In Good Company Blog

Tough Love: 5 Difficult Questions to Ask Yourself as an Entrepreneur

Sometimes our commitment to the ways things are overshadows good decision making. Maybe it’s the whole ‘devil you know is better than the devil you don’t’ kind of thinking. Or maybe it’s that even good change can be annoying and distracting. In any case, this tendency can be particularly dangerous for those of us who work for ourselves. We don’t have bosses or organizations to pressure us into changing our outdated or nonsensical ways. We are in charge – for better and for worse.

In order to challenge myself and keep my own bad habits in line, I came up with this list of tough questions:

1: If you could wave a magic wand to instantly fix three things in your business, what would they be?
(be honest, don’t just say “get more clients”…what do you KNOW is broken)
* What prevents you from fixing these things on your own?

2: What three things would you stop doing for the business if you didn’t have to?
* Why don’t you? What would make doing them better?

3: What are you doing only because you feel like you “should”?
* What would happen if you didn’t?

4: What important thing do you never seem to have “time for”?
* Why? What makes it hard to prioritize?

5: What have you given up for your business or to be an entrepreneur?
* Are you OK with that sacrifice?

Surprisingly as painful as it can be to sit with these questions (and their answers) this exercise has led to some really wonderful changes and improvements that have brought me great satisfaction. I’m planning to revisit them a few times a year.


Pic via.

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