Per My Last Email17 Nov 2025

So You Want to Be Your Own Boss? Here’s What It’s Really Like

In this episode, Kaila and Kyle sit down with journalist, media executive, entrepreneur, and NKA Media founder Nora Ali to talk about the realities of becoming your own boss. Nora gets extremely candid about what pursuing entrepreneurship really looks like in detailing her transition from the traditional 9 - 5 to founding her former startup Mason Media. 00:00 Intro 02:09 Nora’s career trajectory 05:15 Why Nora decided to pursue starting her own business when she did 09:09 The unexpected downsides of becoming your own boss 16:21 The physical toll being an entrepreneur took on Nora 18:12 How Nora navigated the transition from a creative career to having to handle the business side of her own business 24:53 On debating whether or not to re-join corporate America 27:06 Advice for people considering making the leap into entrepreneurship 29:02 The value of having a life or career “theme” 31:40 A final piece of advice for an aspiring entrepreneur This episode was sponsored by Superhuman. You can check out Superhuman today at superhuman.com/podcast. Want to get all of Kaila & Kyle’s career resources? Subscribe to Per My Last Email: https://www.permylastemailshow.com/ Watch Per My Last Email on YouTube: @PerMYLastEmailShow Follow Per My Last Email Instagram: @permylastemailshow TikTok: @permylastemailshow Twitter: @permylast_email Have a question for us? Send us an email or voice note to permylastemail@morningbrew.com Learn more about your ad choices. Visit megaphone.fm/adchoices Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app! Learn more about your ad choices. Visit megaphone.fm/adchoices

Denne episoden er hentet fra en åpen RSS-feed og er ikke publisert av Podme. Den kan derfor inneholde annonser.

Episoder(117)

The Surprising Power of Constraints at Work (with David Epstein)

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...

15 Jun 46min

Following Coworkers on Instagram and Other Social Media Dilemmas

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 ...

8 Jun 34min

The Rise of the Career Generalist (and Why It Matters More Than Ever)

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 gen...

1 Jun 36min

Retirement Has Changed—Here’s How to Plan For What It’s Really Like

In this episode, Kaila and Kyle discuss all things retirement—how the concept of retirement has changed, how they’re financially planning for their own retirements, and what their ideal retirement loo...

25 Mai 36min

Why “Optimization” Is Actually Making You Miserable

In this episode, Kaila and Kyle are joined by author Brad Stulberg to dig into what we get wrong about “excellence,” what true excellence really looks like, and the achievable strategies to achieve it...

18 Mai 39min

Should You Be Friends With Your Boss? + 3 More Career Dilemmas

In this episode, Kaila and Kyle answer listener-submitted questions around career advice and work dilemmas. From just how friendly you should get with your boss to how to ask for remote work accommoda...

11 Mai 32min

The Hidden “BS” Holding You Back at Work (And How to Break It)

In this episode, Kaila and Kyle are joined by Aiko Bethea, Founder of Rare Coaching, to talk about the hidden bullsh*t at work, how it’s holding you back, and what you can do about it. From holding yo...

4 Mai 44min

The 5 Sneaky Ways You Might Be Sabotaging Your Career

In this episode, Kaila and Kyle break down the five sneaky (and surprising) things that are affecting your career, and what you can do about them. 00:00 Intro 02:42 Why your commute is more importa...

27 Apr 37min