OPEN THREAD: Shedding your “Shoulds” at Work

What rules have you set for yourself around work that are holding you back?

I’m just back from a rejuvenating trip with my family. Being a Portfolio-Lifer, I found the initial preparation for the trip challenging; not booking or packing for the it, but the boundary-setting across my various projects.

Knowing what I know about myself, and of my difficulties with completely turning off during a vacation, I brought a book that had been gifted to me by a longtime collaborator and Optionality member, Bryon Morrison, who just had a hunch I would enjoy it: Soulbattical: A Corporate Rebel’s Guide to Enjoying Your Life, by Shelley Paxton. 

Shelley, formerly the CMO of Harley Davidson, decided to step away from her role and from corporate life to clean up internal, soul-level messes that only she could perceive, and only she could address. Through her personal stories and candid insights—wrought from painful life events not related to her job—she shares her journey out of a grind that was emotionally and physically draining to a less-certain but more fulfilling existence as an author, coach, and guide to others contemplating a more soulful existence.

One of the many parts of her book that sticks with me is her advice to “Stop Shoulding on Yourself,” an invitation to look at aspects of your life where you are doing things more out of obligation than intrinsic desire. Of course, sometimes we really are obligated to do things, like pay our bills. But sometimes we make rules around how to fulfill these obligations that no longer apply to us, or that even hold us back.

I thought about the “Shoulds” I’ve harbored over the years:

• I should be making at least as much or more money in every new role. With this as a should it’s very hard to find, or create, fulfilling work. I often found that higher paying opportunities often included a “stress tax” in the way of more pressure, more hours, more politics. Or was that just how I justified taking highly-paid, unbearable roles? 

• I should get a “job-job”: that’s my term for a corporate role, with benefits, versus the more entrepreneurial opportunities I often found myself attracted to.

• I should have stuck it out/made it work at (insert soul-sucking role here). Some say I have impulse control issues; I don’t have a huge tolerance for stagnation, boredom, or any whiff of being exploited. But looking back I can’t really say my decisions to jump, or even when I was pushed, landed me in a worse place.

• I should work straight through my life until I hit retirement age (whenever that is). It never occurred to me to not work, or to not be in pursuit of work until I was incapable of working. Thinking through this Should I’ve concluded: This is really stupid.

So those are a few of my Shoulds. Some required a great deal of excavation, as they have been part of my work philosophy for so long they are no longer perceptible; some I rejected long ago.

How about you? What are some of your Shoulds? Have you overcome any of them? What are new rules you’ve written about how you approach work?