REGRET PROOFING YOUR LIFE

An intimate gathering for parents who suspect they're playing the wrong game.

Snuggle season with your kids is over, or the door is closing fast. Your spouse is more of a roommate than a partner. You haven't seen your best friend in six months. Your body isn't keeping up. You haven't slept well in years. You're following the blueprint for success. So why don't you feel the way you thought you would?

Family

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Friendships

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Health

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Fun

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Purpose

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Money

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Family • Friendships • Health • Fun • Purpose • Money •

I've spent 28 years as a wealth advisor.

For all 28, I've spent about a quarter of every client relationship on things that had nothing to do with money — their marriages, their kids, their health, what they actually wanted their lives to add up to.

That made me an outlier in my field.

And I've come to realize it still wasn't enough. Because it doesn't matter how well your money is managed if the parts of your life that matter most are falling apart.

So let me be clear about what this is. It's not financial advice. It's not a planning session, and I won't be reviewing anyone's portfolio. This is the conversation my industry doesn't have — about everything your money was supposed to be in service of in the first place.

Here's how I've come to see it.

Your life is a portfolio — six asset classes: your family, your friendships, your health, your fun, your money, and your sense of purpose. Most people I see pour nearly everything into one or two of them and let the rest run close to empty. 

Concentration is one of the primary risks we protect against. You would fire an advisor who refused to diversify your money the way you've refused to diversify your life. And you've been running that allocation the whole time.

And here's what you've probably already been feeling without naming it. The kid who used to want to be near you spends more time behind a closed door. The dinners are quieter. The conversations don't last. Most parents accept this as the norm. It doesn't have to be this way.

Here's what most "life optimization" misses. The unfulfillment you can feel isn't a problem in any one domain — it's the fragmentation itself. Your marriage isn't stale because you've stopped loving your spouse; it's in maintenance mode because there's nothing left after work. Your body isn't slipping because you don't know what to do; you've sacrificed it to make the numbers go up. Your friendships didn't fade because you stopped caring; you quietly accepted they didn't fit in the schedule. Each piece looks fixable on its own. The new diet, the date night, the long-overdue text. None of it holds — because the issue isn't any one piece. It's that the pieces don't add up to a whole life anymore. You don't optimize your way to a whole life. You integrate your way to one.

Here's the part that should bother you most: compound interest doesn't only work on money. It works on your marriage, your friendships, your body, your kids. And the cost of starting late in those is worse, not better. You can recover from a bad decade in the market. Your kids' childhood doesn't get a do-over — but you're not out of it yet.

And here's what almost no one in my industry will tell you: the money pressure that's kept you concentrated all these years is mostly manufactured. There's a way to take it off the table — and when you do, the time and attention you thought you couldn't spare for everything else suddenly become available.

  • In 2022, in the middle of COVID, my life cracked open. I sold my practice. My father finally lost his decade-long battle with dementia. And I had a full-blown midlife crisis.

    By every external measure, I'd made it. And I was unhappy. My relationship with my wife and kids wasn't where I wanted it to be. I wasn't experiencing much joy. I had built exactly the life I was told to build — and it wasn't the life I wanted.

    Today, I've never felt better. My marriage and my relationships with my kids have never been stronger. I have real friendships. I have a genuine lust for life again.

    The steps I took to get from there to here were hard — harder than they needed to be, because I was figuring it out alone. I opted out of the game we've all been told to play, and I started playing a different one.

    Now I want to show you how to do the same — without taking as long, or doing it as hard, as I did.

  • Who are we, and why give us a day?

    I've spent 28 years as a wealth advisor and written two books — Networking Is Not Working and Let's Retire Retirement. Melanie and I started CADRE, a community for founders, fifteen years ago, and we still run it together.

    But the part that probably matters more to you: you read earlier that my marriage wasn't where I wanted it. Here's what I left out. Melanie and I did a lot of work to change that — and today it's the strongest it's ever been. She co-leads the part of the day on family — not theory about relationships and parenting, but what it actually took for two people who'd drifted to find their way back to each other and back to their kids.

Our Family Room

What Is This?

A day at our home. In the family room where Melanie and I raise our boys, not a hotel ballroom. The day itself is simple in shape: you'll get a remarkably clear look at how you've actually been spending your life relative to your ideal life, you'll sit with what that's been costing you, and you'll leave with a specific plan to change it, with someone in the room to hold you to it.

Money is part of the day — just not the part your advisor handles. We won't look at your portfolio or talk about what to buy. We'll talk about your relationship with money: the anxiety that has nothing to do with your account balance, the number that never quite feels like enough, and how to use what you've built to live well now — instead of the conversation most planning traps you in, which is forever about a someday that keeps moving further away.

It doesn't end with the day. The group gets back together on a call a couple of weeks later, and you and I talk one-on-one after that — about your life, not your finances.

I wish I could tell you we could do this in an hour. We can't. Five or six hours is what it takes — to look honestly across your whole life, not just one piece of it, and leave with changes that are still holding a month from now. I'm going to tell you what you need to hear, not what you want to hear. If I do my job, you'll leave knowing it was one of the better days you've spent on yourself in a long time — and the people closest to you, starting with your kids, will feel it.

APPLY TO THE COHORT

What You'll Leave With

✓ An updated approach for allocating your time, energy, and attention across the six asset classes built around what matters most to you

✓ The three biggest future regrets currently forming in your life and a plan to prevent them

✓ A plan to meaningfully connect with your kids, including what to say and the first move to make

✓ A plan to restore an important relationship in your life in the next 7 days

Who This Is For

I'm intentionally keeping this first cohort small - just six to ten people.

This is for you if the top of this page reads less like marketing and more like someone reading your mind. If you're a parent whose kids are still close enough to reach — old enough to notice the way you live, young enough that you can still change the relationship — and something in you knows you've been pouring yourself into one or two parts of your life and letting the rest, including them, run close to empty. You don't need to have your money figured out, or anything else. You only need to be willing to look honestly at your life and be willing to do something different. 

Couples are especially welcome — the parts of your life your kids are watching most (your marriage, your vitality, your sense of fun) are far easier to change when you're both in the room. Single parents are equally welcome — this is built for the parent trying to show up differently, regardless of who's at home.

Who This Is NOT For

It's not for you — and I'd rather say so than take your money — if:

  • You're in an acute crisis.

    If a marriage is actively ending, you're in a real financial emergency, or you're carrying something a therapist should be helping you hold, you need a specialist first, not a workshop.

  • You want financial advice.

    We'll talk about money — your relationship with it, how to use it now — but I won't review your portfolio or recommend investments. That's a separate conversation, through separate channels.

  • You want to be hyped.

    No countdown clock, no chanting, no standing on chairs.

  • You want to attend, not participate.

    If you won't do the pre-work, say true things out loud, and actually change something, you'll get little here — and you'll cost the room.

The First Cohort

$1,500 for an individual, $2,500 for a couple.

Honestly, I don't know yet whether I'll keep doing this. I'll see how this one goes — for the people in it, and for me. What I do know is that I'll bring everything I have to this first one, and the value you get will far exceed what it costs you. That's partly why I'm including the one-on-one follow-up — something I doubt I'll be able to keep doing if this becomes a regular thing.

The first cohort meets July 9th. If you're in, just email me — I'll take it from there.

EMAIL ME