Inside the mind of a professional organizer: Coulda, woulda, shoulda

Jessi Bushman PHOTO CREDIT: Contributed

Jessi Bushman PHOTO CREDIT: Contributed

Jessi Bushman PHOTO CREDIT: Contributed

Jessi Bushman PHOTO CREDIT: Contributed

Jessi Bushman PHOTO CREDIT: Contributed

Jessi Bushman PHOTO CREDIT: Contributed

Jessi Bushman PHOTO CREDIT: Contributed

Happy New Year.

As expected, by Jan. 1, we should have our New Year’s resolutions in mind, so we can magically make better decisions.

When it comes to research, we have a greater understanding of our health and how our thoughts affect our physical and mental state. That said, I believe our surrounding environment should be our top priority when it comes to feeling well.

This year, I challenge you to embrace that we are playing the “coulda, woulda, shoulda” game in our head regarding our stuff — what to keep and what to part with. We constantly question our decisions while cultivating what-if scenarios of why we should or shouldn’t keep items from our past.

You might be wondering, “What does coulda, woulda, shoulda have to do with organizing?”


Ironically, our purchases and acquired goods become items of the past.

The greatest feelings resulting from a purposeful purchase include:

The excitement of using said purchase as soon as possible.

The excitement of how something makes us look or feel.

The excitement of how something will function and hopefully make life easier.

The feeling part is where most people struggle. The instant gratification of something new might be filling a void of something deeper.

An easy example would be a shirt we purchase and hang in our closet, tags attached. Every day that shirt is unworn, I see a representation of our lost time, energy and money spent sourcing something truly not needed.

This purchasing habit ultimately will contribute to our sanity when it comes time to deal with our abundance of stuff.

Our inventory also applies to items we’ve acquired throughout the years. Somehow, we just have stuff:

• Where did it come from?

• How long have we had it?

• Why do we still have it?


• We make impulse purchase decisions.

• We avoid making short- and long-term retention decisions.

Right off the bat, we have a lot of decisions to make. This thought alone can immediately shut down our efforts before beginning.

This is why working with a professional organizer is a premier experience.

A fresh set of eyes will emphasize efficient space planning, create solutions and offer suggestions to achieve your current and future goals. We become so set in our ways, it’s easy to continue running in circles unless we make specific alterations to our habits.

Have you had a conversation with your people about desires to achieve life organization? Do you avoid downsizing and organizing primarily because you’ve already played out a negative scenario in your mind?

Don’t let coulda, woulda, shoulda impact your ambition to downsize and organize.

Life organization is a life-long effort. Just remember: The moment we are born, we begin collecting. This is our first exposure to having others make decisions for us, what we want and what we keep. Our entire life is about decisions — ones we make for ourselves and ones we make for others.

This also is our first exposure to developing our mindset in ways we do not understand. Age, experience and knowledge will grace us with the realization of how other people’s decisions have molded us into who we are today.

This takes me back to the conversation needed to move forward with any organizing project. A neutral coach easily can identify coulda, woulda, shoulda concerns and obstacles holding us back.

Recently, I spoke with the daughter of a potential new client.

“I want to gift my mom with your service,” the daughter said. “She is your typical mom — always putting everyone else first. She hesitates to do anything for herself, and she doesn’t take the time to finish projects she’s started.”

Before we spoke, the daughter mentioned the idea to her sister. A source of reason, the sister insisted this needed to be discussed with the mom first.

I 100% agree, support and often suggest that organizing services should not be a surprise but a decision made together when living in a shared space.

After learning a little about this specific scenario, this project sounds like it’s been a hot spot for years. Before seeing the space, I’m estimating this is a relatively small project. The goal is to meet the mom’s needs, make the daughters genuinely happy and show gratitude for everything she has given throughout the years.

See how this cycle begins? One thought easily can morph out of control without a realistic action plan, leading to no action at all. That said, follow through with this project will provide a fresh outlook for the mom and allow others in the space to focus on gathering, not the space gathered in.

To all of the women out there: It’s OK to ask for, as well as accept, help offered. Your people love you and want to support you for all you’ve done for them.

Grab a hold of the new year, and reduce any future coulda, woulda, shoulda barriers. Make the best of your physical space, all while enhancing your mental space.

Jessi Bushman is a professional organizer, member of the Iowa Professional Organizers Association and owner of Organizer Jessi in Dubuque. Visit her at or on Facebook at OrganizerJessi. You also can email her at

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