
A podcast about all the "five year plans" that did not go according to plan. From lawyers turned comedians, to neuroscientists turned chefs, come join Anna in exploring the craziest career pivots and the ups, downs, and uncertainties of being in your 20s and 30s.
| Publishes | Weekly | Episodes | 10 | Founded | 3 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | BusinessCareers | |||

They say misery is reserved for those who hate their jobs, hate their careers, hate their colleagues, hate their bosses, hate their hours etc etc etc.... or is it?
In this episode, Anna explores a different kind of struggle: what it’s like to genui... more
For Henna Choi, leaving her career as a personal injury lawyer was literally matter of life or death.
For years, Henna tried to do everything “right.” She went to law school, built a successful career, and appeared to be thriving in the public eye.... more
How does a corporate lawyer become a famous person? Today, Jules Romano sits down with Anna to unpack the real story behind the transition—from billable hours to building a personal brand on the internet. What started as sarcastic, off-the-cuff video... more
And no, we are NOT referring to the cliche break up line.
We're talking about all the ways you reject yourself, before the world ever gets a chance to (or not!)
In this episode, Anna dives into the invisible limits we place on our own lives—the s... more
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How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
Apple Podcasts | #107 | |
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Apple Podcasts | #65 | |
Apple Podcasts | #101 | |
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Apple Podcasts | #154 | |
Apple Podcasts | #201 | |
Apple Podcasts | #244 |
Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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The show concentrates on non-linear career paths, personal growth, and the realities of pursuing ambitious plans in your 20s and 30s. Across recent episodes, listeners hear intimate stories of leaving traditional professions, pivoting into entrepreneurship, and navigating burnout, identity, and public-facing branding. The conversations balance practical lessons with candid reflections, offering tangible takeaways on making deliberate career shifts, building communities, and evaluating what success really means. A standout thread is the emphasis on authenticity, vulnerability, and resilience as engines for growth, whether someone is transitioning from law, medicine, or demanding corporate tracks into creative, entrepreneurial, or service-ori... more
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The Five Year Plan launched 3 months ago and published 10 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on The Five Year Plan include:
1. Henna Choi
2. Jules Romano
3. Maggie Arai
4. Nathan Ng
To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.