Health + wellbeing

The downside of being your own boss

- February 3, 2008 2 MIN READ

You stroll into your boss’ office, flick your resignation letter nonchalantly onto the desk and explain precisely what they can do with their stinking job. Then you swan out to cheers of your workmates. Or so goes the fantasy of being your own boss.

Much of the appeal of working for yourself and being your own boss is escaping the annoying, incompetent and/or bullying bosses that make your life a misery. But when you leave employment to run your own show it’s not just those bosses that you leave behind.

What about the great bosses? The ones that motivate you, guide you, teach you all the tricks of the trade and swoop in if a project hits the fan.

In any large organisation there are plenty of genuine leaders whose role it is to develop talented employees. If you’re a standout company performer, your progress up the career ladder can become a natural progression.

Being your own boss, it is great that there’s no one breathing down your neck telling you what to do. But there’s also no one patting you on the back, advising your next move and looking out for your career. No strategic roadmaps. No performance review. No career plans. No fast track programs.

So, what do soloists do when it’s time for a change? For me the end of each year brings a period of reassessment. Whether it’s looking for a clear direction or assessing opportunities, these are the times when I miss being able to book a meeting with the boss to map out a solid plan.

Want more articles like this? Check out the working alone section.

One great solution is to find an experienced business mentor who is willing to sit with you a few times a year and be your sounding board.

Is having no leader an issue for you? How do you cope with being your own boss? Do you honestly ever miss your boss? Do you have a mentor? Any good resignation tales? I’d love to hear your views.

I would ask my boss, but I don’t have one!


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  • Andrew Caska

    Caska IP Patent Attorneys

    'Flying Solo opened up so many doors for us - I honestly don't know where I'd be without it"