Cut The Tie | Success on Your Terms
1st - Define your success on your terms.
2nd - "Cut The Tie" to whatever is keeping you from that success
Cut The Tie is not just a podcast; it's a movement. Hosted by Thomas Helfrich, this highly impactful show features short-form interviews with remarkable individuals who share how they redefined success by boldly cutting ties with fear, doubt, bad habits, toxic environments, and limiting beliefs. You'll hear exactly what they cut, how they did it, what it felt like, and how their lives — and the lives of those around them — changed forever.
Each episode is inspirational, motivational, and — most importantly — actionable. You'll gain real strategies and mindset shifts you can immediately apply to your own life and career.
Plus, every day, Thomas drops solo short-form episodes designed to fire you up, challenge your thinking, and remind you that the only thing standing between you and your potential... is the tie you need to cut.
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Cut The Tie | Success on Your Terms
“Comfort Is the Enemy of Growth”—Why Shane Silsby Chose Uncertainty Over a Steady Paycheck
Cut The Tie Podcast with Thomas Helfrich
Episode 285
What does it take to leave a steady government career and build something of your own? In this episode of Cut the Tie, Thomas Helfrich sits down with Shane Silsby, a former public sector leader turned founder of Silsby Strategic Advisors, to talk about cutting ties with stability, embracing ambiguity, and redefining success on your own terms.
After two decades serving in government leadership roles—including as a director at the sixth-largest county in the U.S.—Shane walked away from a reliable career path to build a business rooted in flexibility, impact, and freedom. But the transition wasn’t easy. From navigating the unknown to confronting financial pressure and family fears, Shane shares the mindset shift that made it all possible.
About Shane Silsby:
Shane is the CEO and founder of Silsby Strategic Advisors, where he provides fractional executive services to local governments and strategic guidance to private sector clients seeking to work with public agencies. With over 20 years in government leadership and now years in entrepreneurial consulting, Shane blends insider knowledge with a deep understanding of both operational and policy complexity. He’s also the author of Managing for Meteors, helping organizations prepare for disruptive change before it strikes.
In this episode, Thomas and Shane discuss:
- Why cutting the tie to a steady paycheck is terrifying—and necessary
Shane reveals the internal battle of leaving security behind in favor of more meaningful, high-impact work across the country. - How corporate life wasn’t the answer either
After a brief stint in the private sector, Shane realized real alignment came from doing things his way, not chasing profit-first mindsets. - How to get comfortable with ambiguity
From family pressures to financial uncertainty, Shane opens up about the daily mental challenges of solopreneurship—and how to navigate them. - The silent tie no one talks about: spousal pressure
In a rare moment of vulnerability, Shane shares the honest conversations with his wife about uncertainty, money, and chasing an unclear dream. - Why 2025 requires a pivot mindset
Whether you serve local governments or the private sector, Shane explains how agility and awareness of federal and global changes will define the next wave of entrepreneurship.
Key Takeaways:
- Ambiguity is the price of freedom
Solopreneurship means betting on yourself—even when you don’t know the odds. - Don’t wait for certainty—act anyway
The right time never comes. Move forward, even in the fog. - Corporate doesn't always mean comfortable
Sometimes, the “safe” move turns out to be just another box. - Your spouse is part of the journey
If you’re making big career changes, bring your partner into the conversation. Often.
Connect with Shane Silsby:
📘 LinkedIn: Shane Silsby
🌐 Website: silsby-sa.com
📧 Email: shane@silsby.com
Connect with Thomas Helfrich:
🐦 Twitter: @thelfrich
📘 Facebook: Cut The Tie Community
💼 LinkedIn: Thomas Helfrich
🌐 Website: www.cutthetie.com
📧 Email: t@instantlyrelevant.com
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Welcome to the Cut the Tie podcast. Hello, I am your host, Thomas Helfrich, and I'm on a mission to help you cut the tie to whatever it is holding you back from success. And today I'm joined by Mr Shane Silsby. Shane, how are you?
Speaker 2:I'm doing great, Thomas. Thanks for having me again.
Speaker 1:I appreciate it. You know I've been speaking for several months trying to set this up and I'm looking forward to the conversation. But take a moment to introduce yourself and your business.
Speaker 2:Yeah, thanks, thomas. Shane Sillsbeet. Here I'm the CEO and founder of Sillsbeet Strategic Advisors. It's a solopreneuring journey and I try to help cities and counties across the country, generally speaking, with strategic initiatives and or private sector companies trying to work with government entities to deliver services or projects. That's the high level. And then I try to keep track of federal, state, local elements to try to help those clients.
Speaker 1:It's a tricky thing with everything going on in the world today, with Doge and whatever languages you are, and you're more than welcome to share your take on kind of what the things are with that. Before you do that, maybe tell me why, though, people pick your firm over others.
Speaker 2:Yeah, they pick my firm exclusively because I'm on the Cut the Tie podcast, Thomas. And then they pick me because of my knowledge in the industry and my strategic approach to things, taking advantage of my 20 years in the public side at cities and counties across the country, and then my efforts on the private side to be engaged in national and sometimes global elements to help them with those key decisions they need to make, especially when we've had a ton of turnover in the industry. We talked about that a little bit before, about you got new people everywhere. They don't remember what happened before and they may not have the experience to know where to go next.
Speaker 1:Yeah, and I think that's important. So one of the things I like about your business you served a long time, in the space of which now you serve from the private side. Not everyone has that. Some people may have been like two years in or an intern, but you were like in it, that was a career and you shifted out. So maybe talk about that journey a bit from the public to the private sector and I know you had lots of challenges and things, but what was the biggest tie you had to cut during that transition?
Speaker 2:Yeah, the initial impetus really was to have career growth. After that amount of time on the public side and looking at, you know, when you're in the public sector you're working for an agency. You kind of put all your time, effort, energy into that agency and once you've implemented that good idea or that good project or whatever that can be kind of it for that agency, you got to find something else. So to grow and I wanted to help kind of all agencies theoretically across the country, that was the impetus to do that.
Speaker 2:Now, the things that hold you back from that are the things that we all experience as entrepreneurs or solopreneurs is the lack of consistency of what's going to happen every day. Right, it's a lot of ambiguity and almost all of it is out of your control. Right On the government side, some things you can control, some things you cannot. As a solopreneur, you can almost control nothing other than your effort and energy. So it's really that ambiguity that was the big issue of. If you have a family and you have all the expenses you have to live, how do you go from that standard paycheck, if you will, to betting on yourself for not knowing where that next paycheck might come from?
Speaker 1:Do you remember the moment when you knew you were going to make the move?
Speaker 2:I do remember that moment. It was just pre-COVID, it wasn't because of COVID, I didn't project that. But that's when I did my shift and it was having a discussion about what the next steps might be in my career and seeing that the next, let's say I was six and a half years as a director in the sixth largest county in the country, that the next six and a half years weren't going to be as productive or rewarding as the last six and a half, because it was just going to maybe be a little bit more of the same, and the only thing that would change in my resume is the time, not the content necessarily. So that's when I said I've got to do something different.
Speaker 1:Yeah, and how did you do it different though? So take me through the steps a little bit, of how you cut the tie.
Speaker 2:Yeah, so interesting journey to get to this point. I first shifted to a corporate entity to provide services across the globe, really as global, but mostly focused on the Western United States, and so I had that opportunity when I left from the government side to the private side. I first worked for a global corporation and that was interesting, and then that exposed me. It gave me some stability to start off by my leaving the government side, but it also exposed me to all the things on the business side that you you understand a piece of from the government side.
Speaker 2:Right, you're dealing with contracts, you're awarding services, you're delivering services, you're having oversight, you have legal issues to deal with, but that but, but the ultimate goal is is the delivery under a budget, but then flipping over working for this national corporation, it was more about, okay, the business operations and the profit, right, and so that was a good send off to learn more about that element. But then what ended up happening was that the corporate philosophy was moving way more towards the profit side as the way to balance the scales for what that industry was doing, versus my personal approach, which was trying to help people, treat people well and work with clients that I like to work with, which we all hope that that will lead to money at the end of that road, where that relationship but it's not where you start from which is a little bit different than corporate philosophy.
Speaker 1:And you can this impact question, how you need to, but what impact has it had on your life or customers or your family?
Speaker 2:Yeah, I mean the biggest impact is I've been able to work with people across the country that I wouldn't have been able to support at one level down Right so, if I was a peer for a county or city across the country, and but now what it's done is opened up right the network so people can reach out to me and they do from all across the country to try to have a discussion about whatever it is they're dealing with, and that's a huge shift. It wouldn't have happened before. From my family, a little bit, I do get to spend more time with my kids and my wife, my family Whereas on the government side you're going to the office and there's a reason for that as a leader, 10 hours or whatever it is, and so you're gone from your house for that long, and so that's been a shift also as well.
Speaker 1:Yeah, that's been a big one. If you could go back in time to any part in your timeline, when would you go back and what would you do differently?
Speaker 2:Yeah, good question. When I left my government role at the county, it was in March of 2020. And we all know what happened there. That was the pandemic timeframe and I remember, when I was interviewing for my role with this national corporation which I had a C-suite role.
Speaker 2:I said, well, the biggest issue between public and private is the uncertainty to the market or whatever. And I remember the discussion where they said well, the only thing that could affect your role in the C-suite is like if there's some global phenomenon that happened right, otherwise what you do is necessary, we need it, there's no way it could be impacted. Well, that thing happened and so I don't know what I would do differently. But if I had that knowledge of the foresight, I probably would have put some other security measures in place or whatever it was in the negotiation to try to avoid kind of more the impacts of that. I'm sure we all would to some extent pre-pandemic.
Speaker 1:Well, I mean, on that line, I just go back and buy Bitcoin as soon as I have money, and maybe Apple stock. Yeah, maybe those two things. But I think it's more of a metaphorical question that what are the answers you should do now? So what's the big thing now that could disrupt your world? It's like, well, maybe I should do it now. Yeah, how about some rapid fire?
Speaker 2:So who gives you inspiration? Yeah, I get inspired by people who are kind of in the space, like yourself, that kind of launch out and provide perspectives and maybe aren't necessarily as afraid of the consequences of what might happen. I don't mean being overly negative or whatever, but everybody has a counter opinion nowadays, and so those that are willing to share kind of fact-based approaches to an opinion or observation, I kind of admire those people because it would be easy for them just to stand back and let all this information, or whatever you want to call it, move back and forth and not enter into that fray to try to provide some reality. But those that do that I have a lot of respect for. Nowadays, with so much content out there, obviously it's hard to break through that noise.
Speaker 1:It is very hard to break through the noise. And then I generally find that, like, the more specific you are with what your content and serve, and the less the vanity metrics the more satisfying is, the more effective it becomes when you leave the vanity metrics out. If you truly can get them out of your way, then your ability to be successful, so to speak, is better, because it really defines what you're doing. Am I trying to help entrepreneurs in this space or am I trying to be famous? And the truth is I'm trying to help entrepreneurs. I don't want to be famous. I want to be the rich guy on the beach that no one knows about. I don't want to be you know. So I appreciate that. What's that must-read book?
Speaker 2:Yeah, that's a good one, and there's a lot of authors coming up that are as well known. I mean, you can, obviously you can read my book, right, managing for Meteors, and it's about how to prepare for those things, and we have a new meteor coming on right now with stuff happening a little bit at the federal level with funding. But other than hardcore books, I try to reference sources that are digital but have a way to cut through and try to get you some fact-based information, right. So look at the source, whether it's a national journal or, in my field, I look at engineering elements or infrastructure elements or science-based sources, and then I try to get the facts pulled from that pretty quickly because I need those when I'm having discussions and try to help people with strategy. Right, I need to have that background of where the facts are and try to give recommendations.
Speaker 1:In your recommendations. Maybe you should take that a step further for yourself. Who or what was the best business advice you've ever received?
Speaker 2:Yeah, the best business advice I received was to as in moving into the private sector and especially as a solopreneur was to be comfortable with ambiguity and that was great advice and it's still hard for me to adjust to every day, but that was good for anybody, I think. Trying to enter the arena that we're kind of in, thomas, because I think a lot of people maybe like yourself, they make it look easy but they don't understand everything that happens behind the scenes. In order to have a 15-minute discussion or in order to put out that other podcast or to write that article or to do that presentation, you're seeing the 15 minutes of finished product and not seeing the hours of work that goes behind that and I think sometimes we make it look very easy but people might not understand right what, what it takes to to have that end product or that end result.
Speaker 1:Yeah, that's a really. I think that's some advice. People should realize that if you see something you really like, that may not even be the finished product they expect. But it was not that. I mean, for example, on our show, every 90 days we look at and go what can we do to improve? And this last 90 was let's shorten the show and let's make it more not so much like what you do great, but more about how did you get there, like, what's the entrepreneurial journey and what did you have to overcome. You know and I'll probably take it a level further and being like, how'd that impact your life? What was the meanest thing your wife said to you during that time? Like you know, and the truth, now I probably will take it there.
Speaker 1:I just haven't figured out the comfort level of how to do it with the guest, because I know in your journey you've had some not that you've told me this, just, but I know you've had some horribly tough times talking to your wife about money or what we're going to do. What about the uncertainty of it? You used to be so consistent. And what are you doing If you don't have that? I'd be surprised If you don't have that outside. What the hell are you doing? Why couldn't you just be this and that? You know what I'll experiment with you? Tell me about that interaction as you're doing it, because that is a tie that a lot of people don't talk about.
Speaker 2:I talk about it in my book, but I'll tell you that that is the one that people, that's the silent tie of, oh whole God, spousal pressures yeah, we're just having a discussion this morning about it Right and looking at with recessionary pressures that are happening in the industry and you have to be aware of that, you don't want to be caught on the wrong side of some of that and what that means for our family and what we need to do to adjust and pivot and we can talk a little bit about what some pivoting I think entrepreneurs should be thinking about. But, yeah, to make sure right for supporting our family, our kids and all that stuff that we are thinking about, right, what, what could go wrong or what could go right and how to mitigate some of that and I know my wife's looking for that I'm like I can't.
Speaker 1:I can't even tell you that I'll make the same amount every month, because if every one of my customers goes, hey, I'm quitting, we're kind of screwed for a few months and so like, because they can just do that, like they can, even if you have contracts, you're not going to go after it. You don't have money to go do this. Like. It's like that. Even in this podcast it's right now like a five-day-a-week show. I'll probably move all the interviews to Sunday and just do motivational stuff during the week. I don't know. You always are evolving to try to find the thing that tweaks it a little bit better, to make it a little more impactful, and you'll do that in your business either be a podcaster or consulting, and I think that's really good advice, to get used to that uncertainty. But if you embrace it, that's where the opportunity lies, the opportunities and the uncertainty. So, because a lot of people shed front of it. But if you dive into it and fight your way through it, you'll find something that wasn't found before.
Speaker 2:Yeah, it can produce. A trait that improves your agility and your ability to be agile can be an advantage to your customers, because they are sometimes dealing with something that is outside of their main line or they're outside of that box, and that's why they need somebody that can think that way or be more agile or try to address the issue in a not traditional way. Agreed.
Speaker 1:If there was a question I should have asked you today, and I didn't what would that question have been and how would you have answered it?
Speaker 2:Yeah, I think the main question that's on my mind is what should entrepreneurs or solopreneurs be thinking about in 2025 that they might not have had to deal with in prior years? And for me, we talked about this a little bit it's about that agility and being able to pivot right. So we think about we don't like to talk about politics or what's happening at the federal level, but that does affect especially small businesses. If your business is in commodities, moving products, and your product comes from a certain country, you better know what the impacts are to you and your business going into 2025, because that's going to affect your customers and your business.
Speaker 2:If you're in the position, like what I do, for services, professional services, I need to think about how that or the loss of federal infrastructure funding in my field, for example, is going to affect my clients, my cities and counties, local governments, because if I'm not thinking about how they can react and adjust to that, then I'm not going to have the value, and why would they pay me or give me a contract if I'm not providing them that value? They can do nothing on their own right. They don't need me to be sitting here doing nothing. So to me, it's about that pivot and then in that pivot you can also try to identify, I think, new markets that you might not have thought about before. Whatever it is right, it's the force-counterforce argument. So if something's pushing this way, what pushes against it or what's helping it push, and can you be involved in that space to again help your business and help your clients?
Speaker 1:That's great. Who should get a hold of you and how do they do that?
Speaker 2:I think we kicked off with this, but leaders in government sectors, cities and counties or whatever your agency is that are trying to do strategic initiatives or need what I call fractional government executive support which is what I do they should contact me. And or private sector companies that are trying to work with cities or counties across the country and try to figure out where they can fit and make value out of their asset. So you can get ahold of me through LinkedIn Shane Sillsby contact me there. You can send me an email, shane at sillsby-sacom. You can go to my website, wwwsillsby-sacom, or my book website, managingformeteorscom. Take a look at some free stuff I have in my book and then give me a shout.
Speaker 1:I'm going to have you do your thing again. Your phone was going do-do-do-do-do-do-do-do-do. It was interrupting your thing, but I didn't interrupt you, so do a brevity version of it. I'll ask the question again because I was like it won't be an audible but it'll be distracting when you get to it. Who should get a hold of you and how should they?
Speaker 2:Thanks, thomas. The people that should be reaching out to me are local government leaders that want support from a strategic standpoint. I offer what I call fractional government executive services, so I come and help them with their issue or whatever it is organizational elements, funding elements and then move on that are trying to work with local governments and see how they can better improve their services to provide that value. So it's everything in the local government space, and then they can get to me through LinkedIn. Just type in Shane Sillsby should be the only one that comes up, as far as I'm aware and or you can get to me through my website, sillsby-sacom. Or you can get to me through my book site, managing4meteorscom Some free things you can look at there and then shoot me a note later.
Speaker 1:Awesome. Thank you so much, shane, for coming on today. Appreciate it. Tom, keep up the good work. I appreciate it and everyone listening he made at this point. I appreciate you. I want you to get out there. Go cut a tie to something holding you back. Become the best version of yourself. Unleash the best version of yourself. Don't let anything stop you from success. Thanks for.
