Be Your Own Better Boss

A lot of the entertainment companies I work for are small or solo. Here are some ideas for being your own boss.

Please appreciate that it’s hard

You will never catch up. You’ll never do it right. You’ll always feel like you’re missing something. You’ll have lots of blind spots.

Bosses at companies get paid more (theoretically at least) because it takes an emotional toll, it takes responsibility, consistency, and mostly responsibility. Responsibility is heavy. Anyone can make high level decisions, but it’s not worth it to take responsibility for the fate of the company if you’re getting paid minimum wage.

Separate your boss work

The high level thinking, the big picture stuff, the things only you can do get done when you’re wearing one hat. Maybe literally. Put on a boss hat and figure out where your business is going, what needs to be done to get there. What kind of people do you need to hire, etc.

It helps to delegate work to yourself

… by making a todo list or a bunch of todo lists. I like the Getting Things Done (there’s a short course on Lynda.com) method. You can set up todo lists for your different levels of focus.

  • I want to do my boss work when I’m very focused and have more jellybeans to take responsibility for bold moves.
  • I want to do some communications work, creative drudgery when I’m a little less focussed.
  • I want to do cleanup or fun work when I’m tired.

When you’re the employee

… cleaning your office, sending a bunch of emails, the actual work tasks that are not genius, don’t mesh it with boss work.

You might not feel the wind at your back when you’re working for yourself vs when you’re your own boss, but you can make it easy. Putting in long hours trying to please your boss can be rewarding.

Take the emotional weight out of this work, pretend you have a boss that just wants it to get done, and don’t consider whether it’s the right thing todo at the time. Trust that your boss has already figured out what’s best for the company.

If you think of bigger ideas, write them down somewhere for your boss to review later. Don’t expound on them because you will piss off your boss, or distract your boss from the big picture. Your boss does not have an open door policy.

Block out time to be the boss

If you think of a bigger company, a lot of hours are put into the labor force while there’s only one boss putting in boss hours. Similarly, you’ll want to block out a small percentage of your time to being the boss. It will be not a lot of time, but it will be intense.

This practice of separating your boss time can be really helpful when you’re expanding and taking on more of a boss role. You’ll understand the other roles in the company and will be better at delegating to other people that really exist.

If you never separate, you will never be your own boss. You’ll never have the ability to make the boldest crucial decisions and you’ll also have trouble completing the lower level work.

Stick to the time you allocate. Then, you’re not spending a bunch of time dreaming. You’re the powerful executive.

Understand your employee

A good boss incentivizes the work that helps the business. A good boss knows the weaknesses and strengths of employees. A good boss takes long term plans and turns them into short term projects so employees can be motivated. Think shamelessly about yourself as an employee.

  1. When are you likely to get distracted?
  2. What work are you just never going to do?
  3. Why is some work fun and some not?
  4. How can you improve your accountability?
  5. Where do you flow?

Track something

As a boss, you’re going to track something like audience growth, income, work produced, etc. As the employee you’ll track something like time spent, or whatever other metric your boss wants for representing your labor.

You’re not going to track everything. That gets distracting and tiring. Tracking is for a simple pass/fail scope of the work. Are we meeting our simple goal? Take the next step.

Promote yourself

When things are working, and there’s work that you hate, promote yourself by hiring a freelancer to do that thing for you.

Bosses are usually not at the top

Even if they’re just friends with an outside eye, it can be helpful to have your board of advisors be other people. Check in with them and see how you as the boss can be doing a better job. What are you missing? If your goal is profits, are you meeting your goal? Just talking to someone else about it can make it more clear and more likely.

Written for folks who want to attract and energize groups

Scot Nery is an emcee who has helped some of the biggest companies in the world achieve entertainment success. He's on an infinite misson to figure out what draws people in and engages them with powerful moments.

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