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The Boring Newsletter, 9/20/2026

We Are All the Person Sitting in Their Car, Mustering the Courage to Go Inside

Hi Friendos,

We’re now fully back to school everywhere in the country and lots of us have a bit of a “reset” or “fresh start” feeling this time of year. Like, ok, summer’s over, everyone’s back to work, and now I’m going to finally tackle that thing that I’ve been meaning to get to. Maybe it’s a money issue, like figuring out what to do about some debt, retirement saving, or getting a will – something weighing on you. Maybe you were energized for a day or week or two and then when you tried to look at it, you stalled out or simply decided to do other more urgent things instead. You know that these sorts of money issues don’t solve themselves, but also don’t have a real plan for specific next steps and it is too overwhelming to address.

For years, this was me and getting therapy. Intellectually, I understood and fully agreed that therapists could really help people and yes, that could even include me. But I also had in my mind some truly senseless ideas, like: therapy is shameful; people who see therapists are hopelessly damaged; people in therapy can’t take care of themselves. I would never have admitted that I was buying into these ideas but I know they contributed to my inaction in asking for and receiving help.

Last year, I cried when I searched for in-network therapists in my insurance plan. I cried when I sent messages to therapists to see if they were taking new patients. I cried after phone calls telling me they were not taking new patients, that the Cigna website had it wrong and they didn’t take my insurance after all. Usually for me, making a medical appointment is an administrative hassle but not an emotional process, but this time it involved really so many tissues. And that was just the making-an-appointment part of it, not even the part where I actually talked to a therapist!

I worried about a therapist judging me. What if they, with their professional expertise, confirmed my deepest fear: that I was just a messed up person and beyond reach?

I’m reading a book called “The Trauma of Money” and the author recounts:

I once keynoted an insolvency trustee conference, and one member who works with bankruptcy shared that he would often see people sitting in his parking lot for a year or more before getting up the courage to come in and speak with him about their debt relief goals.

I so wish I could give a big hug to all those people sitting in their cars.

Of course, when I finally did match up with a therapist and start meeting with them, they did NOT tell me I was beyond reach. They told me I was brave and deserving of help and that even though I may have been dealt a couple lousy cards in my childhood, there were lots of things I could do to help make things better now. And then they helped me start doing them and it’s working!

I’ve said many times, “I should have gotten therapy years ago,” or, perhaps more accurately, “I wish I’d been able to get therapy a long time ago,” because I recognize that emotionally I wasn’t ready until I was.

And every time I say something like that, I think about my many clients who begin a meeting by saying they should have dealt with their money issues a long time ago. We’re all saying the same thing!  

If you have a money issue that’s been weighing on you, please know that we all have areas that are hard to tackle so that just makes you normal. That’s why I find it so silly and infuriating when people judge someone else’s financial dilemma, “It’s just math. The answer is obvious,” or “Just handle it and move on,” as if emotions don’t exist or impact people.

If you are able to muster yourself to tackle something hard, please also do something nice for yourself. Maybe some nice back to school supplies.

-Stephanie