Lisa Woodruff: “Every Night When I Am Ready for a Little Downtime, I Challenge Myself to Do One More Thing.”

Lisa Woodruff: “Every Night When I Am Ready for a Little Downtime, I Challenge Myself to Do One More Thing.”

Interview: Lisa Woodruff.

Lisa Woodruff is the founder & CEO of Organize 365, which helps people get their home and paper organized in one year with functional organizing systems.

Outer order, inner calm!

Her new book is The Paper Solution: What to Shred, What to Save, and How to Stop It from Taking Over Your Life (Amazon, Bookshop). Such great questions to get answered.

I couldn't wait to talk to Lisa about happiness, habits, and outer order.

Gretchen: What’s a simple activity or habit that consistently makes you happier, healthier, more productive, or more creative?

Lisa: My weekly Sunday Basket System habit makes my work week less chaotic and frees my brain to think, allowing me to be more productive during the week.

What’s something you know now about happiness that you didn’t know when you were 18 years old?

Happiness is a choice. Circumstances happen to everyone. It is the thoughts you choose to think about those circumstances that create your emotions.

What conclusions have surprised or intrigued you—or your readers—most?

I held the belief that organization was a skill you were born with. Some people had it and some didn’t. After working with hundreds of families, I realized that organization is a learnable skill. We all have the ability to learn to live an organized life.

Have you ever managed to gain a challenging healthy habit—or to break an unhealthy habit? If so, how did you do it?

Habits are so powerful. I find it harder to create good habits than to break bad ones. In doing either, I follow on social media and listen to podcasts by people who already embody the habit I want to have. Watching and listening to them be more productive, exercise, or eat better is a constant reminder of what is possible and to take action!

Would you describe yourself as an Upholder, a Questioner, a Rebel, or an Obliger?

I am definitely a Questioner. I am always looking at problems and situations and thinking through all the possible solutions and iterations for optimization. My mind never turns off. Even when I am sleeping, my mind is coming up with new and unique solutions to situations and problems.

Does anything tend to interfere with your ability to keep your healthy habits or your happiness? (e.g. travel, parties, email)

As a Questioner, I love novelty. The repetitive nature of good habits causes me to lose interest in them. Adding a challenge or goal to my habits keeps me engaged and moving forward.

Have you ever been hit by a lightning bolt, where you made a major change very suddenly, as a consequence of reading a book, a conversation with a friend, a milestone birthday, a health scare, etc.?

Yes! Quitting my job on the Friday before winter break was a very quick decision. After a long day and additional pointless meetings, I questioned the reactive life I was living and decided it was time to take matters into my own hands. Even with the prospect of no job and mounting debt, I quit teaching the next morning and set out to live a proactive life of my own making, no matter what the outcome.

Is there a particular motto or saying that you’ve found very helpful? (e.g., I remind myself to “Be Gretchen.”) Or a quotation that has struck you as particularly insightful?

“Do one more thing.” Every night when I am ready for a little downtime, I challenge myself to do one more thing. One more chore, one more clean up sweep, one more task at work before I shut down. That “one more thing” takes that item off my to-do list, frees up the next day a little, and gives me an added sense of satisfaction as I transition to my evening time.

Has a book ever changed your life – if so, which one and why?

So many books have changed my life. I remember when listening to The Four Tendencies, and identifying that my husband is an Obliger. I remember exactly where I was in the yard weeding when you described Obliger-rebellion and thinking, “Oh my goodness, I better be careful!” As a Questioner, I can definitely push people’s buttons in my quest for more knowledge. I am much more aware now with my husband to keep us far away from Obliger-rebellion!

In your field, is there a common misperception or incorrect assumption that you’d like to correct?

Yes! I remember growing up hearing the phrase, “Only touch a paper once.” This paper philosophy wasted so much of my time and mental gymnastics trying to stay on top of my paper piles following this rule.

Today, I put all my paper and actionable to-dos in the Sunday Basket System and process that once a week. And yet, I still touch each paper numerous times. Rules taken out of context like I did led me to a bigger paper problem, not the solution I sought.

In writing The Paper Solution, I have cracked the code on getting all of your household paper organized once and for all! Americans live a paper-based life. We may never be paperless, but we can have much less paper.

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Find out if you’re an Upholder, Obliger, Questioner, or a Rebel.

The Four Tendencies explain why we act and why we don’t actOur Tendency shapes every aspect of our behavior, so understanding your Tendency lets us make better decisions, meet deadlines, suffer less stress and burnout, and engage more effectively.

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