He Coached the Boss Who Was Firing Him

Dan Smitley got laid off by someone he called a friend. Then he caught himself coaching her on how to do it better.

This Soul Session is about the inflection point that does not come with a clean ending. Dan has been laid off twice, both times by people close to him. The second time, an accidental screen-share showed him what they really thought.

We get into:
- Why the layoff is the easy part, and the chaos after is the real work
- The "five whys" Dan uses to find his core when everything is uncertain
- Separating how you make money from how you add value to people
- Why faith and family drive every decision he makes
- The cost of being the guy who always helps, even when he is the one who needs it

Transcript

SPEAKER_01 0:03

All right, folks, thanks again for joining us. Another soul session. I'm excited for this particular series that we're doing this season. As you know, we're around true stories and inflection points. And um after I've known this guest for about a couple of years now in the professional realm. And so I had an opportunity to connect with him about some of the stories that we're sharing. I'd love to turn it over to Dan and have him introduce himself. And as like we like to say here, um, you know, how would you describe yourself without a job, a career?

SPEAKER_00 0:35

Yeah, so thanks, man. I appreciate the opportunity to chat. Um, how would I describe? I'm first and foremost a curious person, literally in every context that I am in. Um, my family, my faith, my profession, I am a curious guy. I love to ask questions. Um, I'm a people person, as much as I'm an analytically minded trying to figure things out, the analytics that I'm trying to process are always connected to people, trying to understand, right? Almost like a counselor, if you want to think of it that way. Like someone that's curious leans in to try to help others. Um I would say that those are probably my biggest core, it kind of regardless of environment that I'm a part of.

SPEAKER_01 1:17

Yeah. And um, it's interesting, like different people take this question different places. Um, I know obviously you're a dad, your husband, um, and many of that. So it's one of the things we try to highlight is this idea that we're more than one thing or one person, and a lot of things can be true. You hear curious people, um, and under underlee that because like that analytical thing is like trying to understand the why so you can help people. That's I don't know if I'm all off base, but that's how I would summarize it.

SPEAKER_00 1:48

Always. Uh I think right here, Simon Sinek's start with why has been incredibly formative for me. Um, and that is how I process where tension has arised professionally for me, is mine a need for the whys. Uh, some of the conflicts I've had with my wife is about trying to understand, but but why. Um, it's hard for me to move into a what or a how, even with the importance of a who that I love and support or you know, value. Um that why is is critical for me.

SPEAKER_01 2:20

Amazing. Um, all right. We have a couple stories, real stories, really inflection point. I'll turn it over to Dan to just start sharing a little bit, set the scene for us, um, and take us into that place.

SPEAKER_00 2:33

Yeah, so the the setup of it is I have just moved over into a new organization. Um, it's actually an organization, small organization full of people that I've worked with before. I was actually a customer of theirs, and now I'm on the team. Um, small organization that is moving fast, trying a lot of different things, and there's a lack of structure. Um, kind of hard for a guy that loves why, right? Like I love a good heart behind it, reads behind it, but we're we're just shifting, moving, and I'm and I'm trying to do as much as we can. Um, but the moment still comes. The moment still comes where there's my first layoff. And I think it stings a little bit more because what's happening in the conversation is I'm getting laid off by someone that I kind of considered a friend. Again, if I've known this person for 10 plus years, they've referenced, you know, the family motif inside of the professional environment. And I literally had to ask, wait, are you talking so that we're ready for when we might need to do layoffs? Or are you telling me now that I am laid off? Like I was literally giving her advice, thinking about how she's going to lay off other people and how she needs to think about it and the process she needs to go through. No, no, I am getting laid off. Um, and it stung, but that's not even the inflection point. The inflection point came because I said, okay, now what how do I how to provide for my family? That that that is first and foremost my driving value, my faith, my family are the two things that push me to make the decisions that I make. Um, and so that was the starting inflection point. Unfortunately, I don't have this like conversion moment or this like that made everything come into crystal. It was the starting point of something really important, that process that honestly I'm just now, I would say, starting to really wrap up and and crystallize to say, okay, what started two and a half years ago is just now becoming crystallized. There were some refining moments along it. We can dive into it, but yeah, that's the moment, that's the inflection point. Getting laid off, and I'll note for the first time was um was really that my starting point.

SPEAKER_01 4:47

This is this is amazing. And like the idea that um there are different terms, like I have a term where I call the influential low point, or it's it's just the influential point in your life where um you never think things are the same. Like a personal story, real quick, is I graduated from Princeton, a chemistry degree. I thought I was, you know, the it.com, and then I went training for the Olympics. And if you know Olympics, um, you know, most people don't have like great uh sponsorship. I was working at a gym um doing Uber Eaps. I was in Phoenix, Arizona. And I remember there's a point where things were just not connecting. Uh I didn't have sponsors, I was out of job for a couple weeks, and I remember being at a gas station. I was like, wow, I need just five more dollars so I can make it home until this next paycheck drop. And like actually asking people at the gas station for like, man, can you spot me? And I'd like, when I say Dan, like in that moment, I was like, never again. Like, I'm gonna do whatever I have to do. You know, I'm still wanting to make the Olympics, but there was this like visceral thing was just like I not that I was better than it was just like how did I allow myself to be here? And I call that one of those like so influential points where you're right. That's she's that was like 10 years ago, that it's still like gardeners, like how I live my life. So I do have some questions for you as you were you're explaining that. So you um walk me through like so just explain it a little bit more. How small was it? How long were you there? Um, and then the last one I want to ask is like what was that conversation with your wife when you said, Hey, I'm going to a small company.

SPEAKER_00 6:28

Yeah, so maybe start at the end there. My wife has always been incredibly supportive of every professional move that I make, even though this one is kind of the weirdest of them all. So my background call centers, my background workforce management. Um, and this was moving from the operational in the weeds, in the trenches, kind of in the call center, to actually being part of a value-added reseller or vendor, right? So selling the software instead of being in the operations. And it was a pivot. She's like, You're you're crazy smart, you are driven and a hard worker, you can be successful anywhere. Like, yeah, it makes sense. Go for it. So, like, her support is always there all and at every step of the way. Um, how small? Uh, less than a dozen people. So I'm counting them in my head. I think when I joined probably pushed us into double digits because me and one other person that had recently joined. Um, so and they had been around. So as a customer, I was one of their first customers back in 2014. I joined them in 2022. Um, so I'd been had known them for close to a decade. Um, and again, that that relationship was close because as one of their first customers, there's a lot of interaction. They were very close to making sure that we were successful. Um, a lot of hand holding, a lot of relationship building along the way. Um, so it was a tight relationship. And moving over there felt weird, but it felt like a great opportunity. What she was painting, the CEO was painting for me was this like super unique opportunity. I think you're perfect for it. Um come to find out that's kind of just what she does. She's an encourager, she's a galvanizer. She's like, you're gonna be amazing at this. Uh, but she lacked sometimes that structure of making sure that you're successful, not just energized. And I came in energized and realized there's not structure. And I think that structure led to me not being able to be successful because I couldn't show them check, check, measurement of success, check.

SPEAKER_01 8:25

When you say lack of structure, it sounds like not great reporting, things were just out of oc, you know, and especially for someone, someone's like a comfort somewhere bigger. Was there like a specific thing where you're like, if they only had this, or like it was so blatant that a simple type of structure that they didn't have?

SPEAKER_00 8:46

I mean, again, I go back to why is focusing on people. And so something as simple as having a consistent process as to like who's meeting with who and when and why. You have direct reports, you should be meeting with them weekly, you should be having developmental conversations quarterly, we should have some sort of an annual review process that says these are your measurements of success, you did or didn't hit them. And and those sorts of structures I think help clarify whys and what's, but in support of whose. And that was something that wasn't there, something I had proposed, and I was trying to work with them. But there's a great example of that would have allowed just a little bit more structure, I think, for people to feel seen and to feel supported instead of just encouraged at times.

SPEAKER_01 9:29

Yeah, yeah. Okay, super helpful. And now I am assuming most of these happen very quickly. I've had uh it has happened to me three times in my career, Dan. Um, and most of them are 10 to 20 minutes, not even maybe five to 10 minute calls. Um, hop on. And uh I have to I would like to think the third one was yeah, I was a bit more callous by the time I knew it was coming. How were you feeling like coming off of that call? Describe that to me. Like, where's your head at? Like, yeah, look, because everyone goes through it differently. And for your first time, I'd love to hear like how you were feeling, what was going through your head there.

SPEAKER_00 10:12

I think I think the right word is embarrassment. And it's an interesting embarrassment. Embarrassment's important to me. I hate being embarrassed. Um, I know exactly the roots of it, it goes back to my childhood. I can paint the, I can I know the string as to why. Um, but it was embarrassment and it was unique because it wasn't embarrassed, like, oh god, I'm laid off. What will people think of me? There was a smidge of that. It was embarrassment of like, am I so much of a people helper that even as I'm getting laid off, I'm trying to help her lay me off well. I'm literally trying to tell her, now if you need to do this with other people, like this is how you need to approach it, this is what you need to. Have you thought through like this type of communication? How is this gonna happen? How is this? And it was embarrassment of like, I don't know, the an element of are you so others focused that in that moment you couldn't just allow yourself to like feel the feels that you have to and like I'll support you, I'll help you, I'll support even as and I don't know if that's good or bad, but that was the emotion afterwards of just like dude, like chill out with trying to help people so much. Like, just let her suffer. Let let her just flail for a little bit if she doesn't know how to go through this process.

SPEAKER_01 11:26

Yeah, it's a weird that's that's one of the first time I've heard that reaction of um, you know, almost off yourself. And then and I think most people are in this place of like, wow, what does that say about me that I got laid off? Like, will people think it's performance? Yada yada. But you were on the sense of like, wait, I'm not even giving myself time to step back and just honor it. Um, and it sounded like that started a massive journey for you. Um, so there's embarrassment, which was one of the emotions, and I'm sure there's a lot more emotions that you, as you had mentioned, the drive of wanting to provide for your family. How did you even start to think about the next steps? And not just tactically from I need to get a job, but I'm sure you you went on other journeys as well, um, emotionally, spiritually, walk me through that.

SPEAKER_00 12:20

Yeah. So uh the tactical steps were the copy paste of everybody. And and it wasn't unique in the jobs I applied for, how I crafted my resume, et cetera. What was unique is that I had already done the networking, the content creation, the thought leadership prior, so that when I landed on the market, I had a good community around me to support me. Um, and part of that community came in as a consulting gig. And so, again, going back to this kind of flaw of Dan to first thing to help and then something else, someone came to me and was like, hey, we've got these issues. Do you think you can help? I'm like, Yeah, absolutely. Totally get what your problem is, understand how to solve it. Like, let's talk. And so we're talking, and he's like, So, you know, blah, blah, blah. When could you start? And I'm like, Wait, are you are you thinking about like paying me for my advice? Like, is this or are you thinking of it? I'm like, I'll figure it out. And so I started reaching out to my consulting friends, like, how do I do consulting? Like, what does that even mean? Like, do what kind of documentation do I need? Do I need an LLC? Like, what's too much? What's too little? Um, and literally stumbled into a consulting gig that stumbled me into another consulting gig that was the bridge between my layoff to my next W-2. Um, that journey felt, I mean, don't want to over-spiritualize it, but to some extent it felt like support. It felt like support from my community, from my family, from my higher being. I felt like it was hard, it sucked, I didn't like it because of the uncertainty and trying to apply for all these jobs and nothing's landing, but it felt like support nonetheless as I went through that particular stage.

SPEAKER_01 14:00

There's a thought that's coming up for me. Um, because I've done some work where it's my my greatest need is like my greatest fear. And for me, it's to be understood. Um, I think I I've I'm so varied, and people often put me in a box and I really hate it. But I also want people to truly know me. And so it's it's sometimes at odds at each other. And there are times when I go above and beyond and really try to ensure that other people are understood on the level that they want, but I never get in return. And I share that because what I'm hearing also is a part of the thing that, you know, maybe a couple months before you're chastising yourself, like, Dan, why are you caring so much? becomes the thing that continually serves you. And so you're living in this tension of this is the thing that I can't change, but I hate myself in the moment for being so caring.

SPEAKER_00 14:54

Yeah, yeah. Yeah, I don't think I would go so far as to say, like, I that that tension I think it is spot on. Um and I think part of it created confusion. It wasn't at the time, there was in the moment, right? At the layoff, dude, take a minute for yourself. But through the process, I I think I just double and tripled down on no, like helping others, valuing others, thinking of others is important to the extent that my consulting is actually branded and formed after a scripture about valuing others. Do nothing out of selfish ambition or vain conceit. Rather, value others more importantly than yourself. So there was this initial like, why are you this way? to an embracing of this is who I am and how I am, and I'm just going to own it and see where that takes me. Um, so there was maybe a little bit of tension, but that tension I think was resolved fairly quickly in the sense of like, no, like that's important. But what does that mean? How does that live out? What does it mean to value and support others? Is that how I want to make money? Am I comfortable making money off of valuing others? Like, where does that go? And that was really the journey that I've been trying to wrap up since I got out of that first layoff, landed in a W-2. That was the the hardest job I've ever had. Um, not from like um technicality, just an emotional perspective. Um, and then coming into the now where I am my second layoff uh season and trying to wrap that up, um, it's all been centered on what, how, not what, how do I want to make money, and how important is it for me to make money off of helping others? Or do are those two things separate?

SPEAKER_01 16:47

Interesting. That's that's that's so much there I want to pull on. Um the first part, let's actually go back. So you did go back into W-2. I know for myself, the after the first layoff, second, I mean, even you know, I I sort of had PTSD because I'm like, I'm gonna trust these people again. Um you know, anything can happen. Was there anything that you had changed going into the second W-2 or going into the W 2 or you know, like the idea of I don't I don't know if it was a small gig, a large gig, uh where you're like, I don't want this to happen again. And so I'm making sure that I'm these things check the box at this moment in time.

SPEAKER_00 17:31

I would say not into coming out of that second layoff. Yes. As I'm trying to do can contract work now, I'm thinking about a W-2 next and how I show up, how I think. Um, I would say the sting of the first layoff almost felt inevitable. Like, I get it. We're small. Like, if I'm not generating revenue and we're up against the bills, I get it. No hard feelings, like it sucks. I wish we could have done the second time through. There were definitely some hurt feelings, some like sharing of screens and the messages about you show up on screen about what they actually think of you that they're saying behind your back is accidentally shared multiple times. Um, that's that's the triggering stuff. That's the things that I've that is now part of how I work. Coming out of that layoff is absolutely shifting how I show up and how I want to move in my next organization. Coming out of that first layoff, no, it was that sucks. A little bit of uh you should have done a better job, but also like I get it. That second layoff, that one hurt.

SPEAKER_01 18:39

Yeah, oh yikes. It's they they stick around for a bit. I I uh from my experience, different, you know, I always say different people go through grief differently. Um, so maybe I'm just I'm holding on to this one a little bit longer than I I should have. And and then you you you mentioned something which I think is where we want to wrap up. Um I I've thought through the idea of value. Um, and I've been similar to you where I'll hop on a call for someone for an hour. I was like, oh, that's no problem. I don't you don't need to pay me for this. Or um, and it feels easy, right? I think I'm in my zone of genius. I almost feel like this is too easy. Why should they pay me for it? And versus if I'm grinding, grinding, grinding, you know, like that's the thing I want to get paid for when it's like, wait, no, this is a thing that you've like done for 10 years. It should sort of feel somewhat easy to hop. Um, so as you are, and and one of the good things about these sessions is there's not necessarily need to be a bonar, it's not need to be like, oh, I went through this scenario and it's all done and I've learned all my lessons. Like, it's okay to be still going through and refining the process. You mentioned this thing of working through how you want to make your money. I'd be curious, like how did we get to that realization that that is important to you? And as I'm thinking about others who might be listening to this, where might they even start? Because I don't think this is a natural thing people think about, you know.

SPEAKER_00 20:06

Yeah. So the first question before I lose it of just is is the question basically where am I landing on that journey? Like what is the current moment, and then helping people go through that journey, or is your first question a little bit different than that?

SPEAKER_01 20:22

Yeah, I think it's um it's a little bit more on the side of just actually explain it to us. Like when you say how you're making your money, what does that even mean in this context? Let's start there. Yeah, yeah.

SPEAKER_00 20:35

Um, so I am a content creator, I'm a thought leader, I put out stuff, and really what I've been wrestling with over the past say six months since the last layoff is am I doing that the right way? And I'm settling on yes. And what that means is that it isn't generating revenue. I am not creating content to push you into a newsletter that I have your email that I'm doing outreach on. No, no shade to those that do. My approach says no, I don't need to create content to generate revenue, I need to create content to share knowledge and experience to impact and bring up others. That that the value for me is investing in the the community. Um so I've just established where I've where I'm kind of landing and how I've gone through that process is providing for my family is number one, period. I will do just about any kind of crap to provide for my family. I will stay in a quiet quitting job for far too long while I look unfulfilled because I need to provide for my family. That will always be my driving force. I want to try to separate out my value add to the community, to those that I care about, and how I make money. If they overlap, okay. That's not my goal. My goal isn't to try to make money off of the sharing of my knowledge, experience. It's valuing others, impacting, improving others. I want to make my money over here. That doesn't mean it has to be separate, but I want to make sure that valuing others stays pure to some extent. And I would maybe my word of encouragement for others that are wanting to go through the process. It just requires a lot of quiet time and introspection, right? Sit with yourself. Sit with and do five whys. Why, why do I like that? Why is that important to me? Why is that important to me? Why like just try to drill down as much as you can into who am I at the core? And how important is it for me to live out those core values? And then how important is it for me to work in an environment and work in a way that allows me to live out those values? Maybe I'm disassociating, but I think where I'm at right now is my living of values is over here. My getting paid is over here. Now that's not to mean that I ethical concerns are of no issue, but I don't need to say I'm bettering the world with my job. If I can, great, but I don't, it's too high of a bar. I can live on my values and impact my community in another way.

SPEAKER_01 23:17

That's that's that's awesome. It it wasn't until I met my wife that I because you know I drank a lot of Kool-Aids when I was in San Francisco believing that work should be your family. And she was like, dude, what are you talking about? Like work is just work. You can get deep connections and family outside of that, and it has nothing to do with that. And, you know, like work is always going to be work, and they're they're great work environments. Um, but at the nature of the day, if you're venture-backed or you're driven by profit, there's gonna be things that you're gonna have to, decisions you're gonna have to make that's gonna impact you beyond the connections that you make. Um, this has been amazing. There's so much here that we can pull on, and the hope, as always, is that folks walk away. Just number one, having a window inside of who Dan is, and also the stories that we can all relate. Um, it's interesting to see your story, and I know it's like still going on, and there's so many different bit stops there. Um, any final thoughts to share as we wrap up?

SPEAKER_00 24:16

Um, word of encouragement, maybe that's where my mind is going. Of those that are, I will say this. I think in identifying the inflection point is easy, the process is hard. For me, the layoff is the moment, and then there's just confusion and chaos out of out of that. And I think for those that are maybe feeling that to some extent, where like you haven't had that lesson learned, um, just keep diving in and don't check out. I think when there's that confusion and that chaos, sometimes maybe we want to disconnect and just say I can't deal with it. I think there's a lot of great lessons to learn if you lean into that chaos and confusion and to try to do the deep work to better understand and lay that foundation for the next steps.

SPEAKER_01 24:57

All right, that's amazing. Folks, please connect with Dan on LinkedIn. Anywhere else you want to direct them to or just LinkedIn.

SPEAKER_00 25:04

The only thing that I have is a website that has a bunch of my content. If you guys are interested in my other thoughts, sure, but two three consulting, that's the number two of the word threeconsulting.com. But LinkedIn's probably just as good as any place.

SPEAKER_01 25:16

All right, we'll link that below. Thanks, all