The challenges of navigating the digital world when you’re not a digital native


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In this interview I chat with Jim Cirillo – career technologist and recent podcast host.

Find out how Jim found the courage required to leave a steady, well-paying job and what it takes to navigate the digital world when you’re not a digital native.

1:12 - Introducing Jim, what he’s working on, and how he and Matthew met at Podcast Movement.

3:11 - Background details on Jim and whether he ever thought he would have his own podcast.

4:37 - How Jim’s career progressed and ultimately led to starting JimJim’s Reinvention Revolution PodCast; the chaos of the tech world.

8:17 - The effect of the change of pace in technology and how that affected Jim’s career path.

10:55 - Why he didn’t want to be an employee.

12:49 - Starting his entrepreneurial journey as a consultant and making that transition.

13:53 - How the pace of change hasn’t slowed down and leaving his job due to the company not being able to move fast enough.

15:58 - What his approach to staying up to date on technology is and how that works into his podcast.

18:45 - Lifestyle design being the driving force behind Jim’s entrepreneurial journey and where he is on the journey right now.

21:30 - The courage required to leave a steady, well-paying job and what it takes to navigate the digital world when you’re not a digital native.

24:45 - Feeling confined in a corporate career track and that there are more opportunities out there.

26:10 - Taking time to focus on and assess what you’re doing, rather than just being reactive.

28:02 - Creativity as the link between being an artist and being an entrepreneur.

28:42 - The positive aspects of disruption; Matthew’s experience at Block-Con.

31:24 - How different technologies are starting to come together towards a big inflection point.

32:24 - Staying abreast of change and understanding how it may have widespread effects.

33:38 - Using the podcast as a way to stay on top of tech changes.

36:52 - The best advice and education Jim has gotten regarding embracing disruption.

38:34 - Understanding how to react to changes properly by just trying different things in a hands on way.

40:30 - Outcomes Jim has seen so far in his journey.

43:58 - The breadth of possibilities Jim sees in this field.

45:42 - The rapid-fire questionnaire.

52:32 - Contacting Jim and learning more about his podcast.

Resources and Links Mentioned:

JimJim’s Reinvention Revolution PodCast

Podcast Movement

Josh Elledge

Richard Branson



The Power of Now by Eckhart Tolle

61 episodes available. A new episode about every 4 days averaging 47 mins duration .