Episode 37: Burn the Boats
26 Sept 2025 · 18 min
In this solo‑host episode of the Stand Sure Podcast, coach Rob Anderson shares his personal journey through three major career pivots—from military service to corporate training, then to a Fortune 500 instructional‑design role, and finally to a full‑time coaching and wellness practice. He explains how each “ladder” he climbed eventually proved to be built against a crumbling wall, prompting him to adopt a "burn the boats" mindset: deliberately removing any option to retreat so that forward momentum becomes the only viable path. Rob outlines the psychological shift behind this mindset, recounts the fear and inner dialogue that accompany such a leap, and details a concrete, step‑by‑step process he used to execute his latest transition (setting a leave date, running the numbers, inventorying transferable skills, and turning that inventory into a runway). He then delivers three actionable life‑hacks for listeners navigating similar reinventions—converting fear into an immediate plan, tracking personal energy instead of clocked time, and engaging a coach as a thinking partner. Throughout, he emphasizes that passion does not make hard work easy but makes it worthwhile, and he invites listeners to a free coaching call via his website. The episode blends motivational storytelling with practical guidance for anyone considering a career, relationship, or identity change.
Chapters
Hey, welcome to the Stand Sure Podcast. I'm your host, Rob Anderson. I am a coach. I focus in areas of PTSD, wellness, military transition, as well as I have extensive experience in business coaching. And life coaching. You know, I used to think that success was this ladder that you climbed once. You put your head down and you take each rung as it comes, and eventually you'll get there. Except one day I looked up and I realized the ladder that I've been climbing Was against the wrong wall. As a matter of fact, recently I found out it was a crumbling wall. The work I did was—it was respectable. The paychecks were solid. Routine was very familiar. But my gut—it felt like a quiet alarm that wouldn't shut off. I was performing. But I honestly wasn't alive. Now, full transparency, I've actually done this twice in my career, maybe, and arguably 3 times in my career. This one is the biggest one. It's the most detrimental. So let me recap real quick. I did one when I came out of the military, something I was very familiar with, something I was very good with. Stopped climbing that ladder. Shifted over, started climbing the corporate training and content delivery or training delivery ladder. Did that for Fortune 500 company. And then right mid-career, I knew that I wanted to move to Idaho. I wanted to follow a dream and move to Idaho. And I took a pretty substantial pay cut at that point. To do it and start all over again. Climb that ladder again with another Fortune 500 company. Only this time I was, I was more ingrained in instructional design. I was still doing content delivery. I got into coaching. I mean, really, really coaching a lot more so than what I'd done in my previous positions. And then As I was climbing that ladder, making it to senior positions, eventually contracting, the beginning of 2025, that wall, it didn't crumble, it crashed down. And so I've developed this concept of burn the boats. Now, there's times where I've made subtle transitions. But when that alarm goes off and you realize that either that career path is crumbling, maybe you're getting outsourced, jobs going to India, maybe you're getting replaced by AI, and you have to make that change. Which is what I did. That's where I developed this mindset of burn the boats. And it's a bold phrase for a very private moment. Historically, the idea is removing the retreat option to the only direction forward. Now, you can do this in, in a career. I've had to do it in relationships. I've had to do it with changes. It's the idea of removing the retreat option so the only direction that you can go is straight ahead. In personal development, it's not about being reckless. It's about commitment. It's telling yourself, I'm done negotiating with the old excuses and I'm all in for the next version of me. And I got to tell you, I really like this next version of me. On a personal level, I did it— I did this around 2003 and it was through the work of John Eldredge and his book Wild at Heart. It's telling yourself, I'm done. I don't want to be like I was yesterday. I'm tired of negotiating. I'm tired of my old excuses, and I'm all in for that next version. And it's terrifying because your boat— Your boats are comfortable. The boats are what brought you to where you are today. Boats make for great stories about someday. But for me, they kept me circling the same shore. You know, my boats looked like a couple different things. You know, I've had a boat that was Steady career. I had a boat that was steady relationship. I had a boat that was steady lifestyle. I had a boat that was steady mentality. And this last one, again, walking away, it meant a huge pay cut and a huge lifestyle reset. And if you've ever done it, you know the soundtrack. It's going to be asking you things like, hey, are you sure? What if this fails? And I, man, I think about that a lot. This change I'm making, this career change, this life change I'm making right now, what happens if it fails? That soundtrack includes either outside sources or voices inside you saying that you're a loser. That you're a poser? Who do you even think you are? And man, when I— for my pivot, those questions didn't disappear. In fact, they got louder. It's like somebody cranked it from 6 to 11. But the energy of building something aligned with my values, it also got louder. Purpose doesn't silence fear; it outvotes it. I want you to write that down, capture memory, come back to it. Purpose doesn't silence fear; it outvotes it. There is a moment in every reinvention when the old timeline. And the new timeline overlap. I, I'm still having to answer text messages and emails and social media messages and talking to people that are all from my past, and I'm doing it while I'm sketching the dreams of my future. It's about discovering, but it can also be disorienting. I can remember thinking, and you've probably been through this too if you're going through this right now, I used to be the person that people call for X. I was in a meeting the other day with someone who was trying to develop some training. And they're young, but what they didn't realize that in that room, in that room was someone who might, you know, someone that my counterpart was, was a subject matter expert in that area. And I've got 30 years of training and development experience. You know, there was a day where I would get a call Asking about installing learning management systems or designing curriculum or building e-learning or coming out and providing group coaching to someone. But now I'm also becoming the person that they call for Y. They used to call me for X, and that was my specialty. But now they're starting to call me for Y. I have clients now. So the way I set up my coaching is that if you do the month-to-month, once a week we can do a 15-minute check-in call, totally up to you. And I love it when my clients take advantage of that. For one, it keeps me on my toes, keeps me honed, keeps me true to my word. It helps them out. And I love seeing the growth, and I like being there with those steps. I'm becoming the person they call for Y. That's the letter Y, not W-H-Y. I used to get called for X, now I get called for Y. That gap is where most people will turn the boat back around, because in that gap, you don't have— sometimes you don't have the proof yet. Because you're only in the process. So you have to create proof while you're in motion. Practically, burning the boats for me meant drawing a line. No more half— no more half measures. Okay, we'll put it like that. I set a date to leave the old ladder. Actually, honestly, it was set for me. In other cases, I set the date, but for this recent one, it was set for me. The date was set for me. But afterwards, I ran the numbers, figured out what we could live on, what we could cut, and then I listed every skill from my previous world that still had value in my next one. In fact, it became a resume. Communication, curriculum, coaching, storytelling. Operational discipline. That inventory became my runway, became my gangplank. The point wasn't to torch everything I learned; it was to stop letting the past dictate my future. And that's why I'm on the path I'm on right now, and that's the path I'm inviting you to if that's what you need to do. There's a myth that passion. Makes the hard parts easy. And it doesn't. But passion makes the hard— let me think of a way to restate that. Passion makes the hard parts worth it. Passion makes— passion does not make the hard parts easy. I'll say it again. Passion does not make the hard parts easy. Passion makes the hard parts worth it. Some weeks following my passion, and it still, it looks like designing, you know, sometimes it just looks like designing chaos. For some weeks following my passion, It looked like I was designing the pathway or the programs. Are there weeks that look like staring at my bank account, staring at the spreadsheets, wondering how I'm going to stretch out the dollars, looking at what was left in the gas tank, looking at what was left in the, in the cupboard? Now, as I step down, try to figure out how I'm going to do prom dresses and pay for football tickets and for games and all that kind of stuff, right? And it's become a process of stretching faith, even stretching faith in the mission at the same time. And what I'm doing is I'm choosing a later reality because I want my daily work, the things I do every single day, to match my deepest convictions. And I know there's people out there that are doing the same thing right now. Every time I felt the pull to go back to the boats, take the safer gig, Make the comfortable compromise, I ask myself, will this move me toward the life I'm building or back to the life that honestly I outgrew and it was killing me? Burning the boats doesn't mean being irresponsible. It means taking away the option of abandoning yourself and your path. I gave myself non-negotiables that I'm still working on. I want to keep my standards high even if the budget gets lean, which it does get lean. I do things like I protect my mornings for doing the podcast, for doing deep work. I've got protected times where I do coaching. Those things are priorities, even if my to-do list is out there screaming. I'm going to stay connected to the community because reinvention in isolation quickly turns into— it just turns into mind-numbing work that doesn't get you anywhere. So real quick, I want to give you 3 life hacks that are helping me navigate this leap. Number 1, convert fear into a plan you can execute on today. You have to break out of the big scary. What if this doesn't work? And you break it into smaller questions. What result am I trying to create this week? What is the next visible action that proves that I'm serious? And then who needs to know about it? Hack number 2, track energy, not just time. On the old ladder, I scheduled by the clock. I still have to do that to a degree, but now I schedule by energy. I notice which tasks give me momentum and which drain me. I've actually built out a confidence— Excuse me. Confidence impacts That helps to get me through that. Hack number 3, if you're doing this, use a coach. When you're ready to relaunch, restart, or reinvent, you know, you can white-knuckle the transition or you can have a thinking partner who accelerates. A good coach is not going to give you their ladder. That's a mentor. But a good coach is not going to give you their ladder. They're going to help you build your own ladder. They'll ask the questions that cut through the fog, that help you design experiments to create real-world data. And they're also going to help find people to hold you accountable. I'm sitting here thinking as I'm going through this, I want to do a larger series on burning the boats because I think a lot of people are at that point right now. They got a lot of stuff going on. change careers. Maybe they're going through relationship issues. Maybe they're just not happy with who they are today and they want to make that change. Hey, I want to invite you to at least give me a call. Let's do— and I'll give you a free coaching call. Go out to www. And there's a, there's a link that you can click that says access my free coaching. Let's just talk. Let's— I want to better understand what you're going through. If it works out, great. If it doesn't, hey, no pressure. We had a great conversation. Maybe I was able to help you uncover a few things. If it does work out, that's awesome. And I look forward to working with you. But again, no pressure, no obligation. www.stanshirescoaching.com. I hope you have an amazing day. If you're going through this burning the boat Scenario, let's talk. I'm going to expand on this quite a bit. All right. Have a great day.
