Are You Ready to Be Your Own Boss?

“Are you ready to be your own boss?” It’s a question one hears asked by people selling the entrepreneurial dream. And those who are quitting or planning to quit their jobs and start small businesses or freelance repeat it back, “I’m ready to be my own boss!”

But are you? Having a boss sometimes sucks (I’m currently quite lucky with mine but I’ve had bad ones in the past), but having a boss or working for an organization that’s more than just you also means that you have to do everything. Based on my own experience, I came up with four questions to help you assess whether or not you have the personality to be your own boss—or even the interest.

Fortunately, you can work on all of these areas or come up with strategies to deal with your shortcomings by collaborating or outsourcing. The key is to be aware before you start working for yourself and come up with a plan.

1) Who’s more critical of your work, you or your boss? Do you beat yourself up for mistakes or just recognize them and move on?

This can go either way. If you’re not critical enough of your work when it needs criticism and you’re not able to learn from your mistakes, then you’re not going to be able to be your own boss. You’ll always need someone outside of you to tell you when you’re screwing up. That person could be an equal partner, but they’ll need to fulfill something of a boss’s role in this area.

Or you may be the sort of person who beats herself up all the time for any error or potential error. You haven’t yet responded to the guy who e-mailed you 8 hours ago. You accidentally crashed a client’s site for an hour. Whether or not this caused an actual crisis, you’re still thinking about it days, weeks, or months later.

In this case, you’re going to be a much meaner boss than anyone else could ever be. Doesn’t mean you can’t overcome it but does mean you’ll have to work on it. Just don’t feel guilty because you have to work on it. Shame spirals handicap your productivity.

2) How’s your time management?

Can you work on a timetable and deliver products on time? Can you handle multiple clients/jobs at once? Do you feel overwhelmed all the time?

Good time management skills are valuable in any job, but if you’re working for yourself then they’re critical. You’re not on a team that keeps each other accountable (or if you are, you’re all working independently) and you don’t have someone to go to if your workload becomes too much.

You create your schedule, take on your clients, and hopefully deliver the expected results on time. And if it doesn’t work out, then the only person you’ll have to blame is you.

3) Do you like customer service?

You may not have a manager any more, but now every client is something between a customer and a boss. Do you like working with people to solve their problems or would you rather be doing the work itself?

You’ve become customer service, IT support, anything else that could be related to your line of work. If you’re making customized swim suits (and I know a woman who does), you may get some angry phone calls if the suit doesn’t fit right or wears out easily. You then have to solve the problem, if possible, and do your best to make the customer happy.

I actually like this part of freelance work, but that’s because I tend to have good clients with reasonable requests/problems. I’ve never had an abusive client.

4) Do you like sales?

Not only are you the customer service department, you’re also marketing your company. You’ll have to set aside time to apply, pitch, and otherwise market your work, at least until the business takes off and you’ve got enough work from old clients and referrals to keep you busy.

Not only do you have pitch, apply, and market, but you have to do the negotiating as well, or be the person who sets prices and sticks to them.

As I said above, none of these has to be a deal-breaker. Just start thinking now about how you’re going to handle it so that you will be ready to be your own boss.

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