What I do when I’m worried about money

3 strategies for the worried well

I’m a little concerned about sending this email. Money is such a loaded topic, and it’s easy to get it wrong. So please bear with me.

Two caveats before I get to the actionable advice:

First, the strategies I’m about to share may not be useful if you’re dealing with basic survival needs— if, for example, you’re in the fire zone in L.A. (I’ll have something to say about more extreme scenarios at the bottom of this missive.) Instead, this advice is for the worried well—people who fret about money even though they have a roof over their heads. I suspect that might describe many of us.

Second, let me say the quiet part out loud: any advice I give here is coming from a place of privilege. (Not my favorite word, given its freighted cultural connotations—but apt, in this context.) I was born into an upper-middle-class family and went on to achieve a decent amount of success in television news, so I approach this subject as a guy who, going by sheer math, shouldn’t have much to worry about.

And yet, I do worry. Quite a bit, in fact. For reasons that I will spell out in a moment, and about which I have no small amount of sheepishness.

So what do I do when money anxiety hits?

Three things:

1. Practice self-compassion: Instead of criticizing myself for worrying irrationally, I have learned to make peace with the psychological factors that most likely led to my penchant for money anxiety. Said factors include: a. Having a great-grandfather who took his own life after losing the family fortune (and getting investigated by the feds) and b. Being raised by parents who, although they were doctors, were so worried about money that they refused to adequately heat our home during New England winters, forcing us to wear parkas indoors. So now, when I notice myself getting carried away by financial fears, I try to remember to put my hand on my chest and talk to myself the way I would talk to a good friend. Which brings me to…

2. A great technique from Stoicism: Ancient Roman philosophers developed a practice called “premeditation of evils.” Basically it involves picturing the worst possible outcome and then imagining how you would handle it. So when I’m in the throes of money anxiety, I will say to myself: Dude, even if your business fails, you will still have your family, and you will still have the inner resources to figure out a new way forward. For me, optimism is not the blind faith that everything will be perfect; it’s the grounded confidence that no matter what happens, I can probably handle it.

3. What is enough? My final piece of advice comes from my friend and meditation teacher, Joseph Goldstein. He has long advised me to ponder these questions: How much is enough? What do I really need? Are my concerns about money generated by unnecessary clinging? I have found these contemplations to be extremely helpful.

In closing, as promised, let me say something to anyone whose money fears are truly urgent and threaten their basic security. First, I’m sorry—that is really hard. Second, while there may be no easy fix, one thing to consider might be to ask for help. This could mean reaching out to family and friends, or even starting an account on GoFundMe.com, especially for a specific or time-sensitive need.

On my podcast today, you’ll hear meditation teachers Sebene Selassie and Jeff Warren talk about how, counterintuitively, when you ask for help, you are actually doing other people a favor.

Sebene, Jeff, and I also talk about the importance of having awkward money conversations with friends; how to understand the sources of your financial neuroses; and the illusion of security.

Click to listen or watch. It’s a rich (sorry) conversation—and, below, paid subscribers get a cheatsheet with key takeaways and a full transcript.

Also, a programming note: I’ll be doing a series of free, live guided meditations + conversations during inauguration. I’ll start on Sunday, January 19th and go through Wednesday, January 22nd—each day at 3:00PM ET. It’s a reconvening of the “renegade sangha.” There will be special guests. The world is insane—but you don’t have to be. All are welcome, but you do need to download the Substack app to join in.

Episode cheatsheet

The big takeaway

Meditation teachers Sebene Selassie and Jeff Warren talk about our complex relationships with money, and how examining our personal "money stories" and practicing non-attachment can lead to a healthier relationship with finances. The core message is that true security comes not from wealth accumulation, but from cultivating relationships and an open heart.