Practice Management Time Uncategorized

Stop the “shoulding”

Written by Allison Wolf

Our Attorney With A Life contributor Jill Farmer was featured in the Washington Post’s 21 Day Timehacker Project which matches readers with coaches to help them find time for their most important goals.

Farmer was paired with a litigator with a dream: Transforming a foreclosed marina he had recently purchased, into a restaurant and beer garden along with expanding his existing kayaking business and continuing to run his successful legal practice.

She introduced five valuable strategies to help him advance his goals:

  • Shift your perspective
  • Make over your To Do List
  • Define your schedule
  • Sync your technology
  • Stop with the ‘Shoulds’

My personal favourite of the five was stopping the “shoulding”:

Torn between his law office and his growing kayak enterprise, Boyle was always second guessing how he divided his time between the two. “To borrow an oft-used term from twelve-step programs, Chris was ‘shoulding’ all over himself. It was draining his energy and creativity,” Farmer said. “During our conversation, Chris also recognized that the same innovation that has helped him be a successful entrepreneur with the kayak and marina business, can come into play in his law practice, too. We spent quite a bit of time brainstorming ways he could lower overhead at his law practice so he could spend less time there, and give more focus to his kayak company to make it more profitable. (Five Simple Strategies, Washington Post, Brigid Schulte.)

I asked Farmer to tell me more about what lawyers can do generally to reduce energy drain from “shoulding” in their own lives.  Here’s what she told me:

As an attorney, it can feel like your entire schedule is driven by “shoulds”—deadlines, client needs, work assignments from superiors, etc. So, that becomes the default motivation—What should I be doing? The problem with using should as the determining factor for launching all priorities, decisions and actions is that it take YOUR power away. It’s letting someone or something outside of you have control of how you spend every waking moment. That leads to burnout, resentment and a lack of purpose or meaning. What can you do about it? The number one thing is to take a more sophisticated look at your schedule—at a time when you’re not feeling panicked or pressured. Get curious. Where can I make choices that empower me and line up with my values? How can I create space for things that support my physical, emotional and spiritual health? Is there someone else who can help me get creative and give me a different, more positive perspective on how I’m spending my time? The bottom line, carrying around a load of “shoulds” is like lugging around a sack of sand. It’s draining and will deplete your energy much faster. Put it down. Reprioritize based on what you want your life to look like.

Instead of should, what do you want? I have a hunch that some of you may wonder about this: “If I let go of the “shoulds” won’t I simply become lazy and unproductive?”  I have good news for you.  Our “shoulding” selves like us to think that they are essential to our productivity but I know for a fact they are not.

For two lawyers I know, Jason and Andrea, a big “should” that was causing problems was the “I should be responsive.”  This belief that their time was not their own to direct was exhausting them.  The big “responsiveness should” was sucking the enjoyment and satisfaction out of their legal practice.  As a result this summer they are both working to make a change: to set boundaries around their time so that they get blocks of time for them to use during the day as they choose.

Behind all that “shoulding” is your own natural interest in doing well, your creative energy, and a whole set of important priorities. This summer take some time to put aside your “shoulds” and discover what are the choices you can make that will empower you and align with your values.

About the author

Allison Wolf

I am the founder of AWAL and one of the most senior coaches for lawyers in North America. I have helped countless clients over the past fifteen years, develop thriving legal practices and before that served as director of marketing for award-winning law firms. My specialty is uncovering the thinking traps and gaps holding clients back and helping them acquire the mindsets, skills, and habits for growing successful and rewarding legal careers. After a career in legal marketing and business development with law firms in Beijing, New York, and Vancouver, I was trained as a coach in 2004 at Royal Roads University and now coach clients from across North America. You can reach me at or learn more about my coaching practice from the coaching section of the Attorney With A Life Website.

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