Dropping our Work Demons

What would it look like if we let go our our fabulous, monstrous ways?

Back in my 20s I was living in New York City and working for media companies as a writer, producer, and editor. Through a friend I met a co-founder of a recently seed-funded media startup seeking experienced producers to help launch a Website. I had just left one of the pioneering startups in women’s new media; it seemed a no-brainer except for one small catch: I’d need to report to my new headquarters the following Monday ... in San Francisco. 

And did I mention it was a Thursday?

I was only 27, but I had invested over five years building relationships in “big” media: Penguin (now Penguin Putnam), The New York Times, Time Warner. I was getting published in national magazines and newspapers. And the Internet was still a relatively new frontier. By leaving the storied halls of traditional media to join a startup I feared I would blow up my career before it really took off. Back then, there really was no other place to be if you were in print media. And yet, these storied halls were narrowing in on me; something wasn’t working; I wasn’t sure I even wanted to work in traditional media; I felt stuck. 

Still I agonized over whether I should take the role.

I went to visit with Geoff, a senior editor at one of my former employers, at his midtown office. He’d been in the magazine business for over 25 years, and while he hadn’t been my direct manager I considered him a mentor and a mensch. 

I told him about the role. He was supportive, but he also offered words of caution:

“Try it out, but don’t stay away too long or you’ll lose your place in line.”

He said it — what I’d feared most about moving to San Francisco: If I took a new opportunity I could lose my grip on the limited traction I’d generated previously. 

I moved to San Francisco fully expecting to move back to New York in a few years, but I never did. I returned often, after starting my own company and opening offices in New York, and after taking investment from one of the media companies I had worked for in NYC, but that’s it. I never returned to traditional media.

Nearly 20 years later I spotted Geoff at an internet leadership conference and we had dinner together. We lamented the slow painful demise of print media and the death of our former employer.

I joked with him, “I lost my place in line.” 

He joked back, “I think it worked out.”

The unspoken joke: The "line” I so feared losing my place in no longer existed. 

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I try to think back to this story when I catch myself harmfully holding my place in line. Something I do when I come to a crossroads in my working life, and I cling to my reasonably comfortable, if stagnant, situation for any number of reasons:

• I shouldn’t stop working in this industry where I have built so much earning power and reputational currency.

• I should take this opportunity; ten years ago I would have killed for it.

• I shouldn’t waste my years of experience by starting over, doing something else.

Shelley Paxton, author of “Soulbbatical: A Corporate Rebel's Guide to Finding Your Best Life”, calls this “Shoulding over oneself.” Paxton, a former executive and CMO of Harley Davidson, shares one of her Shoulds that caused her great emotional, and even physical suffering during her career as an executive: "I should make personal sacrifices for work."

"Because I get paid great money. Because I’m lucky to have this job. Because it’s what everyone else at the top does. And, because if I don’t go above and beyond, the company will discover that I’m not really that talented or worthy of the role I’m in. Impostor Syndrome was raging, my boundaries were crumbling, and my positive role models were few. An insidious combination, for sure.”

Today, Paxton helps people grapple with their shoulds, which are often rooted in personal expectations and playbooks that no longer serve them. 

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Optionality Open Thread: Shedding your “Shoulds” at Work

What rules have you set for yourself around work that are holding you back? Share yours in this week’s all-member community discussion.

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How do you know when your work playbook is no longer serving you? We see examples every day on LinkedIn of people who weathered illness, external calamity, job losses and are forced to reassess their work lives. But ideally we don’t require crises to signal change. There are smaller, perceptible signs if you take the time to notice them:

• Experiencing insomnia;

• Polishing off a bottle of wine, or a pint of ice cream, to help take the edge off and because, dammit, you deserve it after a day like today;

• Feeling the need to apologize incessantly, or blame others, for mistakes; 

• Feeling distracted, unable to focus on critical tasks;

• Being passive aggressive when pushed to your limit: "It’s no problem! I’ll just order Door Dash for my family and stay all night to get it done. No worries!"

Another way to notice the need for change: Think about a time when you did everything “right”: showed up, over-performed, prioritized work above all else, and things still didn’t work out. You didn’t get the promotion. You didn’t get the funding. You didn’t make your number. You didn’t achieve occupational nirvana. And ask yourself: Knowing what I do now about how it could turn out, would I do it that way again? What would I do differently? How can I adjust how I work, so that, good or less-good outcome, I have no regrets?

This week we focus on de-shoulding and re-examining our work mojo; we ask ourselves: Can I do things differently? Where do I start? Join the conversation.