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Two-headed and three-headed entrepreneurs FTW

By Jennifer Westlake

When you say you’re a consultant or an entrepreneur, you often hear, “Must be nice to be your own boss.”

But the thing is, if you’re your own boss, you are also your own employee. You can be inventive, determined, hardworking and a pile of other wonderful things, but if you can’t assess yourself objectively, how are you going to know when it’s time to start delegating some functions?

My theory – and I must stress it is just a theory, which you are most welcome to counter – is that consultants, freelancers and entrepreneurs all eventually wind up having to fire themselves from some tasks and hire themselves on to others.

When you get to that stage, a sequence of situations that demand increasing levels of savvy unfurls.

Once you recognize the need to focus on your most important tasks and roles, you have to find a way to delegate. Delegating tasks represents a certain degree of risk, but doing it allows you to take on bigger challenges.

When you take on bigger risks and challenges, a feeling of uncertainty is natural and even healthy. Feeling nervous about a new undertaking may be a positive sign that you’re fully committed to doing everything possible to make all the bits and pieces and details come together in one successfully completed objective.

At the same time, “gut feelings” – that niggling feeling in the pit of your stomach –  have been shown to have real significance. So you should probably take those feelings into account, too.

So how do you know when that feeling of being on edge is a sign to keep calm and carry on or get out while you still can?

You’re going to need to worry, and vent and scheme behind closed doors with someone who knows how to keep everything you tell them to themselves. It’s important, too, that this person be immune to the charms of your blue sky visions.

An experienced entrepreneur will see your opportunities and vulnerabilities with different eyes. They’ll see you with different eyes.

See, THIS is why entrepreneurs need trusted confidants. Coaches and mentors are professionally obligated to A) keep everything you tell them to themselves – which is of primal importance in business, and B) not pull any punches when they see you are getting lost in the weeds.

In my next post, I’ll go over a few coaching and mentoring options that are open to Montrealbased entrepreneurs.

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