7 ways to skip the day job

Work + Freedom

I've been earning a living since the Bronze Age (circa 1973), without ever holding a day job. Over the decades I've had my share of money struggles, but I found my way around them and am now, at 65, in the best financial shape of my life.

Here are seven lessons that helped me arrive where I am today.

1. Take risks. My final semester of college, while attending Tulane University, I decided after graduation to leave the swampy lowlands of New Orleans and live near mountains. While researching possibilities, I read an article about the exciting, vibrant city of Vancouver, British Columbia and decided to apply for Canadian residency. To my shock, I was accepted just two months later. After taking the train across Canada, I started my new life in Vancouver in July 1973.

Tip: Avoid rash risks (don't throw all your savings away on the lottery!), but do take strategic risks.

2. Develop a needed skill. After a year of doing odd jobs, I signed up for a one-year course that certified me to teach English as a second language. In 1975, I taught my first ESL class to a roomful of Chinese students. ESL turned out to be perfect for me: part-time, well-paying, and flexible. When I wasn't teaching, I began freelance writing for magazines and newspapers. I taught ESL to adults for 10 years in Vancouver, Boston and Seattle, while on the side I published essays, articles, and columns on self-help and travel.

Tip: Look for needs in the community that you can help meet — and turn into income.

3. Live carefully. Instead of buying a car, I rode a bicycle and used public transit, which allowed me to avoid hefty fees for car payments, insurance, registration, gas, parking, maintenance, and all the rest . When I married in 1978, my husband and I had a joint car, but I rarely used it. I didn't acquire a car of my own until I was 36.

Tip: Question every major purchase, especially those deemed “essential” by our culture.

4. Capitalize on personal interests. While teaching ESL, I lost 25 pounds. Eager to share my strategies, I approached the local university's continuing education department and offered a workshop on alternatives to dieting. The class filled immediately, with a waiting list. After a reporter from The Seattle Times interviewed me, I was invited to lead more workshops and give talks. Meanwhile an article I wrote for Weight Watchers Magazine was reprinted in magazines in the UK, Australia, South Africa, and Brazil. My weight-loss “side” business was doing so well, I decided to make it my primary focus.

Tip: Study your areas of success with a view to how they might help other people, and turn into profit centers.

5. Promote yourself. My experience with The Seattle Times taught me that access to media can work to your advantage. After learning how to write a press release, I approached local print media, radio and TV, offering myself as a guest on shows and inviting reporters to attend my workshops. One journalist who interviewed me about how women could succeed in the workplace wrote a column about a workshop of mine that she attended. Her column was syndicated in newspapers all over the country. Soon I started receiving calls from Phoenix, Chicago, and Boston, and my business went national.

Tip: Take advantage of all media, and don't overlook traditional sources like your local newspapers, radio and TV stations.

Related >> The Essential Guide to Retirement

6. Cross-pollinate. In a weight-loss workshop, I discussed the importance of healthy communication with family members. Afterwards a participant asked me if I'd be interested in leading a seminar on communication skills in her professional workplace. Would I?! Not only did I enjoy working with a larger group, I discovered a new word and a new field: “training.” I also learned it was much easier to get paid generously by a business with an Accounts Payable department than by a string of individuals who often asked for a discount or a delay in paying.

Tip: Be open to opportunities to apply your existing skills to new, more lucrative markets.

7. Find your tribe. After I ‘discovered' training, I joined the American Society of Training & Development, and later the National Speakers Association. In both organizations, I met colleagues, accepted leadership positions, learned about clients' needs, got referrals and business, and gained visibility. Colleagues with more experience helped me avoid “OPM” (other people's mistakes). The more questions I asked of senior colleagues, the more I learned.

Tip: Surround yourself with people who have been in your field longer than you, and ask a lot of questions. Don't be embarrassed to be a beginner.

In many ways, I was lucky. I started off debt-free in an era of economic opportunity. More than once, I was in the right place at the right time with the right people. But I also made smart decisions, said ‘yes' to opportunities, and found allies. These are timeless skills that will help anyone succeed, no matter how old — or young — you are.

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4 years ago

I like your last point about “finding your tribe”. I feel that I recently found mine in the personal finance and more specifically FIRE community and I’m loving it. Freedom40Plan

4 years ago

And I thought you were just into fast cars and designer dresses!

Robert Connor
Robert Connor
4 years ago

Being very conservative taking risks is a hurdle i always need to overcome!

4 years ago

Keep to your own values. After med school I accepted a first job for a year in a smaller peripheral hospital. Some days later a renowned hospital offered me a position I really wanted. They could’nt believe I turned them down sticking to my promise to work at the smaller hospital, but I would like to talk with them. A year later they accepted me right away and because of the experience gained I just flew through the specialist training. Had I taken up the opportunity right away I know I would not have succeeded as most fresh out of… Read more »