The odds are that you will probably consider self-employment at some point: Eighty-nine percent of people in the United States who make more than $50,000 a year are self-employed, according to Entrepreneur magazine.

As with all decision points, the way to make the best choice is to know yourself. If you get bored easily, do a lot of different jobs. If you are a type-A hyperachiever, do one business really, really well. If you have a small tolerance for risk, keep a full-time job while you explore other options. All are great ways to make the shift to working for yourself.

One of the most interesting recipes for self-employment comes from self-employment evangelist Barbara Winter. Winter says that it’s easier to have five jobs that generate $10,000 a year than it is to have one job that generates $50,000 a year — the perfect scenario for opening an eBay business, renting out a room in your condo, writing press releases for your friend’s startup, etc.

This is, essentially, juggling five jobs, but Winter’s book describes ways of making it seem manageable: “The juggler walks out on the stage with ten sticks and ten plates, but doesn’t begin spinning them all at once. Methodically, the juggler positions the first plate on a stick and gets it into motion. Once done, the juggler moves on to the next, then the next, and so forth. Eventually, all ten of the plates are spinning away, each with its own momentum.” (This is how I feel about blogging — it’s like throwing another plate in the air for me.)

If you have spent some time in the workforce, consider becoming a consultant, which essentially is making a single, focused business out of yourself. “You should have at least five years of workplace experience before you go on your own,” says Laurie Young, founder of Flexible Resources, “because you are offering your experience.” Also, you need marketing skills to sell yourself. It takes a certain kind of talent “to show people you have skills they can use.”

Find a market niche that you can dominate. Otherwise there is no way to distinguish yourself from all the other consultants, no way to stand out. (Two good books on this: Small is the New Big, and The Long Tail.) Young did this herself, as a recruiter. She is a headhunter for people who want flexible jobs (she herself job shares the CEO position at Flexible Resources). If she were a more typical headhunter, she would not stand out above the crowd as well.

Alexandra Levit worked in public relations for Computer Associates and then struck out on her own, as a consultant in publicity and marketing communications. In terms of making the transition, Levit advises that you “try lining up a few jobs that you can have before you take the leap,” and be prepared to spend “about 30% of your time marketing yourself.”

Levit provides a snapshot of reality for all entrepreneurs when she says, “Don’t expect the drawbacks to be only financial. You need a lot of self-discipline to sit down in your home office and work without any external pressure. Working for yourself means you’re responsible for every aspect of the business,” and this means, ironically, even some of the annoying tasks you were trying to avoid by working for yourself.

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12 replies
  1. Dale A
    Dale A says:

    Penelope, My background is in manufacturing. I have some very creative product ideas that I would like to pursue as an entrepreneur. I have always wanted to go into business for myself and I think the time is ripe.

    Problem, starting manufacturing business is extremly expensive, it takes at a minimum a small manufacturing site, etc.

    Question, how do I get started? Whats next?

    Thanks for the guidance!

    * * * * * * *

    Hi, Dale. For a business idea like yours, that requires significant startup costs, you need to write a business plan and create financial models to make sure the businss is viable. If it is, use the business plan to approach investors and raise money.

    Good luck with your idea!


  2. Pooja
    Pooja says:

    Hi Penelope,

    Great to read your post on testing waters for self employment.

    I am into software project management and quality assurance since last 5 years – before which I was a technical writer. I have identified my passion in form of writing – and I wanted to get into documentation and quality consulting business without leaving my day job. Your guidance in this would help me go a step further.

    How can I go about it ?

    Thanks, Pooja

    * * * * * * * *

    Try to get some clients on the side that you can work for at night. When you get good at rounding up clients for yourself, that’s when you can quit your day job.


  3. Anchal
    Anchal says:

    Hi Penelope,

    I am new to virtual space , blogging and would like to start working on the sideline to see if I can pull off a full time job for myself on my terms like so many other people here are trying to do.

    My question is going to sound stupid , but then I have come to realise that stupid questions have a tendency of saving the here I go..

    you say “Try to get some clients on the side that you can work for at night. When you get good at rounding up clients for yourself, that's when you can quit your day job.”
    my question is how do I do this? where can I look for clients?

    • uverse
      uverse says:

      juggling jobs is smart. Too many times people focus on 1 skill and are proud of that skill and are employed at 1 job for 40 years – ugg. Constantly need to be developing new skills and working many different jobs. Diversity is the key to getting through a recession

  4. antiaging
    antiaging says:

    You are correct in saying that you need to be self-motivated to be self employed. I started a business from home almost 9 years ago and it was an instant success. My wife wouldn’t let me resign my full-time job until I had 3 months of equivalent or better earnings in my new business. I attribute my success to a free course I completed. The course was published by someone who had been successful in making the transition from working for someone else to working from home with an Internet based business. I have tried to teach friends and family to do what I am doing but with one exception they have all given up without putting in much effort. It made me realize that not everyone is cut out for self-employment. You have to be self motivated, goal oriented, and persistent to succeed.

  5. russ
    russ says:

    This is how I began. Working on the side while you have a full time job is smart for sure. You can build and create your business while still having the security….

  6. Robin Melina Kinsman
    Robin Melina Kinsman says:

    Hi Penelope, I´d like to post this post in my newly formed web page, but in Spanish (I´d do the translation myself for my own benefit). I do this because in general I agree with all your posts/practice. Does it work that way – I just link and translate? Thanks for any comments on that. Best!

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