Using a Donor Advised Fund (DAF) to offset a Roth IRA Conversion

It’s been a while since I’ve wrote out finances, so let’s dig in, and let me preface this by saying that I am not a financial professional; please consult a professional (as I did) before you embark on any significant tax-saving strategies.

Okay, with that out of the way, let’s summarize two things: one, I think charitable giving is important, as I’ve written about before in several different essays. If you have the ability to help others and you’re currently not doing so, or if you wonder if you could be doing more, please consider reading my blogs on this topic, and in particular read about Peter Singer and his philosophy about giving money wisely.

Two, I’d like to have as much retirement income in tax-free accounts as possible - in other words, Roth accounts. I’m happy to pay taxes and contribute to the United States every year, but I also want to do intelligent and legal things to mitigate the tax I pay. Rich people do it, so I figure my family should take advantage of the same strategies when possible.

Now, you’re legally allowed to transfer money from a pre-tax retirement account like a traditional IRA or a 401k into a Roth IRA, but it’s a taxable event, and paying a big extra chunk in taxes is prohibitive most of the time. So even though I want to have as much of our retirement savings in a ROTH IRA so that we can withdraw money tax-free in our retirement, I’m not willing to do so if it means paying taxes now.

With that in mind, I’d like to discuss a method of satisfying both desires - giving to charity and moving money into a Roth IRA - without increasing your taxes.

In 2022 I learned about Donor Advised Funds (DAFs), a device that allows you to move more than one year’s worth of charitable giving into a fund for future distribution. The idea is that if you are able to contribute several year’s worth of charitable giving into a DAF in one calendar year, then you can then itemize the deduction on your taxes. This became especially important a few years ago in states like Illinois with high state and property taxes, because after the SALT tax deduction was enacted, these deductions were capped at $10K. So in 2022, when the standard deduction was $25, 900, it required an addition $15,900 of charitable giving before you could benefit from itemizing your deductions. In 2024 the standard deduction is up to $29,200, so it takes nearly $20K of charitable giving to begin to itemize your deductions.

Now, I’m aware that we should give to give, not to reap financial benefits. I get it. But we can give a whole lot more if we do get a deduction, which is why charitable deductions are allowed in the first place - to spur charitable giving.

For argument’s sake, let’s say you have $100K in a brokerage account somewhere and you like to donate $20K a year to charities (and I recognize that these numbers might be pie-in-the-sky - I’m just trying to make it simple). Depending on your income (there are restrictions, so do your homework) you could take $100K from your traditional IRA or 401K and transfer it to a Roth IRA, and then offset the tax implications for this event by moving $100K from your brokerage account into a Donor Advised Fund. The two events should be close to a wash, and you’ll wind up paying around the same tax as you did last year. And now you have five-year’s worth of charitable giving ready to go!

Even better, you can move appreciated assets into the DAF tax free, thereby avoiding capital gains on that amount. And wait, there’s more! The assets you have in the DAF can grow over time, allowing you to give even more money to your favorite charities!

Pretty slick, eh? To me, it’s a no-brainer, and I’m surprised that this strategy isn’t discussed more on-the financial pages I read.

I studied this method for weeks, wondering if I was missing something, and finally bit the bullet and emailed a financial advisor who I hire from time to time for a flat fee (always a flat fee - never a percentage) and asked him about the above strategy. He wrote: “Love this strategy, we do it all the time. Yes, I approve everything you are planning as described in your email.” He then went on to explain a few specifics to be aware of that were helpful, so please do your homework and get the advice of a professional before you pull the trigger.

If you’re lucky enough to have some assets on-hand that you don’t need immediately and you believe in helping others, consider looking into this strategy. It’s a win win win win.

All Work and No Play

I read Kareem Abdul-Jabbar’s newsletter fairly frequently, and without fail he has something insightful to offer (he’s as smart and as good a writer as he was at playing basketball, which seems a little unfair), often attributing his insight to his old UCLA basketball coach, John Wooden. A few months ago, Jabbar quoted Wooden: “Do not let making a living prevent you from making a life,” and Jabbar expanded on this teaching, saying, “It’s not just about taking more time off work to spend with friends and family, it’s also about how we lie to ourselves and others about our priorities. And how those lies prevent us from making a truly fulfilling life.”

Weighty stuff, that!

I’ve often professed that people are what they do, not what they say. It matters not if you say, “My children are the most important things in my life” if you rarely talk to, write to, visit or even think about them. It may be true that they hold a place in your heart, and I don’t want to diminish that, but the reality is that for many of us, we spend more time watching sports than we do with family, we spend more time working unnecessarily than we do pursuing friendships, and we spend more time scrolling through social media than we do pursuing a meaningful task. The time we spend doesn’t line up with what we claim to be most important in our lives.

Kareem goes on to comment on people who appear on reality shows and compete for money “for their family,” all the while spending more time away from family and begging for attention (like Elton John wanting to spend more time with family, and therefore embarking on a five-year farewell tour to prove it!). It’s a little harsh, but as Jabbar says, “People get married, buy houses, and put their kids through college without stranding themselves on an island or leaping forty feet into the water while grabbing a plastic flag.”

Wow. So how should we spend our time?

At the end of the movie Monty Python and the Meaning of Life, after 90 minutes of insane comedy sketches that include a grotesque live organ transplant and a large man vomiting profusely, the question of the meaning of life is finally answered: “Try to be nice to people, avoid eating fat, read a good book every now and then, get some walking in, and try and live together in peace and harmony with people of all creeds and nations.”

You could do worse! 

But my pithy response to life’s biggest mystery is this: “The meaning of life is to live life meaningfully.”

If what you’re doing at this moment has meaning, you’re on to something. If it doesn’t, stop doing it and move on to another activity. Most of our time should be spent doing things that coincide with what’s most important. I’ve never been inclined to squander away a day, but I’ve been known to throw away an hour here or an hour there in ways I never would have done twenty years ago. Which is silly, because I have less time in this life now than I had twenty years ago! I shouldn’t be squandering another minute.

Or does growing older give you permission to squander some time but somehow feel at peace with it?

If so, I’m not quite there yet.

Time to get cracking.

Crying My Eyes Out

I’ve broken down in tears during no fewer than four concerts in the last 12 months. No shame in that, I suppose, but it does beg the question: why? Is it simply because the music moves me? Is it because of my past? A sense of loss? A realization that the artists I’m watching won’t be around much longer? Probably all of those things and more, but I’d like to delve a little deeper into the songs that had be blubbering like a fool and attempt to understand what the heck is going on.

Peter Gabriel: “Washing of the Water.”  September 2023

I didn’t see this one coming. Last time I saw Gabriel – coupled with Sting in 2016 – he opened with the eerily magnificent “The Rhythm of the Heat,” a song that’s cool as hell, but hardly one that I can relate to. But in 2023, he sat down on a chair with a small keyboard, and beside him sat long-time bassist Tony Levin. Together, they played the quiet, heart-breaking song of pain and grief and a plea for inner peace. That’s probably enough to put me over the edge in any context, but to see these two musicians, together for nearly fifty years, back on stage as a duo? That might have been enough right there, no matter what song they chose to play.

And then there’s my own past to reckon with. Gabriel’s Secret World DVD was on constant rotation in my household when my kids were young. My daughter Jessica wanted to be Paula Cole, a vocalist on that tour from 1993. Envisioning my three young children who watched that concert with me over and over – children who are all now adults living in different time zones – well, that certainly contributed to the waterworks. And to top things off, I was watching the concert with my 21-year-old son, over 36 years after I’d first seen Gabriel on his So tour, when I was an even younger 19. It boggles the mind. It conjures up a time when the future long and wide…you know the drill.

I also knew instinctively that this was the last time I’d see Peter Gabriel live, and that in the not-too-distant future, he’ll no longer be with us.

Geesh. Add that all up – how could I not cry?

James Taylor: “Shed a Little Light” and “That Lonesome Road.” June 2024

I should note first that I can’t listen to “That Lonesome Road” without crying. I find it absolutely heart-wrenching, this tale of a man – much like the man in Peter Gabriel’s ”Washing of the Water” – who’s reeling from his mistakes, untethered, attempting to rise above his pain, to start anew.

But dang, to play an encore of “Shed a Little Light” – a favorite of my wife’s and mine – followed by “Your Smiling Face” and “That Lonesome Road”…I knew, I knew beyond a shadow of a doubt that I would never see James Taylor play again, and I felt a sense of loss for a future without this magnificent artist who so eloquently captures the human condition. It’s like what Mark Twain said about worrying: it’s like paying a debt you don’t owe. I was experiencing grief for a person who’s still living. Kinda dumb. But there it is.

Sara Bareilles” “She Used to be Mind.” August 2024

Okay. Once again, a very touching song.  Sara has about a half a dozen that can set me off in a flash.  She’s got that gift. And here I was on a beautiful night with my beautiful daughter Sarah at the beautiful Hollywood Bowl. I mean, come on! The first time I saw Sara Bareilles was with both of my daughters at this strange venue – the Scottish Rite Center in Milwaukee – where Bareilles played a solo show prior to the release of The Blessed Unrest. I blogged about that concert back in 2013, and here I was over a decade later, watching her perform this wonderful song about self-acceptance. It killed me.

Keane: “Can’t Stop Now.” September 2024

This isn’t a song that would normally set me off, but there were several things going on here. First was the pure jubilation of finally seeing this band after a few failed attempts, the last one a cancelled show in Nashville due to the pandemic. Second, my daughter Jessica was by my side (and yeah, all four of the cry-fests in this blog involve watching a band with a loved one – no coincidence). Third was the sheer power coming from the musicians on-stage, especially the vocal perfection of Tom Chaplin.  Fourth, the fact that in 2020 – just a month after that cancelled Nashville show – I got to play a Keane song with all three of my kids at a little outdoor concert on my neighbor’s driveway while families huddled outside in their safe family bubbles, none of us knowing that this was what life would look like for the rest of the year. And fifth is some serious personal stuff than I can’t delve into on-line, but suffice it to say that I’m aware of life and death, what I have and what I’ve lost, what matters and what doesn’t.

And all of that adds up to tears. Again.

And look, I grew up in a rather undemonstrative family, so I view my ability to cry – in public, no less – as a step in the right directions, generationally speaking. Maybe my kids will have a better chance to be more fearless and open than I’ve been. And maybe in thirty years they’ll be at concert with their adult children, listening to a song that has them breaking down in tears.

The Comfort of Moving On (When to Quit)

A few years ago, I heard former professional gambler and author Annie Duke on the marvelous podcast, “People I (Mostly) Admire,” hosted by economist Steve Levitt of the Freakonomics franchise. In Duke’s book, Quit: The Power of Knowing When to Walk Away, she discusses the art of quitting, and how many of us wait too long to walk away. After all, if there’s one thing a good gambler knows how to do, it’s “when to fold ‘em,” as the song goes. It’s important not to stick with a poker hand when the odds are telling you to quit.

Similarly, it’s important in life not to stick with a job, a pursuit, or a partner when every fiber of your being is telling you to get out. Steve Levitt summarizes Annie Duke’s book this way: “People stick with bad things almost always for too long, and we’d be better off if we quit things sooner.” Waiting too long causes us to stop progressing, to stop gaining ground toward our goals.

How often have you waited to quit an unfulfilling job out of fear and uncertainty, only to find that after doing so, you wound up telling yourself, “I should have done this years ago”?

Getting yourself to quit on time can be tricky. There’s an emotional pull in our society that makes quitting sound weak. We hear accolades for people’s “stick-to-itiveness.” We hear aphorisms like “quitters never win, winners never quit.” But what we might not hear is that a successful person who you admire might have quit three other goals before finding the one that worked, that an entrepreneur had two failed businesses before finding the one that succeeded, that a person left three romantic relationships before finding the one that clicked.

In order to grow, we have to allow ourselves to quit aspects of our lives that aren’t working.

Over the last year, I quit my two main music activities: I stopped playing at a church where I’d worked almost every Sunday for twelve years, and then last week I played my last concert with a local yacht rock band that I’d performed with for three years. In both cases I was playing with good musicians who were nice people. There was nothing awful happening in either scenario. Both allowed me to do what I do fairly well: play the keyboards. Both paid me a little cash that gave me a sense of contributing to my family (albeit, minimally). There were reasons to stay.

But neither musical act was fulfilling. I wasn’t inspired. I wasn’t stretching myself as a player. I was showing up, playing, collecting a check, and going home. That’s not what I want out of music. I think of drummer Bill Bruford quitting Yes, Gregg Rollie leaving Journey, or Sting pulling out of The Police, each at a point when those bands were at their creative peaks. There were all sorts of reasons to stay, but they each decided it was time to walk away.

Now, leaving a church gig and local yacht rock band pales in comparison to the above examples, but despite a multitude of reasons to stay, I quit both of them, and if I’m honest with myself, later than I should have. You know you’ve made the right decision when after quitting you feel a little lighter, a little freer, and that’s how I feel now.

Now it’s up to me to put that new energy into action, and to proudly carry the mantel and say, “Yeah, I’m a quitter.”

Sports Hats Invite Conversation

Spontaneous conversations seem to be a lost art. It’s so easy to avoid eye contact and conversation by peering at the latest headlines on your phone, that chance encounters are less likely than they were a few decades ago. Unfortunately, this lack of small talk can feed on itself until people lose the skill altogether. Each morning, I pass by dog-walkers who not only don’t shoot the breeze with me – a fellow dog-walker – but can’t even garner the energy to say hello, as if they’ve lost the ability to utter the two-word syllable. More likely, they’ve lost all confidence to interact with strangers. Or maybe they’re just douchebags. Hard to tell.

One way to occasionally overcome this trend while traveling is by wearing a sport hat. On a recent trip to the Los Angeles area, I had two delightful conversations with complete strangers, all because of the hat I was wearing. Usually, it’s the Green Bay Packers hat that attracts the most attention, but on this trip I donned the cap of my first-place Milwaukee Brewers. Neither of my conversations came from Brewers fans, but the recognition was enough to start them chatting.

My wife, daughter and I were hanging out at a wine bar in Santa Barbara (it sounds kind of bougie, I know), and one of the guys at a table next to us notice my hat: “That is the greatest sports logo ever, the Milwaukee Brewers.” He proceeded to point out to his colleague that the Brewers emblem is no ordinary baseball glove, but a glove comprised of the letters M and B for the name of the sports team. It is a great sports logo! But it was cool for someone else to notice. For the next few minutes, we talked about my Brewers and his Dodgers, and how the playoffs have watered down the importance of the regular season, etc. Good stuff!

A day later my daughter and I were on the shuttle bus taking us from the Sara Bareilles concert at the Hollywood Bowl back to the Zoo. There were only two seats left, separated by five or six rows, so we each took one, but soon after another group of people came onto the bus for standing room only. I gave up my seat for the first woman who walked on (who said chivalry is dead?) and after saying thank you, she noticed my hat and said, “I was born in St. Louis. Don’t hate me.”  Well, it’s true that the Cardinals have been a thorn in the Brewers’ side since the 1982 World Series, and after she introduced herself as “Ann from Ann Arbor” (she having attended the University of Michigan), we chatted for a bit about baseball before moving on to other things. Ann was a talker, and while it’s true that I wouldn’t have wanted to spend an entire day with her, for a 20-minute bus ride she was a pure delight. She told me about her job in video work, her apartment near USC, her Christmas caroling adventures, and about writing a musical and playing the French horn. When we got off the bus she wanted to meet my daughter and ended up giving both of us a hug.

Yeah, I know. For a lot of people these types of stories only solidify why they never want to leave their homes. Like ever. Conversations with strangers? Eww!

But I’m telling you, for me it was a nice cap to an already terrific day.

You want to spontaneously talk with strangers? Wear a hat. If not, wear the most anonymous clothing you can find.