March 7, 2022  • Newsletter

This Month’s Money Message: Reflect

Welcome to March, the month where tax hypotheticals become real. By now you have probably received a handful of W-2s and 1099s from last year, and you are probably staring at a long list of expense categories (which may or may not be organized as well as you hoped they would be).

Gather them all. We’re using them as an excuse to look back at last year.

Because that is this month’s theme: Reflect.

Normally, I reflect with joy and happiness on the projects I completed, the individuals I served, and the adventures I had, each of which is captured by a restaurant receipt, a plane ticket, or an entry in my “research” category. And I’m still going to do that. I enjoy the pause to appreciate all I was able to do.

I enjoy the pause to appreciate all I was able to do.
But this year, I’m doing another kind of reflection as well, thanks to Jessica Stillman’s article about the “reverse bucket list” (with a hat tip to Arthur Brooks for the idea she reflects upon and the research to support it).

I’m going to reflect on the things that I’d rather not have in my tax file for next year. These may be projects that have run their course, events that were less fulfilling than I wanted them to be, or even subscriptions that I no longer need to pay for. And by taking a moment this month when all of last year is gathered in financial form, I’m going to find what needs to be eliminated from my business life. “Subtraction beats addition” as Stillman writes.

I don’t know that this will magically create more time (it probably won’t) or make the tracking of income and expenses any easier (it probably won’t do that either), but there’s no way I am going to miss the chance to reflect.

With that in mind, here are three things to know, do, and believe this month:

Know: What your stack of tax forms does and does not include.

Your stack of 1099s is probably tall, but it won’t include direct sales to customers. You’ve got your own records… Take a moment to look at what you really earned for the year and celebrate that.

Do: Thank your system.

How well did your system of organization hold up last year? Are there notes to yourself about what categories mean that would be helpful going forward? Do you need to evaluate a new (larger?) system for 2022?

Believe: You’ve got this. Use this opportunity to plan for the 2022 you’d like to have, including subtracting some income and expenses from your business life if that makes sense for you. I’ll see you on the other side.

What We’re Doing

This month we’re (yet again) talking taxes, taxes, and more taxes. Elaine joins NEC, Juilliard, CCAD, and the Cleveland Institute of Art for tax conversations. She’s also joining Nick & Andy to record an episode of Making Art Work, which will be out later this month. It’s also the start of some pretty optimistic spring celebrations, including Holi, Nowruz, St. Patrick’s Day, and the start of Daylight Saving Time.

What We’re Talking About

Client conversations of late have reflected an ongoing sense of languishing and overwhelm, which is no surprise given everything we are all navigating. We’ll keep reflecting with clients, probably using last year’s tax return to check in on items that may need a reset this year.


If you’d like to chat with me to answer your own questions, feel free to find a time that works with your schedule.



I can’t wait until next year when I’m reflecting on 2022 to see what (if any) changes I made and what impact they had. I look forward to hearing about your reflections as well.

Until next month…



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