you know that they received it, come back to and look under “requests” and you’ll be able to see if your contribution authorization certificate has been processed, or is still waiting. And once it’s processed, you’ll have a tax form available under that tab which you can print out or save for when you file your taxes next year.

I know that was quite a few steps. If you have any questions, leave a comment or send me an email and maybe I’ll be able to help you out. But good luck on using this great program; one that helps the kids, helps the schools, and gets you a pretty good 75% tax credit in Illinois.