Against the Herd With John Winsor

Against the Herd is a podcast where I speak with contrarian leaders and visionaries at the cutting edge of the future of work—and living.?

In case you missed it, I had an enlightening chat with John Winsor in my latest Against the Herd episode. A true early pioneer of co-creating the future of work, John is the Founder and CEO of Open Assembly , a company that gives global freelancers unrivalled access to content, community, and strategic advising.

A self-proclaimed “dirtbag climber and surfer”, John has worked this way (that is, from wherever) long before the pandemic. What the future of work means to him is living a great life and working from anywhere, not letting a company’s headquarters be the reason he’s stuck in an expensive city he doesn’t want to live in.?

In the 90s, he sold his publishing company, bought a house in Mexico, worked under the one tree that had cell service, realized that wouldn’t work long-term, bought a satellite dish from someone in a school bus, and set it up with the same person so he could launch another company while spending his days surfing. A true digital nomad!????

He acknowledges the generational differences in this approach during our conversation. Millennials and Gen Z may not be tied down to mortgages in the same way that baby boomers and Gen X are. John refers to the opportunity to work from wherever—perhaps even for yourself as an entrepreneur—as “a whole new operating system” that some generations need to wrap their head around. It’s a fear of the unknown, and I think that’s a really fair and balanced assessment as to why some are rejecting this approach to work; why some are willing to go “back to normal” and return to the office five days a week. It’s all they have ever known… and they bought a house that was commuting distance from the office in the first place.

That’s why economic freedom is such a critical component of transforming the way we work. When John talks about Henry Ford and the industrial age, he mentions that history conveniently forgets the part of the narrative where Ford tripled workers’ salaries and gave them benefits, allowing an entire generation to move into the middle class.?

With a distributed model where companies can actually hire the best people to do very specific things, talent now has the ability to compete. Of course, this means a new work model, which John calls the open talent economy. This is where companies can find the very best talent to work for them. Rather than the role, your job is the tasks.?

With open talent, companies can no longer look at a job like: “I need an SVP of Community, so let's hire someone that can take on all 40 tasks associated with that role.” Hiring should be more about assessing the 40 tasks that need to be done, finding a professional that has built a portfolio of skills around this function, and having that person comb through and pick the 10 or so tasks that they are best at. Rinse and repeat for all 40.?

This only scratches the surface of John’s insights on the changing tides (he uses surfing as a metaphor to navigating this shift, and it honestly works). Watch the full Against the Herd episode to get inspired by John’s journey toward the Future of Living here: https://www.firstbase.com/blog/against-the-herd-with-john-winsor ?