Don’t Be A Bad Boss (When You’re Your Own Boss)

Unless you’re getting a check for turning in what you’re writing, you’re your own boss. But, in this situation, don’t forget that you’re also your own employee.

It can be easier to manage others than to manage yourself. When dealing with another person, you have feedback in their responses to your management. When you delegate work to them, you measure their performance, then focus your attention on other tasks while they do their share of the work. When you set a deadline or goal, they need to work according to your standards. It’s on them.

This isn’t how it works when you’re the whole chain of command. You delegate work to yourself. You need to keep clear on both the big picture and the day to day details. If something is going to get done, it needs to be done by you.

So, how do you avoid becoming your own nightmare boss? It goes beyond being gentle with yourself.1

Think About Your Previous Bosses

No matter what the business, there are general qualities that separate an effective boss from an ineffective one. Look back on the previous employers, teachers, mentors, etc. you’ve had in your life.

What were some of the most succesful ways they motivated you? How did they communicate goals and expectations? Did they work with you to set realistic deadlines and measure your performance accordingly? How did they keep things organized?

Find An Assistant Manager

Think about this person as the XO on a naval ship. Part of their duties involve making sure the captain doesn’t make decisions that will jeopardize the crew or their mission.2 There’s a similar need for that when managing yourself.

Find someone who has an interest in your goals and is willing to keep tabs on you. A significant other, a parent, another writer. Anybody that you have regular contact with and who you trust.

Let this person in on your goals, plans for accomplishing them, and the deadlines you’re planning to work with. The better they know you, the better they’ll be at helping you evaluate if you’re creating unrealistic expectations for yourself (or if you could do more).

At the end of the day, you need to call the shots, but having an outside voice will help you to put things in perspective.

Hard Deadlines vs. Soft Deadlines

A hard deadline is when somebody else needs to see something by a set date. Any deadline you set for yourself with no external force involved is a soft deadline. Period.

A soft deadline can be moved, as needed. Yes, it’s important to set a goal and make the mad dash for it, but if it looks like you won’t make it without multiple sleepless nights, ask yourself if it might be worth it to push things back a bit. This is one of those situations where it’s good to check in with your Assistant Manager, both to remind you when a delay is a good idea, and to help keep you honest if you move the goalposts too often.

Keep Everything Outside Of Your Head

Use a calendar. Find a task list method that works for you. Make countdown signs on a whiteboard when a big deadline is coming up.

The more you try to just remember, the harder it is to remember it all. Save your brain power for the things that really matter and keep hard (and/or digital) copies of all your planning and administrative information.

Give Yourself A Day Off If You Need It

You can’t fake calling in sick when you’re your own boss. You are completely aware of any reasons you decide not to work on a given day. You aren’t just Ferris Bueller. You’re also Mr. Rooney.3

But you can’t let yourself take the attitude of a Mr. Rooney. If you feel you have a completely valid reason to have a Me Party,4 or take care of something else that’s come up, do it. Unless it becomes a nine-day bender of Netflix Watch Instantly and cookie dough straight from the tube, it’s not the worst thing in the world.



  1. See previous post on being gentle with yourself
  2. For examples of this, see every naval movie, ever. Also, most space movies where there are more than five crew members on a ship. 
  3. If you’ve checked this footnote, it may mean you haven’t seen this movie. If that’s the case, please fix that as quickly as possible. It is so choice. 
  4. A party for one. 
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