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My Boss is a Pushover

I’ve been a little stressed at work lately because there’s a big project due. There’s no firm deadline, but it’s clearly my top priority to finish it, and there’s a lot riding on its successful completion. Yet every day I end up working on secondary tasks, not the big project. They’re easier. And it’s rewarding to cross several concrete items off the to-do list not just inch a millimeter down an enormous task list for a single project. The lower priority projects also have less at stake. The pressure to get the big project right puts a lot of weight on every step of the work.

I feel guilty about avoiding what I should be doing, but not guilty enough to get myself to work on the big project. Compounding the matter–my boss is letting me get away with it. Week after week, the big project is not done, but I settle in with the little stuff. Nothing is said. No pep talks. No earned reprimands. No redirects. No refocusing of my priorities. So this failure is partly a management problem—my boss is a pushover.

I’m betting most of you have guessed the trick–I’m a writer. I am my own boss. And my only staff person. And I am letting myself get away with murder on the job. I know this because I have very different work habits at my day job than I have at my own writing desk.

On the day job, I am efficient, focusing on the highest priority tasks first, even if they are not the most fun. Even if they are tedious. Or difficult. Even if I’m stuck on how to get them done.

At my writing desk, however, I am the queen of spontaneous googling; keeping the inbox empty; tidying unnecessarily; finding more research to do; or exploring ideas for the next project (once this big one is finished). This lackadaisical approach to work is sabotaging my writing career before it even gets started. I need to figure out how to motivate myself; how to stay on task; how to focus. How to stop doing the easiest, most comfortable, or most straightforward tasks first.

As they say, awareness is the first step towards change. What, exactly, needs to change, however is not clear. The problem isn’t ‘me’ per se, or my skills—I can be effective–the day job proves that. What I lack is self-management—how to get myself to do what needs to be done on my own work. I have to become a better self-boss.

There is lots of available information on business management strategies for the self-employed. It mostly provides guidance and advice on the ‘business’ side of the deal—managing finances, clients, legal issues. If anything, my problem with the writing job is that there is no ‘business’ to manage. Just a number of projects of varying size, at varying stages of completion. No income stream. No external deadlines. No clients. No clear incentives for completion.

And that lack of ‘business’ proved to be a big cause of my poor writing job performance. If I am effective at getting myself to do all the dirty and difficult work on the day job it is because the work is low stakes and brings regular rewards. The opposite is true of the writing job.

On the day job. I receive a guaranteed rate of return for effort expended. The larger the task, the more hours worked, the greater the return. When I am stuck on a daunting or unsavory task on the day job, I have a motivational trick of calculating how the hours of work will turn into the funds to purchase something tangible. The projects also hold little personal risk. None are hugely important to me, or have much personally at stake. Finishing them earns me my boss’s approval, makes me feel efficient, and ensures that I can keep doing the job. The payoff, in proportion to the risk, then is relatively high.

On the writing job, it is the reverse. There is certainly more personal joy in the doing of the tasks than on the day job. But any reward is abstract, distant, elusive, unspecified and uncertain. At best finishing a writing task brings me a happy feeling. Nothing tangible. The stakes, however, are abnormally high. Every word matters. The quality of my writing, the story, the plot, the characters, the voice, all of them might or might not add up to something that will eventually determine success or failure. All of the writing, every single bit of it, is also a direct personal reflection. Who I am. What kind of writer I am. How well I can ply my craft. How well I can make something appealing. And erudite. And sensible. And . . . you all know the deal. You are what you write–in a way that will never happen with a job that is just a day job.

No wonder I have been a pushover boss and an awful employee. I have been putting in endless hours for no tangible rewards and working under the oppressive expectation that my work defines me at more levels than I care to admit. There is no chance for success in that formula.

So I am attempting to alter the formula. I am embarking on an experiment to improve the risk/reward ratio of the writing job. I am creating (and delivering) immediate and tangible rewards to myself for completed tasks and projects, and I am working to lower the stakes of writing.

So far it is working. There is no perfect. But it is good to be back to making steady, if slow, progress on the main project.

How about you—do you ever struggle to get yourself to work on the most important aspect of your work? Do you find yourself stymied by the high personal stakes of writing? What are your strategies to get yourself back on track? 

“Two Girls Are Sleeping On a Table” by Stougard [1]

About Jeanne Kisacky [2]

Jeanne Kisacky trained to be an architect before going back to her first love--writing. She studied the history of architecture, has written and published nonfiction, and has taught college courses. She is the author of the recently published book, Rise of the Modern Hospital: An Architectural History of Health and Healing, 1870-1940 [3]. She currently fights valiantly to keep her writing time despite the demands of a day-job, a family, and a very particular cat.