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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.

{ 2 trackbacks }

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Miranda April 28, 2010 at 9:11 am

Great points! I think a lot of people forget all of the extra hats that one has to wear when being one’s own boss. I never really figured myself for customer service, but I do it all the time when working with clients.
.-= Miranda´s last blog ..Review: Retirement Calculator at =-.

Tyler WebCPA April 28, 2010 at 5:12 pm

I really see myself in the being more self-critical than worried about my bosses criticism. In fact, sometimes he has to tell me not to be so hard on myself!
My recommendation is to jump on in and see how you float. Perhaps work on your own moonlighting while working on your current job or perhaps quit it all and sink or swim! Whatever happens, it can’t be worse than never having done anything.

Small Budget Big Style April 29, 2010 at 7:22 am

I believe I have some of the skills you mention above, but I’m honestly not sure if being a full time entrepreneur is for me. I like the fact that I can count on my pay check every two weeks. But I also like the idea that I can increase my income by being a part time entrepreneur. Maybe I’ll change my views as I get older and become more confident in m professional abilities.
.-= Small Budget Big Style´s last blog ..Reasons to buy organic: Scary sized fruit =-.

Mrs. Micah April 29, 2010 at 7:28 am

@SBBS the qualities can also make you function excellently in a lot of work places or make a good boss of other people. You need them to do well as your own boss, but they’re definitely not exclusive to that. 🙂

I like part-time entrepreneurship, myself, because it gives me a place to outlet certain creative energies, it supplements our income, and it’s nice to know that even if I lost my day job I wouldn’t be helpless or peniless.

Jackie April 29, 2010 at 10:05 pm

These are some great points that people often don’t give enough thought to before going off on their own. The sales one has always been my stumbling point…
.-= Jackie´s last blog ..How I Learned the Secrets of Traveling Light (& Saving Money in the Process) =-.

Guy G. April 30, 2010 at 12:17 am

Thanks for the great post. I am always aspiring to move into not only self-employment, but business ownership where I’m managing my own sales force. I think I can say yes for 3 out of 4 of your questions. I lack in time management, so when I can get that in check, I’ll be able to get my own business moving.

Thanks for your advice,
.-= Guy G.´s last blog ..How To Manage Money Tips has joined the Yakezie Challenge! =-.

eemusings April 30, 2010 at 12:50 am

My beloved boss, who left a couple months ago, was the best manager I EVER EVER had. New replacement has been named and starts soon. I’m wary. Also, because it’s a woman, and to be honest, I tend to prefer male bosses. (Single Ma, does, too and does a great job articulating why!). But I’m happy to be proven wrong and hope I am.

I don’t think I would want to work entirely for myself – don’t have the temperament or skills. Am I critical of myself? yes – sometimes I feel I just can’t get a task right by my standards…but I admit I sometimes miss the ball entirely and need a second pair of eyes to get me back in line.

I always get the job done, but I often feel overwhelmed for sure! I hate selling, have never done sales, let alone selling MYSELF. I don’t mind interacting with others – sometimes my phone manner is out of this world! but generally I much prefer to put my head down and get on with my work.

Yep, I think it’s pretty obvious I’m not cut out for this, at least not at this stage.
.-= eemusings´s last blog ..Life in the spotlight =-.

Izrada sajta September 26, 2013 at 3:49 pm

I like to work as a freelancer and really like people with workoholic habits. And I think that self-employed people works better, harder then “9-5” guys. 🙂

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