On Horses and Bookkeeping

By: Stella Orange

There’s a phenomenon that’s been kicking around in my head for awhile now.

Let’s call it “The Pleasure of Paying for the Ride You Want.”

Years ago, I used to host writing workshops in one of my chosen hometowns, Bozeman, Montana. We’d gather a dozen business owners around a big wooden boardroom table, and everyone would present a project to the group for input and feedback.

At the end of the three days, I invited those inclined to stay and socialize to go ride horses, soak in the hot springs, and eat at one of my favorite out of the way joints.

I always felt like a queen, being carried on horseback. The work was done. There was space between horses on the trail so you couldn’t carry on much of a conversation. It was just you, your horse, your thoughts, and big sky country.

To my mind, this was the perfect way to end a work thing.


Fast forward to last year. Last January, I’d parted ways with my bookkeeper.

I tried to hire another one, only to have it fall through. Then the pandemic hit. Then I had babies. Then the uprisings and the helicopters came, when people took to the streets for George Floyd and Black Lives. Then. Then. Then. You know the year we’ve had. I let the chips fall where they may.

By the end of last year, my accountant emailed me a list of what she needed to do my taxes.

“I don’t need a bookkeeper! I can do it!,” I declared.

And I did. I poured myself a Manhattan one Saturday night, and did the data entry for a year’s worth of books in about two hours. Thousands of dollars of work! “Look at me!,” I congratulated myself. “I’m a flipping genius!”

Then I needed to file reports for payroll. I did a quick internet search. Everything was written in a foreign language I do not speak.

“I am resourceful! I can do my own payroll filings!,” I proclaimed.

I stepped back, thought through what I was trying to do, and picked up the phone to call a past vendor and colleague to beg help. She answered my questions, told me exactly what I needed to do, and refused payment.

So I sent her a box of chocolates from my favorite Montana chocolate shop.

It was only when I started printing out end of year reports that my confidence ground down to a nub.  

Were the numbers right?

I had no way of knowing.

That’s when it hit me: I was definitively, decidedly, and unequivocally out of my depth.

End of the trail!

So I called Sarah and asked for a bookkeeping referral.


This may sound odd, but the feeling of riding a horse and the feeling of having someone who knows what they are doing do my historical bookkeeping for 2020 is exactly the same.

It is the feeling of being carried.

It is the feeling of having the ride I want.

Bookkeeping-wise, I wanted two things:

One, I wanted to prove to myself that I could figure it out on my own, because in the past I have been known to go all Victorian-lady-on-her-fainting-couch on bean counting details.

Two, I wanted it done correctly – and to do that, ultimately, it would cost money. Interestingly, once I took it as far as I could by myself, I was okay with spending the cabbage. More than okay, actually. I desired the experience of being cared for, taken care of, and being the queen on horseback again, allowing herself to be carried.


I’ve worked with enough people over the past twelve years to understand that letting go of doing what’s not yours to do is a skill that doesn’t come naturally.

It is hard to know our lane. Let alone stay in it!

I’ve also bought enough services, eaten at enough restaurants, and had the good fortune of staying at enough high-end hotels to know what the pleasure of being taken care of by professionals who give a hoot feels like.

It feels like being carried by a horse. And I’m old enough to see that there are times to save money, and times to spend it. And what good would keeping that two thousand dollars in my pocket be, if my taxes were wrong because of it?

Stella is cofounder and copywriter at Las Peregrinas, a creative and consulting agency. As our resident word nerd, she writes copy and points out the stories everyone is living and telling through their work. She is also fun at parties.

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