Wisdom and Giving in 2026

 During the 2020 quarantine, I was reflecting on my life...and feeling different. When I was in my 20s, self-reflection led me to be more active in the arts, politics, and protests. When I was in my 30s, self-reflection was about healing myself and becoming a better person. When the quarantine started, I was in my 40s, and my 40s brain was saying, 'You need to make more money. Now.' 

I didn't expect that. I like money, but it was never my primary motivation. I went into debt for an MFA in playwriting so my lack of financial concern was obvious. 

But there's something about the mind shifting into another gear while still having the 20s spirit of rebellion and the 30s spirit of healing going on. The 20s voice is like 'you should be ashamed of yourself...thinking about money' and the 30s voice is talking about its inner child. A 40s voice is saying 'yes to all of this...AND make more money,' with some expletives thrown in there.

Don't get me wrong: yay to protests, self-expression, and personal discovery. But that midlife brain is reptilian and direct: how can I accumulate as many resources as possible so that I die indoors and on a mattress...ideally 40-50 yrs from now?  It wasn't screaming as it would be in my 50s or weeping if I were in my 60s.  It was just a clear knowing combined with seeing far too many talented artists wrecked on the shores of medical bills or just not having enough to live. When I was at Juilliard, I was broke and still donated what little I had to artists who were a part of past avant-gardes: Andy Warhol factory artists and downtown theatre gurus. And I thought 'wow this is the life. People sacrificing everything for their art.'  And then later on I realized 'I admire that so much...but I don't want to be that.' Yes, it is possible to love the people who made the sacrifice but not want to emulate it, just like you can love Jesus for his sacrifice but not want to be on the cross. 

Seeing people get dumped out in the streets and lose their homes hits different when you're at the midway point in life.  Hearing people obsess about unpaid fellowships when you know several esteemed artist who died with gofundme campaigns to pay their rent...hits different. 

So I did two things, I got my basic financial stuff in order. I paid off all my debt and started investing. Depending solely on salary is not enough in this country. Even if you work for 40 years straight, most people will still need a retirement fund to not feel the financial pinch of expenses later on in life. I started playing the stock market. It seemed like a better way to keep myself busy than playing video games. 

And yes, I went back to wisdom. I re-read "The Diamond Cutter" but this time from a midlife agenda, which felt like I was reading it for the first time. 

Wisdom is knowing money comes from giving. Not begging or taking or scheming or the 40 Dark Laws of Lucifer or 25 Ways to Manipulate Others. Giving. That's it. That's the entire ballgame. So I started the Squire Foundation to provide a solid platform for philanthropy and dedicated a percentage of whatever I earn to organizations that help others by combining resources with wisdom. 

Now I have 3 retirement accounts and a WGA pension. I have a side STASH account that has a return on investment in the range of 75-85% over the last few years. I have high-yield savings accounts so I can earn a few thousand dollars back every year, rather than letting it sit in a checking account with no interest. I am becoming my dad. He was focused on money but not in a greedy way, but with a clear understanding that having greater financial ease made him able to give to others with greater ease. And the greatest thing to give is wisdom so...

No more GoFundMe donations this year. I'm giving through Squire Foundation and only the Squire Foundation for the rest of the year. I'm giving to groups, orgs, and collectives that help other people and use wisdom. Money is the platform but it's not enough. A farmer giving food to someone without teaching them how to farm is a dysfunctional model. It sets up a feedback loop of codependency and resentment. The greatest gift is to teach people how to farm so that people can grow their own crops. It does require patience but it's more satisfying for the village to have a collective of farmers than one farmer and a collection of beggars waiting for their handout. And I feel like our arts community is becoming more beggars than farmers. 

And I'll teach with wisdom. On the topics of writing and finances and health. Only wisdom in 2026. We need more resources which means we need more knowledge on how to make that happen.