David speaks with Jenny Blake, an international keynote speaker and author of Pivot: The Only Move That Matters is Your Next One, winner of the Axiom Best Business Books award in the careers category. She hosts two podcasts with over one million downloads combined: Free Time for heart-based business owners, and Pivot with Jenny Blake for navigating change.

They talked about:

๐Ÿš€ Jenny Blakeโ€™s early career experiences

โš–๏ธ How to manage competing interests

๐Ÿ“ฑ How social media shapes perspectives

๐ŸŒŸ Career fulfilment beyond mere results

๐ŸŽฒ The power of taking risks

๐Ÿ—๏ธ Self-discovery through pivoting

๐ŸŽ™ Listen to your favourite podcast player

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๐ŸŽง Listen on Spotify:

๐Ÿ“น Watch on Youtube:

๐Ÿ‘คConnect with Jenny:

Twitter: @jenny_blake | https://twitter.com/jenny_blake

Instagram: @jennyblakenyc | https://www.instagram.com/jennyblakenyc/

Website: Pivot | https://www.pivotmethod.com/

Podcast: Pivot with Jenny Blake | https://pod.link/pivotmethod


Pivot: The Only Move That Matters Is Your Next One | https://amzn.to/3xvBdxl

Free Time: Lose the Busywork, Love Your Business | https://amzn.to/3Unh05U

๐Ÿ“„ Show notes:

[00:00] Intro

[04:25] Jenny's early professional journey

[08:00] Balancing work and personal interests

[11:40] Finding a sense of control within your schedule

[17:05] We learn what to desire by looking at other people

[21:48] How social media can be deceptive

[26:41] From side hustle to full-time passion

[32:27] Lessons from 'Pivot'

[35:06] Success is not instant

[37:19] The importance of nurturing a diverse skillset

๐Ÿ—ฃ Mentioned in the show:

Google | https://about.google/

Medill School of Journalism | https://www.medill.northwestern.edu/

University of California | https://www.ucla.edu/

Daily Bruin | https://dailybruin.com/

Palo Alto Networks | https://www.paloaltonetworks.com/

Career Guru | https://careerguru.teachable.com/

Parkinson's Law | https://amzn.to/49BnjXT

Andrew Wilkinson | https://awilkinson.medium.com/

Shane Parrish | https://fs.blog/about/

Wanting: The Power of Mimetic Desire in Everyday Life by Luke Burgis | https://amzn.to/4d31DqA

The Kardashians | https://en.wikipedia.org/wiki/The_Kardashians

Suits | https://www.imdb.com/title/tt31122751/

Kentucky Derby | https://www.kentuckyderby.com/

The Legend of Success | https://theknowledge.io/issue34/

Battle of Thermopylae | https://theknowledge.io/legends-an-immaculate-deception/

Steph Smith | https://stephsmith.io/

Andreessen Horowitz | https://a16z.com/

Full episode transcript below

๐Ÿ‘จ๐Ÿพโ€๐Ÿ’ป About David Elikwu:

David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.

๐Ÿฃ Twitter: @Delikwu / @itstheknowledge

๐ŸŒ Website: https://www.davidelikwu.com

๐Ÿ“ฝ๏ธ Youtube: https://www.youtube.com/davidelikwu

๐Ÿ“ธ Instagram: https://www.instagram.com/delikwu/

๐Ÿ•บ TikTok: https://www.tiktok.com/@delikwu

๐ŸŽ™๏ธ Podcast: http://plnk.to/theknowledge

๐Ÿ“– Free Book: https://pro.theknowledge.io/frames

My Online Course

๐Ÿ–ฅ๏ธ Decision Hacker: http://www.decisionhacker.io/

Decision Hacker will help you hack your default patterns and become an intentional architect of your life. Youโ€™ll learn everything you need to transform your decisions, your habits, and your outcomes.

The Knowledge

๐Ÿ“ฉ Newsletter: https://theknowledge.io

The Knowledge is a weekly newsletter for people who want to get more out of life. It's full of insights from psychology, philosophy, productivity, and business, all designed to make you more productive, creative, and decisive.

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๐ŸŽž๏ธ Descript: https://bit.ly/descript-de

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๐Ÿ“œFull transcript:



Jenny Blake: But it's true and it's hard to do is that if we don't appreciate and be grateful and enjoy with the way to get there, in free time I say, how we bake is as important as what we make.

If how we bake is with agita and angst and envy and stress and burnout. Why do we think that what we're making is going to be good? Why does anybody want to engage with a product that was made with like self martyrism? You know, with martyring ourselves and killing ourselves and then being like, oh, here, I killed myself for this. Do you want it? I just don't even think it's going to create the best possible end product. And yet it is just so much easier said than done. It is so hard to be ambitious as a person, like you said, not hold ourselves back, but still be totally content with what is.

David Elikwu: This week, I'm sharing part of my conversation with Jenny Blake. Jenny is an author and podcaster. She's written three books, but two, her most recent ones that we talked about in this episode are Free Time [00:01:00] and Pivot. And she also hosts podcasts of the same name. So Pivot with Jenny Blake and the Free Time podcast.

We talked about this idea from her book pivot about being able to make incremental changes in your career and really move yourself into a direction that aligns with what you really want to be doing and how to find joy in your work.

And we also talked about her book free time and some of the ideas from that. I think it's applicable, not just for business owners, but also for busy professionals and really being able to carve out and maximize time. And use time in the way that is most productive for you and makes your life one that can be filled with joy and where you can make the time for the things that matter most to you.

So if you're an entrepreneur, it's about how you can unravel yourself from busy work and really create time for intentionality.

So like I said, I love this episode. I think you're going to love it too.

You can find Jenny on LinkedIn @JennyBlake and on Twitter at the same name.

If you love this episode, please do share it with a friend. And [00:02:00] don't forget to leave a review because it helps us tremendously to reach other listeners just like you.

David Elikwu: Thank you for making time with your book tours and everything that you've got going on. I know that it's a really busy schedule.

Jenny Blake: You know what, there's nothing I love more than podcast conversations in either direction, whether I'm interviewing people or they're interviewing me. And I was just thinking today, how lucky am I that I get to do my morning reading have coffee, and then what we just hit record. And I get to know you like an awesome new person. I always joke that it's the introvert's guide to making friends because we actually don't just schedule a random coffee. We're doing this for some functional purpose, but at least other people can listen in and then we get to know each other and it just feels like this is one of the parts of what I do. What makes me pinch myself and just say, I get to call this work.

David Elikwu: I love that. And actually, that's a perfect segue. You, okay, so you've had this whole journey and we're going to get into it in second but what I'm really interested in, obviously you wrote this book called Pivot, [00:03:00] and I know that you left Google at one point, which was like your dream job at the time, and I've actually done the same. So, you know, there's like some good parallel that.

So I was working in corporate law and that is what I always wanted to do. So I'll just going to my a bit of backstory into

Jenny Blake: Please do. Yeah.

David Elikwu: So I actually came to the UK from Nigeria many years ago when I was a lot younger and I came to do some school here.

And originally I started doing like design and marketing, and that was more out of passion, that was just skills I taught myself and I could use to make some money. And it was a lot of fun, but obviously the immigrant dream is you have to become like a doctor or a lawyer or something along those lines.

And so I decided from, I think when I was 14, that I was going to become a lawyer and I've never met one until university. So I was already at Uni, it's the first time I actually met a corporate lawyer, even though for years and years, I've been saying, this is exactly what I want to do. And while I was at uni, I was still working in marketing. So actually I did some work with Amazon and a bunch of other brands and startups, and then I ended up getting what I thought was my dream job in corporate law at one of my dream firms. [00:04:00] And I worked there, I was there for like five years. And then I reached a point where eventually I felt like it was time for me to make a pivot of my own.

I want to start maybe as far back as you can go, I'd love to know what some of your early career experiences were like. And what started taking you in this direction and this trajectory? Did you always have kind of like, what I just shared clear vision of what you thought you might want to do, or was that something you were figuring out as you go along?

Jenny's early professional journey

Jenny Blake: I thought I was going to be a journalist. So I started this little family newspaper when I was 10, 11 years old that I produced. This is called the monthly dig up, every month all the way through high school. I won this California journalist of the year award. I got to be the top four finalists in the country, in the US that year. And I applied to all these colleges and even the Medill Northwestern was like the holy grail school of journalism, and they rejected me. And I was so shocked. I was like, I'm top four in the country and this still doesn't get me in? And that was a kind of rattling moment because [00:05:00] I was so convinced that I was going to be a journalist.

I ended up at UCLA, which is, I was actually very thrilled to go to school there, even though I thought I would end up on the East Coast. I was a news reporter for the Daily Bruin for one year and the lifestyle of that was so stressful and so intense because they would call with a deadline that was two days from now and I'd have to drop all my schoolwork. And I realized even then that the pressure of that, and I couldn't quite see financial abundance on the horizon as a journalist, this would have been in 2001. So I kind of put it aside. And that was a strange moment of just thinking, well, yeah, here was this thing I hung my hat on my whole childhood of what I wanted to do. And then who am I? What's interesting to me without that I ended up adding, I was a comms major, ended up adding political science. I almost minored in computer science, but my poly scie advisor, she offered me a job at a startup in Palo Alto as the first employee. And I think that the founder of this really brilliant Stanford Economics [00:06:00] Professor, I think he just was kind of skeptical thought I was going to be filing papers. And as soon as I got there, he started giving me all this work, because I was also indicating that I could handle all kinds of stuff. So the startup was really fun. I left school, I ended up finishing at UCLA kind of a little bit remotely, a little bit through Stanford classes. And the startup was really where I learned.

I mean, we grew from zero to 30 people. It was in the now famous stretch of university Boulevard in Palo Alto. And when I hit a plateau there, that's when I started interviewing at Google and moved over to Google. So it was interesting to go from a teeny startup doing political polling and then Google, which was at that time had 6,000 people. So I was there as a grew to 36,000. All the while during that time on the side, I started blogging and that let me kind of express my computer nerd side, teaching myself coding and HTML in order to do some of my job at the startup. But blogging is where that journalism thing comes full circle.

And now [00:07:00] podcasting, which is the current love of my life. It's the same thing. It's like journalism, even coaching that I ended up doing at Google. Coaching, journalism, podcasting, blogging, they'll have curiosity in common and communicating with people and taking in ideas and then packaging them and synthesizing them and publishing back out. The common threads are there but the actual forms they've taken have changed over the years.

David Elikwu: I love that. I wanted to ask how you found during that period, managing all of these interests that you had, because I think that's one thing that people more so I would say maybe very early in their careers, but actually it carries on through later in their careers, people that have competing interests, but they still work and they want to be able to balance. It might not necessarily be a side hustle, but it's a hobby, right? You enjoyed doing this journalism, you enjoyed, you started this blog. I'm sure maybe the blog started to grow. People were reading it and you started to find a passion in doing and publishing that. How did you find being able to [00:08:00] balance that with what you were doing?

Balancing work and personal interests

Jenny Blake: It was tricky, always. I talk about this in Free Time. My third book that the inner time blueprint that I was raised with, whether nature nurture society I grew up in San Francisco was just this frenetic pace, like day was filled from A to Z morning, noon and night with activities that was like the form of childcare, you know? And then I did it to myself. And then as I got into high school, I put the pressure on myself and college and Google. And so I always had this overflowing plate and I was always hitting burnout.

In some ways it was very satisfying to juggle that many things, I felt fulfilled doing that. And then also, I probably took on too much and I did that over and over again until I started to be able to have full autonomy over my time and craft more balanced existence. But in the early days, I think, I mean, still to this day, I learned the hard way. Who are we kidding? It's not like there's ever a there, there. [00:09:00] I find that even if I get my sort of work patterns under control, then my life complexity grows like, oh, I got married. Oh, we have a house now. Oh, we have a dog. So I joke that it's like the number of browser tabs open at any given time is five X. What it was when I was in my twenties.

In my twenties though, I had a tremendous amount of just overall anxiety. And I joke that I have 10,000 hours of neurosis under my belt. Like if I was a master at anything, it was worrying. And at least the blogging and the side hustles helped me work through some of that. And I was always so afraid to post the really vulnerable writing and I call it now truth while it's fresh. And yet those would be the posts that people would share the most. Those would be the ones that people would write in the most. Those would be the ones that even had coworkers coming up and talking to me.

So I started to realize that we all crave that, nobody really wants to hear about someone's like state of perfection. I mean, yes, that [00:10:00] can be informative too, but I find it more interesting to talk about the process and the imperfection and the insecurity and the uncertainty. That's really, those are some of the big themes behind Pivot. It's not like, oh, here's this process that you'll never have doubt again. It's like, if you're racked by uncertainty and anxiety and insecurity, like I often am, here's a process that will still help you move forward and do creative things even with those things carried up alongside you.

David Elikwu: I really agree with that. And I think there's a few things that stuck out to me from what you were sharing, but I think, okay, so one is finding this sense of control within your schedule. And I think that's one thing that I personally found hard and I'm sure a lot of people would probably empathize is that it can be, it can feel really difficult when you hear, so I have a lot of people on, on this podcast and I'm sure people have a lot of other points of reference that they see out in the wild where, it's very easy to see people that are completely in control of their time and they're not completely working full-time. Or they're working [00:11:00] full-time on their own thing, like of something they've created. And so they are able to set their schedule and say, okay, I'm going to work on this, I'm going to work on that. And so a lot of the advice that some of those people might give, or a lot of the perception that you might see is from people that have complete control.

Whereas there's also a lot of people like you are once upon a time that you feel like all of that time pressure is being imposed on you and you are almost subject to everyone else's timing. You have to follow everyone else's clock, that's how it can feel.

So how did you maybe start to disentangle yourself from those feelings and start taking active control of your time? Even when, at least at first you were still on other people's clocks to an extent.

Finding a sense of control within your schedule

Jenny Blake: One of the things working at a company like Google. And I'm curious to hear about your experience too, is that there was a saying, even working there, the bar is always raising and we were, at that time, I know they've shifted how they do performance evaluations in recent years. But at that time you get [00:12:00] two performance reviews a year. And the goal is to be always exceeding expectations and always working toward a promotion. And even if the managers weren't reinforcing that idea, because often it was the early in career, people who were obsessed with promotion. And there's only one CEO, like at some point in your career, you got to realize promotion isn't the end all be all to happiness. It's actually quite a stressful goal.

So there was a point around year four of my Google tenure out of five and a half. Where I realized that striving to get promoted again, was not serving me. And I had been promoted twice quickly, early on when I first joined, but that next level, the amount of stress and pressure that I was putting on myself, even beyond the time boundaries placed around me just by nature of working at a full-time job in a very intense company.

The obsession with getting to the next level and the next and the next was actually hurting me. And there was this moment, this aha moment where I said, you know what? I'm earning enough. My title is fine. Like I was a [00:13:00] level four. That's not going to mean anyone to anyone else, but I was not even qualified. I co-created and launched this global dropping coaching program called Career Guru. When I created it, when I was training the managers and directors on how to coach others, I was not even qualified to be a career guru of this program of my own design and yet when I realized I don't care if I get promoted again, it was so freeing. And I actually thought to myself, what's the worst that can happen if I stopped trying to get promoted? I thought, well, maybe they'll fire me. Okay, well that will take at least six months because for the first three months, they'll start to notice, then they'll put me on a performance plan. Then we'll be another three to six months before they give you the boot. If I don't turn things around. And I was willing to have that be a consequences on some level, instead I kept exceeding expectations.

So then what that taught me was that actually I could scale back my obsession a little bit and the burnout and still perform, so [00:14:00] that this association of just pure nose to the grindstone hard work, it does not always correlate to performance and results. Especially as you get to higher levels, especially when you run your own business, there is not a linear correlation between hard work and results. And in fact, sometimes it's harder to work less because you have to be more strategic and you have to delegate more and more creative and think outside the box.

So, that was really something that helped me even when I was still within corporate was just relaxing, the sort of arbitrary standards. I mean, on some level they're not arbitrary because they're associated with salary and other kinds of benefits. But at some point I think it's helpful to realize and be grateful that what I have is enough and this is okay for now.

David Elikwu: Yeah, I love the idea of finding enough. I think that's something being honest. I've struggled with quite recently as well, being in, maybe, I don't know if it's exactly the same position, but a similar position where this reminds me of, and I think you talk about this in free time as well, which is Parkinson's law where essentially, you know, the amount of [00:15:00] time you spend on something expands to fill whatever time you've allocated to it.

But I think the same applies to hard work in some ways where, or to ambition, right? Whatever ambition you set, the work that you do to fill that can always expand and because a lot of people, and I think even for me, right now, I'm kind of at an inflection point where I'm thinking about that now is because for most people, there is not a specific concrete and finite level that they are expecting of what their ambition might be or, or what they're hoping to reach. And it's not to say that you should limit yourself, but it's to say, you know, okay, if you have this objective, what fulfills that objective right now? And at what point will you allow yourself to be happy? I think that is the real critical issue is that a lot of people end up feeling like, because they haven't achieved something and they don't yet know what it is.

They can't be happy and they can't allow themselves to rest and they have to keep pushing the boundaries and keep pushing whatever it is. And so you're doing all this work and I found that as well. Where I do all this work and [00:16:00] long, long ago, I've probably already achieved three or four of the things that I said, were going to be the prerequisite to me being able to happy and me being able to relax.

But as soon as you hit that, you kind of move the boundary out again. And then you're like, ah, now I'm so far from where I could be or where I should be. And so you're on this perpetual treadmill.


We learn what to desire by looking at other people

Jenny Blake: It is so tricky. I'm just reading a book, I heard Andrew Wilkinson talking to Shane Parrish on Shane's podcast about this book, and it's blowing my mind too. It's called Wanting the power of my mimetic desire and everyday life by Luke Burgis. And it's the idea that we learn what to want, what to desire by looking at other people. And I think now with social media, the way that it is, and even the sexiness of startup culture or entrepreneurship, and, oh my goodness, same as you David. Like, I find that, oh, it is so hard not to just constantly be comparing myself to others and measuring, oh, how many podcasts listeners do I have? How many newsletter subscribers? How much money am I making? How much money are they making? How much money should I want to be making? You know, like every metric, it is so hard not to just look over the fence.

And I do, there's even a chapter in free time, a [00:18:00] sidebar Eyes on your own paper where I try to remind myself, okay, keep your eyes on your own paper. You're on your own project, you're doing your own thing. And what you said, what's so hard is not to say, I'll be happy when, because that bar is always changing. Oh, I'll be happy when I'm earning this much from my podcast or this much in my business, or and then the irony of that as well is that if we're not happy in the building process, and I know this gets to all the mindfulness self-help cliches, but it's true and it's hard to do is that if we don't appreciate and be grateful and enjoy with the way to get there, in free time I say, how we bake is as important as what we make.

If how we bake is with agita and angst and envy and stress and burnout. Why do we think that what we're making is going to be good? Why does anybody want to engage with a product that was made with like self martyrism? You know, maybe that's a redundant word, martyr, you know, with martyring ourselves and, killing ourselves and then being like, oh, here, I [00:19:00] killed myself for this. Do you want it? I just don't even think it's going to create the best possible end product. And yet it is just so much easier said than done. It is so hard to be ambitious as a person, like you said, not hold ourselves back, but still be totally content with what is. It's like, I think it's a polarity that is almost ever present.

David Elikwu: Yeah, and you make a really good point by referencing Wanting as well by Luke Burgis, I've talked about that a few times in my newsletter. And it's such an interesting idea because I like how he talks about, I think it's negative and positive models, but the point being that, so you have models of people that are close to you that kind of give you desires, so that could be your parents or people that own very close proximity to you. But then through social media, we also have these models that are a lot further away. And the difficult part about that is that you have no idea, the actual content of the rest of their lives, because what social media allows people to do is to curate what you show, right.

And it's so funny. Okay. I'm not sure if you've seen, but on Twitter quite recently, and [00:20:00] through TikTok so I've seen some people within tech make these TikToks it's typically like a gen Z thing of like, oh, here was my day as a product manager or something like that. And people show their day as this glamorous, you know, I came out of bed, I took an Uber to the office, we had some, some biscuits and some granola and you know, a completely healthy day. We had all this fun, we went to this party off, all of the highlights of the day. And people are hate it, and people are so angry and everyone's in the comment, lambasting them and just talking about how terrible they are and how terrible it is that we just pay people to do nothing. And it's like, I don't know if anyone else is like watching in between the gaps because this day started early in the morning and ended late at night and although the only clips that you see in this video are the parts where, you know, they went and had some free lunch. Clearly, this is not a 12 hour video for their entire workday. This is literally just the two seconds highlights, the entire video is 15 seconds long or however long. And so I think that is the [00:21:00] part that it's so easy to miss, right? It's so easy just to see and notice and be hung up on the highlights and you see someone is having this kind of success. You see someone's having this kind of fun and it feels like you're not having it. And it can be easy to become angry and feel dissatisfied as a result of that. But you're not seeing everything else that comes with that package and all of the other work that they're doing and everything else that they might have to do.

And I think that is when it can be easy to start feeling drained by what we have to do. And the things that we put ourselves through just like you were saying, this self-flagellation where we're flogging ourselves and making ourselves do all this work. But very often, you know, we are trying to create something that actually doesn't exist coz what we're trying to create is what we think is someone else's reality and that reality is not even that person's reality. So we are all ending up chasing fantasies.

How social media can be deceptive

Jenny Blake: it's true. and we make the assumption that how they feel on the inside is how it looks on the outside. But there's nothing telling you that, that person isn't racked with anxiety throughout that entire day. And [00:22:00] then that's what I find so interesting too, that we assume that if we have all those things, then we'll feel really good all day long, all day, every day.

And that's not true, like just yesterday morning, I had funny experience. I was walking my dog and they're filming a movie in my neighborhood and we ran into a celebrity. She's like a list, you know, you would know her, and she had her dog with her. And so we start talking, she's talking to my dog and I'm asking her about hers. I didn't like let on that. I knew who she was. But I said like something about her dog, he looks like such a good boy and she's like, he is a good boy. He's 13. And he just came through chemo. And I thought to myself, you know what, this woman, who is this a list, gorgeous celebrity. First of all, at 7:00 AM with her coffee looks just like anyone else on the block. If she wasn't instantly recognizable it's she's like anyone else and then nothing, no amount of money can prevent her heartbreak that her dog is 13 or that he [00:23:00] just went through chemo, that she still has her heartstrings pulled in every direction by life, the same way that any of us would. And even though she's there shooting a movie and it has this like glamorous job, but also the mechanics of shooting a movie are you get arrive at 7:00 AM and she sits in a tiny trailer all day that's parked on our block. You know, like, I don't know, it was just this moment where I really thought about I'm like, she's probably making a gazillion dollars for this movie but, so what? Like here we are running into each other on the street, like it's nothing.

And it's just a reminder, it's a constant reminder that we can never know the interiority of somebody's experience no matter what they have and the reason I'm reading Wanting. It's so cool that it's already on your radar is because I keep struggling with this.

And I heard on a podcast the other day that people will hate listen to a podcast twice as long as the ones who like it. So like the ones who don't like what's being said will engage with content for twice as long. And [00:24:00] the catch I'll make here is that I was always resisting watching the Kardashians. And finally, I just watched the latest season cause I couldn't get it out of the algorithm of my Hulu account. And like, I was just drawn by curiosity. And the amount of wanting that, the show invokes of like how many followers, how much glamour, how much cosmetic procedure, how much clothing, how much interior house decorating? Like, oh my God, I just, and of course, you know, I watched the whole season after that, David, you know, I didn't just stop at one episode. I watched the whole thing, like almost mouth agape at how much wanting, it was sparking in me. And that it must be doing that for gazillions of people because they have such a ginormous platform around the world.

So I feel like they are a real expression of this idea of mimetic desire of we see what other people have and

David Elikwu: Yeah.

And funnily enough, so exactly what you were saying also brings me back to what I was saying about when I was working in law. I think you have these shows like Suits that really glamorize it. And obviously I [00:25:00] was you know already working by the time that that started and stuff, but it's really funny how, so people have asked me or at the time. So before I started working in startups, when I was still working in law, they were like, oh, is it like Suits? And I'm like, actually it kind of is okay, take out all of the drama, all of the exciting stuff and again, this goes back to what we were saying before. If you watch Suits again, you will realize that the majority of the show happens at night. The reason it happens at night is because people are working. So without the drama and all of that nice stuff, the reality of that show is that the majority of the time they're just working from early in the morning late at night, that's it. So imagine that is your life and it's not, there's nothing wrong with that. And I did it for five years and it's great, but I think, you know, for me, it got to a point where I, I was looking at partners and people that was my original desire. I was like, okay, I'm going to come into this law firm. One of the biggest law firms in the world, I want to be a partner at blah, blah, blah.

And then you just watch people saying goodnight to their children on FaceTime [00:26:00] and having to like, they would go on family holidays and then come back after two days. And that the rest of their family is still on holiday and they have to change their plans and they have to come into the office and they are voluntarily coming in on weekends, even though no one has to do any work, I don't know. It was just not what I ended up in visioning for what I wanted my future to be. And so it's really interesting where you start to have these kinds of crisis points or pivot points where the vision of what you thought you wanted starts to diverge from the reality.

And so I'm interested to get to know maybe for you. I know you touched on this, but maybe at the point where you then ended up leaving Google and obviously going on to right pivot as well. What made you realize it was time to make that changed?

From side hustle to full-time passion

Jenny Blake: Well, yeah, my first book, so I was an early blog-to-book success story, if you will, because I had a tiny number of newsletter subscribers, I think 500 in 2010 when I got the book deal. But at that time it was a lot just to have a blog and a newsletter was like, oh, you're already onto something. But sure enough, [00:27:00] it got me a book deal. I was rejected 27 times. Someone said, yes, that's all it takes.

So I was working on the book on nights and weekends, and by the time it was coming out in 2011, I intended only to take a three month sabbatical, very quickly about a weekend. I realized, oh, this side hustle could take all day every day, and it is, and it would not be fair to myself to the new direction, which at that time was life after college or to Google or to my team, if I keep trying to do both. I will completely burn out and I will not do a good job at any of it. And that's when I felt that I really had to make a choice.

And I was 27, I felt like if I'm not going to bet on myself now, when will I? I got to try. It was the first time in my life that I thought I had six months of savings in the bank. And it was the first time I was willing to spend every penny of it, run it to the ground and know that I tried. Because up until that point I had been very frayed. My inner CFO was really strict. It was like, saving birthday money [00:28:00] since I was eight. I was really meticulous about money and really kind of paranoid. And finally I was willing to spend that little savings account. And sure enough a month after, so I gave my two weeks notice toward the end of my sabbatical. And I didn't need to dip into that savings for two years. So my sheer paranoia and motivation not to prove everybody wrong, who said I was an idiot to leave, just got me through the first two years, but surely enough that type of motivation to earn, it's going to fizzle out, cause it's more running away from fear rather than running towards something. That's a more of a magnet.

I think at that time it was the right move for me. And I also was ready for a simpler career setup and also I wanted to have a bigger impact. So I knew that I could, at that time I could impact about 33,000 Googlers by working internally and people operations. And I just wondered what would be possible if I could speak out to the world? And Google is still a client to [00:29:00] this day and they have been for 10 years. So I love Google. They're still like, I call them like my angel corporate Alma mater like that so much in my life to this day is thanks to Google. So I'm truly still grateful and I just like working from the outside. And the amazing thing is that they run pivot programs globally, internally. It was so cool to hear Googlers experiencing the material, and I think that for them, my story is a Google success story in the sense that you can pivot in and out of the company and within the company and so I think it kind of fits the whole idea of pivoting as well that we still work together just in a slightly different container.

David Elikwu: Sure. And I'd love to let's, let's dig into some of the principles that you discuss in pivot, because what you were just sharing actually is very similar to my story although I think it, it didn't end differently, but okay.

Jenny Blake: I'm also curious what you're doing now, what your current context is?

David Elikwu: Ah, okay. So yeah, so I left, my job in law, I did a very similar thing, saved a six month runway because, so for more context, [00:30:00] when I was working in law, like you actually, I started developing my own interests. I taught myself some photography and started being able to shoot like lots of really interesting things. I was going to fashion weeks. I did like London fashion week, New York fashion week. I was going around and doing all kinds of cool stuff or fun stuff.

But then I was also consulting for businesses and startups as well. So I mentioned I'd done some consulting and had done some marketing before as well. So I was consulting for startups in a blend of like legal staff, marketing staff, and brand strategy, growth strategy. And so I was doing all of that on the side and it got to a point where I thought okay, you know, I'd love to be able to, I'm doing a lot with the minimal time that I have, like when I say minimal time. So what I used to do, and it was, it was tough. I was thinking about this earlier. So I had a full-time secretary at work, so you have a full-time secretary at work and then I also hired someone outside of work that was also working for me, that was helping me just to manage all of this stuff. So I had all of this support and it was still not that much. And I'm still having to just work like super early mornings, that was pretty much [00:31:00] my time and it's still is, that's exactly how I still do things now. I just wake up a half four and it means that I have time to, like, I almost have my own mini day before I go to work.

But even at the time I was just thinking, okay, if I can do this much with this little time, what if I had the whole day? And so I was like, okay, I saved this a six month runway. I eventually quit, that was a process of its own I think it had been in the back of my mind since the beginning of that year. And then it got to towards the end of the year and I was like, okay, fine. This is enough. We're done. And so, yeah, I left and I started and it was going okay. But then after I think, so I had the initial six months, that was okay. And it was like seven months, eight months. Okay. And then this is actually just before the pandemics. I remember we had, yeah, like a few months going into Christmas and then coming out of Christmas. And then suddenly I had to extend that six months to like 12 months plus, and then that was like a really tough period where, you know, I still had consulting clients, but it was stretched. And so I did that in total for maybe about 18 months [00:32:00] before. So now I joined a startup full time. So first as chief of staff and then now in product strategy.

But it is, I mean, that was voluntary. So it wasn't as a result of any poor circumstances. But what I wanted to dig in with you is, thinking about a lot of what you discuss in pivot and some of those principles, I think a lot that stood out for me is about how you think about pivoting in advance and you start thinking and planning for what you want to do and what you're going to go on to do before it happens and before you're almost forced to do it.

Lessons from 'Pivot'

Jenny Blake: What I found most interesting with pivoters that I spoke with was that they always said, in hindsight, it was so obvious what the next move was like. In hindsight, the answer was right underneath my feet and that we're often so close to ourselves and our career that we don't see it. We feel confused, we're having this existential crisis. Who am I? What do I want? What's next? And so I learned two big things about pivoting.

One, it's not productive though it is tempting that we just obsess over what's [00:33:00] not working, what we don't want, what we don't have, it goes back to the thing of wanting. But we're focused on the negative. What's not working and we complain to friends and family about work. Ultimately that doesn't produce a pivot output, it just keeps us stuck.

So the first secret is you just look at what is working, even if it's five or 10%, what is the part that you are enjoying? And if we can double down on that, even if it's not a full-time role that starts to grow and it starts to expand, and we naturally grow into the next direction, especially in technology, especially in startups, I've seen so many people create their own roles. It's just absolutely one of my favorite phenomenon to watch of somebody starting something small. Even my career guru project that I mentioned started as a 10% project. And then only later when a career development team was formed, one did not exist when I started that. When the team was formed, I was able to move on to it.

And the Second part of pivoting, it's more of a continuous process. Like we don't have the [00:34:00] answer upfront. We actually don't just solve the pivot and say, oh, now I know what's next. And boom, boom, boom. Let me move into it. It's actually that you run a series of pilots or experiments. I compare it to race horses at the Kentucky Derby or you don't get to know the winner in advance. You actually just run these experiments and then they show you which one takes off and gets momentum. And only by experiencing that momentum among one of the many pilots, do you then are you shown you're shown what has energy, where to go next and where to double down. As all those are I would say two of the big learnings from the pivot process.

And the third that I kind of mentioned is just this idea that, it's not a surprise. The reason it's a pivot and not a 180, is that it is connected to something you're already doing. And that's where we just got to get curious and look at, okay, what's here already. What's here now? Acknowledge that and then dive in. So sometimes it's a process of stripping away what's not working, like cleaning out a [00:35:00] closet. So cleaning out a closet. It's like, you know, what's not a fit and you got to do it every couple of years because clutter accumulates.

Success is not instant

David Elikwu: Yeah, exactly. And i think that's exactly what I wanted to highlight from what you just shared as well. Cause it was really interesting to me just thinking about, so I was talking with this girl called Ama and she started a business during the pandemic as well, actually, but she had been fired and then started this business and made, I think at the time about 2.6 million pounds. Like literally just in that period, which is incredible, but it's the fact that it wasn't instant and it sounds instant, but it wasn't because even when she was working before that, she already started building some of these skills and actually. I'll take it back, two steps. I think she was working in a previous job, had started learning some copywriting skills, then that led to being able to get a copywriting job. And then while working in that job, she's still building skills. So my point is just that all of these things are still incremental and it's really easy to [00:36:00] draw a straight line in retrospect, like you said, you know, everything was clear when you look back.

And I remember writing a newsletter a long time ago, which was about, I think it was called like Legends of success or something like that, where I was talking about, I think what sparked it was, I was listening to someone that was that they read some book or they were telling me about like ninjas and Spartans and stuff or Spartans, yeah.

And it was really interesting reading into that for myself and realizing that when people think of spartans and they think of, wow, this, you know, the battle of Thermopylae and all of these great stories, but the irony is that that is not necessarily, I mean, it's the truth, but it's not the whole truth. Because before that battle, that was not what the Spartans were known for, they had a completely different reputation, but you know, there was this inflection point and then that started to change how people thought about them. And so it's in retrospect that we're able to draw this line and say, ah, this is how it was, and this is how it always was.

And I think in careers and in our lives, it can be very much the same where in retrospect, we can draw this straight line and say, ah, yes, of course, you know, I did this and then I did that and this is the story. But in [00:37:00] reality, there's often many inflection points on the way where you're learning things and you're taking these small incremental steps. And actually, maybe it's the fact that you've been building this skill in the background that doesn't seem super relevant now, but it's something you enjoy that if you spend more time on it then you know, one or two steps down the line, suddenly that is what leads to opportunities.

The importance of nurturing a diverse skillset

Jenny Blake: Yes, so true. I call those interim pivots or leapfrog pivots, where you actually know what you want to moves out, but you're not ready yet or you don't have the experience yet. And so it's okay to take something that's not the end all be all. I think we're doing this more now than ever.

It's funny, you mentioned the Spartans because my husband has a giant Spartan tattoo. So he's like really into the wars. I'm like thinking. Hm, tell me more because it was such a curious choice that he made a really go all in on Sparta.

I have been thinking lately, I wonder what your take is and also I think chief of staff is a very fascinating job title. So I'd be curious to hear more about that.

But, I think now what I'm finding is getting a little further [00:38:00] along in my career, I'm turning 39 this fall is it starts to narrow what I'm qualified for like actually, you know. I don't know. I was just for fun I was looking at Google's jobs the other day and I thought, what am I even qualified for at this point in my career where other people have an MBA and they have all this corporate experience. Meanwhile, what have I been up to? I'm like podcasting and writing newsletters. And yes, there is plenty I've learned about running my tiny media company, but it was kind of wild to realize as well that you do make choices about what to get better at, what's invest all this time in, and where to build the network and that it does kind of over time, it opens many doors and it also closes other ones. And I just think that, that's a very interesting thing to realize, like all the sliding doors, careers that when you're really early on in your early twenties, you can kind of pick anything and go in any direction. And then I'm finding now as [00:39:00] approaching kind of mid-career zone, the niche it gets as my, one of my mentors has an inch wide and a mile deep, but like really starts to specialize. I don't have any grant aha or conclusion on that yet. It's just something I've been pondering.

David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.

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