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EP 234: Leaving Apple’s “Siri” Team for a Second Career Break with Prabha Kannan

Prabha Kannan headshot

Episode Description

Market researcher Prabha Kannan took a seven-year career break before relaunching at Apple, ultimately as the Managing Editor for Siri – which means, as Prabha describes, “head writer and character lead for Siri”. After four years in this role, Prabha published a LinkedIn post that went viral, talking about her decision to take a second career break. This post has over 95,000 reactions, 2,000 comments and more than 1,500 shares. She was also recently featured in a Business Insider article writing about her career journey. We will discuss how Prabha relaunched her career at Apple, how she progressed once there, and hear more about her decision to take a second career break and write about it.

Read Transcript

Carol Fishman Cohen: Welcome to 3, 2, 1 iRelaunch, the podcast where we discuss return to work strategies, advice, and success stories. I'm Carol Fishman Cohen, CEO and Co-founder of iRelaunch and your host. Today, we welcome Prabha Kannan. Prabha took a seven year career break before relaunching at Apple, ultimately as the Managing Editor for Siri, which means, as Prabha describes, head writer and character lead for Siri. After four years in this role, Prabha published a LinkedIn post that went viral, talking about her decision to take a second career break, and this post has almost 7 million views, over 95,000 reactions, 2000 comments and more than 1500 shares. So talk about going viral! And we're going to talk about that viral piece in a little bit. And we're also going to talk about the details about how Prabha relaunched her career at Apple, how she progressed once she was there, and hear more about her decision to take a second career break and write about it.

Prabha, welcome to 3, 2, 1 iRelaunch.

Prabha Kannan: Thanks for having me. I'm excited to be here.

Carol Fishman Cohen: Well, we're very excited to hear from you. And can we please start by hearing a little bit about your career path and what you were doing professionally before your career break, and then what led to your decision to step away from the full-time work force?

Prabha Kannan: Sure. So I built a career in user experience research before I took my first career break in 2010. I had spent about a decade running internal research departments, so primary research, consumer research and consulting to companies who wanted to understand their user base better. So think focus groups and online surveys and any other primary research methodology.

I was living in Boston at the time and I had two major life changes that precipitated my career break. One, I was diagnosed with multiple sclerosis and I had to take disability leave to recover from a bad relapse. And two, I gave birth to my first child. So looking back, I think I may have been able to hack it if I'd had one of those life changes plus a full-time job, but not both.

So I went back to work after a four month maternity leave and I really just wasn't ready. I didn't feel like I was doing a good job at work. I certainly wasn't doing a good job at home, but most importantly, I wasn't doing a good job of taking care of myself. And I was also really fortunate that I was in a position where I could take some time off and know our family would be okay financially.

So I decided then to leave the paid workforce for a bit.

Carol Fishman Cohen: So Prabha, that does sound, there's a lot of transition there, there are a lot of things going on at the same time. And I'm, I want to know if you can, give us a sense of what was happening. While you were on career break and ultimately you transitioned into working as a freelance writer.

And I'm wondering if you could tell us some details about how that happened.

Prabha Kannan: Sure. Yeah. So how did I transition into becoming a freelance writer from a user experience researcher? Very different careers in many ways, although there's a lot of writing and analysis and observational research, that's similar to both and common to both.

I would say the transition required a little bit of skill, a lot of hard work. And just a truckload of luck. In addition to giving birth twice and raising kids and managing a busy household with a spouse who traveled for more than a third of the year, I also used my career break as a period of self investment.

And that's very important. That was really, that's a really important part of my narrative. And my journey is that period of self investment. I took a lot of writing courses through some writer's collectives, one in Boston called Grub Street. I took a number of courses after we moved out to California at Stanford through their continuing education program.

And then I just started writing. I just started writing a lot. I started pitching editors and I started getting rejected over and over and over and over again until finally I got accepted. And it's funny to say this, but I've never actually worked as hard as I did when I was on that career break.

Those seven years, I was juggling family. health, household and developing a new skill. Those were the toughest years of my career. And they happened to coincide with when I wasn't working full time.

Carol Fishman Cohen: And I just want to call out here a couple of things. First of all, originally, when you said, you were in a financial position to be able to take a career break and we want to stress the financial planning, the financial assessment of peace of, being able to take a career break or career breaks of different lengths. So thank you for acknowledging that at the beginning, and then what you call this period of self investment. So, was there something lurking in your background where you thought I've always wanted to be a writer, and then you want to explore that.

And that started the course work and the writing or was it triggered by some other experience?

Prabha Kannan: Yeah, so I started writing actually pretty soon after I was diagnosed with MS. And I initially used it as an outlet for just the pain and the anxiety that I was feeling and the way that I've always coped with stress in my life is through humor.

And so I started writing humor. I started writing satire. I would satirize things that were happening in the news. I would satirize things that are happening in politics. And after I moved to Silicon Valley, this place is, just a as city that's filled with satire and

Carol Fishman Cohen: There's a lot of material.

Prabha Kannan: It was an easy target. Yeah. And so I started satirizing everything around me. And, at some point the work that I was writing was interesting enough that an editor thought it worthy of publishing and which isn't to say that it was easy. And I certainly don't want to gloss over the hard work it took from me to get to the point where I was able to publish something and also the rejection. And I think frankly, anyone who's in a creative industry will resonate with this. I've been rejected far more times than I've been accepted. Then, and still today, anytime I write something you pitch over and over and over again.

And frankly, nine out of 10 times, I still get rejected. But, every so often when you pitch something and it gets accepted and you get a platform for your work, then that's just so incredibly meaningful. And I was lucky that I was able to get a platform that would publish some of my satire, but I also really worked hard to be lucky too.

Carol Fishman Cohen: So you're talking about, a lot of rejection with occasional acceptance and the acceptance was super high. That was a super high of being, in freelance writing, but that we should not minimize the persistence that you have to keep going forward when you're in that long, series of rejections.

Prabha Kannan: Absolutely.

Carol Fishman Cohen: And then how long were you working at your freelance career before you realized that you're actually ready to reenter the full-time workforce?

Prabha Kannan: So I had been freelancing for about seven years before I decided that I was ready to come back. And the trigger point for me was really when my youngest was ready to go to full-time kindergarten.

I figured that it would be a good time for me to start looking for full-time roles just as he was getting ready to go to full-time school. And actually I got approached by a recruiter for Google Assistant at the time to apply for a role. I ended up not being qualified for that position. They needed someone who was an Indian native, who spoke English.

And I am a child of Indian immigrants, so not an Indian native, but it opened up my eyes to the possibilities that existed. And so I checked for similar open positions at other voice assistance, Alexa and Siri. And I saw one for a Siri writer serendipitously and I applied immediately.

Carol Fishman Cohen: And do you think that you were identified by that recruiter because the person saw something that you published or how did that person get to you?

Prabha Kannan: From Google Assistant?

Carol Fishman Cohen: Yeah.

Prabha Kannan: Yeah. I would bet that it was a combination of my name. So an Indian name as well as the work that I publish and I'd written work that had gone viral in the past, some of the things that I've written for The New Yorker and Huffington Post have gone viral. So I think my name was out there a little bit as it was associated with those pieces.

Carol Fishman Cohen: I see. And we're going to talk about going viral in a little bit, but before we get there, so I, so you saw the Siri opportunity and you applied for it. And then what happened? How did that lead to your first interview?

Prabha Kannan: Yeah. So Apple is a giant company with over a hundred thousand employees. Six degrees of Kevin Bacon, it didn't take a whole lot. It didn't take a lot of time for me to find someone in my network who could submit my resume internally.

And that I think is really critical. You can apply for positions via job boards, but really having that internal connection is so valuable. If you can have someone who can submit it directly to that hiring manager or to a recruiter, then that's just so much more powerful. And so I had someone do that for me. And that personal connection was really helpful in ensuring that my resume got seen.

Carol Fishman Cohen: I see. So, I just want to emphasize for our audience, we talk about that personal handoff, that personal connection being so important. And here's a perfect illustration of that. Prabha, when you were applying, do you think that because you had the freelance writing career and that was over the period of your career break, even though the pieces that got published were occasional, although it sounded like they were pretty high impact and they went viral and that was that's amazing.

So it, it looked as if your career break was really a period of freelance writing. Is that how it appeared on your resume?

Prabha Kannan: Yeah, exactly. I was able to smooth over my career break, if you will, with the combination of freelance writing that I was doing, the humor writing that I was doing, as well as the consulting that I was doing as a UX researcher.

So again, I continued to consult a little bit, part-time, really just when my kids were napping during the week, so a handful of hours a week. But I was able to do that to some pretty marquee names. I worked with Google. I worked with the Mayo Clinic. I worked with Amazon, specifically their Alexa division. I worked for so many companies, a number of healthcare companies as well, anything having those big names, even though I was just doing some very small projects at a very light workload, was very helpful to smooth over that career break in my resume.

Carol Fishman Cohen: And how did you get those user experience roles? Was that through people that you knew from your first, from your first job, your pre career break career.

Prabha Kannan: Exactly. Yeah. So I had worked at a company called C Space, which is a division of Omnicom, the giant media and branding agency.

And I'd worked there full time and again, relationships matter. So when I left. I had good and strong relationships with the wonderful people who worked there. And they were able to find a way for me to continue working at this very light level of effort during my career break.

Carol Fishman Cohen: I have to interject right now that the founder of C Space is Diane Hessan, who is a dear friend of mine. So shout out to you, Diane. I'll have to tell her we're talking about her in this podcast. Getting back to your, the Siri role in that application process, did you have to have any technical skills in order to be qualified and to move forward in the interview process for that role?

Prabha Kannan: So between the time I found out about the job and interviewed for it, I hustled to read everything that I could about speech recognition and natural language processing and the voice assistant space, Siri, its competitor.

So not just mainstream publications, but I was reading academic papers, technical papers, really doing a lot of self study to educate myself about this space. So as someone who is applying for a job with the title writers, so that the title of the position was Siri writer. I knew I wouldn't need the same technical skills as someone with the title engineer, but I still needed to be able to prove that I could speak that language and learn the industry jargon, because I knew that I'd be working very closely with engineers and other designers and that in order to prove myself and get this job, I'd have to speak that language.

So I was pretty familiar with the tech stack before I even interviewed. And that, frankly, at companies like Apple, you're going to have to work hard in the job. So you'd better prove that you can work hard to get the job too. So I worked really hard to prepare for that. And then after I got the job, there was a ton of internal training and mentorship to help get me up to speed.

And frankly I needed it. I was a PC person before I got to Apple. I, the last time I had used a Mac was in middle school. I, as soon as I got there, I had to take Mac Skills 101 and really get up to speed quickly. But they were patient and there was a lot of internal training to help me get up to speed.

Carol Fishman Cohen: Got it. And again, I want to call out for our audience what Prabha is talking about in terms of that self-study. It reminds me of myself when I was applying to finance financial analysis jobs after an 11 year career break, also went through a period of deep immersion in all the things that I knew needed to know and get updated on, in, for a finance career.

Now, in my case, I was reviewing things that I had done before. In your case, you were doing a deep dive into subject matter that was fairly new to you, but I just want to emphasize to people how important that subject matter expertise piece of the equation is, when you are going into an interview. And not only does it give you a leg up in terms of the level of conversation that you're going to have in that interview, but it helps improve your confidence. Prabha, did you feel that there, that it impacted your confidence in, in terms of the interview process there? Or how else did it, did it impact you?

Prabha Kannan: Yeah, it hugely impacted my confidence when I could go in there to that first round of interviews and really speak about what I've learned.

And see the reactions on the other side, they could tell that I knew what I was talking about. And, then we could really engage in a deeper conversation about the sorts of ways that I could contribute after I got there.

Carol Fishman Cohen: And then once you had to learn some of that technical piece, when you're on the job, did you find that, like you talk about yourself being a lifelong learner, were you applying that perspective to this kind of learning or were there moments where you're thinking, whoa, I hope I can really figure this out.

Prabha Kannan: I have always had a growth mindset when it comes to learning new things. And so I, I always try to approach complex concepts that are challenging to learn with the same sort of, okay, I can master this attitude. And I knew it would take a little bit of time. I also knew that I had it in me to do that. And frankly, I had spent so much time on the sidelines that I wanted to prove myself. After, as part of this re-entry I really wanted to prove to myself more than anyone else in my circle.

I needed to be able to prove to myself that I could do this, that I could learn something new, that I could learn something that was at the cutting edge of technology, artificial intelligence and machine learning, and to learn something that frankly, I say my job didn't exist when I graduated from college two decades before.

And I needed to learn something completely new. And I approached that with that growth mindset of, okay, I can do this. And that was huge.

Carol Fishman Cohen: I want to fast forward to recently when you had spent about four years or so at Apple, and then you've decided to take a second career break.

Can you talk to us a little bit about that decision process?

Prabha Kannan: Yeah. So I just kicked off break number two and I'll admit that this was a tougher one for me. I loved my job at Apple so much. The people, the work, it really wasn't an easy decision. But ultimately I decided that I needed to clear some space for myself and my family.

After these last couple of years. Pandemic parenthood is no joke. Managing a team of people at work during a pandemic is no joke. Self care during a pandemic is no joke. And the way I put it as this, I wasn't running away from Apple, I was running to my family and that was an important decision for me. And it's a really important distinction to make.

I didn't leave because I hated my job. I loved it. And frankly, I was pretty good at it. I left because I felt the pull of parenthood a lot stronger in this particular moment. So my plans are to take some time off. We've got some family vacations planned. I'll also be doing some writing, some advising, some consulting, some speaking. People are pretty shocked when they hear that I'm not jumping to a different, bigger role immediately, but I actually think that there's a lot to be gained in a non-linear, non-traditional career path.

And I think that's something that companies are starting to value a lot more now.

Carol Fishman Cohen: I agree. And accelerated significantly by the pandemic and the experience that companies have had during that time. I want to jump now to that, to the post that you wrote about your decision to take the second career break, which is how we met.

And also it went viral. So I'm very interested in, first of all, what made you write it? Was there something about going public with this personal decision, but also you feeling there was something important to put in the public domain. And can you talk a little bit about what about it you think made it go viral?

Prabha Kannan: Yeah. So I wrote that post on LinkedIn for a couple of reasons. One, I wanted to acknowledge specific people who had helped me at Apple. And I wanted to do that in a public way. And two, I wanted to acknowledge the challenges of relaunching a career and the biases against relaunchers. I think that it went viral because of one particular line in the post.

And I will quote that line here. And it's got an expletive in it, but I'll say it anyway.

Carol Fishman Cohen: Go for it.

Prabha Kannan: But the line is, "If you want to get shit done, hire a woman. If you want to get everything done, hire a mother." And that's a powerful rally cry if you ask me. It's really this perfect, bite-sized quote that people could copy and paste and easily share.

And I think the key to virality is as you've got something that can, that people can rally around and that they can share very easily.

Carol Fishman Cohen: And so did, was this something that one you woke up in the middle of the night and thought I'm going to write about this or is it something you were pondering for a while and then you spent a lot of time writing it. What was the timeline?

Prabha Kannan: I knew that I wanted to post something the day after I left Apple. So my last day at Apple was January 31st. I believe I posted this on February 1st or February 2nd. I retired the same day that Tom Brady did. He posted on LinkedIn the same day. I knew that I wanted to write something.

I didn't have anything drafted until the morning that I posted it, so it was pretty spontaneous.

Carol Fishman Cohen: And when you're talking about what made something go viral, you had said that there were prior things that you had written in the past that had gone viral. Do you also think it was because there was some sort of a high-impact soundbite that people related to that made that happen or were those for different reasons?

Prabha Kannan: Those were for different reasons. I'd say those articles were not personal in the way that this was. I think this had the resonance of one, a personal story and two, a relatable story, right? This is my personal story. But two this is something that a lot of people can relate to when they leave the workforce for whatever reason.

But, there is potentially a way to come back. And I think that in showing and proving that I could come back after an extended career break and not only come back, but to pivot my career into a different industry and to grow and succeed at it, I think that was very powerful.

Carol Fishman Cohen: Yeah. And from our perspective, to have a powerful story like yours in the public domain, it's not only inspiring for other relaunchers who might be in the early stages of relaunching their career, but also a great example for employers to see what's possible, when high caliber, high performing professionals leave their careers and then decide to go back again, what can happen.

Prabha Kannan: Absolutely.

Carol Fishman Cohen: Prabha, can you tell us, we talked about the numbers in terms of the viral response, but what happened personally? Did people start reaching out to you? You mentioned that you might do some speaking, is that because people want you to speak now, due to the post or for something else?

Yeah. I think people are interested in someone who has a Siri writer, it's a weird quirky job, and people are interested in it. I think the LinkedIn post helps, again, accelerate the name recognition and the association of that job title with me. And folks are reaching out to me.

It's largely, I'm speaking largely at women in tech conferences, to groups of women in college or professional women who are not in tech or interested in getting into the industry, but really the common thread there is that everyone is really interested in increasing the numbers of women in the technology industry.

And I'm speaking largely about my own experiences there and hiring and recruiting and retention.

Yeah. And you think about that incredible job and title you had and you're bridging this world, bridging the world of writing and technology. It's really an unusual opportunity too, so I'm sure there's a lot of fascination with that part of it.

Prabha Kannan: Yeah, definitely.

Carol Fishman Cohen: So, Prabha, we're coming to the end of our time, our conversation time right now. And I want to close by asking you the question that we ask all of our podcast guests. And that is, what is your best piece of advice for our relauncher audience? Even if it's something that we've already talked about today.

Prabha Kannan: Yeah, so I would say my most important piece of advice is to really use your relationships. Relationships are the key to the job hunt. They're important for making sure that your resume gets seen by the right people. They're important for reference checks. So really making sure that you foster those relationships is critical.

You'll never know when you'll need them and when they'll need you. Frankly, I've helped so many people I know submit resumes to various roles and connect them to people that I know, and people have done the same for me as well. So when you sincerely help others, they'll help you in your time of need as well.

Carol Fishman Cohen: That's fantastic advice. So Prabha, thank you so much for speaking with us and for joining us today.

Prabha Kannan: Thank you for having me, Carol. This has been a lot of fun.

Carol Fishman Cohen: And thanks for listening to 3, 2, 1 iRelaunch, the podcast where we discuss return to work strategies, advice and success stories. I'm Carol Fishman Cohen, the CEO and Co-founder of iRelaunch and your host. For more information on iRelaunch conferences and events, to sign up for our job board, and access our return to work tools and resources, go to And if you liked this podcast, be sure to rate it on Apple podcasts and your favorite podcast platform, and be sure to share this podcast with a friend on Facebook, Instagram, and other social media. Thanks for joining us.

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