27. “What Do I Want To Do?” (And How Often Do I Already Know The Answer?), With Jason

Jason Siegel spent most of his adult life trying to figure out “what do I want to be when I grow up” - except, turns out, as a young kid, Jason already knew the answer.  Today, in what is best described as a *boomerang leap,* a return to your roots - that original 'knowing' of what made you tick - we’ll hear how Jason: 

• Had an early passion but, like many of us, didn’t pursue it;
• Went from, as he describes it, ‘floating’ from one career to the next, to really taking ownership over what he wanted;
• Realized what he wanted was - turned out - right in front of him all along; 
• Was - and is - willing to make a change when things don’t feel right;

And finally, Jason’s story really reminds us all to ask ourselves: how often do we ask what we want to do, but some part of us kind of already knows the answer?  Or, as in Jason’s case, it’s there but we just don’t see it yet.

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Transcript

27 - Jason Siegel

Jason Siegel:  [00:00:00] what I did when I was really young was probably what I should have done all along.

Life Leaps Podcast: Welcome to Life Leaps Podcast. Hear inspiring stories of ordinary people who made extraordinary life changes. What drove them, what almost held them back. Insights for the rest of us considering life leaps big or small, because hearing someone else do it reminds us that we can too.

Happy Wednesday, everyone today. We're with Jason Segal, who like many of us spent most of his adult life trying to figure out what do I want to be when I grow up, except turns out. As a young kid, Jason already knew that answer. Today in what I'm calling a boomerang leap, a return to your roots, that original knowing of what made you tick. 

We'll hear about how Jason number one. Had an early passion, but again, like many of us didn't pursue it. To went from, as he describes it, floating [00:01:00] from one career to the next, to really taking ownership over what he wanted. Three. Realize what he wanted was turned out, kind of right in front of him all along. 

Number four was and is willing to make a change when things don't feel right. And finally 

 Jason's story really reminds us all to ask ourselves. How often do we ask what we want to do? 

But some part of us kind of really already knows the answer. Or as in Jason's case, it's there, but we just don't see it yet. 

Jason Siegel: I grew up in Orlando, Florida and

I went to college in Houston, kind of like went back I guess to my roots in a way. My, my dad went to Rice University in, in Houston, and he kind of talked about it his whole life and really wanted me to go, and I don't know if it was the best fit, but I ended back there 

and I didn't really know what sort of path I was on.

and that kind of started changing a little bit. When I first studied abroad, I went to[00:02:00] Copenhagen, Denmark, and I didn't really know anything about it. I could hardly find it on a map. and all of a sudden I felt like I was just exposed to. Completely different perspectives, on just how to live life and what's important and,what sort of country I was even in my whole life.

And I started questioning a lot of the assumptions of the way that I was raised. So that's, I guess how it started. That's like the moment I guess, where I feel like I started to become myself and start making my own choices and question a lot of, the assumptions that I had about who I was and what I wanted to be.

It's 

Life Leaps Podcast: funny how travel will do that, or just even a change of, of scenery, 

Jason Siegel: yeah.

 It started then because I had just floated for a long time.

 I had done things that were interesting to me when I was fairly young.

I taught myself how to code. I think first, actually in elementary school there was this coding program and I like was building these [00:03:00] little games and things and a language called basic, which is, I don't think anyone codes in it anymore. And then in middle school I taught myself how to build some websites just cuz I thought it was fun.

And in nights and weekends I was like building these small businesses and online communities. And I dunno if you've ever played like Rollercoaster Tycoon. Which is this, it's kinda like a Sims game. Do you know it? Okay. 

Life Leaps Podcast: I've heard of Sims 

 you basically create a theme park and you can put roller coasters in it and you put like hotdog stands in it. And the idea is you try to create a really exciting place for these little fake people to come to your park and you can decide how to charge them.

Jason Siegel: Okay. Yeah. One of those tycoon games. So I thought it was like super fun, but the reason why I bring it up was I started doing it like for real, where I had like a real business and a real website, a real community and like real people were coming and they were, spending real money.

And I had built these sorts of things myself. So I just found it really fascinating. So I would like sometimes play games like that, but then I would also have these. Little side businesses [00:04:00] where I was dealing with real people. but I had never really thought about it too deeply, like what I was doing.

I just thought it was fun and 

Life Leaps Podcast: you told me once that when you were in high school, you.

Were so in the flow when you were coding that you could stay up all night and you wouldn't even know what had happened because you were in such like an entrenched state of building in this like online computer language that most of the world definitely didn't then still of course doesn't speak.

Jason Siegel: Yeah. There was this magical moment with computers when they, first started coming into homes. I remember I would raise home and I would literally throw open the front door and run to my computer and then hit the power button because the computer would take, I don't know, a few minutes to turn on and I think there was even like a turbo button on some really old computers trying to make it go a little faster.

And I would just raise home and I just found it Just super cool. I don't know what it was about the technology, but I just found it [00:05:00] fascinating and,

I didn't know there was such thing as like a. Tech industry, and I didn't know that you could make a career in coding. I didn't know any of these things. I just followed what I found was interesting and I had discovered there was such thing as coding where you could build programs.

And I was like, Hey, let's do that. Or, I learned that you could build your own websites and I tried it out and you could, make a button pop up on the screen if you type some weird text. And I did it and I was like, Hey, that's so cool. So I just, one thing led to another, I started buying some books and reading some online resources where I could teach myself to be better at it.

And before I knew it, I was a full stack developer, but, never because there was much intention other than doing what I found was fun. and to your point on the flow, I would find myself not just at the end of the school day running to the computer, but I would look up and it would be, three, four o'clock in the morning and I had been.

Learning or coding [00:06:00] for hours and hours 

Life Leaps Podcast: okay. So even though you loved this coding thing, and even though I remember it was in, I think it was in high school, you ended up actually building a website or two, monetizing it, selling it, like making money. this was a real thing for you and you were quite good at it despite all of that.

You didn't go into coding, you became a teacher. Like what, that was your first leap, frankly. Like what happened there? 

Jason Siegel: Yeah, looking back, I don't feel like I had a lot of great models for the sort of careers that maybe I should have gone into.

there were a few people I knew who were a little bit into tech, but I think being in Orlando, 

there's a lot of tourism there. There is, I mean, who knows? I don't even know what the industry is there, but wasn't surrounded by the sort of people who could give me a lot of guidance, or at least I didn't know how to find them.

And so I found myself as college was coming to a close, interested in a lot of things.but I didn't really know [00:07:00] what I wanted to do. And there was a program called Teach for America, which recruited heavily from my school and Teach for America, 

they would basically recruit people out of college and give them some training and then send them to some of the toughest like schools around the country, to help teach kids. And the idea was that it would. Help provide to them a great education.

And then you would also personally learn a lot and take that knowledge that you learned out into the world to help make the educational system better. And I had never really thought of my teach myself as a teacher before, I was curious in so many things. I was like, Hey, like this sounds really meaningful and I could really be into this.

 I don't really know what I want to do yet. So why don't I, spend some time doing something that's meaningful and try to make some people's lives better. I think there was a certain naivety ni naivety. [00:08:00] Naivety, naivete to it. And that,looking back, I'm just shocked that they would send.

Kids essentially, which is how I might refer to people who just graduated from college, at least in hindsight, to teach other kids. I didn't really know what I was doing and I tried really hard, very successful program. Okay. But you did, it's very successful. Yeah. I ended up in, in California.

 I ended up on the east side of San Jose, which is nearby Silicon Valley, but a very different kind of, kind of part of the city.

And, I tried really hard. I was super passionate. I loved my students. I did my best and yet I. I never felt like kind of one, it was really right for me. which in hindsight, again, I should have known better because I didn't really put a ton of thought into whether it was right for me.

So I had really mixed feelings about that experience. I'm really glad I did it. at the end of the day though, I think it, after a year or so, it was like, you know what? I don't know if this is right for me. And I think that there's a lot of people who could do it much [00:09:00] better. 

Anyway, so I was starting to think around that one year mark, what to do next.

Life Leaps Podcast: So you are teaching what age group of kids are 

Jason Siegel: these? In California? I taught eighth grade language arts. Okay. So 

Life Leaps Podcast: yeah, techie still trying to figure life out as our most post-college kids. Jason Moves who grew up in Florida, went to school in Texas, moves to California and you're in a really challenging by definition cuz it's Teach for America, school district.

 teaching eighth graders and you're like, oh my gosh, I should have known this wasn't for me. 

Jason Siegel: Yeah,

And I, I started soliciting advice from people I trusted 

And someone told me that you can do anything with a jd. 

Life Leaps Podcast: Durst doctor Law grave. 

Jason Siegel: Oh boy. I'm realizing as saying this out loud that it makes me seem a bit, I hate to say naive again, but [00:10:00] it's not like I took that advice and I just ran with it. But it was one of those things where 

Life Leaps Podcast: I really, cuz I did, Jason, you don't have to pretend you knew what you were doing at 24 when you decided to go to law school.

Oh, I didn't. None of us did or do, so just carry on. Okay. Don't try to church it up. My friend. 

Jason Siegel: You know, growing up, my father had said occasionally, you'd make a great lawyer. And I think he said that probably because. We like to debate each other a lot. We had somewhat different worldviews and I don't know that he really meant it like you should go to law school.

I think he more meant it like he told you that later much, by 

Life Leaps Podcast: the way, son was a figure of speech, 

Jason Siegel: didn't I think that's right. Take it literally. Okay. but it kind of embedded itself in me and I was like, you know what, I'll probably end up a lawyer one day. And so, you know, I had explored going to grad school, going to B School, getting a PhD, jd, everything.

Maybe I don't go to school. I just try to find some other career. I really don't know. [00:11:00] And. Nothing really seemed to resonate except, hey, you can do anything with the jt and law sounds really interesting too. And I always liked, politics and all that stuff and it seemed like it would help me understand how the government works and how I don't really know exactly, if I felt like I wanted to be a lawyer, but I thought, hey, it would be really fun to go to law school.

And so I committed and I like many other things that I do. I got really excited about it. And I would go to coffee shops on weekends and take my students like papers and grade them and then I'd put them to the side and then I'd take out my LSAT study materials and I'd practice some LSATs getting ready to go to law school.

That's how I spent my weekends for quite a while. And I got into Georgetown Law and ended up there, which brought me to dc. And I thought [00:12:00] law school was just really interesting, like everything else, I don't know that I was great at it.

I think I was an average student. but I tried really hard. I wrote on to Law Review. I, had some really cool internships at the S e c and, actually with now Supreme Court Justice Kaji Brown Jackson,And I really dove into it. But at the same time, there was something that wasn't quite right. And I started to sense it because a lot of my friends were not just passionate about doing well in school and learning, but also about working for law firms. And they were doing all of these things to take the next steps to work for a great law firm to.

Worked for a judge and I just didn't wanna do those things and I kept dragging my feet and I didn't really know why. And in hindsight, it's probably cuz I didn't wanna be a lawyer,

which I can laugh about now, but it's a little sad too. law school's pretty expensive, so to be in law school,at [00:13:00] the same time, I think this is a realization, more 

Life Leaps Podcast: expensive mistake. People have a more expensive mistake. My friend would be spending the next 30 years doing it.

Okay. Expensive in other ways besides just financial. All right. Like in terms of your time. Yeah. Your energy, your lifeblood, you know? Okay. You go. Yeah. You're not the first follows lawyer. It's all 

Jason Siegel: Okay. I'm not, 

Life Leaps Podcast: There's something. To the fact that I realized it maybe sooner rather than later. a lot of what I was sensing was that there was a lot of unhappiness.

Jason Siegel: Not amongst everyone, some people really loved what they did, but there was also a lot of people it seemed like, who just really felt trapped or were passionate in the beginning and, didn't find the career to be what they wanted it to be. And then reflecting on what I wanted for myself, I think I liked the intellectual kind of problem solving aspects and the learning aspect of law, but I didn't really.

Think that the day [00:14:00] of the day would be particularly fascinating to me, waking up in the morning and getting excited to go to work. 

Life Leaps Podcast: Jason, where is your head space at when you, I know we're talking about you were such a baby in your twenties, whatever, and we're making these decisions. We all are, right?

 We're such babies, and yet that's when we start these trajectories, which can last a lifetime, Because you've now gone from a kid who codes and like very easily could have gone into that field, but you say, you didn't quite have the same career guidance you might otherwise have.

You didn't really know it was an option, you didn't do it, you went to teaching and then you're leaving from teaching to law. And then sounds like in law school you start to realize oh boy, this isn't for me. Like at this point are you having in your mind all right, growth mindset, it's okay, I'm gonna make this work.

Or are you having your head like, oh my gosh, I'm a failure, I'm never gonna figure it out. Are you ping ponging between the two? Something different entirely.

I should say actually, spoiler alert, you do start practicing law. I practice, I practice for three years.

Jason Siegel: when I took a step back, sometimes I would think about the fact that you got [00:15:00] one life and. If you spend too long doing something that you're really not passionate about, then you can very quickly find yourself looking back at life and realizing that you wish you had done something different.

And so there's always some costs, and maybe it's better to keep following your interests so you don't have regrets. Now, that's a somewhat maybe privileged thing to say. Not everyone has the privilege to be able to make changes, or they have a lot of responsibilities that keep them from doing that.

But I tried to take advantage of the opportunities that I had to make changes. I think what I wish I had was a better radar for. When I should change and when I shouldn't, because what I found at the end of the day was that what I did when I was really young was probably what I should have done all along.

And I, I [00:16:00] probably didn't need to make quite as many changes had, I just realized that I should have pursued what I originally found myself drawn to. Wow. 

Life Leaps Podcast: Okay. So in a lot of ways,your story is really about like a leap.

which is a return to your roots.

Jason Siegel: sort of like a boomerang and you hit a lot of bumps along the way, Maybe you need those bumps along the way, Something like that?

I don't know that I regret entirely the path that I took. In fact, I wouldn't have met my now wife had I not taken that path. Because when I was an attorney, I would be done for the day and I would sign off and. I would go just explore and try new things.

I picked up meditation and I would go exercise and I would make new friends and, I would date. And this period of exploration, because I wasn't really passionate about the day-to-day of my [00:17:00] job, allowed me to, meet new people. And I met my wife that way, during that period. And she's incredible.

So, you know, it's really hard to think backwards and say, I wish I did things different, because you don't really know what other path you would've taken or where you would've ended up, or who you would've met. And so it's not really worth dwelling on too much. you can go down this rabbit hole and convince yourself that you did something wrong.

You could go down a rabbit hole and be. Absolutely convinced you did things perfectly. Like it. It doesn't, it almost doesn't matter to, I think, go back and try to figure it all out sometimes. And 

Life Leaps Podcast: Jason, you said something, you said, the fact that I wasn't passionate about my day-to-day work at that time in law allowed me to do other things.

I almost wonder if it pushed you or drove you because you were like, I'm not finding a spark or meaning or purpose, which let's be real. Purpose [00:18:00] is what we all want and need on some level, wherever we're gonna get it. I'm not getting that in my job 

 And so maybe it almost pushed you to go out and then try and find it in other places, which allows you to develop more holistically as a person. 

Jason Siegel: It did, it definitely pushed me. There's that sort of leaps you make where the door closes behind you.

sometimes you need that to happen and that can be, sometimes you do it to yourself but I think there is something to that, that sometimes you get a little push.

And I've, I guess one thing that I am a little proud of is that I, I do take those risks, which is actually not how I was raised at all.

I was raised to be really conservative with decisions that have to do with career and money. My dad grew up like really poor in New York City and this story he likes to tell is how he like wore the same pair of pants for like a year or two in school and, applied to college. this particular one just cuz it was [00:19:00] free and worked his way up, until he had a nice lifestyle and living.

And he always taught me that you have to be so careful, and be very conservative with your investments and not rock the boat too much. try really hard, work really hard, but not risk your livelihood. And for some reason it, I just, I. It's not me. So I kept jumping, I kept trying new things and so I found myself once again thinking, all right, what do I do with myself?

Because I know law is not right for me either. I was gonna say, 

Life Leaps Podcast: so Jason, and you already touched on this, so you're in law school, you figure out it's not for you, but you decide to practice law anyways. 

I gave it a shot. I really did, I tried to make every day really interesting. I looked for the new things and the people that I worked most closely with. I looked for the things that we could do to kind of innovate and find the.

Jason Siegel: parts of law that would get us excited every day to [00:20:00] solve problems really, to kinda like figure things out, take things apart, put things back together. But I never really felt like the amount of excitement doing that was anything close to what I had experienced before.

And there was a certain like I didn't like feeling like buttoned up. I had to be like this serious lawyer who's doing serious things. Sometimes it was two high stakes, where you feel like the sense of responsibility that if you don't.

Kind of do your job really well, that it's gonna have a really serious negative repercussion on someone's life. that's a lot of pressure and it's not that I didn't like being responsible for things, but it didn't make me happy to be in that position. And sometimes 

Life Leaps Podcast: the higher, for someone who really thrives on innovation and experimenting with new things and like taking chances and risks when the stakes feel so high in that way, that can really stifle both [00:21:00] organizationally and for you personally, the ability to do that.

And 

Jason Siegel: that makes sense to me. Yeah. I think there's something about, at least the part of law that I experienced, which was inherently risk averse. You have to be careful. You don't wanna break things, you don't wanna hurt people, you don't want. People to be wronged. It's a, I won't say that law is negative because I don't think it is, but I think the experience that I had was like more trying to prevent bad things from happening than to create great things.

Okay. And I wanted to be building things that would get people excited. You wanted to create great things and Yeah, I guess so. And so I just started to feel that a bit more day by day until I was like, you know what? I think I need to do something different. Was there one moment 

Life Leaps Podcast: when 

you said, cuz now we're getting to like more recent in your life, right?

Jason Siegel: this is like these are real, this is no longer baby Jason. These are like adult life decisions. Was there a moment when you were like, I don't wanna do this anymore? Or was it just a [00:22:00] slow burn and build? There was no single moment, but when I looked forward at my life and I thought about.

What I would, feel, what would I would be doing in 10 years, 20 years. The thought of being a lawyer, it didn't make me feel great. I didn't think it was like who I was. If there's such thing, I don't know that we all have a destiny, but I didn't feel like that was the sort of identity, or at least my professional identity, where I would feel truly at peace with the life that I had made for myself.

And so at this point, I was starting to not feel my mortality exactly, but realize that you can't keep changing forever. So I was like, all right, this time I need to be really serious about this and be more thoughtful about what it is I'm going to do next. I know I need to leave, but what do I do next?

And despite the advice that I had received, [00:23:00] Years earlier, you can't do anything with a jd maybe in the conceptual sense, right? You can have a JD and then you can go, whatever, get a different degree or navigate to some other job. But it's not like someone looks at your resume and they're like, oh, you have a jd, so you're perfectly qualified for this non-legal job.

It doesn't work that way. Yeah. Sounds like not like what you 

Life Leaps Podcast: wanted to do. You wanted to do something in a very different field, which sounds like JD didn't matter so much for 

Jason Siegel: Right. W right. And it would come as no surprise to those who listened to my story so far. I still didn't know exactly what the next step was, but I did learn that I probably belonged in the business world or something to do with business or tech by that point.

and how do you know, 

Life Leaps Podcast: how did you know that? tell me like what made you feel that 

Jason Siegel: I started networking with folks. I started. Reaching out to people I knew or online, I would just surf the internet until I found some groups that seemed to resonate with me and I started contacting people asking if [00:24:00] I could chat with them about what they did and how they got to where they were 

 how were you finding things that resonated with you to even begin to know what was 

next? I wish I knew. I felt so lost, to be honest, because it sounds silly that I had gone this far in life and I still didn't really know how to navigate my career. But I didn't, and I didn't know how to really network well, I don't think.

And I didn't know, I, I just, I didn't know what I was doing. I'll be honest with you, I don't even know how, but I managed to chat with some people who were working at consultancies, and I learned enough about consultancies to learn that they hired people from different types of backgrounds.

And I also learned enough to know that consultancies would allow people who joined to navigate their organization and kind of swim over to different types of careers because consultancies have so many [00:25:00] different aspects of what they do. and you're talking about like 

Life Leaps Podcast: big consulting firms? Is that what 

Jason Siegel: Okay. That's right. So for instance, like Boston Consulting Group or Deloitte, which is where I ended up, and. I realized that if I could join a consultancy and there was a chance I could get hired with the JD as an attorney, then I could spend a few years trying out different things, working for different organizations and businesses, and it wouldn't be seen as a bad thing that I didn't know exactly what I wanted to do because a lot of consultants, are generalists, you know?

Or you were looking swimming around the organization. Yeah. You were 

Life Leaps Podcast: looking for something that would allow you to not know yet and make it okay that you could sort of try being a jack of all trades, master of none and experiment along the way without inviting you. It's a total cop. It's not a cop. Think it's brilliant.

You're like, [00:26:00] It seems to me that I feel like I have this more like business rational, building blocks mind that's not fitting in what I've done before. And, but I don't know where I wanna use that. Buildings block building blocks mind. So your idea was, I'll go to a consulting firm where they don't specialize in anything.

Anyways. I can try moving around to all these different places, see what works, see what fits, and it, I, I won't be dinged for it. It makes sense to me. 

Jason Siegel: Okay. It makes sense. 

Life Leaps Podcast: I'll say this.it, it was a good move because I was able to use that experience to find what I was really passionate about. And pretty quickly, it was this first or second project that I had, which was just fascinating.

Jason Siegel: we were hired by a very large organization that had relationships with farmers around the country and was trying to increase adoption of what's called precision agricultural technology. So these are things like [00:27:00] drones and smart sensors, really the forefront of technology in farming. And they wanted to improve adoption.

And in order to do that, they hired us to, Talk with farmers, basically do ethnographic research. We actually went around the country to farms and interviewed farmers and watched them do their jobs to learn about what the pain points were that they had and the blockers to them. Adopting more of this technology more rapidly, which would, unlock just a ton of economic value.

And I didn't know anything about farming. this was totally 180 from anything that I knew, but I got to really experience a totally different world and really empathize with, people who are very different from me in so many ways, lifestyle, politics. And I just found it so cool. And I was like, you know what?

Even though I can be interested in so many different things, this really reminds me [00:28:00] of when I was young and there were people online who had this. Interest in, how would I put it? I guess just like learning about what other people need in their lives and helping to provide it to them. Building something, creating something, providing more opportunity to them.

It sounds fairly vague, but at a certain point I realize that's actually a lot of what the technology industry does in particular and what product managers do, which is what I am now, where a key part of your role is to identify a particular target user or target customer to learn about them and they could be anyone, and then figure out how to solve a really important problem for them.

And the people that I had met traveling around at farms, although I knew very little [00:29:00] about them in the beginning, had really grown to learn a ton about what they needed and. What was important to them and how to help them. And I used my five years at Deloitte to navigate to a career where I could do that all day long, which is the career I'm in now, product management.

Life Leaps Podcast: Wow. Okay. So who knew that it was all gonna begin with farming. so you start back at ground zero with this project where you're working with these farmers and it makes you realize that, I could be doing something with farmers or someone in Timbuktu or someone you know, at the president of the United States, whatever the point is.

I, Jason realized that I love coming up with solutions for people. I love finding ways to optimize, solve problems, fix things for people, and maybe it matters less who they are or what the problem is. As long as you're able to use some skills [00:30:00] within your world to fix it, like that seems to be what makes you tick and it you grounded yourself back in your early once again, when you come back to this high school time, your early like high school coding days where you had this online community of people that you were trying to do that for and with.

That's what made you not even realize, but just remember that.

Jason Siegel: Yeah, actually, I think that what's neat about being a product manager is that what you could become really good at is walking into a room or having a call with someone and knowing almost nothing about them. And then very quickly asking the right questions and being a good enough listener to be able to distill what are the most important things to them and what are the biggest problems they have and how can I make their life better.

These are also similar skills [00:31:00] to the ones that I practice as an attorney, where I would actually interview people all day long in a different context. In that context, they were whistleblowers who were reporting various types of wrongdoing, but much in the same way. You had to build trust with them. You had to really understand.

What their lives were like and why they were so passionate about the issue they wanted to talk about and what they needed. And we would help to solve problems for them. And that was the part that I found really interesting. It wasn't law, for example, when I was an attorney, but there was something about learning about people and what they needed that I found fascinating.

And there is a tie-in, to all the things that I've tried over the years where I want to do something meaningful to help people. It's not in any particular industry that gets me excited, it's just learning about people and what they need and how do we solve problems for them. Now, at a certain level of abstraction, that's every job, right?

I don't know that, but I found something that I, that ties into what I, when I [00:32:00] was very young, found myself drawn to, which is technology. 

Life Leaps Podcast: So it's not only wanting to solve the problem, but for you, I, it sounds like there's an extra piece to what you said, which you just filled in the gap, which is, it's not just.

Finding and learning about people and solving their problems, which is a huge important part and takeaway in realization. But then that really important add-on, cuz you were doing that with teaching, you were doing that as a lawyer and you were doing that with these farmers, but the piece within that goal that made you tick was using your technology tools to do it.

Does that sound 

Jason Siegel: right? That's right, yeah. I think there's something that I always just found exciting about technology and I had just strayed from that path. And again, no regrets necessarily, but it's what It's what just felt right to me. And so once I noticed it, I was like, Hey, I think I need to do that.

And I think this one will actually be for a long time. 

Life Leaps Podcast: [00:33:00] and it was great. I learned a ton of Deloitte.

Jason Siegel: At the end of the day, though, I wanted to be a technology at a technology company. 

so, After five years, like five years, So I decided to leave and talked to a bunch of tech companies and ended up at one 

 for almost a year and a half. 

 And I was finally at a place where I felt like I really belonged and is where I had been guiding myself too for a really long time. I am. And yet, as is very common, apparently for myself, I found, all right, it's not the best fit forever, but it's exactly where I needed to be at the time.

So 

Life Leaps Podcast: Jason, I just need a flag. So you left your job at the consulting firm for this tech company, but this time when you left, it wasn't as confused, Jason. It wasn't as, self whatever, berating Jason I should have [00:34:00] known this earlier, or I should have, maybe I shouldn't have done this.

Oh my gosh. This time that you left, it was like, I've taken what I need to know. I did this whole generalist experience, try these different things and now I really know finally that I really wanna dive back into the tech world, which is where I came from in the first place. I. So when you move to this new tech place, it's knowing what you wanna do.

Jason Siegel: And that's a big change. That's a sea change from the Jason who's left in these other ways. I did come full circle, right? And I had, there's a certain, I don't know what the word would be, but a certain completeness maybe where I felt like I had been on this path to find something that really resonated with me.

And I do think I, I found it in the end. I was out of really cool tech startup. I was in a line of work that I really enjoyed. I had a ton of colleagues that I really respected and I would wake up, maybe most importantly, [00:35:00] so many days, excited to solve the problems we were solving.

And I would put in like extra time on nights and weekends like I did when I was young because I was so interested in what we were building and the problems we were solving. And so I knew that there was something about it that finally was exactly what I was looking for. 

Jason, 

Life Leaps Podcast: I was gonna ask you how did you know Cuz some people might think how do I know if this is right for me But it sounds like you already answered the question. You were like, I was excited.

I wanted to put in extra time because it excited me and lucky for you, and actually I think many of us had this experience of having been in flow before in our lives doing something and you used that as a baseline to evaluate whether things were or were not the right fit moving forward.

And this keeps coming up again and again. An interview that I did months, ago. With [00:36:00] Astrid Baumgartner, who's a Yale professor now and is a career coach and does all kinds of amazing things.

She's actually got a Ted talk on this. Anyway, I interviewed her and one thing that she said, it was almost like a little mini coaching session. and one thing she said that she tells people to do who are trying to figure out their lives? I e all of us? And she was like, picture times in your life when you've been in flow and flow is that feeling where you're focused on nothing else.

That time is not existing in the moment you're feeling totally connected. we often have one or two extra voices in our head that are running like little tracks at the same time that we have our main voice. Flo is the time when most of those other voices are silent. Okay. And it's it's those really special moments.

And she was like, and if you've not had that experience, Start experimenting and see and pay attention to when you do or don't have those moments, because that's the baseline you need to pay attention to for every other goal and thing you do in [00:37:00] your life, career, personal, whatever else, use that baseline because without it, we're kind of lost sometimes as to whether something fits or not.

And Jason, you were doing that all along, whether did you realize it or not? 

Jason Siegel: I think that's right. And what was particularly tricky for me is that I really am genuinely interested in so many things. you can come up with some random topic that I knew nothing about and I would read a whole book on it or would love to talk about it for hours.

and what really resonated. When I came back to product management and technology is, it was like the one thing where it's not that I was just interested in it, but when I get really into it, it almost feels like nothing else matters. It's that certain like mindfulness that you might experience if you meditate sometimes, where you can enter that flow and time passes really quickly and you don't feel like your attention is drawn to anything [00:38:00] else that's going on in the world because you're not just interested or fascinated, but you're just totally focused.

And that's a great feeling. Wow. 

Life Leaps Podcast: You know, for some people, like a lot of us wanna find that in our careers and maybe just as many of us don't need to find it in our careers, But I'll say I pretty much every one of us needs to find that somewhere in their lives, whether it is through some sort of religious practice, whether it is through a volunteer thing, a hobby, a certain, I don't know what it is.

A lot of us, I think as millennials, want it to be our careers. But I just wanna flag, like that is something that I feel like is so vital that all of us are searching for and trying to connect with in whatever we do. and I realize that the most after you and I had a call a few weeks ago to talk about having this conversation when you just off the cuff mentioned like how you had felt that feeling.

And I was like, [00:39:00] okay, Jason's there. Jason gets it. Like Jason. Anyway, I think that's really special. 

Jason Siegel: thanks. I hope we can all experience it. 

I don't even know sometimes how I ended up where I ended up and who knows, maybe in five years I'll be somewhere different. I hope not. I don't think so, but you really never know, and maybe that's sometimes what's great about trying new things, that there is a bit of an unknown and. There's an excitement sometimes of not knowing Exactly, what the future will look like.

Life Leaps Podcast: I love it. okay. And Jason, just real quick, so you mentioned that you found this company that you felt all these excited things about. Ultimately, it sounds like the company itself wasn't the perfect fit. not for your craft, but for different sort of like internal organizational reasons.

Whatever you decided to move from move on from that company and for the [00:40:00] first time in your life right now, 

 tell me where you are. 

Jason Siegel: Yeah, I did something I have never done before and I'm not gonna lie, it was terrifying. I was working really hard and very long hours, but I wasn't really proud of how it made me feel in the day-to day.

And so I wanted to keep doing what I was doing, but do it in a place where I felt like I really belonged. And so I did something that was really scary. I don't even know what, in the end, what made me pull the trigger.

But after thinking about it for a while, knowing how hard I was working and how it's really difficult to work. Full-time and then look for a job full-time. And at the same time, I could see if you're following the headlines. Now, the tech industry is really not in great shape. I knew it would be really difficult to find an next job if I couldn't give it my all.

And we had just bought a house my wife and I like a couple months earlier. And so [00:41:00] we had this new mortgage and it was a big risk. But I decided, you know what? I've done this many times before where I decided to jump without knowing what was next. And I needed to trust myself that I would figure it out.

And I already had 90% of what I needed, which is knowing exactly what I wanted to be. And all I needed to figure out was. Where it would be ands the place to do it. And the place to do it. That's right. So I gave notice, they asked me to stay a little bit longer, which I did. And then I jumped and had spent the last month or two thinking about what I wanted and where I wanted to be and organizing my life through.

Those are all these things that I was so busy that I couldn't even take care of them. So I just, this really long to-do list of getting my life organized and then preparing to interview again and [00:42:00] starting to interview again. And that's where we are now. So I hope that pretty soon I find my next place. I think I feel fortunate though, that I don't feel quite as lost or I don't feel lost anymore.

And in a year or in two years, the kind of. Persistent anxiety I would get sometimes that I hadn't really found a path yet is something that's hopefully behind me. 

Life Leaps Podcast: Wow. And Jason, how did y'all make the money work?

That's obviously something that a lot of people would ask you are currently married, but you just said you started a mortgage. are you guys just cutting down expenses? Did you have significant savings? 

Jason Siegel: Yeah, I definitely feel fortunate that we were able to make this decision. My wife was actually really encouraging of this.

I asked her, I said, should I quit? And she said, do it. just do it. Don't worry about it. we'll figure it out. So I'm very grateful to her [00:43:00] for that. Fortunately we had enough savings to be able to make it work without any real immediate impacts. We've certainly cut back on our spending a bit.

we're not planning some big vacations and we're being mindful of going out and things like that, but we have enough that we can keep things going for a while without any sort of catastrophe happening. So if this turns into, a year or two, then I think we're gonna have a problem.

But I have to believe like I have before that it'll work out. And sometimes you don't know what's next, but sometimes you just have to take risks. So ask me, I guess in a year how I'm feeling about this. And Jason, I'm asking and hopefully I'm like, it was a great decision because now I'm at a place where I'm really happy and it all worked out and, there's always a chance it won't.

But Jason, I can't think about that too much. 

Life Leaps Podcast: Jason, I'm asking you before a year, like I'm checking back in with you. I wanna know what happens in a couple of months, I'm gonna track you and we'll see. but for [00:44:00] now that sounds great. Before I release you into the wild to go and continue to figure out your life path,as we all do,

what advice, insights, reflections, things you wish you'd known, done, whatever do you have for the rest of us looking to make life leaps?

Jason Siegel: I think it's important to notice when something isn't right in your life. sometimes it's easy to. Push those feelings away of something isn't right. It's not always actionable. Sometimes you need a year or two to plan for how you're gonna deal with that, but noticing when something isn't right and you want to make a change is I think the first step.

 And so maybe if you can notice those moments, then you can think through what are the ways in which I can get some distance and perspective

Maybe I need to work on myself. Maybe I need to take a vacation. Maybe I need to have conversations with those [00:45:00] whose opinions I respect. Maybe you need to do all of them. Maybe you need to take a year. Maybe you need to take a week. Whatever it is, taking the time to find that perspective and look at your life and decide whether it's situational, whether it's a mindset.

Whether you need to have a multi-year plan to get to a different place, or whether there's a really quick decision you can make. It's really hard in the moment or when things are rough or when you're confused or have any real kind of very strong emotion to make great decisions. So first noticing and then finding a path to a broader perspective on your life, I think is really important to decide what's next.

[00:46:00] And I can't promise that, of course, based on my life, right? You'll always know what is next, but hopefully you'll at least know whether it's time to really go do something about it and maybe what that next thing is. 

Life Leaps Podcast: Thank you all for being here. We're a brand new podcast, so if you enjoyed it, go ahead and follow rate and review us in your podcast app so that we can know what you liked and others can find us. It would mean a lot. Last but not least, we'll keep you posted on brand new episodes each week when you follow us on Facebook or Instagram at you Guessed it like LEAPS podcast.

Till next time.