Break Free From the 9-to-5 Grind With a Portable Income

I’ve been helping people to kick-start their life as online freelancers for over 12 years, but I still find it incredibly gratifying when someone writes me an email, or approaches me at a conference to tell me how different their life is now that they have broken free from their 9-to-5 job.

I remember one woman who sent me an email saying, “Get me away from my microscope.” She was a pathologist, and she was tired of only looking at the world of microorganisms. She wanted time to look at the bigger world too. Now she’s freelancing for companies in Latin America, helping them to write webpages in English for the North American market.

Then there was the schoolteacher that said she wanted M&M money. When I first heard that, I thought to myself that she hardly needs to start freelancing just to buy candy. It turned out that for her M&Ms were massages and margaritas…much sweeter. To fund her relaxation she wanted to work just a few days every month and take the rest of the month off. And rather than draw the money out of her savings account she wanted to earn a little bit instead. I helped her do just that.

Then there was the lawyer who was concerned about the legal implications of the whole freelancing thing. He was worried he could be sued if he gave advice to somebody in a state that he wasn’t licensed in. But after talking with him and explaining about how he could use his skills without getting into legal difficulties, he’s now giving business advice to start-ups based on lessons learned over his 30-year career.

And finally, there’s the funny one about the corporate marketing guy who spent most of the last 10 years of his corporate career making slideshow presentations (think Microsoft PowerPoint) for his company’s products and services.

He told me he was “ready to vomit” if he had to make one more presentation. But it turns out, it wasn’t so much making presentations that was the problem, it was making them for the same company for a decade—he was just burnt out on the subject matter.

He found out he actually relished the opportunity to make presentations for different businesses, explaining different things, presenting different products and services, and bringing new ideas to market. He found a freelancing life that taps into all his PowerPoint and presentation skills, plus, he enjoyed the freshness of working on exciting new projects with multiple clients.

Over my 12 years of doing this, I thought that what I was doing was simply helping baby boomers learn how to freelance effectively. Now I realize that there’s more to it than that.

We baby boomers are going through one of the most profound and difficult changes in our lives, as we transition from our careers to the great “what’s next?” And though freelancing creates a way to bring in income, it’s not solely about that.

Being able to share the things we’ve learned also brings us meaning and joy, and it allows us to stay interested and engaged over the coming decades in a way that no generation before us has had the opportunity to.

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