In this episode, Kaila and Kyle debate whether or not taking a real vacation even exists anymore, and provide tactics for how to protect your off time. Can you ever really fully log off in a world with flexible working conditions? And how can we reclaim PTO? 00:00 Intro 02:20 How we got to the state of the working “vacation” 06:59 The real vs imagined expectations of your employer 11:08 Setting clear expectations with your team 14:32 Flexibility’s pros and cons 21:27 The other reason we can’t fu

In this episode, Kaila and Kyle are joined by Cherry Miao, CFO of Hightouch, who gets into the art of conducting an effective job interview, how she susses out a job candidate’s mindset, and what she thinks should be changed about the job interview process in general. She also breaks down the skills that are most important to hone in each stage of your career—from your first entry-level job all the way to the C-Suite. 00:00 Intro 01:06 The art of the interview, and how Cherry identifies top tale

In this episode, Kaila and Kyle are debating ambition: do you really need to be super ambitious to have a successful career? What level of ambition is the ideal amount? And can you be ambitious in both work and life in equal measure? 00:00 Intro 01:21 How we’re defining “ambition” 05:42 Can you succeed without ambition? 13:30 What is the opposite of ambition? 17:05 Kaila’s framework for thinking about the qualities necessary for career success 18:18 How ambitious SHOULD you be? 24:04 Can you be

In this episode, Kaila and Kyle are joined by author David Epstein to discuss the topic of his latest book, Inside the Box: How Constraints Make Us Better . Listen to hear why constraints increase both productivity and creativity, and how to implement them on your own to help you in work and life. 00:00 Intro 02:05 The story of General Magic 06:02 Additive bias 09:14 Brooks’s Law 12:34 How Bell Labs is an example of useful constraints 14:48 Can removing constraints ever be beneficial? 19:31 How

In this episode, Kaila and Kyle dig into the unspoken rules of social media at work. When is it okay to follow a colleague on Instagram? When is posting about your company empowering vs. harmful? And is it okay to have no social media presence at all? 00:00 Intro 00:58 Which social platforms you should and should not follow your coworkers on 08:05 A good rule of thumb for deciding whether or not to follow a coworker on Instagram 09:58 The most important thing to keep in mind when it comes to fol

In this episode, Kaila and Kyle are joined by Milly Tamati, the founder of generalist.world , to talk about the benefits of being a career generalist (vs. a specialist), what people get wrong about generalists, and how to start building a portfolio career. 00:00 Intro 01:29 Defining what a “generalist” is 02:27 What does a long-term generalist career look like? 04:42 What people get wrong about specialists vs generalists 07:39 How do you figure out your strengths and fit as a generalist? 14:52 W