Category Archives: Delegating

Cruel and unusual management (or, how to stop being the worst boss you’ve ever had)

Be done with cruel + unusual management (photo from (c) David Morch)
Be done with cruel + unusual management (photo from (c) David Morch)

Most entrepreneurs place a high value on freedom. And most of us can tell bitter tales about “that horrible boss” we once had, back in corporate days of yore.

But was that “horrible boss” anywhere near as demanding, critical, and unforgiving as YOU are, as your OWN boss?

Did she make you stay up till 2am, proofreading blog posts?
Or deny you your god-given right to a 2-week vacation + paid sick days, every year?
Or strap you to a chair and forbid you to go to dinner with friends until you’ve cleared out your inbox, completely?

I’m guessing … not.

Those longs hours often begin when our business is new, and we’re crazy in love with everything about it. Can’t stop talking about it. Thinking about it. Working on it.

But as with other loves, that ardor for a new business eventually cools a bit. What we’re left with is a few habits we once overlooked but we’d now like to change.

Life partners can be hard to change. (What’s so mysterious about where the dirty socks belong??) But you can have a sane + humane boss right away, by becoming one. Here’s a baker’s-dozen steps to becoming your own best boss:

  • Maybe the bad boss expected you to be available 24/7. But that ends now. Establish work hours. Make them reasonable. No more going back to work for a couple of hours at 11 pm, unless you get to sleep until 9 AND you like it that way.
  • Your bad boss may have sprung things on you at the last minute, but you work from a plan. Is your one-person business too small for a written business plan? No, it is not. It just needs a special kind of plan — one that fits you and your business.
  • Use your plan to make a task list. Your bad boss may have assigned busy-work and pointless projects, but you won’t.
  • Learn to say “no.” It’s the only way you’ll be able to say “yes” to what you really want.
  • Have you already said “yes” to some things that don’t contribute to your plan? Clearly, quickly, professionally and gracefully renegotiate those commitments.
  • Get out of your chair every hour. You are never too busy for exercise. As a good boss, you know that movement is actually what your brain needs to function better.
  • Never skip a meal. Google is famous for launching as the only start-up in Silicon Valley that was not littered with empty pizza boxes. They had a great chef from the beginning; now they have several great restaurants. Take a lesson from Google and feed yourself well.
  • Invest in professional development. Make a list of 10 things you’d like to learn, or 100. Choose one, find a teacher/coach/class, and do it now.
  • That bad boss may have expected you to handle everything yourself, but you’re a better boss than that. Be strategic about developing your team. Figure out what kind of help can contribute the most directly to your bottom line. Hire that help first.
  • Don’t go it alone. Find an accountability partner, or two. Hire a coach. Form a board of advisers. Or all of the above.
  • You don’t need your bad boss’ evaluations at the end of the year. Give yourself credit for everything you’ve tackled, every day, every week.
  • Pass out rewards. Lots of them. As the best boss you’ve ever had, you know how to show appreciation, even when the budget is tight.
  • Your bad boss was only interested in avoiding disaster and covering her backside. You had to hide mistakes. Now you can freely admit mistakes, learn from them, and keep going. No shame.

Kiss that horrible old boss good-bye. You’ve got a new boss now, and this is just the start. She’s definitely someone who’s going places, and taking you with her.

For more on how to be your own best boss, see

The Most Powerful Word In Productivity

Sitting Is The New Smoking

What’s In It For You? How to reward yourself for meeting your goals

We All Do Better With Help – 8 professionals that can really make a difference

What’s Better Than Perfect? Escaping the perfectionism trap


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