The only way to achieve true job security

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Laurie Lewis ran Patagonia’s SoHo shop, the brand’s highest grossing store, for six years. She then built the retail operations for Organic Avenue, described as “the only organic plant-based grab-and-go brand in the U.S,” to 12 retail stores. But then the capital structure of the company changed, they reorganized and she was jobless. Fretting over her sudden unemployment, she gratefully signed onto her first freelancing job, which soon led to multiple jobs. It’s been an exciting and also nerve-racking transition for her.

I hear desire in so many friends’ voices who want to learn how to freelance, and my heart burns for them. Money is freedom, and not feeling in control of how much money we can make on our own, no matter what changes in our lives, keeps us in situations that no longer serve us.
 
“I’m a consultant now, and the freedom that it gives me is priceless,” Lewis told me recently. “I don’t have to settle. I am not in pursuit of just any job.  I [know] what my value is as a retail executive specializing in building happy and profitable employee and customer experiences.” 

I started freelancing in 2002 as a Web developer, and it was both easy and hard at the same time. It was easy in that there was always more work than I could handle. It was hard in that I had to deal with the pay cycles of my clients — do the work in June, for example, but not get paid until September. Cash flow was forever my enemy, followed close behind by the enormous tax bills resulting from how little I knew about self-employed quarterly tax payments.

But over the years I learned how to manage the work and build support teams. I could work when I wanted from wherever I wanted as long as my clients felt cared for. Mostly it gave me the peace of mind to know that I wouldn’t ever worry about getting a job or losing a job because I could always generate projects and make money when I needed to. Shouldn’t every woman be able to have that kind of security? 

We go through so many events and phases in life during which it would be comforting to know that we can still earn a living while also having total control over our schedule. But it’s scary — the idea of not having a guaranteed paycheck.

Ramit Sethi teaches a program called Earn1k, and has helped many men and women transition from full-time employment or unemployment into freelance work. I sat down with him recently to ask: What holds people back from spreading their wings and jumping into the big blue sea of opportunity? And how can we identify and develop our skills as freelancers? Here’s what he shared. 

1. Believing that no one will hire you or not knowing what you can offer.

Feelings of being unwanted or unable to provide anything of value are far more a matter of your own self-confidence, but likely have little to do with whether or not you can provide a service people will pay money for. Yes, finding your first few clients will be hard, but when you find the right product-market fit, you will find them. 

Everyone has a skill that others would pay for. Maybe you're an Excel whiz...or amazing at dog training, or organizing closets, or tutoring math. It’s all about how to find that skill, then "package" it for the market. Finding clients is really about learning the basic art and science of selling. Once you learn that, you’ll succeed.

2. That your job will become all about sales.

This concern is actually true, but the issue isn’t that you have to become a salesperson. It’s that you need to change your relationship to selling. When you sell a product you believe in, that supports you.

Sales simply means sharing authentically about the quality of the services you provide and finding relationships through which money is exchanged for these services. If you want to experience the freedom of freelancing, consider changing your relationship to the idea of selling.

Being a saleswoman doesn’t mean being sleazy or dishonest. It means communicating with potential customers so that the people who need you can find you.

3. Feeling like you’ll lose your work-life balance.

If you have self-employed friends, you probably see them working on nights and weekends and fear you’ll lose “me” time. Ironic when what you’re going for is freedom. Truth is, every decision you make has a cost and benefit.

You are trading the security of a full-time job to be able to decide when you work and where you go. There will be periods where you’re working day and night to deliver for a client. And, there will be weeks where you have less work and you can do … whatever you feel like. That’s the trade.