The Happy Engineer Podcast

046: How to Be Happy AND Successful with Diego Rebosio

What is success? Is life about being happy now, or big goals like Elon Musk? Do you have to choose?

How can you have BOTH?

In this episode, you will be drawn into the wisdom of Diego Rebosio, the CEO and Founder of Oshyn, Inc. My mind is blown every time I talk with this guy, and yours will be too.

Founded in 2001 to help customers achieve digital transformation, Diego’s team at Oshyn is helping brands achieve breakthrough sales and interactions via smarter technology. He is an engineer at heart, and a powerful leader.

We cover nuggets of wisdom ranging from why engineering leaders struggle so often with anxiety, how the engineering mind interferes with happiness, to the art of saying “No” at work.

Get into the head of an engineering leader who is very happy, AND very successful, and maintaining that balance over the long term.

>> So press play and let’s chat… because this is your engineering class on happiness!


The Happy Engineer Podcast




Listen on Apple Podcasts // Spotify // Android // iHeartRadio


Let’s unpack the philosophy of this really powerful conversation with Diego and put it into action. I have been so blessed every time I get to talk with Diego Rebosio, he has such a unique perspective versus many of the engineering leaders who I have met and talked to over the years. He brings a calm, peaceful confidence, and certainly came through a lot of ups and downs. 

Here are four really simple, practical applications of how you can put this conversation into action. Make sure and listen to the entire interview before reading.

Number one, celebrate the success you already have. 

You are in one of the highest paying fields in the world as an engineering leader. You make more than enough money to be very happy financially.

A huge percentage of the world would love to trade places with you. Not that it’s a comparison at all, but just remember how far you’ve come and do something to celebrate! 

Now, let me be really specific. When I say do something to celebrate, I literally mean DO SOMETHING!

  • Make plans to celebrate the success in how far you’ve come
  • Go to your favorite restaurant 
  • Order that bottle of wine that you’ve never splurged on before
  • Do something intentional for the sole purpose of celebrating the success
  • Include your family, invite some friends, make it a meaningful celebration!! 

When we celebrate, it’s got to be bigger than just a little nod. Classic engineering move. We set a huge goal. We hit it, and then we go right onto the next thing. 

So take some time and go celebrate that success. I’d love to hear what you do. Shoot me a note!  Email me directly at [email protected] and share. I’d love to hear about your celebration. 

Number two, say NO to something that you KNOW needs a NO. 

What is that thing you’ve been saying yes to that has been a huge problem? It’s causing all sorts of frustration. It’s overwhelming and overloading you, it’s not aligned with the strategy and the vision of what needs to happen. It’s not a priority. It’s not moving. 

Go say no to that thing. 

If a senior leader is asking for something that you already are certain cannot happen for whatever reason, say no. Provide the data and reason, let them know that you are a team player, you do want to succeed, but that this is a no. 

Diego’s example was so powerful. When you say yes to things that are completely unrealistic, things that you don’t have any belief can happen, that is a huge, huge disservice to yourself and the organization. You’re not doing anyone any favors by staying up all night, working all weekend and, busting your chops for something that you are already certain isn’t going to work.

Go have the courage to draw that boundary. Now we can have a real conversation. If somebody disagrees with your “no” then talk about it! 

Number three, go build something. 

There’s a part of you that is wired to build stuff, to be creative. You may have that opportunity in your job right now. If so, double down, lean in and be like a child again! Be that young, excited, passionate engineering version of yourself again. Or, you may need to choose something outside of your core job to tap back into that part of you that loves to build.

Go explore. 

Get creative. 

Be inventive. 

Have some fun!

Number four, go take a walk.

Get away from work. Get out of your office, get out of your home office, and take a walk. Do me a favor too, don’t listen to another podcast episode, even if it’s The Happy Engineer Podcast! 

I want you to take a walk without any inputs. Just observe things. Take a walk and enjoy it. Take a walk and notice as many things as you can, down to the tiniest details. Use 100% of your focus and your mind to simply observe and notice your surroundings. Notice what you see. Be like a scientist. 

Allow yourself to break from constant inputs, constant learning, constant stress and anxiety about the things that we need to get done. Take a walk with the freedom and permission to do nothing other than walk.

Enjoy it. Let me know how that goes for you. 

For some people. This is the breath of fresh air and the sigh of relief that they’ve needed. For others, it can be a little stressful the first time! Why? Because your brain is hungry and trying to go down those same pathways that it always goes down. It starts saying things like this:

  • “Why am I not searching for the next thing to do?” 
  • “Why am I not checking my email?” 
  • “Why am I not listening to something productive?” 
  • “Why am I not scrolling on Facebook or Instagram?”

I’m challenging you to shut off all those things. Go for a walk and just observe. 

I appreciate you. I love you. I hope that you continue to crush comfort and create courage in the journey of your career and life. We’re here to help at OACO and at The Happy Engineer Podcast. 

Remember to SHARE this episode with your peers, and ask any questions that you want us to dig into in our future Q&A episodes via email or our contact form.

Let’s do this.


Previous Episode 045: Master Your Mental Edge with Nerd and Navy SEAL Josiah Kauffman




Diego Rebosio is the CEO and Founder of Oshyn, Inc.

Founded in 2001 to help customers achieve digital transformation, Diego’s team at Oshyn is helping brands achieve breakthrough sales and interactions via smarter technology. Their superpower is Sitecore, and they’ve been doing it for years.

With a strong focus on the aspects of tech that make great websites reliable, they help customers achieve sales and visibility, while making big improvements to customer interactions. Customers in today’s marketplace expect connected experiences where every interaction informs the next interaction.

By providing services, technology, and platforms they enable creative talent to focus on what they do best: create amazing work.





Please note the full transcript is 90-95% accuracy. Reference the podcast audio to confirm exact quotations.

[00:00:00] Zach White: Diego. It’s awesome to see you, man. Thanks for making time to be on The Happy Engineer Podcast. Welcome to the show! 

Diego Rebosio: Thank you. 

Zach White: I want to set the stage and transport back in time, about a month ago, when you and I were standing in your backyard.  Beautiful, serene waterfall there, trickling, having a cup of coffee at the abundance retreat weekend

Expand to Read Full Transcript

[00:00:24] that your amazing wife, Brooke and Leslie Thorton held. Leslie, who was a guest on our podcast, not too long ago. And I was sharing with you some of the things going on in my journey, the growth that I’ve been experiencing, the personal development, all of the challenges that entrepreneurship and being a CEO has brought up in my life and just got to unloading to, to use some of these things and then was so struck by.

[00:00:51] how you were able to share wisdom nugget after nugget, about how the years of growing as an engineer and now CEO of a much larger organization than mine has reshaped the way that you approach life and work. And, and this day-to-day experience that we’re all seeking to optimize and maximize as the engineering minds that we have.

[00:01:10] So I would love it if, if you would just grab back onto that thread and say like, what are those things. That has shifted and changed for you over the years that have had the biggest impact in the way you approach leading as a CEO today versus years ago, when you might’ve been in the shoes of the young engineer, Diego, just trying to figure it all out.

[00:01:34] Diego Rebosio: Well, I don’t know. I guess I can try and, uh, come up with some pearls of wisdom. Um, an an interesting thing about me is I have, I mean, I don’t think I’m unique in this, but I think I have a relatively terrible memory. Like I don’t remember exactly what we were talking about. Right. I remember that we were talking, but you know, uh, Eh, maybe it’s part of the being in the moment thing.

[00:01:47] Right. And I’ve tried not to hold on too much or into, into those kinds of things. But, so I think the way I look at it is okay, you’re saying, okay, here’s a form where you can give. Other engineers, some advise people that essentially have been engineered years and as, as they go through their career, you know, what kind of challenges that they come up with.

[00:01:52] Right. Um, and I guess I can just maybe grab a handful of these and discuss them. 

[00:01:52] Zach White: You know, I would love that. And, and before we even start pulling out your favorite nuggets, what you just said, and it came up before we were recording. I think it’s such a powerful approach to why hanging out with you is so rewarding that you’re just here with me in the moment, you know, that day in your backyard, not really thinking about anything else, just totally present, and it’s added massive value in that discussion, but then just kind of moving on next.

[00:02:12] What’s the next, the next thing. So can you. How do you stay so present? What, what, what trained you or helped you to become that kind of a present individual? You 

[00:02:23] Diego Rebosio: just learned that you enjoy things more. It just feels better and you’re more likely to do it if it feels good. Right? I remember years ago, um, when I was working with one of my first clients in this company, you know, it was basically a one man band at the time.

[00:02:40] So I was there doing some coding for this client. And I remember just getting just this inner joy that just came to me from just doing what I was doing. I’m doing a good job, right. Something about that just felt good. And I was like, huh, that’s interesting. I don’t know where this comes from. It’s a new feeling, but it just shows up on its own.

[00:03:00] Right. And I think it’s that feeling that just little by little stays in there and grow. I don’t know when it comes to comes. 

[00:03:07] Zach White: I love that. What, where are we in time? So you’re one man band starting that business. What year was this? Uh, this was 

[00:03:13] Diego Rebosio: probably 2000 to 2000, maybe 2000. Yeah. 

[00:03:18] Zach White: So here you are just doing the work and you’ve had this moment.

[00:03:24] Maybe someone would call it a flow state or a deep moment of presence and passion show up. What was that inquiry? Like, we were like, Hey, where’d this come from? Did you actually really chase that? Or, or was it just kind of, it came and went 

[00:03:38] Diego Rebosio: and like you say, now flow state or whatever. And those, those were not words I would have used.

[00:03:43] I would have be like, oh, that’s funny. It just feel good. Like I wonder, is it, is it something I ate? Is it the coffee that I just had? Is it like, what is it? Right, because it was almost like a little switch just turned off. I just felt good. And I think it just came from doing what I’m doing and being present while doing it and just doing a good job for blind.

[00:04:07] Zach White: Did you then learn more how to create that feeling more regularly or more frequently, or like, like, it sounds awesome. Maybe somebody’s like, Hey, I want that, you know, how do I get that? What, what would you say? How do you get to that? 

[00:04:21] Diego Rebosio: Well, now that I have more of a, an understanding of this, I know that it’s almost like, uh, that’s the kind of thing that you can’t get by trying to get it right?

[00:04:30] Because your logical mind trying to obtain something keeps you away from actually enjoying the things that are in front of you. Right. So I understand it that way now. Um, but back then, no, I wasn’t chasing anything. It’s just like, oh, okay. This is interesting. And it would just be there from time to time.

[00:04:45] Right. And it’s, uh, maybe the closest thing is just, you know, if you, if you’re doing something you enjoy and you’re doing a good job at it, there’s a satisfaction in that that builds over time. 

[00:04:57] Zach White: So, this is a perfect segue back to your backyard then. And I do remember the conversation because it was really impactful for me.

[00:05:04] And, uh, one of the things I was telling you is I’ve begun to let go of my intensely high pressure relationship with time and how I always want the bigger goal to come sooner. Yeah. I’m a very ambitious individual. I’d love to see my business grow. I’d love to see my clients succeed. Historically, especially back in my engineering career days, put massive pressure on myself related to time.

[00:05:30] And I described to, Hey that I’m starting to learn how to release that pressure more and just show up in the moment and do the work. And the, the harder I try to grab for the result that I want in the future. Now, the further away it seems to go and the more I release it and just forget about it. So that’s the direction, but here’s, what’s in front of me.

[00:05:52] The experience of it feels so much more abundant, feels so much more joyful and this, this kind of emotional state that we’re all seeking. And so that idea of when you hold it tight or try to figure it out logically, consciously you block yourself from actually getting there. That’s a really counterintuitive thing for engineers because we spend our time.

[00:06:14] All day, like using our minds to figure out problems. How do you approach something that you want without thinking about it and try to like help us disconnect. What’s that journey, 

[00:06:25] Diego Rebosio: maybe this, this is helpful, right? I’ve never heard of anyone or any college offering engineering classes for happiness, right?

[00:06:32] There’s no such thing. Like, okay. Here we go here, you know, you got to have some math background. Maybe you need to know multi-variate calculus and you know, linear algebra. And then we’re going to be able to, through this map, show you how to get happy. Right. It doesn’t make any sense. Right. So why is it that so many people try to obtain happiness that way?

[00:06:55] Right. It doesn’t make sense if you look at it that way, it’s just, it’s just silly. you know, going back to, you know, what you’re saying, success is, is, um, I think when you get, when you really think about it, success is a feeling it’s not really so much an accomplishment of a or B it’s. It’s not getting what you want is wanting what you’ve got.

[00:07:11] And maybe it’s even more than that. It’s just, you know, um, again, it’s just a feeling, right. and that’s why you can’t really chase it in an engineering kind of way. Right. I mean, you may be able to accomplish X, Y, or Z, you know, like, I don’t know. You can say to your, well, your way into a few million bucks if you want.

[00:07:26] Right. But is that going to make you happy? Right. Well, maybe that’s. What our logical minds want to believe. They want to believe that, um,

[00:07:38] by doing certain things, you’re going to get certain results. And it’s the results that make you happy. Right. But what you want as a feeling, not the actual things. Like if I told you, okay, you want a billion dollars. Okay, great. What if I told you that you get a billion dollars, but all of your relatives will be there.

[00:07:54] Are you going to be happy about that? Right? Well, no. Well, why not? Well, because I want to feel good and have the billion dollars. I don’t want to feel like crap. I have a billion dollars. Right. So how about you feel good without the billion dollars? Right? Well, your logical mind will say, well, no, that’s for losers, right?

[00:08:14] But at the end, you do get boats. If, if you just kind of balanced, 

[00:08:18] Zach White: So I want to come back to that statement that in the end you do get both, but before we, we do, I think it’s appropriate may to set the stage a little bit for your journey in terms of engineering and your, company and building that. And can you just describe in a few words from 2002, that one man band to today, The the growth and the changes and what you do and now a CEO, just what your company looks like today.

[00:08:42] Diego Rebosio: Yeah, sure. I mean, maybe I can share a little bit before that too. I mean, so I came to the U S for college, right? then I got a job in a little consulting company and that was out of Boston and I was like the seventh employee. And, uh, they needed someone to work here in LA within an account. So, uh, I came over here, um, and, basically fast forward a few years that company, you know, grew organically like crazy and it went public and it made a ton of money. And I had a few stock options that I made a bunch of money. Right. Uh, then, uh, At the height of that, you know, it was the internet bubble. And I had all my money. I had cashed in all my stock options and everything, and I became a day trader at a big, made a bunch of money with that.

[00:09:19] Right. And I had enough money, so I didn’t have to work anymore. Right. So there I am going to work and I’m wondering, I’m asking myself, why am I here? Do I actually want to do this, that my bosses would want me to go work on accounts that weren’t in trouble. And I was like, I’m sorry, I’m not going to fix that.

[00:09:36] That’s a loss of waiting to happen. And indeed that client did Sue the company, but I was like, I’m not working on that. Right. And my boss would be upset. but so eventually that, you know, that company started having layoffs that I wasn’t the layoffs because obviously my boss didn’t, wasn’t happy with me.

[00:09:52] Right. I didn’t need a job. So then for a while I full search figuring out, okay, so what do I want to do? Right. And in the meantime, the money that I had, which I thought was safe, went down the tubes, you know, with the internet bubble busting, right. Oh, And, you know, I was pretty heavy, leveraged, like traded on margin.

[00:10:09] So I basically lost everything,

[00:10:12] but, you know, I had enough to, to start again and so, and maybe not be able to not work for a couple of years. And so I started ocean the company that I’m in now. 

[00:10:22] Zach White: this moment that you had, where you, you did literally have enough money, that you didn’t have to work.

[00:10:28] A lot of engineering leaders who I need, describe that moment as kind of this dream place to reach, you know, but call it financial freedom, call it whatever you want, or they, they imagined, you know, if I did actually have. That kind of money. I would do all these different kinds of things. Right. I wouldn’t work for this company or I wouldn’t put up with this crap at work, I have not personally been there, but do you believe Diego that it’s possible to make the decisions or to get the benefit of that type of thinking without actually having Moment all it’s cracked up to be, or I don’t know. I’m just kind of curious, like, would you say, yeah, that’s a really great place.

[00:11:00] Everybody should try to get there or like in the end, maybe it’s not what we think it is. I don’t know, just from the outside looking in, it’s like, Ooh, that’s a really interesting moment where you can, you literally can do whatever you want. Money’s not an object. What’s that 

[00:11:11] Diego Rebosio: like? Well, I mean, I think you’re starting with an assumption that is off.

[00:11:15]  I think as engineers, right? I have news for you in case you already know it, you already make good money. You know, you, you can’t not make good money if you’re an engineer, right. It really is. Okay. You’re maybe comparing yourself to your peers and maybe there’s ones that are doing better. And some that, you know, you know, start, you know, big companies and make a ton of money.

[00:11:36] Right. But at the end of the day, everybody in this business that, you know, That has some, kind of aptitude for it is able to, to do. Okay. Right. I mean, all those jobs pay well, um, you can get nine to five jobs that pay well and you just kind of safe, safe, safe, and eventually you do retire. So that’s, something that, you know, um, is in there.

[00:11:54] The other thing that I learned is, uh, okay, so I’ve made a bunch of money. Um, that was nice. What I noticed is my lifestyle. Dramatically change, you know, is just the question of you. Um, you realize you don’t have to work to maintain the lifestyle. Right. So I didn’t go out there and, you know, buy a Ferrari, right.

[00:12:13] I mean, I got myself a nice car, but it wasn’t, you know, something of that caliber. And I think most, most engineers probably would do that. Right. You don’t need to have a middle east crisis and. I get three Ferrari’s and, and, and get lots of lame friends to be somebody. 

[00:12:29] Zach White: Right. Yeah. 

[00:12:31] Diego Rebosio: so, um, so that was that, um, 

[00:12:31] Zach White: could you say ocean begins that, 

[00:12:31] Diego Rebosio: but hold on.

[00:12:31] There’s another key thing in there is what I, what I noticed was the biggest shift is that whatever problems I had were magnified. Right. So, okay. I wasn’t getting along with the person I was with at the time, those problems became bigger. Right. Because all of a sudden you have a bigger Eagle. You think you’re on top of the world.

[00:12:48] You’ve made all this money. Cause you’re so smart. Right. And all of a sudden, you know, you, you want to control things a little bit more anyways, that was my issue. But I think whoever, whatever problems you had before. Just become magnified when you have more money. Right. So if, you’re not ready for it, then it’s going to be tough.

[00:13:08] Right. Um, so that was, that was really the main shift, but, um,

[00:13:08] yeah, I don’t know. 

[00:13:08] Zach White: That’s something, a lot of people I’ve spoken with who’ve achieved. High levels of wealth have described, you know, money itself is neutral. But what it does is has this amplifying effect, you know, whoever you were before you had money, it’s kind of just show up. More acute, bolder way. So if you, if you were a total jerk or an idiot before, and you’re just smelling a bigger jerk after the fact and likewise, these other problems.

[00:13:34] So I think that’s great. Me. Do the work on ourselves now to prepare for that abundance to flow in. 

[00:13:45] Diego Rebosio: And, and, and so I think if you do what you love here, right. And you’re, you’re good at it sooner or later, you’re going to make probably a lot more money than you need. If you’re an engineer right now. I mean, if you were a musician, for example, I like music too.

[00:13:45] Right. But you know, to, to be. Uh, musician that makes a lot of money, right? You have to be like, you know, in the top, you know, 0.01 percentile, right. Or 0.1% out to be, to make a decent living as a musician. Right. But when you’re an engineer, you just have to be an average engineer to make that kind of money.

[00:13:45] Right. 

[00:13:45] Zach White: I think a lot of us forget how fortunate we are in that way. That’s a great right. 

[00:13:45] Diego Rebosio: Um, so 

[00:13:45] Zach White: yeah. So fast forward, we’re in the growth stages of now your own business. So you had it all your lost, most of it. You started your company and just really quick, describe that, that journey of these last couple of decades.

[00:13:59] Diego Rebosio: Well, I mean, it’s basically also been a bunch of up and downs. Um, but most of the ups and downs, where relationship wise with me, I had a lot of personal drama deal with the company that have some really bad years as well. You know, like You know, like there, 2010, 2011, those were particularly hard.

[00:14:15] Um, just with the economy also collapsing a little bit with the, the housing prices and how it affected everything from that. Right. Um, it. But, you know, 

[00:14:15] Zach White: um, can you actually describe just in a couple moments, the work that you all do? I know for me as an engineer, everybody wants to kind of understand behind the curtain.

[00:14:23] So what is the business and who you serve? 

[00:14:25] Diego Rebosio: Yeah, so we do basically website for large companies, right? We specialize in some software that large companies. related to web content management. And so normally they find us because of those niches, right? Like the people here, oh, you the websites they think, oh, great.

[00:14:39] I need a website. Or, you know, I know a restaurant that needs a website. Can you guys do it? It’s not that kind of what the development is really more like big corporate websites, you know? Right. Several hundred thousand dollar websites, sometimes millions of dollars. And, um, you know, those customers have very specialized needs and that’s what we’re able to service.

[00:14:59] Right? So we found that niche over time. Like it wasn’t always our niche, but little by little, you find your niche, right? Like when you start a company here, is that, you know, in, in marketing, you know, uh, Uh, bullet works better than a shotgun, right? So you don’t want to go all over the place. You want to be specific, but it’s hard to find what that specific thing is for, for a long time.

[00:15:16] Right? So, but, you know, there were a lot of numerous lessons that we learned and, and now over the years, right, the company is doing great. Um, and, uh, I have no complaints. I make a good living and I have happy clients and happy employees. that’s pretty good. 

[00:15:25] Zach White: So then I’m going to come back to what we said before I got into the quick history of Diego, which was, you said, you know, in the end.

[00:15:33] We have the success, the object of success, you know, whether that’s the car or the house or the bank account balance, whatever that is the title in our career. And then there’s that emotion and experience the feeling of success. And you made a statement earlier in the end, when you’re mindful of going after what really matters this, this state, this feeling you ended up getting both.

[00:15:56] So tell us what you mean by that. 

[00:15:57] Diego Rebosio: Well, it’s really more than finding that are going after. It is much more realizing that you’re able to access that when, when you kind of are out of your own engineering mind, ironically, right? The way to, to be the happy engineer is to stop being an engineer when it comes to being to being happy.

[00:16:08] Right? So it’s like, um, when you realize that you’re able to access that inner peace, joy it’s like, it’s always in you. It’s just that sometimes you don’t realize it’s there. So, but when you do that and you’re able to always access it, then you already have what you want. Right. And then it’s almost like having, you know, the money to retire.

[00:16:27] Right. You already have it, right. Maybe act as if you already habit, fake it till you make it type of thing. so if you could do whatever you wanted right now, what would you be doing? If you could quit your job right now, what would you be doing? What kind of job would you have? Right. You’re going to say you’re going to go play the guitar.

[00:16:44] Okay. That might be nice for a month or two, but after that, what? Right. You’re an engineer, right? If you’re really an engineer. You probably going to go do something else. That’s building stuff. Why? Because you like building stuff, that’s all there is to it.

[00:16:57] Zach White: So I love this because I hear from a lot of people who are burned out and frustrated or stuck, or they’re in a negative state, they’re in a tough place. And you ask that question, you know, what do you really want? And it’s like, I just want to go on a vacation. Like I want to sit on a beach and sip my ties.

[00:17:13] I want to stop working. But in the end, Th that’s really not true at all. Like, we don’t want to just sit on a beach and sip my ties for the rest of our life. You know, if you’re, if you’re 35 years old, eventually that gets pretty boring or your engineers for a reason we liked to, to your point, we’d love to build stuff.

[00:17:29] We love the challenge. We’d love to actually go solve. New and novel problems. And so for you from the CEO lens, you know, you know, if there was a young engineer or somebody, maybe they’d been engineering for decades, but they just feel that kind of disconnection from the joy and the passion of like, I just love doing engineering.

[00:17:47] I love building stuff. What would you coach somebody or, you know, how would you describe to them that journey of reconnecting to just that place of love? I mean, I don’t know. 

[00:17:57] Diego Rebosio: It varies by person what their challenges as to why they are stressed or unhappy. Right. But for example, a common one that I saw over the years, both in myself and as a manager of engineers, because I did manage engineers before I started the company.

[00:18:13] Right. Is, uh, you know, Learning how to tactfully say no, when it’s warranted is a really important thing. And you’re doing everyone a service when you do that. Right. Brooke had me watch the other day. I don’t know if you’ve seen this documentary on the fire festival. Have you heard about that? No. Okay.

[00:18:32] So it’s this festival that these, these intrepreneurs came up with that was supposed to be like. Like south by Southwest, like the biggest musical thing. Right. And it was a total flop because of poor planning, right? Like completely oversold dreams and expectations. Right.

[00:18:50] and eventually landing with the harsh reality that these people were underfunded. They didn’t have enough time. They didn’t, they had terrible logistics and it all fricking collapsed, like with a bunch of people sitting in an island in the middle of nowhere, without being able to even get flights to go back, you know, they rented like villas in this new place.

[00:19:11] And they basically had tents where everybody was fighting for food. Right. That’s how bad it was. Okay. Wow. It’s terrible. So that’s, it’s actually a good movie to watch because what it teaches you is this is. Saying yes to your boss when it’s unrealistic is a sin, 

[00:19:31] Zach White: right? Hold on, hit the, uh, exclamation point on that saying yes to your boss when it’s unreasonable or just the wrong thing to say yes to, 

[00:19:41] Diego Rebosio: well, if it’s unrealistic, it’s unrealistic right now.

[00:19:45] Sometimes the answer is just, you just don’t know. Right? It takes a long time for you to feel confident about your estimates. Right? Everybody’s always asking an engineer. How long is it going to take to do this, right? And sometimes you just don’t know, or sometimes you can just give a wild guess, but you tell them, but it’s not reliable.

[00:20:03] Right. And that might change tomorrow. I might uncover that there, there is a lot more risk in this than I realized. Right. But this is my guess right now. That’s okay to say. Right. Um, but you know, learning how to say no is really important because, you know, it’s kind of like the. You know, You know, in the airplane, when they say you got to put on your own mask before you put that help anyone else with them.

[00:20:22] Right. If you don’t put on your mask first, then you’re going to say yes a lot and no one’s going to win. Right. Your boss is going to look terrible to his or her management, right. It, because, you know, they didn’t set the right expectation and it’s okay. You’ll find out that 99 times out of a hundred, they know.

[00:20:41] It will be fine, you know, just everybody needs to know, okay, it’s going to take an extra few weeks months, whatever. Right. It is. What is. 

[00:20:48] Zach White: one of my clients, we just had a group coaching conversation and, and he shared a celebration with our group that he had just said no to his boss for the first time.

[00:20:57] And, and we all kind of cheered and celebrated. And so I asked him, so what happened? And his answer was nothing. Exactly. Nothing exactly. He said, he said, I, for the very first moment, my boss kind of looked at me with. New. Like what what’d you say? Like, cause it caught him off guard, but then he said, you know, he explained why the answer was no and why it was clearly something he couldn’t deliver right then.

[00:21:22] And his boss said, okay, that makes sense. You know, I’ll find someone else. So talk to you tomorrow. It was just over. And I was like, wow, we have this idea of what’s going to happen. Our fear paints a picture and it’s almost always completely. 

[00:21:36] Diego Rebosio: Yeah. And you don’t need to go crazy with that either. It’s not about pissing off your boss and getting the reputation for being the angry engineer.

[00:21:43] Right. They wanted us always saying no. Or the one that’s always giving on realistically conservative estimates, right? Yeah, exactly.  It’s just, you know, you’re in a business where, you know, project based work is always, you’re always building a new one of a kind right. You don’t go and build the same bridge twice.

[00:21:59] You don’t build the same computer software twice the same way. Otherwise you would just need to copy paste. Right? The reason you’re there is because you can’t just copy paste. So it’s always a, one of a kind. 

[00:22:11] Zach White: Where else would you aim someone to, as they’re building their engineering career and looking for the places that drive us into that frustration or burnout?

[00:22:21] So saying no is a great one. What other pearls of wisdom do you have for somebody who’s in that place?

[00:22:27] Diego Rebosio: Uh, I mean, I don’t know. I think if, if you’re just doing what you love and doing a good job at it, you know what I mean? Don’t don’t have acid, maybe. I don’t know. I’ve never been the kind of engineer. Okay. Cutting corners, right? You don’t need to go overboard and do what, what some call gold-plating either.

[00:22:40] Right. Which is to, put way too much detail more than anybody cares for. But, you know, like to feel good about what I’ve built, right. And I think we all do you don’t feel like you’re doing a good job at what you’re meant to be doing, then why are you doing it? Of course, you’re going to feel bad.

[00:22:55] Right. I can’t think of why else you would feel bad it’s either that, or you would just have too much pressure, Eh, you can also, I mean, there’s, there’s also, you know, I mean, I dunno a lot of engineers also maybe have trouble with anxiety, you know, because when you’re very smart, sometimes you’re able to.

[00:23:07] Understand situations and so much more precision Of everything that could go wrong, that you worry about all the details, right? Like you’re, I don’t notice that you’re making a bridge while you’re not going to know the 65 different reasons why that bridge could fall, that no one, you know, would have a clue when they’re driving through it.

[00:23:26] Right. And so maybe now all of a sudden, every time you’re on a bridge, you start freaking out. Right. And it’s just your mind going on overdrive and analyzing. Right. And so there’s learning how to deal with that as good. You know, meditation is good. He has a way of quieting the mind learning how to do that.

[00:23:42] Well, exercise is great, you know, just, you know, it does a, there’s something about it, right? Maybe those endorphins or whatever. That again, just helps you settle. Right. Uh, and just being a little bit balanced, you know, go out, walk in nature right now with COVID. I mean, from what I know, most companies that are doing any kind of engineering, people are working from home and they’re staying that way even after COVID.

[00:24:00] Right. I think a lot of the reason for that is that people have figured out that without their boss breathing down their neck every morning, They’re able to do their job and find that better work-life balance. And no one wants to give that back. 

[00:24:14] Zach White: Yes. Diego, how do you under, like, when you think about work-life balance in your own journey, what does that mean to you?

[00:24:22] It’s a phrase that’s really thrown around a lot. Everybody wants better work-life balance. What does. Main or what’s it look like in your world? 

[00:24:31] Diego Rebosio: Well, I mean, I meditate and exercise in the mornings that that comes to me before everything else. Right. A I also, you know, uh, I have my kids part of the time. So when I, when I have them, I like to enjoy that.

[00:24:39] Right. And so, for example, with Wednesday afternoons, I don’t work. I mean, I I’m the boss. I can do that. Right. Eh, but I, I spend them with my kids. Right. Eh, um, that’s really Mo mostly it, you know, then normally on a weekend day I also, you know, broken. I like to do pick a day that we just absolutely don’t do any work.

[00:24:56] Right. And that works for us. So, I mean, you gotta find what works for you, but for me, uh, I would say the meditating and exercise is probably the, the absolute minimum. 

[00:25:03] Zach White: The non-negotiables. 

[00:25:04] Diego Rebosio: Yeah, because after that I have energy to do everything else. I’m more 

[00:25:08] 048 – Diego Rebosio – The Happy Engineer Podcast: productive 

[00:25:08] Zach White: that way. Yeah. So energy. I want to go back.

[00:25:10] Another thing that you’ve said before that really struck me was how seriously you take your energy and just how you show up this idea of, you know, your presence, your intention around, you know, moments above it and that as a CEO of a large and growing organization, You see, you know, managing your own energy and state as one of the most important things that you do as a CTO.

[00:25:34] Can you describe that? How you came to that place to just what it looks like and why, why energy before something like strategy or tactics or leadership. These other words that get thrown around like energy. Talk to me. 

[00:25:48] Diego Rebosio: Well, I mean, everything that you create, I mean, you’re, you’re a creator when you’re a manager, right.

[00:25:53] Or you’re an engineer or any of these things, right. You’re, you’re creating things and everything is going to have a blueprint of how you feel. Right. So if, if you’re pissed off at your boss, right, the output is not likely to be as good. It just isn’t right.

[00:26:06] likely to take longer and so on. Right. And so the same thing maps for me, right. It’s like a for example, I mean, maybe it becomes more obvious when you do sales and that’s where, it’s where it started. Right? Like Like in, in what I do, I do a lot of sales. Like a lot of, I talked to a lot of customers, especially new potential customers.

[00:26:21] Now, if I’m trying to, um, eh, I, I learned before that if I wasn’t in a good state of mind, customers were not really likely to want to work. Right. Like if I come across as pissed off or upset about something, then, you know, in a way sales is a transfer of excitement, right? Like I can only get you excited about something that I’m already excited about.

[00:26:42] Right? Like if I tell you, Hey, look, you want to buy an apple watch and I’m all excited about it. I’m not going to be like, yeah, I have an apple watch. You should buy one too. Right? That’s a terrible, no, no. One’s going to be excited about. so you gotta be excited in order to sell or be effective at it and be able to transfer that excitement.

[00:27:00] Right. You also can’t. I mean, unless you’re okay being a dishonest person, which I’m not, and most of us are the same way you can’t be. Um, you can’t really sell something you don’t believe in. Right. Like, um, for example, let’s say that you work in a company that does something you don’t believe in, or you’re selling something that you don’t believe in the customer sees.

[00:27:19] It is like, you don’t believe the shit. Your body language is saying you don’t believe the shit. Why should I? Right. Like it get out of my face. You know, you’re not even artists here in, in telling me what you really feel about this product. Right. Everyone has a smell for. Right. And, and so you’re not good at selling something that you don’t believe in and similar year, you’re not good at doing something that you don’t believe in or something you don’t are not excited about.

[00:27:45] So, you know, that’s why it’s important for you to get in your old state of mind where, you know, you’re able to, to feel good and be happy before you actually take any action. Right. A and so whatever actions you’re going to take throughout the day, They’re going to be infused with that. It’s almost like having an extra battery pack in there.

[00:28:03] You’re going to be able to get more. You’re going to be able to do a better job at it. When you are in a leadership position, your people are going to be more excited to do their job every day. When they see that you’re excited and you believe in it. Right. and that’s why it’s just obvious to me, but maybe it’s not obvious to everybody, but it’s how else would you do this?

[00:28:22] Zach White: I wish that you had come along in my career, you know, 10 years ago. And I had somebody telling me this. Recount the number of times that I let a situation or another person or my own self manufactured pressure and anxiety about performance, put me into a negative state of mind of negative energy, and then just plow through the day in that state.

[00:28:46] And to your point that those days are looking back. It’s easy to see. They were ineffective. I, I negatively impacted the people around me in the workplace. There’s just, I mean, like, I think about Zig Ziglar’s old quote, you know, positive thinking. Doesn’t make all your problems go away, but positive thinking gives you a better output than negative thinking.

[00:29:05] Well, every time it’s so like, let’s, let’s still go to that place. You know, I definitely did not know that when I was a young engineer, but, um, state of mind. As a priority before you get into action consistently allows you to get more done, do better than 

[00:29:23] Diego Rebosio: maybe another analogy is, I mean, if, if you’re, if you’re an athlete, let’s say that you’re going into, I don’t know, the, the Olympics or something, and you’re a runner, right.

[00:29:32] You’re not going to try and, do the race, with a hangover you’re also not likely to do well when let’s say something really terrible happens. So you, that really brings you down. Right? If, I mean, I do sell, for example, in the Olympics, there was that whole thing with Simone Biles, for example, right.

[00:29:46] That she was not under the right state of mind. And she knew that she wasn’t going to be able to perform. That’s why she just found out. Right. So similarly, right. I mean, for, for us, we’re not able to perform. Our job as effectively for ourselves. That for everyone around us, if, if we’re not just happy, I mean, this is why you call your podcast, the happy engineer, not the angry engineer, right.

[00:30:07] Zach White: That’s right. Absolutely. You know, the thing is I’m yet to find somebody whose actual authentic goal is to be an angry engineer for one, but also, unfortunately, Diego, I have found that it’s somewhat rare to find. Truly happy, uh, you know, folks in our, in our discipline because of some of the things you described, you know, the anxiety, the pressure, the living in our engineering mind all the time and not finding that other side of ourselves, learning how to tap into these things.

[00:30:34] So it’s a really important conversation before we wrap. I am curious, are there any favorite resources or tools or books or things that you recommend, for your, for your team at work or for engineers that you mean. To help them in terms of their development and growth or anything that really served you along your journey, that you would recommend people to look at?

[00:30:55] Diego Rebosio: Nothing, I would say specifically for engineers. Um, eh, yeah, nothing comes to mind. Uh, not as fight as far as that. Um, I mean maybe just going to more general advice. Something else that might be important. It’s not, everybody’s supposed to be a manager. You know what I mean? You’re not, and you’re not supposed to be also the next Elon Musk either.

[00:31:09] Sometimes it’s perfectly okay to just be really good at being a really good engineer. There’s nothing wrong with that. And you can make really top dollar with that too. Yeah. Um, So, but you know, it depends. I think you’ll, you’ll just find your own way. I mean, the stuff that, um, I mean, I, I don’t give it to my people or anything like that, but I find that just anything more like spiritual, not, not, not religious, but more spiritual.

[00:31:34] Like I like a lot of the stuff. Yeah, totally. I liked a lot of Buddhism like Alan Watts and stuff like that. Learning how to meditate. I think some of these things are relatively, how can I say compatible with just about any kind of religious beliefs and they can help you find that piece. Um, Um, um, that worked for any kind of career.

[00:31:56] I think it was just for engineers. You know, we have such a big brain that we are very much in our mind and we want to solve it, like to do like an engineering problem. Yeah, 

[00:32:05] Zach White: totally. So if you’re going to invest even more time into development, don’t, over-index on more of that analytical thinking, you’re focused on developing that other side of yourself, that the soul and spirit, 

[00:32:18] Diego Rebosio: yeah.

[00:32:19] Take a walk in nature. Yeah, 

[00:32:23] Zach White: you don’t need another book. Take a walk. 

[00:32:25] Diego Rebosio: Exactly. Don’t read a book while you’re on. Okay. Just actually do the walk. Right. Look at, look at, look at the, I mean, I have a beautiful neighborhood. It right here, you know, it’s like, there’s lots of nice, nice trees and front yards that people have.

[00:32:40] Zach White: Yes, I am so guilty of this. Diego I’d have. And instead of actually taking a break, I want to listen to another podcast, which, you know, here I am recording one. So I was like, I hope, uh, the engineers listening, realize, like this isn’t the most important thing, but feel free to turn off this podcast and go for a walk.

[00:32:59] You have Diego’s permission and mine right now. But, but yeah, it’s like always wanting to just keep feeding the intellect, keep feeding the intellect because it’s a. Of mine. And it’s the strength of the engineering leaders sitting and it’s working. Yeah. So I 

[00:33:13] Diego Rebosio: thought that, yeah, it does work for a lot of things.

[00:33:17] Just don’t use it to try and. Make it your step two, not your step one. Oh, 

[00:33:22] Zach White: there you go. I love that. Well, I want to wrap this up and thank you again for your time and your generosity, Diego. I mean, we could go for days with wisdom I’ve heard from you and your stories, but I always get curious at the end here around questions and great engineering.

[00:33:41] It’s like great coaching. The questions, lead answers, follow. And if we want to get better answers, we want to ask great 

[00:33:48] Diego Rebosio: questions. Um, Terry, that the last, the last 10 seconds were cut off. No problem. I got, I had a video issue. 

[00:33:48] Zach White: All good. Let me back up great engineering. Diego to me has in common with great coaching, that questions lead and answers follow.

[00:33:48] And if we want to get better answers in our life, then we want to add. Better questions. And so for the engineering leader, you’re frozen 

[00:33:48] Diego Rebosio: again. Oh, no. Sorry. 

[00:33:48] Zach White: That’s all right, man. Not your fault. Let me actually make sure it’s not on my end. We can edit all this. It’s not a big deal. Uh, sometimes the router here does, uh, it will automatically switch without my permission, which I hate.

[00:33:48] Uh, no, it’s it looks good. Weird. What can you hear me now? Okay. I can 

[00:33:48] Diego Rebosio: hear you fine. Exactly at the wrong. Okay. That’s 

[00:33:48] Zach White: all right. Um, what was the last thing you actually heard? And I’ll make sure I back up far enough.

[00:33:48] Diego Rebosio: Ah,

[00:33:48] Zach White: I am. What a pain we need, like two more minutes, you know, and here my, my internet seems to be beautiful. Here you go. You have 

[00:33:48] Diego Rebosio: it. Two engineers, not being able to figure out their router. 

[00:33:48] Zach White: Oh man. It’s

[00:33:48] uh, stinking, zoom played me. It says it’s the, it looks pretty good. It’s it’s on my end. I don’t know what’s going on. It’s uh, given me all the bars and none of the love, so. Well now I’m back. It does say it’s still recording. So we’re going to see, hopefully zoom connected all the dots and I’m a backup we’ll.

[00:33:48] We’ll see if we can land the plane here. Um, okay. Did you hear any of the last question? I’ll just start it over, start it over. Okay. So Diego, thanks again for your time today. I know, man. There’s so much more. I’d love to ask you, but we always end in the same place and it’s around questions. The questions that we ask in our life matter.

[00:33:48] If we want to get better answers. And we want to ask better questions. So if there’s an engineering leader out there, who’s been listening to this chat and they want to get more of that connection to happiness and the joy in their life and have the, both get the results as well. What would be a question that you would lead them with today?

[00:34:09] Diego Rebosio: Why are you an engineer?

[00:34:12] Just ask yourself that. Why are you an engineer?

[00:34:14] Zach White: A very 

[00:34:16] Diego Rebosio: simple, right. But with that, you’re going to find a lot of answers as to where you’re going to get that, that happiness, regardless of, how good or bad your boss is and, and, and everything else amazing. They’ll help you find that joy in, in doing just a good job at what you’re doing.

[00:34:39] Zach White: Why are you an engineer? I hope everyone out there takes some time to sit with that question today and dig up. If somebody wants to either that maybe they need a million dollar website, so they want to talk to you about business, uh, or they just want to connect or, or follow the amazing work and life that you have.

[00:34:57] Is there a place that someone can, can follow Diego and, or connect? 

[00:35:01] Diego Rebosio: I guess he could find me on LinkedIn. Eh, I don’t really use my Twitter much once in a while I post something there. Uh, those are probably good, good places. Um, that’s pretty much it. I mean, what I have is too specific to kind of do more like a general pitch about.

[00:35:15] But what we do is we basically implement websites for large companies. Like I mentioned, we specialize in some web content manager, software, specifically some tools called Cycore. We’re probably the best shop out there to do that kind of thing. and that’s pretty much it. 

[00:35:30] Zach White: I understand that, which I know in our audiences, a high percentage, more than most, uh, and that fits what you need in life connect with Diego and their team, but also, uh, just a tremendous leader and someone that I’m sure, uh, you would never regret connecting to.

[00:35:44] So reach out on LinkedIn, we’ll put the links in the show [email protected] and Diego. Thanks again for your generosity and the time today, it’s been awesome to have you on this. 

[00:35:54] Diego Rebosio: Thank you, Zach. Thanks for the opportunity.