Corporate life vs. Entrepreneurship

Posted on 07 Jun 2022
Founder Stories

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About this episode

What's it like leaving the corporate world to start your own business? And what about going back? Is that hard?
In this episode, Lena Sesardic and Anthony English share their experiences with working in corporate, switching to running their own businesses, and then going back to a corporate job.
Lots of wit and wisdom from these two mentors at Growth Mentor.

What they talked about:

  • What if the timing isn't right for you to leave corporate
  • Skills from big companies that help when you're on your own
  • Entrepreneurial skills that can work in corporate life
  • Working solo vs. working in a silo


Anthony English: Well, Lena, okay, so it’s it’s it was wonderful trying the entrepreneurship, the roller coaster. But you at some point, you sort of say, You know what? It’s this, maybe this isn’t working? Is that? Is that something that you have have seen before in other people or yourself?

Lena Sesardic: Yeah, definitely. I mean, I think, I think, you know, you see it around all the time, really, if you kind of just take a look. But I think for me, it happened multiple times throughout the journey. So each each pivot within the entrepreneurial journey, like let’s say, the first product idea, the second product idea, the third partnership and all that kind of stuff. Every time, you know, there’s a moment like you’re working, I’m working on my first product video, for example, there’s a moment where you’re kind of like, you know, do I keep going with this? Or do I switch gears? So it happened every time I was kind of at the end of some sort of project, or maybe I was trying to decide whether I should keep going with a product idea. But then the final, the final moment, I think, was when I eventually decided to go back to corporate and that decision took it took about over a year, actually, because when I first quit, to go into entrepreneurship, I had a six month timeline, I was like, you know, I’ll just do it for six months, and then I’ll see. But once you get into it, you know, just things started happening. And it’s a roller coaster and like, you just feel like you haven’t had a good shot. And then you just kind of keep going it’s like gambling, like are you just kind of count stop. But there’s moments where I was kind of like, maybe I should, you know, there was a few months in where I was like, oh, like, I don’t know, is this for me? Should I just like maybe I did three months? Like maybe I just close it, my husband was just kind of like, well, no, like, do it properly, like don’t just do three months. And then you know, there’s a few times where I was applying for jobs and really considering some offers, but like just didn’t end up pulling the trigger that was kind of leaning towards like, No, I think I just need that one more. Shot that one more, hey, you know, and then eventually, eventually just kind of, you know, realized very soberly that it was just, it was just not happening anymore. So yeah, definitely very familiar with that just state of limbo, and it’s very portress.

Anthony English: It can be and you know, even a bit you just seen, but I’ve told everybody

Lena Sesardic: Yeah, this is my identity, right?

Anthony English: Ah, you’ve sold out, you’ve gone back? And it’s not that at all? It’s so I’ve got some some Yeah, well, I’ve got some questions around around there, which is, especially around the relationship between you as the entrepreneur, whatever that means. And then your corporate person, whatever that means. How did they cross fertilize? How does corporate experience? How has your experience working for the man, you know, in the big, the big company? How has that helped? How did that help you with the entrepreneurship? And then part two of that question is having been there having, you know, dived in and then, you know, got out? How does how has that improved or affected your, your approach to the corporate life?

Lena Sesardic: Yeah, good questions. I think for the first one. I mean, I think my corporate experience before I went into entrepreneurship, like I was really lucky. And then I worked in a few jobs where we were either in a startup or a startup like teams, so I kind of understood that idea, like the concept of, you know, a little bit of hustle to get things done, like lack of resources don’t have all the roles, like when I was building early prototypes and fintech we didn’t have designers and didn’t really have a proper dev team. It was very just kind of side of the table type of project. So like, you know, doing what you can so I think that kind of experience taught me how to just you know, have the grit to just figure things out. It’s like, you know, don’t have a designer figure it out yourself. Don’t have a copier to figure it like it was very just I was like, Yeah, that’s what I’m used to like I’m not used to working with a bunch of resources that the massive org right so I think in that way I was I was pretty prepared to understand like the concept of you know, you have to do a bunch of different things. Do what you can type of things so I think that was helpful and and just generally like basic confidence, you know, even just knowing that I had seven years of corporate under my belt, you know, I wasn’t like a fresh University grad doing my first startup. Although that has advantages too, but it was like, you know, I have some experience, I can know, I know how companies work. I know how decisions are made, I can maybe sell some things, you know, I’m not, I’m not completely green. So I think that helped. And then on the other side, it was, which I guess I’m going through that right now. So I’ve only been back for about, you know, four or five months. So it’s like, what really skills that I learned are relevant in corporate and it’s a tough one, because my job right now like, I’m actually in a very, very big Ward, which is probably, you know, I’m actually in order to like, I’m not in a startup team, like within it. So I’m really just in the regular org. So that’s something that I haven’t experienced per se before. But I think just generally, like, I’m able to weather disappointments more, I think, I know, I think I know what the other side feels like now. And that’s kind of why I went out, I wanted to see the other side. And because before I was like, oh, like I, you know, corporate, so complicated and so slow, like, I’ll just go do my own thing. It’ll be great. And then you do it, and you’re like, oh, my gosh, it’s really terrifying. So you kind of realize, like, you know, each side has its pros and cons, to the knowing the challenges on the entrepreneurial side, even though it’s great, but it’s like, it’s really tough. I kind of don’t get as affected by the corporate issues, because I’m like, at the end of the day, I can log off. You know, I’m not the only one responsible for everything. And that that really helps. But yeah, I think I think those are some of the things that come to mind in terms of that cross cross skilling? Yeah, I’m curious to hear your experience.

Anthony English: Yeah. So I’ve actually had a very, very mixed career, although I’ve worked on extremely narrows the specialization in in it, not not a developer or anything like that. And it’s a very old school kind of technology that I work on. And so, in that sense, it’s been extremely narrow. But because I worked for an outsourcing company, we ended up having clients who were, you know, government departments and, and tiny, tiny printing businesses with, you know, and, and so we were able, so I ended up getting some exposure through my clients to, you know, quite a few different industries, especially in manufacturing and, and in a little bit, even of education, but mainly, yeah, yes, manufacturing will finance whether to write. And so, for me to get involved into into project on a bigger, a bigger company was like, it was not such an adventure for me, there was not such a something so new. But one thing that really struck me really shocked me when I worked for a bank was we have this idea when we’re when we talk about corporate, when we’re outside of it, we sort of think, wow, that’s the big building with and everything runs like clockwork, and they’ve got massive names. And, and if one thing goes down, say on a computer system, just flick a switch, and it will automatically walk in, when you can’t actually get into it, you realize it isn’t my goodness, come on in everybody. It’s awful. You know, it’s just such a, you just think, Wow, you can see from when we when you it’s so I suppose here’s the thing is that when you’re a announce when you’re thinking of a business, when you think of a business owner, when you’re contacting a business, if they’ve given you some really bad service. And you’ll get through to a help center. And you might sort of threaten now I’m going to be taking my business elsewhere. And in the call center. Like if if somebody said that to you as the business owner or an entrepreneur, you just, oh no, this is a disaster, I need to fix this. But when you’re actually through to the coals and they don’t care, KPIs or something to you know, or some SLAs they don’t care. I should explain what KPIs and SLAs are. But by key performance indicators and servers. Agreements, yeah, service level agreements. So how fast they’ve got to answer the calls. And you know, they don’t care. And so that’s one thing that kind of shocked me when I was actually in corporate. And now that I’ve gone back to it is, is that people are not all sailing in the same boat. They don’t they’re not sort of for the good of the company, and some of them are there by so for example, let’s say a project is big project is coming through. And it’s like, you know, $2 million project, some of the people, their motivation, from everybody will say that their motivation is I want to keep my job, okay. But beyond that, some of the people are saying, well, actually, we’ve my team. I’m the team leader here, and my team already has too many projects. We’ve all we’re already swamped. They’re already working extra hours. And so my job is basically to get out of this project, because we’ve still got our work, we’ve still got these projects that are not getting delivered on time. And so they don’t really, they’re not as invested the way that you might be if you’re the actual business owner. It’s projects.

Lena Sesardic: 100% percent no. I think you’re hitting on honestly, a really important point, which I was just talking to one of my mentors about just last week, actually. And yeah, I think that’s the biggest differentiator for me as well. And I think, for me, you know, I’ve, I’ve never really worked in a company and not felt true ownership over what that company is trying to do. And I think the point at which I ended up leaving a company is when I just don’t feel truly aligned anymore. I don’t believe in what they’re doing. Or I don’t believe in you know, like, what leadership is doing. I don’t believe the way that the teams are, but like, I don’t think it’s, you know, it really, I struggle. I struggled to just clock in and clock out. And I think there’s a lot of people in corporate and and, you know, this, this speaks to, I think, the compensation systems, because, of course, like, why shouldn’t the majority of people really care? Like, it’s not like, not a lot of companies have, like, you know, bonuses closely tied to performance? They don’t, I’ve never had one, that’s for sure. And like, I’ve worked in tech for, you know, nine years. So I think it’s just the way the system is designed, like, what How Could everyone feel accountable? Like why at the end of the day, when they’re just paid the same? If I if they just leave, leave? As long as the end of the day, you will? Be ready to go, right? So.

Anthony English: Yeah, as long as, as long as I’m not gonna lose my job, you know, I’ll just do what I need to do. But then people are drawn by.

Lena Sesardic: Exactly, yeah.

Anthony English: But then people are drawn by well, I need to help out my colleagues, something like this right. Now his his perspective for those who are not in corporate and have never gone to corporate and, and probably sort of the feeling the mystique Wow. If only if only I’d ever worked for a big bank, or a big insurance company, or big government or government. But he finally had done that. Is that from both of us, we’re saying, Well, I’m saying it anyway, is that like, is no big deal. And we’re not saying that because we’re the corporate kings, but because we can say actually, things are just are in quite a mess there as well. And the proof of that, is that when you call a company, let’s say you have to call a company to cancel something or to get a refund or to get find out if an order has come through. Just check next time that happens or call the government for something, you know, Rekha, find out the next time that happens, where you get, you get told the one answer, and then when you contact them, again, you get told the different answer a contradictory one happens all the time, which would not happen if you’re dealing with one person who is who’s got, you know, he’s on top of, yeah, yeah. So it doesn’t matter that you don’t necessarily have corporate experience. You don’t have to get however, I want. I also want to mention something that’s a real advantage. If you are going from that entrepreneur journey through to or, you know, you do a bit of dabbling, and then you come back in and maybe you take a job for a while a six month contract or something that happens to be in a bigger company. Is that when at the beginning of a big project, let’s say a $2 million project, okay, now, there might actually be a tiny project, but for us, in the entrepreneurial world, we just say, wow. Yeah, at the beginning of a project, here’s what happens first, I said, we actually need to do this. And there’s some brainstorming sessions and they can be quite tense. And you’ve got before we live, all the technical people come in and just say, this is the way we’re going to do it. Early on, it’s like we could do it this way. We could do it that way. And then everybody’s got their opinions and so on. And here’s where your experience even if you’re a solopreneur and is only really just started out and just learning about marketing and so on. This is where it can come in super handy. When you feel like you’re the junior in this massive in this meeting of like 12 teams or something, and they’re all saying that I want to go this direction another saying no, we want to go that one that direction is that people are all at cross purposes, they’ve all got different motivations. Personally, they want to keep their jobs. But some of them are looking, you know, maybe a bit more ambitious, some of them want to get rid of this project, some of them want to embrace this project, there’s a whole lot of different motivations. And that’s where the tension comes. And if you can learn to ask questions, just in a very gentle way, not run the meeting, but just ask a question just here or there. Just before we go into this direction, can I just ask a little bit around the risk of it, you know, just ask very gently, that can bring such peace and wisdom to the whole situation. And you think, well, and it makes it look like you’re a genius. It’s really amazing. But that’s really comes from the little bit of learning about marketing, and how to talk to people and sell on when you’re when you’re out on your own. It’s valuable.

Lena Sesardic: Absolutely, absolutely. Yeah, I think I think when you’re on your own, at least, this is my experience, you kind of have to really drive the conversation. Like, I think in corporate, it’s, you know, each each job is different. But generally, it’s like, you know, the, because everyone is part of the system, it’s like, you kind of just slot in with your own like, wave, right. But I think when you’re on your own, you’re creating that, or you’re creating everything without you doing anything, nothing exists. So you have to really put it all together and, and facilitate. And again, it’s just, you know, creating something with your bare hands like on your own, there’s no help no one knows the answer. You just have to kind of trial and error. And I think that’s the other piece of it. Like, you know, I think being an entrepreneur, I am so much more aware of how important experimentation is. And so I think a lot of the time, someone asks, you know, should we do it like there? Should we do like dive? It’s just like, well, you know, like, what, what, what could an experiment look like? Like, we don’t know, like, I’m so I feel like, I’m so familiar with the fact that like, we don’t know anything. So it’s like, it shouldn’t be? What is this? It should be like, how can you run an experiment to figure this out? Like, how can we get to the answer as quickly as possible without just relying like, on our mind or whatever?

Anthony English: Yeah. So this is this is a really, this whole idea of taking responsibility, taking ownership of, and, but allowing others to take the credit. And then that’s, that’s really, yeah. Because excellence. You know, it can’t be hidden. Right. And so when you see that, as I’ve seen, you know, with many people, and I just see, like, in so many different contexts, and I just think, wow, she really knows how to write and so on on Earth, it’s really amazing the way that they asked that question or they, they defuse that tenses, tense situation, they, you know, should be a police negotiator, that person, it was just so, so tense in there, in that Zoom call that we had, you know, in corporate, whatever. And I think that there are just so many gifts and skills that you can translate that you don’t have to wait for permission to, to, to give something a go, to try something and then for people to say, well.

Lena Sesardic: Yeah, I feel like corporate is a very kind of permission-based environment. And again, like we’re totally generalizing here. It’s just the tendency, right? And I think it tends to be a more like, permit, you know, you have your role. You have your job description, like senior, like, Who’s this director? Who do you report to what organization like there’s so many constraints. That it’s just easy to kind of swim in your lane and do your own thing? Right. And so, I actually have a question for you, which I’m very curious as to what what the answer would be is, what types of people do you think get promoted in corporate jobs? And do you think an entrepreneurial type of personality is at an advantage or a disadvantage? Or? Because there’s a tendency, there’s a notion that, you know, like, yes, people get promoted, and that’s not really the entrepreneur because, you know, we’re always questioning things and just getting to the truth, you know, we’re not just like, let’s, let’s do it just so I get paid. It’s like, Is this really the right thing to do? Not that non entrepreneurs don’t do that. It’s just tickets again, tendency, right? So like, what’s your view on who? That’s promoted. And are we at a disadvantage or loss?

Anthony English: Yeah. So taking apart assuming that everybody is treated fairly men and women and so on, okay, and I know that that’s, that’s Yeah. Put that put that question aside, and just look purely at the skills and what I found that now that I’m back in a in a corporate setting on in an IT role at the moment, I’m mum it’s very project based. And who gets promoted? Well, I haven’t been there long enough to see who gets promoted. But I would say that the more, you know, Jay Abraham said probably in the 1970s, or something, you know, one of these sales guru guys said that, if you can understand people’s problems, or if you can explain people’s problems or pains better than they can, they will assume you’ve got the solution? Yeah, it’s a brilliant piece of marketing, but I have found not been promoted at all. But I have found that it has that ability, when you hear them talking, like if you hear some technical people talking about the technical side, then I switch straight into tech mode. And I’m talking the jargon with them. But once we get an application owner, who, whose responsibility is if this goes down, it’s going to be on my my head right? And is not too interested in the technical side, then I’m going to be speaking to them about risk. I won’t be talking about the technical side at all. They won’t hear the jargon unless they ask me. And even if they do ask me, I’m going to explain it using a very human example from cooking or something else. So what I’m saying here is that if you can talk their language, and I’m not saying to be a yes, person united, yes. As I’ll agree to everything, but if they feel that they are understood, because you’re the only technical person talking about risk, instead of just talking about the technical How do we do this? Well, you’re the only person who’s saying look, we need to balance the you know, the budget or about the about the project, if you can start to talk their language. That is, is it’s it’s like, it’s a Get Out of Jail Free card. It’s amazing. That happens in interviews, too. I love job interviews, I’ve had the done any in my life. They’re like a podcast interview here. I just, I I’m always asking when they ask a question. I’m asking, what’s behind that question? What are they?

Lena Sesardic: What’s the motivation? Yeah, what do they really want to know?

Anthony English: Why are they trying to trap me? Like if they ask you a question in a job interview? You know? What’s the question? Tell us about yourself? Or tell us a situation where you’ve, you know, we were you had a clash with with your boss, and you know, how did it turn out? You know, what? Those questions are not there to trap you. Ideally, they are there to say, well, here’s how I turned around, here’s how you’re going to be able to work with me when we get into a similar situation. To see how quickly I think and so the entrepreneur side definitely has got a huge advantage over the corporate. But the problem is because things are so siloed if I went in and told them like I’ve got a YouTube channel, which has had like 2 million views on it. I haven’t even told my colleagues. They wouldn’t even be interested anyway. You talk to them about marketing or copywriting. It’s like they wouldn’t have a clue. Yeah, yeah, they don’t. It’s not they wouldn’t have a clue. They wouldn’t have an interest in it. Yeah, yeah. Why? Because in their lane, that’s where they’re focused. I don’t need that at all. But that’s not part of the zone free his his were an example is that like, if you’re trying to document something, right, the big problem, you know, it is that we’re terrible at documenting. So in a job interview, I always say I love doing documentation. You remember that guy said he loves documentation? We got a high. Yeah, nobody would ever say that. And unless they’re a technical writer, but I realize why they’re motivated, why they don’t like documentation. First, they feel self conscious about their writing. But more importantly, they are people who are generally very good at figuring things out. You know, maybe late at night. With the team are on their own, and they’re figuring it out, and they’re just going to be basic. That’s where they get their buzz. That’s their motivation is let’s just plan, let’s just work it out, we because we’re great. Whereas my attitude is, I’m going to plan everything ahead of time. And if the project we’ve we had a change that was supposed to, you know, bring a system down to four hours, if I can get that done in 20 minutes instead, in the middle of the night, then that’s great on I don’t want it to be four hours. So it’s two different motivations. One is, I want to be there, I want to be the hero. And the other one is, I want to be the hero that so much so that it can run without me.

Lena Sesardic: Mm hmm. Yeah, no, that’s a really great way of putting it. I really appreciate that. Yeah. Um.

Anthony English: So if you understand people’s drives, when they ask the question, and you know, I do this in my children, I’ve got seven children. And when I ask a question, you know, how old do you have to be to learn to drive and or whatever? I’m going to find out what’s behind that question. You know, what, Dad? Have you got any, any money? Wait a minute. You don’t want money? Money for something? What’s going on? Why? Yeah. So the question behind the question I said, I think is, is a very powerful skill, whether in entrepreneurship, in corporate in family life, whatever. And, and so when people are asking a question, because they’re really afraid, sometimes to ask the real question, because they’ve been embarrassed or whatever. If you can answer that real question in a very gentle way. Yeah, that’s, that’s like a superpower. In corporate in all sorts of situations.

Lena Sesardic: Mm hmm. No, it makes sense. Yeah. No, I really like that. You know, the why behind the why. Question behind, the question behind the question.

Anthony English: Yeah, that’s right. So here’s a perfect example in entrepreneurship. Right? This is saying mentoring, somebody will say, What’s the best platform for a website? How do I set up a website? Where do I do? I’m a technical guy, do you think I don’t know how to set up a website? I can figure that out. But the real question is, why do you think you need a website? And why do you think you need it right now? Like, is this are you just stalling? Because your market is and you think, Oh, well, I’ve got to I’ve got to learn website before I go out and create anything.

Lena Sesardic: Oh, yeah. What are you avoiding?

Anthony English: What are you avoiding? And so that’s really,. So, so I won’t say what are you avoiding had day you asked me about the website. But I want to jump into, Oh, well, you could do it in Squarespace or Wix or in WordPress? I’m not gonna do that. I’m going to wait. Why is this on your radar right now.

Lena Sesardic: When you’re trying to do Yeah.

Anthony English: Yeah, the why. And being able to do that being able not to answer the direct question, but answer the question that was really behind it. That is, yeah, that that is extremely helpful in pretty much every contest. In law.

Lena Sesardic: Yeah. No, I like the way that you’ve put that I’m going to try and start implementing that into my daily life and my my work life and everything. Yeah,

Anthony English: Yeah. So pull out a gun and say, Why are you asking that? Why you asked him if he wants to know. But as soon as you can do that same thing, when people like I find this with mentoring, if people are saying something, if they drop a little hint ahead of time. At the beginning of the conversation, they just are sorry, I’ve been so busy. Or I didn’t get that time to do this or something that they’ve kind of promised themselves, I promise you that they would do want to know what, what else is happening? What’s behind that? Because those things that apparently are on the periphery of very often the real issue.

Lena Sesardic: Mm hmm. Very true. Very true. Yeah. Yeah.

Anthony English: Well, we’ve sorted the well’s problems in our other.

Lena Sesardic: Yeah, nothing else can be done now.

Anthony English: So none of that anymore. And in this one, we’ve given you a complete roadmap to go either intercorporate or to get out of it.

Lena Sesardic: Yeah. No, no, not going to tell you which way to go.

Anthony English: We just asked you why you want to do it.

Lena Sesardic: So Exactly. Yeah.

Anthony English: So we’re both available on GrowthMentor, Anthony English.

Lena Sesardic: And Lena Sesardic, yup anytime, mentor profiles

Anthony English: And we work across different time zones as well and so yeah, and I’m a technical guy anyway so.

Lena Sesardic: Yeah and then Anthony and I have you covered for all times

Anthony English: Yeah we do everything yeah perfect marketing is for every kind of business is for every client

Lena Sesardic: Wherever you are, whoever you are

Anthony English: Everyone Yeah

Lena Sesardic: We will ask you the why behind the why’s.

In this episode

Anthony English Impostor Syndrome Coach

If you’re finding it hard to see what value you’re really bringing to your clients, you’re not alone. Maybe you’re a creator, or you’re technical, but the sales side, and impostor syndrome can hold you back. That was me, too.

Lena Sesardic Product Manager, Content Creator & Speaker

Relentlessly focused on helping you with product management challenges (strategic, tactical, organizational), building an authentic personal brand on LinkedIn, and writing captivating content that stands out AND sounds like you. Reach out! I’m happy to help. 🙂

A talk by Lena Sesardic
Product Manager, Content Creator & Speaker
Hosted by
Anthony English Impostor Syndrome Coach

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