Self Employment: A Popular Pathway in the New World of Work

April 14, 2023



Self Employment: A Popular Pathway in the New World of Work

Self Employment: A Popular Pathway in the New World of Work

Jeffrey Shaw has never had a traditional job. He started his entrepreneurial journey as a teen, grew a successful business for 25 years, then became a coach for those who want to be or are self-employed. Jeffrey founded the Self-Employed Business Institute and authored “The Self-Employed Life” and “Lingo”. He discusses the fundamentals and key rules of engagement for entrepreneurs that he learned along the way and how he helps people transition to self-employment and build their own businesses. From recognizing your value to finding your customers, and “deprogramming” your corporate mindset Jeffrey shares his insights for the swelling ranks of the self-employed.


[03:15] Jeffrey has never had a traditional job.

[03:35] Started his entrepreneurial journey at 14 years old, Jeffrey wants to be independent.

[04:18] Jeffrey's father's words were pivotal.

[06:17] After receiving multiple awards for his photographs, Jeffrey decided to become a photographer.

[06:49] Jeffrey focuses on buildings then falls in love with portrait photography on location.

[07:33] At 20, Jeffrey has to make it work to support his wife and life.

[08:34] Jeffrey realizes his value/offering and target audience do not match.

[10:15] Jeffrey works out who his audience should be and where they are.

[10:40] Three months should be all he needs to figure it out!

[11:34] How to learn critical intelligence about your target audience.

[12:55] A saleswoman at Bergdorf Goodman shares critical nuances about customer behavior.

[14:05] Jeffrey's book “Lingo” is about his clientele’s secret language.

[14:42] The power of asking questions and seeing things in others that we don't see in ourselves.

[15:40] Achieving success in his business, Jeffrey decides he wants to do more.

[16:25] Jeffrey discusses self-doubt and starts to pursue the idea of coaching.

[18:22] Why did Jeffrey hire his first business coach at the peak of his success?

[19:30] Why had the business plateaued?

[20:25] After 9/11, Jeffrey thought everything was at stake.

[21:33] With every major struggle that business owners go through, there is a shift in values.

[24:15] Crises speed up the process of change.

[25:15] Jeffrey's older clients want to transition quickly to have more freedom through self-employment.

[27:29] To gather useful insights from prior experiences, Jeffrey asks what compliments people have repeatedly received throughout their life.

[28:44] Most people want to set up a business to optimize what they have been doing--there's a catch.

[29:38] How does Jeffrey help people shift from the corporate mindset?

[30:31] The self-employment ecosystem has three components.

[32:35] How Gen Z’s can pursue the self-employment.

[33:34] What Jeffrey thinks the Future of Work looks like. Jeffrey encourages employees to push corporate America to offer a better way to work.

[34:10] What percentage of people are solopreneurs who Jeffrey works with?

[36:10] Is the cycle of contracting, over-hiring, layoffs, and re-contracting changing at last?

[39:10] We shouldn't overlook the fresh perspectives and creativity that come with hiring self-employed specialists.

[39:50] Jeffrey learned how to employ and questions the effort many companies put into hiring.

[41:10] What it means to be self-employed, from real-estate agents to sales associates.

[43:30] IMMEDIATE ACTION TIP: To speed up a typical 12-month transition to self-employment from a corporate job, identify your passion first and build a side gig to test it. You want to know if you have enough passion for what you want to create that’s going to keep you going and get you through the frustrations.


“I used to say, I never had a real job. And then anybody else that was self-employed would look at me and say, you need to stop saying that because there's nothing more real than running your own business.”

“I think you can change everything in life in three months.”

“I didn't know if I could handle having a traditional job because I would live in fear of the rug being pulled out from underneath me. And I always felt like the advantage of being self-employed is that it would at least get slow painful death, but it wouldn’t be sudden.”

“You get to a point in life where you want to get to where you want to go quicker. We all felt like we had all the time in the world in our twenties and maybe even our thirties. You get in your forties, fifties, and sixties, and you're like: ‘Give me the goods so I can get to where I want to go because I don't wanna figure this all out on my own!’”

“I think everybody wants the agency of self-employment, but not everybody wants the burden of responsibility that comes with business ownership. Therefore, let's also make it feel that way in traditional jobs.”