10 Things I Learned At A Joyfully Jobless Weekend

I have been recommending Barbara Winter’s book, “Making A Living Without A Job,” for years, so when I discovered that she was coming to the city where I live for a Joyfully Jobless weekend, I jumped at the opportunity to participate in her event. I wanted to learn new resources for self-employed clients and also to explore ways to ramp up the writing and product development sides of my business.

Here are my favorite 10 things that I learned:

1. In person, Barbara (she gave us permission to call her by her first name!) is the same feisty, irreverent, passionate advocate for self-employment as she is in her writing. Her calling in life is to help people leave jobs they hate for self-employment they love and she has spent 20+ years learning to do this effectively.

2. Barbara told us that Sophia Loren once said, “I am successful because I was willing to give up being anonymous.” This idea really struck me as important because I know that I’ve felt ambivalence before about putting my most creative work “out there” in the world, open to critique, and I know many clients feel the same way. It is essential to learn to forge ahead despite the fear because as T. Harv Eker says, you can’t go very far when “one foot is on the gas and one foot is on the brake.”

3. Credentials no longer impress customers or clients. They prefer that you have real world experience. While this isn’t such a fun realization for someone like me who spent a decade in school to acquire specific expertise, the good news is that when I want to master a new skill set, I probably don’t need another degree but I can instead learn through doing. (Tempting as a degree in instructional design or non-fiction writing may be!)

4. There has never been a better time to build a business because the demand for products and services is global. Barbara told us about Dr. Joyce Brothers deciding that she wanted to teach but she wanted the world to be her classroom. Since I am already convinced of the advantages of location independence, I love how much this creates infinite possibilities.

5. People who think that they hate marketing may be reassured by the reality that when you find the right audience for what you offer, sales are a natural by-product. If you focus on developing relationships, then there is no need for the obnoxious type of self-promotion. The goal is to find people who share your values. Barbara cited Paul Hawken, the entrepreneur who founded the Smith & Hawken gardening company, who says that gardening is the best training to be an entrepreneur because in both cases, you plant seeds and then nurture them.

6. Many people with jobs are frightened by the idea of self-employment so they will give you all manner of bad advice. Ignore the dream bashers and learn from people who are happily and successfully self-employed, such as Barbara.

7. Don’t focus so much on “how” you will do things but instead keep the end rewards in mind and then learn as you go. You don’t have to know everything when you start.

8. Barbara joked that “guidance counselor” is an oxymoron. While I observed how much her audience appreciated the humor, I think it is important to acknowledge all the wonderful guidance counselors who are enthusiastic about self-employment and will help students/clients explore and pursue entrepreneurial paths (I personally know some of these guidance counselors).

9. Barbara also joked that “good job” is an oxymoron. This is funny and I laughed, but neither Barbara nor I believe everyone should be an entrepreneur. I think there are three types of people in the world: (1) Those who are primarily suited to be business owners / entrepreneurs, (2) Those who are primarily suited to work in salaried jobs within organizations, and (3) Those who can adapt to either situation, perhaps alternating between the two or landing jobs as “intrapreneurs” and running autonomous departments and divisions within larger organizations. The important thing is to figure out which one you are.

10. Don’t struggle alone. In building a business, even introverts benefit from connection. Whether you are brand new to self-employment or you are an experienced solopreneur who wants to meet other “joyfully jobless” people and learn some new things, a Joyfully Jobless Weekend is a fun and educational thing to do. I highly recommend it.