Press Pause to Leave: Sean O’Rourke on Knowing When It’s Time to Step Away

How do you know when it’s time to leave, even when you’re the owner ? 

In this episode of Time To Press Pause, Ellen Williams is joined by Sean O’Rourke, a cyber liability consultant, CFO, and former IT company co-founder, who shares the moment he realized he could no longer live in a millisecond-by-millisecond business. 

After more than 25 years in technology, including 12 years running the IT firm he co-founded, Sean made the difficult decision to step away from day-to-day operations. 

Not because he couldn’t do the work, but because it no longer aligned with the life he wanted to live. 

Together, they explore what it means to pause without quitting, how identity and motivation shape leadership decisions, and why being honest with the “reflection in the mirror” matters more than external expectations. 

In this conversation, you’ll hear: 

• How to recognize burnout before it defines you
• What it really means to leave, even when you’re the boss
• Why technology became a 24/7 pressure cooker
• How Sean reshaped his career without walking away from his expertise
• The importance of being honest about what truly motivates you

This episode is a powerful reminder that pressing pause isn’t about stopping, it’s about choosing what comes next.

📘 Ellen Williams’ upcoming book (pre-launch):
Creating Time: The Key to Productivity and Peace
👉 https://shopbooksdirect.com/product/creating-time/

Learn more about Sean O’Rourke and his work at Combs & Company:
 👉 https://www.combsandco.com
 

📰 Subscribe to Ellen’s newsletter for updates on new episodes, insights, and the book launch:
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Transcript

Time To Press Pause - S3E10 - Sean ORourke 

Speaker:[00:00:00] How I was reacting to the alarm clock every day, and it just was no longer something that I knew I wanted to do. 

Speaker 2: Welcome to Time to Press Pause, real Life Stories from the C-Suite. I'm your host, Ellen Williams, CEO of the salient strategist and author of Creating Time, the Key to Productivity and Peace. 

Now in presale today, my guest and I are talking about knowing when it's time to leave even when. You are the owner. My guest, Sean O' Rock, is a cyber liability consultant for Combs and company and insurance brokerage and consultancy for small and mid-size businesses around the us. Sean works with companies to mitigate the myre of risks posed to their technology and data by internal and external threats. 

Sean spent 25 plus years in the IT arena. Which included 12 [00:01:00] years running the IT firm he co-founded. So he has a unique perspective on the financial, legal, and reputational disruptions faced by businesses in today's interconnected world. Sean also sits on the board of pancakes for Roger, a veteran focused nonprofit and has served as board member for multiple private companies. 

He's a long time mentor to students and new entrepreneurs. He's a CrossFit and Spartan coach and competitor and has recently taken up endurance events. 

Speaker 3: Welcome, Sean to this episode of Time to Press Pause. 

Speaker: Thanks very much, Alan. It's nice to see you again. 

Speaker 3: It is nice to see you again too. Sean, you and I have known each other for a very long time. 

In fact, I think I was on your podcast many years ago. 

Speaker: You were. You were? 

Speaker 3: No, not that many. Let's not overdo that. Anyway, you and I, it's 

Speaker: longer than either one of us want to admit. 

Speaker 3: So we did a lot of networking [00:02:00] together and when I was in New York and I was so pleased when you reached out and had interest in being a guest on my podcast, and I'm really excited to hear your press pause story. 

Speaker: Yeah. Uh, technically my pause is still in effect. When you and I met, I was still running my IT firm that I co-founded, and my pause event was telling my business partners I was done being in the day-to-day morass of technology. I had been 20 years by that point doing different. Forms of it, technology, however you want to refer to it, and I just decided it was going in a direction. 

That no longer fit with the lifestyle that I wanted given my age at that time, and where I saw myself going subsequently. So they were very [00:03:00] cool about it and I was able to not retire, but I was able to pull myself out of the day to day. Technology space that was becoming more of a millisecond by millisecond business. 

Seven days a week, you had to be on available and ready to respond to any of the chaos that might come up. Whether it could be simply, I can't get internet, or all my documents are saying they're encrypted and I owe people however many tens of thousands of dollars in Bitcoin to get it back. And that was no longer. 

Appealing to me. I loved being one of the bosses of the company. I loved my business partners and our employees, but it was just no longer palatable for me to get up every day and have to handle what we have to handle when you're taking care of other people's infrastructures. And [00:04:00] given all that's transpired over the last decade, I'd say I made a pretty good call. 

I still talk to my former business partners on a pretty regular basis 'cause we were friends first and are still friends after and they are two tired individuals. COVID certainly didn't help. And the new distributed workforce environment added more pressure and more complexity to what they had to do. 

I'm glad that I've left that industry. Now. I'm still connected to technology. I still work. I still enjoy getting up now, going to work every day, but I have a more normalized, manageable schedule I'd say, than I had previously. 

Speaker 3: I hear you. Cybersecurity and everything that's going on. Now I can understand that it would be a millisecond business and how that could take its [00:05:00] toll. 

You mentioned that you're still in the pause, but then you said you still get up and go to work, so can you reconcile that for me? 

Speaker: Sure. So when I say I am still in the pause, it means I have not gone back to technology, but I'm still connected to technology. I now do business development for an insurance brokerage firm, and my area of expertise is on cyber insurance. 

And insurance to help protect technology companies. I am still a bit of a unicorn in that I am a technology person or somebody with a technology background who understands insurance as opposed to insurance person who's trying to understand technology and everything that's going on, and that's evolving with it. 

Head starts on blockchain and crypto, and now AI and whatever. The next piece will be, I've had experience growing up with [00:06:00] that, and so I have a very unique understanding of the challenges of ensuring that how to properly translate what a company does. For as a business and how they earn revenue and translate that to an insurance carrier so that carrier can understand the box by which they need to assign risk. 

And sometimes you can leave companies exposed if you're not really sure what they do or how they do it, and in which case, I take great pride in that. I can understand pretty much what most companies do to earn revenue. And then how to properly say, okay, this is what we're going to have to cover to do. 

So again, I'm still connected to technology. I'm just no longer taking care of it except our company's technology. You can't necessarily escape it fully, but at the end of the day, taking care of one company's, it is far different than, let's say a hundred different clients. [00:07:00] 

Speaker 3: Yeah, I've been in technology for 40 years and mm-hmm. 

Wiggled my way in and out and it's, I've done some marketing and. Some, sometimes it's hard to escape your past those tasks and those questions come up and you're like, I've got the knowledge. Alright, I'll do it. Yeah. So what was the gap of time between leaving the IT firm and then starting with the insurance company? 

Speaker: So, that's funny. The insurance brokerages was founded by my wife. Exactly a year after I founded my IT company and back then, so this was around 2016, she had just started a new line or expanded the business into an arena of consulting. And so she needed some new systems in place. To help her better track everything, because the insurance side was growing. 

Now this new consulting avenue was growing, so [00:08:00] she didn't have a great picture of the two of them, so I was supposed to be there for two weeks, putting in the new systems, training her team up, here's how to use it, here's how you have to put in the data and whatnot. Showing her how to pull the reports. 

And she just casually mentioned one day, you keep telling me how important cyber insurance is and it's going to be, why don't you see if you can start a practice built around that? For us, when I left my IT firm, it was not retirement type of deal. It it was just to gimme a new opportunity to do something else. 

And so I thought, you know what? I don't have anything. Else to do. My wife would probably be pretty bored of me sitting on the couch and twiddling my thumbs, trying to figure out the next step. So sure, I'll do this as an iterative step. And that was almost 10 years ago at this point. And now I've expanded my role on the [00:09:00] PNC side of the business. 

I'm now the CFO. Of the company. That's also another primary role and like I said, I'm also responsible for the it, but believe it or not, we use my old IT company as our outsourced IT provider. That's how I also get to stay in touch with what's going on in the the IT arena. 

Speaker 3: That's a great full circle story that you paused or basically said to yourself, done with the getting up and. 

Putting out fires every day. Mm-hmm. So I'm going to step back and it all worked out great. And then now that you know, that never really goes away. You could hire someone else to do it. Lo and behold, you know exactly who to hire. 

Speaker: Exactly. 

Speaker 3: So that, that's a great story. That's a great story. 

Speaker: So, and the beauty is I have to work around an insurance carrier's schedule, [00:10:00] and the beauty is insurance carriers like to work nine to five Monday through Friday, unless there's a claim process. 

There's not much I can do on weekends. So it's, it's a new way of working my life that I hadn't known in almost 20 years before that. 

Speaker 3: So a combination of I don't have to put out fires and I don't have to work weekends. 

Speaker: Yes. Yeah. 

Speaker 3: Yeah. That's a great outcome for a change of lifestyle, for sure. So how is it working with your wife? 

Speaker: So the funny thing is that we don't, we don't really work together, quote unquote. I'm in our office right now. She would be sitting there on occasion, but even if we sat in his office together for 10 hours, once we went home, we'd have to ask each other how our days went. I do one part of the business. She is now almost [00:11:00] exclusively on the consulting expert witness work that she does. 

And so at the end of the day, unless there's something of a historical client nature that she's been connected to, 'cause we have some clients that have been with us for 20 years now. She turns it over to the team that she's put together and I end up talking to the VP of benefits. More than I end up talking to Susan on a daily basis because I don't do benefits. 

You do not want me doing your benefits. And so when somebody comes to me and says, Hey, I need help on a group plan or an individual plan, I say, here's the benefits team. You want that expert doing that? I'll take care of all your. PNC questions, and so that's how we communicate with each other more often than we actually communicate with Susan. 

Speaker 3: That's really interesting because we hear stories. Some family businesses work well and some [00:12:00] families should never be in business together. 

Speaker: Yeah. 

Speaker 3: So it really interesting that, I don't know that your situation would really lend itself to, I work with my wife because it's not really a daily engagement on at the business level that you have with her. 

Speaker: No. No, and I think that did. I don't think we'd have a problem working together though. We are too. Very opinionated, very strong-willed individuals when it comes to certain things. We're also, we understand that, hey, you can't see every tree or every forest, so you need another set of eyes. But in this situation that we've evolved into, it's actually given Susan the ability to do what has really become a national exposure for her. 

And that would be tough to do if she was constantly dividing her tension among all the parts of the [00:13:00] business. That's how it evolved to where I became the CFO. Is because she actually hates that part of the business, the bookkeeping, running the reports, trying to figure out budgets, and that's not what she likes about being an entrepreneur. 

And I said, fine. I did it in my old IT firm. I can do it here. No problem. I enjoy that part of the business side of things. So it's actually worked out perfectly for both of us. She gets to focus on what she really likes. I get to focus on what I enjoy doing. And while insurance is not nearly the sexiest business you could find, at least for me, it's always interesting because a prospect coming in that's a doctor's office is different from a new startup tech company, different from a mom and pop cafe who needs coverage on things. 

So at least every day I get something different. I have to figure out. Different [00:14:00] threats or risks to certain businesses. So at least it keeps me engaged, keeps me thinking, and people oftentimes realize, in fact, I talked to somebody earlier and I was talking about certain elements of a coverage they were interested in, and they said, I had absolutely no idea that existed. 

And I said, why would you, unless you had to investigate it like you do now. Pretty much 99.9% of the populace would never know that type of coverage exists, and that's why it's enjoyable for me because it's always something new. Going back to why I took the pause originally, it is not to use your term, putting out fires your life and you're able to breathe, think, and come up with a solution for somebody that will work for them. 

Speaker 3: Able to breathe and think. Yes. Mm-hmm. That is truly the core of pressing pause. 

Speaker:[00:15:00] Yes. 

Speaker 3: Is to be able to think and breathe. 

Speaker: Yeah. 

Speaker 3: And you definitely did that in the first place to make that initial decision. And I'm so glad you landed in a place that was custom made for you to move to deliver what you're looking for. 

So now what do you do with your weekends? 

Speaker: Oh, I do a lot of things. I, I try to put my body through various physical. Endurance tests a lot of weekends. My wife and I are big into CrossFit. I'm, I'm a CrossFit coach. I do obstacle course racings like Spartan races, so I'm a Spartan coach along that line. So a lot of times the weekends are spent around either doing something physical on Saturday and then Sunday is all about sitting on the couch or sometimes both days are about being outside and doing a little bit of challenge, because I will say this. 

Where it, you could be a little bit more mobile in having to go to client sites [00:16:00] and whatnot, doing insurance. It's this all day front of a screen, hands on keyboard. So the ability to get up and move is, is very valuable to me. 

Speaker 3: So were you a CrossFit coach when you were with the IT firm? 

Speaker: No, I got my level one about, uh, 2018, I think, and then I got my level two actually just about a year ago. 

Uh, I started coaching just about six, uh, actually seven years ago now at this point, 

Speaker 3: it sounds like your pause changed your life. It. 

Speaker: It did. I made the right decision. It was difficult because it's something you found, it, you grew. I was doing it for with friends for 12 years. We had grown it in a way that it, we were all proud of what we were doing. 

It's just that I could see what was coming. I could see how I was reacting to the alarm clock every day, and it [00:17:00] just was no longer something that I knew I wanted to do. I could have done it. But I had the capability and the wherewithal, the self wherewithal to know I didn't wanna do it anymore. And I figured I've developed a lot of experience, a lot of skill sets. 

If I leave, I'm sure I could either start something or find something that would fit those skill sets and a want. And so I decided that was the time. 

Speaker 3: Congratulations on that decision. 

Speaker: Thank you very much. 

Speaker 3: So I have one last question for you, Sean. What advice would you give other leaders as to when they would identify it's time to press pause. 

Speaker: So I would probably give the same advice that I give to a lot of students and want to be entrepreneurs. I've mentored over the years and still do. Is that the easiest person to lie to? Is that reflection in the mirror? And if you can [00:18:00] be honest with that reflection as to what motivates you in your life will be so much easier. 

My brother and I are the perfect examples. My brother likes toys and he likes experiences, and to do that takes money. And so he's been in banking his entire career, but he's had to deal with. What you have to deal with being a banker, both in the internal side of things and with your customers, and while he makes a great living and will retire long before I will, he's had to deal with a lot of headaches that there's just no way. 

I would've ever dealt with. And for me it was always I wanted to be the boss. I wanted the outcome of a situation to truly be dependent on my capabilities and the decisions I made. And once I came to that realization that I would be a great [00:19:00] worker, but a terrible employee, everything I always did. Was geared around doing my own thing and being in a position to be quote unquote, the boss. 

And so I tell people all the time, you have to be honest about what motivates you and not be shy about it. And so if it's money. Pursue what will make you the money and be ready to deal with that. That if it's, you want to be the entrepreneur and you have a great idea or want to give it a shot, you have to pursue that. 

You have to work toward that, but that honesty with your reflection, I think is the most important piece of advice I could ever give. 

Speaker 3: Be honest with your reflection. I think that's an amazing piece of advice and really not one I've heard on any of the other episodes, so I think, 

Speaker: Hey, I'm original. 

Speaker 3: Thank you. 

You definitely original, and I have to say I'm probably a better boss than I [00:20:00] am employee as well. My career has been, yeah, 

Speaker: back and forth. I was a terrible employee. I was a great worker, but I was a terrible employee. I didn't know when to keep my mouth shut and yeah. Being the boss, all you do is argue with that reflection, but that's much better in my opinion. 

I 

Speaker 3: love it. Sean, I am so glad that we had the opportunity to have you as a guest. 

Speaker: I really appreciate it. 

Speaker 2: Thank you for listening to this episode of Time to Press Pause. If you're interested in learning more about Sean, go to combs and co.com. That's C-O-M-B-S-A-N-D-C-O. Dot com. If you're interested in learning more about his veterans nonprofit, go to pancakes for roger.org. 

If you're interested in learning more about me, please visit the salient strategist.com and be sure to sign up for my newsletter to get the up-to-date information on my new book. 

And please listen again wherever you listen to your podcasts.