If you’ve been immersed in the tech world for some time, you probably have heard one specific YouTube channel mentioned more than once - Learn With Jason. It’s a project started by Jason Lengstorf, a former VP of developer experience at a web tooling startup (he was a head of developer relations prior to that too), that is aimed at helping everyone navigate the always changing landscape of developer tools and frameworks. Which, by the way, according to Jason do not matter.
In this show, we dive deep in Jason’s career path and focus on the less known aspects of climbing the career ladder - things like amassing political capital by doing great work, building visibility by meaningful means that can help cement your reputation, and being able to address business problems as a mechanism to build trust in your own leadership abilities.
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The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
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Transcript
Den Delimarsky:
Welcome, Jason Lengstorf, to The Work Item. So good to have you here.
Jason Lengstorf:
Yeah, thanks for the invite. I appreciate it.
Den Delimarsky:
It’s been a while since we chatted and I am so excited to learn more about your career because from all the people that I know, you have a very, very remarkable career. And I say remarkable. This is not an understatement. You do have a remarkable career. Maybe before we get into kind of the meat of the conversation, you tell us more about what are you working on these days?
Jason Lengstorf:
Yeah, so these days I am running a company called LWJ or Learn with Jason, where I help companies make developer focused media more or less. And what that has turned into in practice is that I’m kind of running a reality TV network for developers, having a blast and partner up with a lot of cool companies. And I actually couldn’t imagine something I enjoy more.
Den Delimarsky:
And if you have not subscribed to Learn with Jason, go to YouTube. It’s there. The links are going to be in the show notes, so you can always check it out. Highly recommended. And Jason, you are one of those people that combines a lot of the technical acumen with the ability to teach people, like you’re very good at explaining complex topics in very easy terms that make people grok at. But what bootstrapped your own interest in tech, like what was that starting point that you said, you know what, this is something I want to build my career in?
Jason Lengstorf:
I kind of came into tech sideways. I was trying to make it as a musician and I was touring. We were playing around 200 shows a year back in 2006 or so. And, prior, like when the band started, I couldn’t afford help. We didn’t have money. We were always living on, you know, just enough off the door so that we could afford gas to get to the next city. So there was no hope that we would be able to hire someone to make us a website or to customize our MySpace page or any of those things that a band needs if they want to promote themselves on a a tour. So I figured out how to put up a custom banner on the MySpace, and then I wanted to put our music up. I wanted to add a little bit more.
So I, you know, started designing our merch. I started… I got a job at a screen printing shop so that I could secretly make our t-shirts when nobody was around. All sorts of little things where I just started learning skills to support this this goal of becoming a musician. But after a few years, I was in that band for about five years, we broke up in 2007 or so, and I realized that, you know, I’m not going to make it as a rock star. It’s just, you know, the lifestyle was too hard. And also, I don’t think I was that good. I think the best thing, like the thing that I was worst at in being a band was the music part of it. But I’d learned all these other skills. I was basically running an agency with a single client.
So I could build websites, I could do design, I could do all this other stuff. So when the band broke up, I looked around and I was like, what am I going to do next? And I made the decision that I really liked all of these things that I was doing for the band. So what if I just tried to do those for other people and I started an agency and that’s what I did for the first 10 years of my tech career.
Den Delimarsky:
Right. And so it all came from a place of need that you actually needed a solution, right? Like it’s not like you just jumped in it because like, “Oh, tech sounds fun. I’ll do that.” It’s more like we actually needed to solve a problem. Tech seems to be the avenue to do that.
Jason Lengstorf:
So I think the unique cocktail that kind of powers me is a combination of my great upbringing, like my parents raised me very much to be somebody who says, “I can probably figure that out”. And I got good education and encouragement in that direction. And on the other side, I’m just the most extra at anything, right? And so I have this this combination of - if there’s a problem, I’m not willing to back down and say, well, I can’t do that. That’s not me.
But also, I can’t look at something and just do it halfway. So of throughout my career, I’ve had these moments of of looking at something new. And I say, OK, well, I don’t want to just do something that’s going to get it done.
I want to do it well. And then I fall down the rabbit hole of trying to get really good at whatever the thing is.
And you know, to varying degrees of success, if people have seen that you know my music or my art and my my web development, you’ll see there’s there’s some variance there in what well means to me. But as as Aaron Francis would say, I’d like to try really hard at things and and to see how far I can push it.
Because that, to me, is a lot of the fun of learning, is you know, can you do this at a world class level and and how much effort and time is required to get there?
Den Delimarsky:
Right, right. So you’re taking the kind of the bit of a, you know, Ron Swanson approach, like never half-ass, you know, two things, whole-ass one thing and you’re whole-assing many different things. Whatever that domain is.
Jason Lengstorf:
Sequentially.
Den Delimarsky:
Yeah.
Jason Lengstorf:
Yeah, so the way that it’s kind of worked for me is that I tend to get into a field and then I’ll spot something new that… The concept that I’ve heard that I repeat constantly is, it’s from Steven Johnson is where I learned about it, it might come from somewhere else, but it’s a concept called the adjacent possible, where you you don’t get to an invention immediately. You have to get there in step. So you don’t go from inventing the wheel to a jet engine.
There’s a lot of things that happen along the way. And each step on that journey unlocks the next step and so I think of it is sort of like opening doors. I walk through a door and when I get there I can see new doors that I can see before and whenever I open one of those it exposes me to new doors and that’s how my career has run more or less is that, you know I started out in the band and I realized that I can do some cool stuff with computers and then when I got into the agency world I realized that there were things I could do there and then I got a job as a consultant and that led me to playing with some of the stuff that got me my job at IBM, which got me into open source, which got me into Gatsby, which got me into Netlify.
And when I was at Netlify, I got into the marketing side of things, which got me to where I am today. And each one of those things I don’t think could have happened if they hadn’t happened in sequence, like it was the act of getting into the thing and then trying really hard to get good at that thing and realizing that there were additional opportunities that I could explore adjacent to where I was.
Den Delimarsky:
Right. And so it sounds like from the description that you just gave us is that a lot of this feels almost serendipitous. Like you started down a specific path, you discover something else, you start seeing new patterns that are of interest, you follow that path that opens your new path and so on and so forth.
Have you ever thought about mapping out your career in any capacity? Because something that I hear often from folks is, well, should I have some kind of career plan? You know, if I go in five years, 10 year increments, like where do I want to be? Is that something that you did or more? Did you follow your interest and then see where that goes?
Jason Lengstorf:
I think goals are an interesting thing because I don’t think it’s necessarily good to not have them. But I think that a goal can also become really stifling if it’s too prescriptive. And so I like to think about it in the abstract of my goals are always to look back at where I was and know that I’ve done better.
And and so a concept that I that I’ve heard that I repeat a lot is this idea of like 1% improvements. You can do 1% better every day. At the end of a year, that’s… It looks nonlinear if you look at the graph of 1% improvements over 365 days.
And that sort of thing isn’t, it’s a goal in the sense that I know that what I’m aiming for is higher than than where I am. But it’s not a goal in the sense of like, I’m aiming for this specific role at this specific company, because I don’t know what’s like, if I say, “Oh, I’m going to go become the CEO,” like, all right…
So here’s a good example, I’m currently I’m moving into media and I know that what I wanna do is make things that are higher production, higher effort, more scale, more more people, more timelines, you know, that kind of stuff. But if I were to look at it and say, all right, my goal is to become the CEO of NBC so that I can direct the programming and make the stuff that I wanna watch. That would achieve what I see in my head, but there are so many unknowns between what I’m doing right now and what it would mean to be the CEO of a media company that setting myself on that goal is kind of walking through a dark hallway without a lot of information on what’s gonna happen between point A and point B.
So instead I think of it as like what I’m looking for in five years is I wanna have the access and autonomy to build something, to make something at the scale that I wanna make. And maybe that means getting into traditional media and working my way up the ladder to have influence.
Or maybe that means something entirely different. Like in my case, I didn’t move into traditional media at all. I’m kind of using the tech connections I have to end around traditional publishing because that’s the access that was available to me, right?
And I would love to get into traditional media and learn more about it and and kind of get involved because there’s so much fascinating stuff going on there. But if I had said my only path is this goal I’m gonna work my way up the corporate ladder it would have cut off all of the things that I’m doing now.
In a way that would have been really restrictive so, directionally I have goals, prescriptively - I don’t, and so the map is more of a go that way than it is like a go to here than here than here than here and then you know X marks the spot.
Den Delimarsky:
So it’s an approach that is primarily driven by what do I want to achieve and accomplish more so than I want to have this particular role or this particular position because that’s… I think the mistake that a lot of folks do and maybe it’s not a mistake that is intentionally made but more especially as you are junior in your career you think like okay well right now I’m Software Engineer 1 and I want to get to Software Engineer 2 and then I want to become a Senior Software Engineer and the title carries that kind of torch for you because that’s what you’re aiming for but ultimately that can only get you so far because at some point you’re gonna be capping out and it’s like well okay now you want to become a Staff Engineer - what’s the path to Staff, okay you don’t really know because there isn’t one.
Jason Lengstorf:
Well, and I think the other thing too is that is that a title itself, it turns the goal not into an achievement, but into a checkbox.
And the thing that gets really challenging about that is I’ve done this in my career and I remember I had set a few goals that were really important to me. I was like, I want to make $120,000 a year.
Like that was a big milestone for me because it meant I was making $10,000 a month. And I knew that that like that was going to be it when I when I felt accomplished.
I knew I wanted to work for a tech company that everybody had heard of, like the IBM job. And I knew a couple other things that I had set as these goals, like I want to work for a big name, I want to make a certain amount of money, I want to have a certain amount of whatever.
And then I hit those goals. But the day before I hit those goals and the day after I hit those goals didn’t feel particularly different. Like there were changes where I, obviously like crossing a monetary threshold is a big moment, but it wasn’t like I did it and then confetti cannons popped off and I got a trophy and everybody said, okay, congratulations, you’re done. You don’t have to do anything else. You’ve accomplished the things that you set out to accomplish. So here’s a big comfy chair and you just wait out the next 70 years of your life until you die.
That isn’t how that typically goes. Instead, we cross a threshold and then it’s, I think of it as sort of like walking through mountains, right? You see a peak, you walk toward that peak and when you reach it, it’s not the end of the world. You don’t just look off into the abyss. You just see more mountains that you haven’t climbed yet.
And so then it can feel really, it can be a disillusioning moment to accomplish a goal because you basically realize that like your ambition stopped here, but look at everything that you didn’t even know existed. And so now there’s this sort of vacuum that needs to be filled by the absence of a goal. And and so if instead, what I’ve adopted is is sort of directionally constant improvement, then there are milestones.
I got hired at IBM, which was a milestone for me, but it wasn’t the goal. Like that. That was a milestone that enabled me to do more stuff. But then when I you know decided that IBM wasn’t the right thing, it didn’t mean that I was like letting go of this lifetime achievement to climb the corporate ladder at IBM.
It was that I had found a way to chase something that held more value, more meaning for me in the sense of small startups where I’d have more autonomy more influence on the roadmap, right? And each of those decisions was it… Was a goal and it was a milestone. But I wasn’t putting the value in the checkbox.
I was more thinking of of “How do I feel like” - do I feel like I’m doing something that’s valuable? Do I feel like I’m doing something that I’m gonna be happy about and then it’s, you know, if I’m, if I’m proud of myself, every time I go to work, then that’s every day you wake up and you go, am I proud of the work that I did today? And you say, yeah, okay. I don’t know. There’s no, there’s no like end to that.
You just keep doing it. You always find a way to go one step further and be proud of what you’ve done. And I feel like that that’s a little more sustainable for me, at least.
Den Delimarsky:
I think it goes back to what you were talking about in one of your recent videos too, it’s what actually motivates you to do this. Because for some folks, it very well could be that the title is the motivation, like that is your end goal. But then, as I mentioned earlier, like you’re gonna be capped at a certain kind of ceiling that you might or might not know about, because the more you think about the title as the core goal, the more you miss out the opportunities that come around you. And this is where that overly rigid map of I wanna hit this title and then this title and this title, it makes you have almost like those, the blinders that you’re… You’re looking ahead of you at the thing that’s like, okay, here’s the check boxes that I need to do for this title. And you miss out on all these other opportunities that can take you in a completely different direction. As you just described for your own career.
And that actually leads me to Learn with Jason, because this is something that again, I love the work that you’re doing on your channel. I love the work that you’ve been doing like since we worked together at Netlify. And what was the origin of this effort? What started the YouTube channel, the kind of the educational material and then Jason’s life wisdom in video form?
Jason Lengstorf:
So there’s a little bit of a few different things happening as I mentioned I was a musician before and I’ve always loved that aspect of performance of the sort of community gathering around something, and so being able to find a way to fit that into the things I was doing felt good I had been looking at things like speaking at conferences I had done at IBM a bunch of internal training so I was I sort of the person running through internally, that’s how I got into DevRel actually was I had built some open source at IBM and worked on some stuff to fix a major problem and at IBM.
And then there were so many teams that we needed like internal DevRel to go around and convince these other teams that the tool was good, safe, actually going to remove work for them and not create more, you know, all the things that that devs worry about, especially at larger companies where there’s a lot of legacy code and pager duty and stuff like that.
There’s always some young hotshot like me who comes through saying like, I rebuilt the whole thing, let’s just switch to this and all your problems will go away. So I learned DevRel, I learned positioning. And then when I went over to Gatsby, I realized that the so Gatsby kind of hired me without a job, if that makes sense.
They said, Come over here, we’ll hire you as a principal engineer. But We don’t know what you’re working on yet. We want you to figure that out, which in retrospect was absolutely bonkers from a founder standpoint.
But from from my standpoint, it was kind of the best possible outcome because I got to show up and survey the company and see what everybody was working on. And then I noticed a gap. And the gap was that Gatsby had this really healthy community that had sort of emerged, but nobody was taking care of it.
Nobody was was making sure that it stayed healthy, right? And as as anything grows, the you know the product will build the initial community, but then when it hits critical mass, the community starts to turn into something that can go a lot of different ways if it’s not actively cared for.
So I kind of opted into being the person who was going to build the community system. So I built out some stuff to like automate GitHub, automate giving anybody who committed to the repo, if we merge your PR, we’d make you a maintainer, and we would give you some swag.
And there was a whole thing, right? But that got me thinking about, well, how do we scale this, right? Because it can’t just be, I do everything manually. And that’s how community works. So how do we how do we expand this out a little bit, I’d started having calls with people in the community to coach them on stuff.
Jason Lengstorf:
And I’d started having calls with with other people to learn how to integrate their products with Gatsby. So I was like, Okay, what if I just live stream this?
And I had a couple of iterations that failed before this, where I did things like live streamed internal maintainer meetings. They were dreadfully boring and nobody wanted to watch them. So those kind of faded into the ether.
But then I had a call with Nader David, who at the time was working at AWS and I was like, okay. Let’s deploy Gatsby to AWS, show me how this works. And I just live streamed it and people enjoyed it. And it was a Zoom call. It was just, you know, my window and his windows sitting on top of my desktop, streamed it live. And it seemed to do well. So then I took a few more iterations of, you know, I talked to community folks and I realized that I didn’t want the format to be me being the smart person and somebody asking me for help because they’d already had to sort of take a risk by asking me for help in the first place.
So me saying, okay, well, will you take that risk by also being vulnerable in front of a live studio audience? That didn’t feel right. So flipping the format to where I’m the one who doesn’t know things, bringing an expert in to teach me sort of emerged from experimentation and then I polished it up and I got more into it.
I learned more about AV, got really excited about that. And so over time, it just it was like each thing was a logical next step.
And that kind of became like, all right, I’ve done all this AV gear for my live stream. What if we did stuff that wasn’t live or what if we expanded it up to be a conference. Like when I was at Netlify, we we tried to live stream an entire conference with multiple tracks and all sorts of stuff, learn some valuable lessons like you can’t plan on having electricity.
So we had a… A bird sabotaged our conference.
Den Delimarsky:
The little things.
Jason Lengstorf:
That was a a fun one.
Den Delimarsky:
Wow, there’s a story there.
Jason Lengstorf:
Um, yeah, that was a, that was a fun day. Good 5AM call to find out a bird took out the power to the neighborhood that you’d run at a house in to do your live stream from.
Den Delimarsky:
Goodness, that that makes that makes the job very appealing. Why wouldn’t you want to work in that field?
Jason Lengstorf:
I mean, I think, but the thing that’s fun about all this stuff, right? Is that it’s the same kind of chaos that you run into with anything, the demo gods and and all that.
But it’s like a new interesting set of challenges. And so, like you said, you know, with engineering, you go up and you hit that principal engineer and then it’s like, okay, what do I do?
I become a CTO. Well, what if I don’t want to be a CTO, right? And so then you start to look at how else you can apply this.
And and in my case, it was like, okay, so I’ve… I feel like I’ve done really well in engineering and front end. I’m confident that that’s a thing that I do really well. How can I expand? Can I get better at talking to teams?
Can I get better at talking to people, get better as an educator, get better as an entertainer? It was All of these different spaces where I felt like there’s still room to grow there. Like that’s a ladder I haven’t climbed.
And so as I started to expand these out, it became less important to demonstrate growth as an engineer because that wasn’t the area that needed tending.
It wasn’t the part of my career that felt like I was struggling, right? Like I got lots of opportunities to build. I got lots of opportunities to try stuff. And and I’m by no way implying that I’m like done as an engineer, that I’ve learned all that I can learn, but more so just that it felt like I’d hit the plateau of like incremental gains in my own journey as a technologist where I can. There’s a million things that I can learn that will make me incrementally better as a developer, but there were so many ways that I could make more impact as a community leader, as an internal leader, as a mentor, as a coach, as as a manager, whatever it was, those things all felt like I could have an outsized impact versus getting you know a little bit better at at the technology that I was working with.
Den Delimarsky:
And especially some of the alluded to is like that, that plateau oftentimes it’s very hard to know. What does it actually take to get to the next level?
Because nobody talks about it or maybe people talk about it. I don’t want to say nobody, but generally it is so taboo to kind of talk about what do you optimize for to get to that next level after you hit the principal bar or staff bars and companies, right? From your experience, somebody that actually carried the title of vice president, how did you figure out what were the required next steps for you to kind of make the jump to the truly the kind of executive level?
Jason Lengstorf:
I mean, I think this is one of those things that’s so steeped in in survivorship bias, right? And so I wanna be careful about how I frame this, but for me personally, I think what has, what laid the foundation for me to get but to get tapped as as an executive in the first place is that I had a a long history of being willing to assume responsibility for the outcomes of things. And so when my team was working on something, at the time my my VP was Sarah Drasner, and every time Sarah had something going, she would say, all right, here’s our list of objectives.
What do we want to do? I would but I was willing to own one. I was willing to plan it. I was willing to take the responsibility, lead the team. And if something didn’t work, I was it was my fault. It’s not the team. I’m not letting somebody fall under the bus there.
And I also think that you know part of it too with executives is recognizing and embracing that nobody knows what’s going on. And every single job is the same as the job you have But as you go up the ladder, the number of things that are our you can be confident in diminishes significantly.
So as a software engineer at the you know the junior level, you’re getting a list of tickets. And you don’t feel like you know what’s going on, but there’s a clear list of like, somebody wrote down a list of what you need to do.
Jason Lengstorf:
You check those things off the box. When you get up to principal engineer, the things on that list are like, “We’re losing customers and we don’t know why”. Here’s a stack of research from the product team. Here’s a stack of of requests from the support team. Here’s a stack of ideas from the design team. Do you know what’s going to make us make more money? And as a principal engineer, you’ve got to be able to think through like, okay, well, technologically speaking, we can get XYZ done. And through my experience, these things are actually feasible and will make an impact. And that’s supported by the research.
Now I’m going to go have a meeting with the marketing team and the product team and the engineering team, convince everybody that I think everything we want is met by these goals and prioritization. like So suddenly you’re in this role where you’re. you’re you’re evangelizing technology, you’re you’re going out and you’re saying, I have a plan and you’re pulling it out of completely undefined spaces, right?
Then you go into an executive space and you’re not only expected to do that, but also you’re like horizontally managing a bunch of people who also don’t know what’s going on and are getting even less concrete things.
Like they have to decide what should we green light for the product team to even spend money on to go and get research?
How do we know? And they don’t have the skills to do these things. You find yourself managing. I was acting as the VP of developer relations and marketing. And my history is not in marketing. I don’t know how enterprise marketing works. I don’t know how how to run a good email campaign or all these things that I was being asked to oversee. Somebody was just coming to me and saying, OK, what do we do? And so as an executive, you have zero clarity, you have zero playbook, and so much of that job is being able to confidently say, I don’t know, but I have information from these experts that report to me, and based on the information I have, I’m gonna make this bet, and then having enough spine to stand behind your bet long enough to let the team follow it through, right?
So, that to me is what really makes the difference between a good executive and a bad executive. And I think that if you show those qualities when you start getting into the senior plus rungs of your ladder, if you want to get into executive leadership, that’s where it starts to show is that you’re you listen to people, you’re willing to change your mind, but you also are willing to make a plan and commit to that plan, despite all the noise, because you know, right, we’ve all learned and and internalized, I hope that changing the plan every other week, doesn’t make… There’s no good outcome to that, right? Following a bad plan for for six weeks is better than changing good plans every two weeks.
So hopefully you get good at making good plans and you get good at sticking to them so that you’re getting good results by letting people follow through on plans and not jerking them around, not making them panic, making people feel like they’re trusted and secure in their jobs and doing good work and getting feedback and all the things that are important in an organization If you can start to exhibit those qualities as you know as early as possible and and really try to internalize what it means to and have no idea what’s going on but listen to an expert, trust them and play your job on the line to let them do the thing that they said is going to work, that’s that’s leadership and it’s terrifying and I hated it and that’s why I don’t do it anymore.
Den Delimarsky:
Yeah. I’m asking you for advice from a person that’s like, I don’t want to do this anymore.
Jason Lengstorf:
No, but but I do think like you know the direction that I decided to go with it is I decided to start my own company because I don’t like the risks of being responsible for somebody else’s wellbeing. If I screw up as an executive, I might have to lay off my team. If I screw up as me, I have to go apply for jobs. The downsides to me are drastically different.
Den Delimarsky:
Yeah, I totally buy it. Now, when you were kind of making this jump, what’s interesting is that the balance that you just described of being a technical leader versus a people leader kind of shifts, right?
So you’re no longer writing as much code.
You’re no longer reviewing pull requests. You’re no longer contributing to open source as much. Not saying at all, but probably not as much. How do you navigate that transition where now you need to think about strategic items and not try to get in the middle of, oh, this engineering team is building this. I know how to fix this thing. I’ll jump in on help. Like you kind of have to let go a little bit. How did you navigate that?
Jason Lengstorf:
I wish that people who reported to me were here to say whether or not I did a good job but I think that the hard part of moving into leadership is that you are moving from a doer to a well that’s not okay it’s that I don’t want to make that distinction so let’s make a different one you’re moving from somebody who is building the thing to somebody who is clearing the path, right? And so your effort shifts from how do I clear enough space for me to create this thing that is planned? And instead your effort shifts to how do I clear enough space for all of these people who report to me to get the things done that they were told to do?
And all of the things that have to happen for that to be true, they need to know what’s expected of them. They need to know how it ties up to business goals. They need to know that they are not going to be told midstream through a DM and Slack or something that a different executive wants them to do different work and it’s P0.
They need to know that they have clear expectations of timelines, but not so unreasonable that they’re panicked. They need to know that you you know the workplace is gonna be safe for them and they can offer feedback and constructive criticism without being retaliated against. All of those things are really, really, really important for somebody to do good work.
And as an individual contributor, you can create that space for yourself, right? That’s what makes a lot of us really effective, is that we can manage up a little bit. We can talk to our manager and make sure that our manager understands what we need and create our own space.
As a team lead, right, if you move into the staff or principal roles, now you’re starting to look at how can you do that for your immediate team, the people who are clearly like around you, but you still have a manager to sort of deal with all that stuff.
Your ability to do the technical things, I think, in my in my opinion at least, the path of individual contributions peaks at senior. Because once you get beyond senior, now it’s not like, how much can I do? But it’s like, how do I make the people around me more effective? Can I build better tools that make the other engineers like less likely to make mistakes? Or that make the code base more maintainable, or help them onboard into some complicated thing. And then as you go up the ladder, you get to staff, you get to principal, you get to distinguished engineer, you’re you’re now… You’re not thinking about day-to-day code anymore. You’re starting to think about building tools that help the coders do the day-to-day code. Or you’re thinking about systems, or you’re thinking about structure, you’re thinking about architecture, all things that aren’t you directly writing code, or that are you writing code that helps people write code, as opposed to building the actual end product for the user. And so when you move into executive leadership, it’s just the next thing up. Okay, how can you make people good at code without writing any? Right. And so so it’s sort of this gradient, right?
When you’re a junior, all you do is write code. And when you’re an executive, all you do is help other people write code better. And and so I think that’s sort of the It’s to me, it feels like a very natural progression.
And then it’s it’s on you as a leader to remember that, you know, your job is to trust experts to be experts. Your job isn’t to know everything and do everything. And if that’s what you’re doing, quit and start a company.
Like if you want to think about it all and do it all, that’s a great sign that maybe you’re a founder and not not an executive.
And that’s what I found about myself is that I was feeling a lot of tension and and like, stress, I wasn’t sleeping through the night because I was so worried that my people weren’t taken care of and I felt all this tension in myself because I wasn’t building, I wasn’t creating, I was spending all my time sort of clearing space and I didn’t like that, I missed the building and I didn’t like that, I felt like it leadership is sort of an exercise in constant failure because you’re never, once you get past even like three reports, the likelihood that you’re gonna make all three of them happy at all times is approaching zero. When you get the 30, 40, 50 reports, you’re hosed. Like somebody’s mad at you at every minute of every day for an extremely valid reason, right?
And that is not because you’re a bad person. It’s because companies are inefficient and somebody had to get deprioritized and it is not cool that they got deprioritized, but you literally have no control over that.
Right? And so now it’s your job to be as diplomatic as possible while telling somebody effectively, I’m not going to make you happy yet. So sorry, but you’re gonna have to stick with me.
I hope you don’t quit. I can’t tell you exactly why because that’s confidential, right? These these conversations are terrible.
They’re really, it’s hard. It is a very, very, very hard job. So maybe the first thing for anybody who’s looking at being an executive is to really examine what it is that you want out of that job.
Because I think that for a good executive, it really gets into that idea of of you know the servant leadership. You are effectively, you are martyring your own mental health to help other people have better careers.
And for some people, they’re extremely good at that. And they’ve got a good good grip on how to properly compartmentalize and protect their own space and give themselves things to help them stay disconnected.
It was not working well for me. I could feel myself starting to spiral into some pretty bad mental space.
Den Delimarsky:
Yeah, what stood out from what you just said is there’s an interesting aspect to leadership that it’s not necessarily about even delegation because I think that what’s I think a lot of people mistake leaderships like, oh, I just need to learn how to offload things to other people.
But in reality, it’s not just the offloading part. It’s how do you make sure that you are the catalyst so those people are more effective so they can operate at scale so they can spot gaps and processes or interpersonal communications or any of those potential areas that might need improvement, right?
It’s not just about, “Oh, I have a plate full of things. How do I find five people to give them the work that otherwise I’d be the one doing it?”
Jason Lengstorf:
Yeah, I can give you a really good example of what I think good leadership is. And it’s funny to me because I feel like I did very little. When I early in my my stint as a VP at Netlify, I started talking to my team about taking over the marketing team. I was like, what’s the biggest blocker? They were telling me about the internal systems they were using to build the .com page.
And then I heard from the app team that they had similar issues. And I knew from, I was managing the docs team as well, that the docs team couldn’t get any support because they were on a completely separate system. And I asked, you know, why aren’t we all on the same system?
And and we had three completely different designs, right? Like the docs, the homepage and the app looked like three separate companies because of the way that they’d been designed and managed.
And I and everybody, everybody hated this. This was like a years old complaint at Netlify, where it came up in every sprint planning, it came up in every retro, like we need to fix this problem, we need to fix this problem. So when I got this job, I was talking to the other leaders and I was talking to people who were like the leads on their teams and I said, okay, what’s going on? Like why, why doesn’t this happen? And they’re like, that’s just too complicated. We need the marketing team and the engineering team and the product team and the design team and all these other people, the docs team to all come together and like coordinate on this effort. And we just don’t have the bandwidth for that.
And I said, okay, can I have like three people off each team for five days and I’ll fix it? And they were like, what do you mean you’ll fix it? I’m like, give me give me three people from each team for five days and I’ll fix it. And I went to each of the leaders and I said, look, this is on me, like I’m gonna do this, but I need your full buy-in, like leave these people alone, let them do the job and give me the people that I need, not the people that you think you can spare. And we got a week, we called it Web Cohesion Week and we were able to bring together the design systems of the .com, the docs and the app. Not because I did anything, but because I basically went out and I blocked with the other leaders and said, let me let these people do the job that they’ve been saying slows them down.
And it had exactly the effect that we wanted. Everybody left super, like the morale jump was huge. The quality jump was huge because the designers didn’t feel like they were working on a system they didn’t like anymore.
They were doing something they wanted. The autonomy jump was huge because people who had been asking for something got trusted to do it. And they were willing to keep doing that, right? So the momentum we built off of this was enormous.
And the only thing I had to do was corner all the other leaders and say, give me a week, but five days, you know, and and I pulled 15 people together into our previous VP of marketing, Lauren, Lauren Sells’ house. And she was willing to give us her living room. And we went and worked what everybody else thought was impossible, just by giving the right people the right space, and not a lot of time, just a clear directive and a clear buy in across the entire company. And I think that’s what really good leadership is, isn’t like, I’m going to build the right team. I’m going to come up with the right project.
It’s listening to what the team’s been begging for and clearing out space for it and making it happen.
Den Delimarsky:
How do you build that? I want to call it, for lack of a better word, political acumen, because on a surface, it sounds fairly easy, right? Like, well, you’re VP now, you can go to other VPs and ask for people and say like, Hey, here’s what we’re trying to do. You hate this, right? Right. All right. Give me three people. But I’m sure it’s not as easy. It’s not as obvious. How do you build that ability to convince other people say this is the right thing we should be doing. This is something that I need your support and convince those people to provide you with the resources. It’s not just about kind of clear out the way for me but actually give up some of the work that you’re doing so I can do it.
Jason Lengstorf:
The probably the single most important thing for me was was realizing that we all want the same thing. Every company exists for a reason. Literally everything we do is serving that in some way and we have differing opinions about how we should do that about what it’s worth about who should be buying but ultimately we’re all trying to do the same thing and so if we take what we want. If we take what our cross-functional organizations want and we start looking at what they’re asking for, you’ll start to see dots connect, right? And and this is why I think my willingness to sort of try hard in different spaces has really been a force multiplier for me is because I’ve learned a little bit about product. I’ve learned a little bit about marketing and about engineering and all these different things.
And how an organization functions, and so now when I go into a sales team meeting, I’m not trying to convince the sales team that we need to do some technical thing.
I’m trying to explain to them that what they’re trying to do is get more leads, and here’s a way that we can reduce the turnaround for their leads to get custom features so that they can close deals, right?
That sort of, like, because that’s all they want. They’re like, why aren’t you shipping more features? If you want us to sell, we need more features, right? So go in and speak to them on that level.
Don’t go in and say, well, we can’t give you features unless you give us time for technical debt. Because we say tech debt, we say, you know, we need we need to pause on features so that we can clean up the mess that we’ve made trying to rush features out the door.
And they go, absolutely not, we can’t take time off to go and do features.
But if you go in and instead say, okay, here’s what we’re gonna do, we’re gonna do a big feature push on like stability and polish, which you’ve said, one of the reasons people go to our competitor is that they feel like their app looks and feels better.
So we’re gonna do a feature to upgrade the look and feel of the site. Now you’re speaking their language. You’re you’re saying something that they can sell. you’re You’re talking about things in a way that they talk about things all the time.
And you didn’t change what you’re doing. You’re not like hoodwinking anybody. You’re not running a running a gamut here.
You’re literally just saying, I understand what you want. Let me say things in the way that you talk about them so that when you hear what I say, you’re going, oh, hell yeah, I want that, right?
And if you can do that across all the different departments, then suddenly you’re not having a conversation about what I want versus what you want. You’re having a conversation about what we all want and how can we get there together. And that to me was huge.
I think the other thing that was really important, people say this a lot and I don’t think they explain what it means. You have to not have an ego. And what I mean by that is not don’t care about whether or not you look good. It’s don’t make that the primary thing that you care about. Like you getting credit as the person who created the thing or led the effort or whatever it is, that’s not important in the time of planning.
Because everyone will remember who made it happen, right? And so you like, if you really want to be the person who gets things done, don’t worry about the specifics of the credit in the planning because that will kill momentum on any project.
If you’re saying like, okay, well, let me stop you there because what you just said was you’re gonna bring your team and I wanna make sure that you say that I said that you brought your team and and then they’re like, okay, I don’t wanna work with you anymore. you’re way too You’re being weird about this, right?
And so the the embracing of like second and third order effects in leadership is so important and and recognizing that if you do something well, there is no way people can ignore you. But if you won’t let things happen unless you get credit, people will go out of their way to ignore you.
Like we’ve all worked with that person who’s unwilling to move forward until they’re the center of attention.
Den Delimarsky:
Oh, a hundred percent.
Jason Lengstorf:
You will do anything you can to work around that person. They’re terrible to work with. But the person who’s just there to get stuff done, not only do you try really hard to make sure they’re involved in everything, but you tell everybody how great they are because they’re so wonderful to work with.
So the the removal of ego in planning is actually the best way to feed your ego as a leader. So it’s not an unselfish act of martyrdom. It is quite literally the most effective way to grow and to build political capital is to not worry about the credit and just get shit done.
Den Delimarsky:
And you know what? That’s one of those points that’s again, counter-intuitive. And if you look at a lot of corporate training, a lot of the typical advice, there’s one word that gets thrown around everywhere.
And that word is visibility, visibility here, visibility there.
And what a lot of people do is they take that to the extreme where, oh, your visibility, I’ll be sending you weekly status emails with my name attached to them that this is, oh, your visibility.
I’m going to be the one talking to VPs. Don’t you dare talk to other VPs. It’s me who’s presenting this, right?
Jason Lengstorf:
Yes.
Den Delimarsky:
It’s that. And that is the absolutely wrong way to go.
Jason Lengstorf:
Right. Yeah, I think, cause I mean, the way that I think about it too is if you if you look at the best teams, It’s not like one person and they’re entourage. It’s like, you look at a team and you go, man, this team just get stuff done.
And then later, when you’re trying to figure out how you get the other teams to get stuff done like that, who are you going to go talk to? You’re going to go talk to the tech lead.
You’re going to go talk to the manager. You’re going to talk to the executive and you’re going to ask them, what are you doing? Right? And a good executive is going to say, well, we’ve got a great team and I just support them in getting their work done.
And now you’ve got like, you’re not, you know, the team feels so loved and supported. They’ll follow you anywhere after that.
And, and the company, a well-run company is going to recognize that. And they’re going to want that to expand. And they’re going to want you to have more influence because you create a team that if you create an environment rather, that allows teams to feel healthy and productive and like they’re the you know, badass technologists that you hired in the first place, right?
Den Delimarsky:
Yeah, exactly. And and that’s the part two where it’s not necessarily about your name being thrown around, but about building that reputation that people know that you can get shit done.
Jason Lengstorf:
Yes.
Den Delimarsky:
People know that the stuff you do is high quality and actually delivers on what the company cares about because that’s…
Jason Lengstorf:
I think… Yeah, there’s a phrase that that I hear all the time, like a a lot of my friends are on black tech Twitter, right?
And you’ll hear them talk about like, “don’t talk about it, be about it”, right? And that phrase just every time I hear it, I’m like, yeah, because it’s such a like, such a great encapsulation of everything that we’ve just said in a thousand words in what, five? It’s such a perfectly summed up way of just saying like, look, if you want to be visible, if you want to have people talk about you, do the work, like constantly deliver things.
Don’t take credit for other things that are delivered. Don’t make sure that people see your name a lot because I’ll tell you what, the leaders that I was least impressed with were the ones who seemed to have a lot to say and nothing to show.
And and people get very good at making sure they their face shows up on every slide. But like being the worst performer in a group project is not something you want to brag about.
You want to be the person who is consistently like people when people are not in the room with you, they should be saying, I mean, honestly, I couldn’t believe how much we were able to get done because they were there.
That’s those are the conversations that you want to have. You want people to be championing you not on a slide, but in back rooms, because that’s where those promotions happen. That’s where. the reputation where somebody will leave the company and then they’ll desperately try to poach you over because they know you’re the secret sauce.
That’s the network you want to build, especially when you get up to that higher level, is you’re the reason that this department was able to get so much done. You created an environment where these people could be great.
Come over and do that again for us, right?
Den Delimarsky:
Nobody is looking at how many status emails you sent.
Jason Lengstorf:
Never.
Den Delimarsky:
Those backroom conversations never go about. Well, who did we see in our inbox the most last month? Oh, is this person? Well, should, should we put them up for promotion? It’s never that it’s literally never that.
Jason Lengstorf:
And I guess it is worth saying like there’s a way to go too far in the other direction on this where you like constantly ship and and you’re a ghost and no one’s ever no one knows that you’re there.
You wanna make sure that you’re visible in the sense of like when you’re doing work, show people the work that you did.
But don’t take that to the extreme of I’m going to show people work that I didn’t do just so that I can have my name on it, right?
Den Delimarsky:
Yeah. Right. Now, you ran Learn with Jason for some time now and you’ve built those skills to be a good communicator, a good presenter. Do you think that contributed to your career growth?
Jason Lengstorf:
Oh, 1000%. I have never… being able to communicate being able to tell a story being able to connect with the person that is listening to you and understand what they’re into so that you can shape the message a little bit. That’s like, at the core of everything. I think that is the biggest superpower you can have.
Regardless of your industry or your career or anything. I mean, just as like just in a relationship. If I can look at the person that I’m with, romantically, or platonically, or professionally, and and I can understand what their motivations are and I can talk to them about my motivations in a way that takes theirs into account, we’re going to have a better relationship.
I’m gonna have a better understanding of what they want.
I’m gonna be able to shape my desires to match up with theirs in a way that makes both of us happier in the long run. right And in business it’s the same thing like we are always trying to get these vague. Sort of you know like roughly project shaped ideas out of our heads and into a big organization full of a bunch of people who all have a project shaped ideas.
If we’re not good at communicating, then we either don’t ever get to work on the stuff that we don’t want that we want to work on because we can’t communicate it well enough to get anybody on board, or we become the kind of person who is impossible to work with because we won’t do anything that isn’t exactly our idea because we can’t communicate about how you know somebody else’s idea could fit into what we want or something.
That ability to think abstractly to communicate on multiple channels to think about you know outcomes and not necessarily specifics of implementation those sites those sorts of skills are are so critical. At every level like you know if I’ve hired fresh out of bootcamp engineers who were really, really good communicators. And it’s several years later now, and they are significantly further in their careers than the folks that I hired who weren’t great communicators at a same at a similar level.
Den Delimarsky:
Were there any unexpected side effects or learnings from Learn with Jason? If you look back at it.
Jason Lengstorf:
I mean, I think one of the biggest ones is that It really cemented, like we say this a lot as engineers, that the tools don’t matter. And I think that Learn with Jason has cemented that more than anything because every week somebody comes on and they show me something really cool that solves a problem.
And then a few months later, somebody with a completely different tool will come on and will build the same use case. And it’s always like the tool isn’t the point, right? Like and in in a company, our job is to understand an outcome and build that outcome.
How we get there, is an exercise in efficiency and taking advantage of what we have on hand. We’re not going to drop one stack and adopt another stack and suddenly be a different team.
We can make ourselves more or less efficient, but it’s a matter of a few percentage points, not a matter of night and day different.
I think that I would put that argument on anything like I think some people might say like, Oh, yeah, but if you’re on like an old, you know, an old app that’s built in Fortran or see like you could make huge gains if you were to switch over to Rust or Go.
And my answer to that would be I don’t know how many C engineers do you have to retrain to become go engineers, you have to fire everybody in your company so that you can hire people who can work in the new stack.
Like what’s the contextual domain knowledge loss. How many of the edge cases that are built into that Fortran code base do you actually understand and would be able to rebuild in the new stack that you’re trying to port?
The tools are not the point, right? The point is always what we get to the outcomes.
And again, that comes down to that communication and stuff that we’re talking about. And and so I love new tools. I love new technology. And I’m constantly I mean, that’s the whole point of what I do is to be able to have an excuse to constantly play with new tools and new tech and see what’s happening. But I also think it’s it’s had the opposite effect of what I thought, which is I thought it would make me more opinionated.
And it’s made me significantly less opinionated about tools. Cause if I walk in and you’re like, Oh yeah, we’re an Angular shop. I’m like, great. You all know Angular. Let’s use Angular. I don’t care. It gets, you know, it’s not going to stop us from building what we need to build.
Den Delimarsky:
Tools are not the point. Yeah, for sure.
Jason Lengstorf:
Yes.
Den Delimarsky:
It resonates now more than ever, especially because technology moves so fast and there’s feels like there’s something new every week and you just can’t switch to something new every week.
Cause then you’re not shipping any product. You’re just going to be doing fiddling with tools.
Jason Lengstorf:
Exactly. I often have made the joke that you know if you if you’ve gotten an app built to the point where you’re on that last mile of all the weirdest, fiddliest, hardest things to solve, the best way to avoid doing that work is to rebuild the app in another language so that you can punt that last mile another two years down the road so that you can then try to not solve it in Rust.
Den Delimarsky:
Right. And you know, by that time, there’s going to be a new language. Who knows?
Jason Lengstorf:
Right. You’ll just rewrite it again, right? Like it’s a, it’s a great way to kick the can. If you’re onto the really, really hard problems and you’re like, ah, I don’t know how to solve these problems. I know let’s rebuild the entire app in a different language so that I don’t have to worry about that.
Den Delimarsky:
Or as we call it job security.
Jason Lengstorf:
(Laughs) There is that, but I think too, you know, I was talking about tech, but I would say the same is true about management styles and all. If you want to bring in.
Linear versus Jira versus who cares? It doesn’t matter. What matters is that the team uses it. I’ve seen teams that run objectively well on Google Docs, which is it has to be scientifically the worst way to manage and discover data.
But they’re consistent, and they follow a pattern, and they all do it the same way, and they run great. And then I’ve seen teams in these incredibly complicated and incredibly full-featured tools, like Linear and Jira and you know Notion and et cetera, et cetera, and they have no systems, and they all do things differently, and it’s impossible to find anything or get anything done.
Again, the tools don’t matter. What matters is the team agrees to do a thing and follow follow a system and work together, right?
Den Delimarsky:
In a very cliche way. It’s when people look up for, you know, tech leaders and visionaries is like, Oh, Steve Jobs this Steve Jobs that, I’m going to wear the turtleneck. The turtleneck is not the point. Like you’re totally…
Jason Lengstorf:
Yeah, you you missed the forest for the trees there for sure.
Den Delimarsky:
Yeah, exactly. It’s like, but if you look like him, surely people will buy your product. That’s not… Now, how do you feel as a founder? Now that you have transitioned to this role where you’re your own boss, how is it?
Jason Lengstorf:
It’s the kind of chaos that I like. I think that, again, I was talking about this earlier with the executive thing, like you you move in as an executive to a kind of chaos that is largely out of your control.
And it becomes sort of an exercise in you know… You’re on a leaky boat because any company is always a leaky boat. There’s something that’s on fire, something’s going wrong, and as soon as you plug one hole, another one opens up. And you know your job is to is to not stop that. It’s just to embrace that it’s gonna be constantly happening and know how to pivot and change. And I think when you’re a founder, it’s it’s the same, but I think of it like being on a surfboard. You’re not gonna control the ocean. You’re not going to change the direction of of how things work.
Your job instead is to is to sort of find the right balance where you can go where you want to go using the momentum of everything around you. And if you fall off the surfboard, you just kind of go back over and get back on it.
You didn’t accidentally you know kill half your crew because you didn’t plug the right hole in the boat, right?
And so to me, there’s a lot more at risk, personally, like if I get this wrong, I you know I would have to go rely on my my network that I’m very lucky to have like my my safety net with my family and and stuff like that to bail me out if I like really screw this up and don’t have any income.
There’s professional risk like if I get this wrong, everybody knows it was my fault. I don’t have a scapegoat. It’s like I had bad ideas and they didn’t work, right?
That’s the outcome if I get this wrong. But at the same time, that sort that sort of chaos feels more comfortable to me than if I’m in a position where somebody who I don’t control, who is not reporting to me, can go on social media and have a completely unhinged rant, and now it’s my fault.
I suddenly have to make a new career decision because somebody who is not my responsibility decided to go say some heinous stuff on the internet. Or, you know, whatever, like all the things that can go wrong in a company that you just you literally have no control over that, right?
So I’m embracing the idea of everything is my fault, and everything is my problem. But I get to choose which problems I’m going to take on if I don’t want to deal with a problem, I can just stop doing that part of my business.
Den Delimarsky:
Yeah. It sounds like you gain more freedom and purpose.
Jason Lengstorf:
You gain more freedom, you you gain more autonomy at the expense of the ability to delegate, the ability to not pay attention to something. Like if there’s a problem, I can’t say somebody’s probably got that, right?
Like it’s only me here. I got it. If I don’t got it, then it’s either something I’m willing to take that damage or it’s going to become a really big problem later.
Den Delimarsky:
I think it’s great that you’re calling out the fact that it’s good to have a network that you built over the years that if things do go wrong, like I said, like what’s the worst case scenario?
Well, you have to apply for jobs. Is that really that bad?
Jason Lengstorf:
Well, yeah, right. I mean, like everybody always talks about oh, but if this goes wrong, I’ll be, you know, I’ll be destitute. I’ll be out on the streets. I’ll be panhandling. It’s like, no, you won’t.
You’re a professional, right? You were able to start your company because you had the ability to do this job for other people and you did it so well that other people were willing to pay you to do whatever it is you found at a company to do.
So the likelihood that you will hit the absolute disaster scenario is virtually zero, right? And if you’re being realistic, you know, like this is what my books look like. This is what my leads look like. I you know, I think I should be able to hit these, you know, this level in the budget and I can cover my expenses and all that kind of stuff. So if you’re if you’re doing a good job with your books, you’re going to see it coming a few months minimum in advance if something’s about to go off the rails.
And in that time, you can reach out to your network, you can reach out to, you know, anybody, any of your former clients, et cetera, and say like, Hey, it looks like this business probably isn’t going to do what I wanted it to do. I’m starting to, you know, put feelers out.
You know anybody, chances are you’re going to find something. You’re going to get some interviews, things like that.
I mean, the market’s tough right now. But if you’ve got that network, if you’ve made those friends, if you treat people well, like, I mean, I know some, don’t get me wrong, I know some founders who have, they’ve burned every bridge they have.
And if if this company doesn’t work out for them, there’ there’s, who knows what they’re going to do.
But the folks I know who who are respectful and treat people well and and recognize that like the value of your career is the network that you’ve built, not the number of dollars that you’re your startup is valued at, those folks are pretty resilient to downturns and to changes.
And I know a lot of people who have swung on the pendulum, they they worked for a company, they founded a company. They either sold that company off or shuttered it, and then they took a job at a different company. And now they’re going to do that for a while, and I bet they’ll found something in the future.
And I think that that’s just an an embracing of like, this industry is small, these careers are long, and you don’t have to have it all figured out, you can have a good idea now, that won’t necessarily be a good idea in five years. And that’s okay, you can you can take an adventure, and then take what you’ve learned from that adventure.
And just apply it somewhere else. I think that’s the really big lesson for me has been recognizing that there’s no such thing as wasted time if you’re learning and moving.
If you’re making something happen and you’re gaining new knowledge and you’re gaining new experience, that will be applicable somewhere. You’re not wasting time. You’re you’re building a set of experience, even if a all you’re building is a great list of things to never do again.
It’s still experience. It’s gonna make you better in the next thing that you do.
Den Delimarsky:
Love it. And, you know, as we talked to this podcast, is that your reputation is extremely important because if people know you as somebody that is toxic, somebody that steals credit or whatever else, you’re not going to have an easy time finding that next gig.
You’re not going to have that easy time falling back.
But because people know Jason is the guy that helps us. Jason is the guy that taught us all these things like, yeah, of course you want to work with Jason. Why wouldn’t you?
So, to close this out, I want to ask one question that I ask of all the guests. Unconventional advice for somebody that’s listening to the show and things that they want to follow in your footsteps. They want to reach the same heights that you did. What would your advice be to them? Some Jason-style life wisdom.
Jason Lengstorf:
Be unapologetically weird. and And what I mean by that is… I have spent my whole career doing stuff that when I first start talking about it, people look at me and kind of go, are you sure?
And it’s, you know, I see something that I think will work. I see something that I think is interesting and I start kind of moving toward it. Right. And when I first… For example, right now with what I’m doing with, with Learn with Jason in the media, I remember my first conversations where I started saying like, I think I want to make a game show.
And the first conversation I had, they they borderline laughed me out of the room because they were like, why? There’s no reason to ever do something like that. But I knew I was right. And so you know this was in 2019, 2020, something like that. I first pitched this idea. And every year, I got a little bit better at explaining what I wanted. I got a little more insight into what I could do. I did a few more projects that taught me more about how this thing worked.
And now this this weird thing that I was doing that nobody understood, I have a waitlist for it and I have constant inbound interest in because I found something that’s working in a way that the old playbooks weren’t right. Like I saw, I saw a way to go that would work in a post pandemic world where the old playbooks of of meetups and conference booths and you know the sponsored talks those those sorts of things are all starting to they’ll probably come back someday but they’re not working right now and so companies are just dumping thousands and thousands of dollars into these playbooks that don’t work.
But and anybody who’s working with me, they’re getting the results that they used to get from their meetups and their conference booths and their their stuff like that because we found a different path. right So suddenly, the weird thing doesn’t seem weird anymore.
And I’ve got a head start because I’ve been looking at it for five years now. It’s, you know, it won’t last and I’m sure that given another, you know, two, three years, I’ll be looking at the next weird thing and people be looking at me sideways wondering what the heck I’m on.
But right now, you know, it’s… And this isn’t the first time that I’ve done this in my career, I’ve kind of consistently trusted my gut and done the thing that felt like I can feel that this is where I’m supposed to go. Even though it doesn’t make sense to everybody else. But like I see the path and I see the reasoning so gonna stick with it. I’m gonna you know, not at the expense of… I’ve never been uncomfortable. I’ve always kept my job. It’s always been on the side.
But I apply constant, gentle pressure toward whatever outcome I think I should be working toward. And every single time, when when I feel it strongly, I’ve been right.
And I’ve been able to do something really interesting in my career because of trusting that that urge to do something weird.
Den Delimarsky:
That’s some excellent advice. Jason, thank you so much for being here. Where can folks find you online?
Jason Lengstorf:
The easiest place to find me is to go to lwj.dev. That’s where I kind of have the core of everything going. That’ll lead you to the YouTube and all those places where I post the stuff that’s not Learn with Jason. Or if you want to see just a list of where I am on the internet, jason.energy/links is a LinkTree for me.
Den Delimarsky:
Excellent. And we’ll make sure to have those in the show notes. Thank you again for being here.
Jason Lengstorf:
Thanks so much for having me.
