501: Climbing Down The Corporate Ladder To Discover Career Happiness

Dan Ruley 00:01

If I have to wake up tomorrow morning, and do this specific thing, and then turn around and do this specific thing every day for the next 10 years, is this something that I really want to keep doing?

Introduction 00:18

This is the Happen To Your Career podcast, with Scott Anthony Barlow. We help you stop doing work that doesn't fit you, figure out what does and make it happen. We help you define the work that's unapologetically you, and then go get it. If you feel like you were meant for more and ready to make a change, keep listening. Here's Scott. Here's Scott. Here's Scott.

Scott Anthony Barlow 00:43

Getting promoted is usually great news. But what if you were promoted beyond your ideal role? Many people don't ask themselves what they truly want out of their career before they automatically begin climbing the corporate ladder. In fact, that's one of the most common things I've heard over and over again, even when I was interviewing people who wanted new jobs, they'd say, "Well, I want growth" and usually by growth, they meant promotions. It's not uncommon to work for years to get to the top, only to realize it's not all you wanted it to be. For example, if you're great at sales, you may get promoted to sales manager. But those skill sets are completely different. And sometimes those roles are completely different. So what do you do if you feel like you've surpassed the role that would actually fulfill you?

Dan Ruley 01:31

You know, I'm tooled for chasing money and you know, chasing really high paying sales jobs and things like that. And I just finally came to the realization that I don't have to, you know, I can do something that I really want to do, something that I truly enjoy doing.

Scott Anthony Barlow 01:45

That's Dan Ruley. Dan worked hard to climb all the way up to Director of Sales for a large corporation, only to realize it wasn't what he wanted. When he was unexpectedly let go after taking time off for a family emergency, he took it as a sign to change the trajectory of his career, even if that meant climbing back down the corporate ladder. So it turns out, Dan did make a move, but he was able to also move up in pay and get the right type of role for him. Here's Dan discussing what led up to his surprising termination from his last role.

Dan Ruley 02:23

I had to take some time off at the end of the year to take care of some family things. And when I came back to my previous employer, things were just a little bit off, you know, I mean, the whole time I was gone, they were rooting for me, they're like, "Take care of your family, everything's gonna be fine. We're here for you. This is the culture that we have" yada, yada, yada. And then when push comes to shove, they're like, "you're the director of sales. It was the end of the year, and you weren't here." And I'm like, I mean, my family is going to come before my director of sales position, because it's my family.

Scott Anthony Barlow 02:52

Yeah, as it turns out.

Dan Ruley 02:53

Yeah. So ultimately, they ended up kind of blindsiding me and saying, "We're gonna part ways." And I was like, "wow, that's surprising, considering I am literally the face of your sales organization," which it is what it is, I took it with a grain of salt. But it kind of gave me that push that I needed to just say, "you know what, I need to do what I want to do, rather than continuing to do things that pay me well, but don't give me the satisfaction that I want." I'm too old for chasing money and chasing really high paying sales jobs and things like that. And I just finally came to the realization that I don't have to. I can do something that I really want to do, something that I truly enjoy doing, and I don't really have to stress out about, I don't know, sticking with a plan that I felt was subpar for myself.

Scott Anthony Barlow 03:40

Well, I think what's so interesting about what you said is that may have been, potentially, could have been a good plan for you many years ago. But what you want has changed. And clearly you have other priorities now, as well. And the plan... Exactly, exactly. Shocking surprise, right? But I think that that is what happens to so many of us is we keep operating on a plan that may have been good in parts for years ago, and now is no longer good. So I think that that is really amazing that you recognize that and came to that conclusion that hey, like "I've worked hard over the years, so I don't have to do it in the same way."

Dan Ruley 04:27

I think one of the problems, one of the pitfalls that people get themselves into is that they become comfortable and comfort kind of leads to complacency, right? Like so, you get stuck in this comfort zone, you're like, "You know what, I've been doing this for so long. I'm good at it. I'm comfortable with where I'm at, you know, I make enough money", whatever the case may be, and you don't really think about the bigger picture like, "What is my life going to be like five years down the road if I'm still doing what I'm doing? If I'm still stressed out every single day, because of what I'm doing, because of who I'm working with, etcetera." They don't think about the long term goals. And I think that this, while it was a shock, and it was surprising, and it was stressful, I think that it allowed me the freedom to realize that. Now, and don't get me wrong, not everybody has that same ability, because some people are struggling financially. I was in a good position, because my wife makes good money, and I didn't have to, like, really stress out about like, "crap, I have to find a new job tomorrow." So I think I was fortunate in that I had the space to be able to make the decision that I don't want to go back to doing the same thing. You know, I want to pivot my career in a different direction. I mean, it's a direction that I had been in previously as well. But moving back into this direction was, it was very fulfilling. And I think that my happiness level at this point kind of speaks for itself.

Scott Anthony Barlow 05:51

So here's what I'm curious about, then. I know, you had just earlier said, hey, you're glad that this happened. "I'm glad that it happened in this way." And it forced you to, it sounds like, look forward to the future and say, "What do I really want?" What were some of the parts and pieces that you were then able to identify that you needed and wanted that had been missing before? Or the areas that you really wanted to focus your career and your work in?

Dan Ruley 06:21

That's a great question. I think one of the biggest things was my primary goal being in sales leadership was always to mentor and to help people grow. That's one of the things I'm very passionate about– is professional development, personal development, and kind of the psychology behind human motivation. Those have always been things that have been very big passion points for me. And when this whole situation happened, that was the one thing that I looked at more than anything else is like, "what do I actually love about sales leadership?" And that was the mentoring thing. And I look back at my career, and my career has been pretty long, and it's been in sales for the most part, for the entire 27 years, I've been doing what I'm doing. And I realized that the only times that I was truly happy in what I was doing, was when I was teaching. And I realized that I had a career in sales training before, and I was happy, I didn't make very much money. And that's ultimately the reason why I pivoted to a higher paying director type role. And it worked out pretty well for a while, obviously, things change, your priorities change, your wife all of a sudden decides she's going to be a software engineer and does it all on her own. And she makes plenty of money. And you're like, "Well, crap, I don't have to make that much money now." And you know, ultimately, it just boils down to, I decided that teaching was what I wanted to do. So I really kind of went full force into finding a job in sales enablement, or training. And that's where I'm at now. And it's pretty amazing.

Scott Anthony Barlow 07:46

First of all, I think you did a really wonderful job working through all the pieces and parts and challenges of that type of transition. So kudos to you on one hand. And then the other thing I'm really curious about is, as you went into this transition, and started moving through it, what was the biggest struggle for you or what was hardest for you?

Dan Ruley 08:07

Honestly, the hardest thing was probably getting out of my own way. I mean, in the back of your mind, when you spent the majority of your career trying to make sure that you're in these larger leadership roles, it's hard to fathom stepping outside of an executive leadership role and into, still a leadership role, but not quite at the same executive level. And I think that was just a hard pill for me to swallow, because I have so much experience, and I've been doing this for a long time. But ultimately, it doesn't really matter. Titles don't matter, your happiness with what you're doing is what really matters. And interestingly enough, I now make almost three times what I made before as a director of sales with a smaller title. So I can't complain about financial compensation at all when the title doesn't matter, because I'm doing something that I really liked doing.

Scott Anthony Barlow 08:55

I think that's fascinating, because that happens so many times where we have in our heads a specific way that we're thinking about this, like in your case, you just said, "Hey, I had a hard time being able to really orient around. Is it the title? Or is it happiness?" Essentially, that's what I took from what you said. And when you start to remove it and say, "You know what, I'm not gonna focus on that. I don't even have to think about it that way." And it opens up new doors and possibilities where you essentially got what you really actually wanted and a whole lot more too, if we're talking about the monetary side, and in a completely different way.

Dan Ruley 09:31

You're absolutely right. I think that that's the biggest thing when you're thinking or dreaming of making such a big change in your career, I think that you have to pick things apart and figure out what is the most important thing to you, right? Like, is a title the most important thing to you? And if it is, that's fine. There's nothing wrong with that. At one point in my life title was the most important thing to me. If compensation is the most important thing to you, again, that's great, then you need to go after that. If finding happiness in what you're doing is the most important thing to you then do that. If you can get all of that wrapped into one pretty little package, hell yeah, go for it. That's fantastic. But I think that you have to be able to pick out what is most important to you, and then put everything you have into going in that direction.

Scott Anthony Barlow 10:21

That is... Here's what I've learned about that exact thing, both for myself, and many of the people that we've helped over the last many, many years. I guess, at this point, is that that is easy to hear and it sounds logical and simple when we're talking about it on the podcast. However, in reality, it's so much more difficult to prioritize for ourselves, what is actually most important, and it doesn't... just because we're prioritizing doesn't mean we're giving up hope on other things that are also like secondary important or third important, but it is incredibly difficult to prioritize that this is most important to me and declare that, like, that takes courage to do that. So I'm curious what helped you be able to do that for yourself?

Dan Ruley 11:11

I mean, I think that my wife had a really big part of tha. Having the ability to step away and not have a job for a few months while I was looking for the right one, and having the support of your partner, I think is extraordinarily important. And I think that you're absolutely right, it sounds really easy. It sounds great in concept, in theory, but putting that into practice is a whole different story. And I think that for a lot of people that are out there, they get stuck in this analysis-paralysis almost. Where they're like, "This is what I really want to do. But I don't know if I'm capable of doing it, maybe I don't have enough experience doing it." I mean, when I was, gosh, when I was in high school, my original plan in life was I wanted to become a marine biologist.

Scott Anthony Barlow 11:57

Was it really?

Dan Ruley 11:58

That was my biggest dream in life– was to be a marine biologist. And then I realized that, well, at that point, I lived in Arizona, so that was just not going to happen. Close enough to me to be a marine biologist. And it's like, you have to evolve what you want to do and figure out why it is that you want to do this specific thing. I mean, 15 years ago, I never would have said that I wanted my ultimate goal in life is to be a sales trainer. That's not something that you think about, but you think about what it is that brings you happiness and joy in what you're doing. And for me, it's like it's helping other people. So helping other people succeed at what their goals are, has always been a really big part of my life, whether it's with my kids, whether it's with my wife, whether it's with my friends, I just like to help people get to where they want to go. And you just kind of figure out, okay, well, step one is like, let's start in my career in sales, it was an easy one to get into sales. Salespeople are a dime a dozen, and you're either good at it, or you're terrible at it, and you'll fail fast, or you'll succeed. And I was able to succeed. And I did really well. And I realized that mentoring younger salespeople that aren't quite as seasoned as I am, was really fulfilling for me. So I just latched on to that for a while. And you just keep building along your career and picking up little bits and pieces of what you really find joy out of. And then you get to a tipping point in your career where you're like, well, "Here are the things that I really love doing about what I currently do. Here are the things that are kind of terrible about what I'm doing right now." And then you have to weigh the good and the bad, like, "Does the good of me being able to help Junior Account Executives, or whatever, succeed, does that outweigh the massive amounts of stress that I'm under, because I'm managing way too many balls at the same time, right?" And then you just have to make the decision to pivot because there are other things you can do that removes the bad and keeps the good. And maybe there will be more bad, maybe, but it could be different. And why not give it a shot? Right? If you have the ability to try, then you should. I mean, if you're stuck in a situation where, you know, and so many people are right now, you know, they're stuck in situations where they're struggling financially, and they can't fathom making a huge jump. And if you are in a situation where you are living paycheck to paycheck, and you're trying to feed children and whatnot, like, maybe that's not the right time, because you've literally can't afford it. But you have to do everything you can to prepare yourself for the moment when you can. And I think that the important thing is that you have to prepare yourself, you have to follow your gut, and what you want to do. Because ultimately, what's best for you is also what's best for your family, because my family is a lot happier now that I'm a lot happier. And that's just kind of the way that a family dynamic works, right? Like you live your life and you work your tail off for your family. And if you're unhappy in what you're doing while you're working your tail off, you're not happy, thus making your family not so happy. And it's just...

Scott Anthony Barlow 15:00

I love that for so many reasons, and I definitely very much resonate with... for me, it is my family that drives a lot of what I do, I really not only want to show up in a different way for my family, for sure, which is part of what I hear you speaking too. The other side of it, too, part of the reason why I do what I do is I want to role model for my kids that, like, you don't have to just be stuck in a situation that really isn't wonderful for you or for their families in the future if they choose to go out and have families, like, I don't want it to ever be a thing for them where they feel like they need to stay stuck. So kudos to you because I know that it is so much harder to actually do than it is to think about. And also marine biologist, are there any inklings of pieces that are still true to this day? I'm curious.

Dan Ruley 15:53

I mean, I think that a lot of it comes out and like what I do for volunteering. I don't think that I can really equate much of what I do in a professional sense to marine biology. I mean, I did get to work with the Benioff Ocean Institute in my previous role, which was a phenomenal thing that I've done. But I think that what I've done since then to kind of, I don't know, I guess, plug that gap or fill that need, whatever you want to call it, is a lot of the volunteering that I do is surrounding animals and marine life and things like that. Living in a suburb of Portland, the ocean is an hour and a half away. So I can volunteer with organizations to clean up the beach or to help monitor different things. And I think that I've been able to fulfill that need. Will I drop everything on the planet to go learn how to be a marine biologist now? Maybe not. But I would definitely do it as like a side gig. That's part of my retirement plan. When I retire one day, I'm gonna become a marine biologist. I don't know if that's a thing, Scott, but I'm gonna give it a shot.

Scott Anthony Barlow 16:57

I think that if that's something you want, you absolutely should give it a shot. Well, I love what you're saying, though, because, like, you still have found through volunteer work a way to be connected to what you really wanted, even way back then as a kid. And I think that that is pretty amazing.

Dan Ruley 17:15

I think that too many people, they have their dreams when they're a kid– I want to be an astronaut, I want to be this, I want to be that. But when they become adults, they don't take what their dreams were seriously anymore. So I got it as a pipe dream. I never could have achieved that. But maybe you didn't achieve exactly what that was. But you can still achieve a lot of different aspects of what that dream was. You just have to reframe the way that you think about things.

Scott Anthony Barlow 17:42

Yeah. Or even dig in, like you've done and identify what was it that I actually wanted out of that. Very cool. So here's another question that comes up for me. I know that you did a really wonderful job with this transition. But I don't know all the pieces of it. And I'm curious, you know, when you think back, what made this type of transition really work for you? Get into the nitty gritty for me just a little bit, like, what was something that ended up going really well in the end, but was maybe more difficult at the beginning?

Dan Ruley 18:19

I feel like the transition for me was probably easier than it is for a lot of other people only because I basically transitioned into doing something that I've already done before, and that I have a lot of experience in. So I mean, I think the hardest part of the transition overall was just finding the right place to go. Finding the right opportunity for me, was probably the hardest part. Because there's obviously thousands of positions out there and hundreds of different organizations that do what I do now, and it was really sifting through it all to find out what made sense. But I think that digging a little bit deeper and understanding what other organizations bring to the table and what other organizations, what their values are, there's a lot of other options out there, not just *insert dream company here*. There's a lot of other companies out there that can do what you want them to do. And I found that with Sage Intact, I think that it's an organization that I had worked with in the past as a partner, in a million years that maybe I want to apply to work there. It's a financial SaaS company. I don't know anything about financial services. That's not my gig. So I never would have thought about it. And then when you just kind of explore the different options that are out there, and you kind of decide between these different organizations, and if you're in a position where you have the experience to be able to pick and choose what organization you really want to work with, I think that that makes it a lot easier as well.

Scott Anthony Barlow 19:49

What caused you to begin, not even where you're like, "oh my goodness, obviously this is the organization for me. I have to work here." But even long before you got to that point where you started to have an inklings of "wow, this actually couldn't be something that I had might be interested in as an organization", what were the pieces along the way that caused you to start becoming interested or start realizing that this could be right for you?

Dan Ruley 20:13

I think it started, you know, there's a lot of people that are like, you know, they talk about company culture, and a lot of it is to be perfectly blunt, pretty BS. You throw a pool table in the office and give people some snacks, and they think that's culture. And it's not the same as organizations I'd have in a real company culture where they actually care and nurture their employees and things like that. And I think that once you're researching organizations that you want to work at, you know, that's when you hit the glass doors, and you hit up the reviews on the organization's and you do your research, you make a list of all the different companies and all the different positions that are out there. And these are positions that I want. And then you see this is the company that it's at. And I mean, I think I made a spreadsheet of everything that was like, "Here's the company name. Here's the position that I wanted to apply for. Here's their rating on Glassdoor. Here's what some of the more impressive reviews that they have. This is what their hiring process looks like, et cetera, et cetera." And you just become very prescriptive about what you're looking for. The more you know about an organization, the more you know, whether or not you and your own personal feelings and your own personal... The things that are important to you are also important to that organization. And throughout my research, I narrowed it down to about like four or five different organizations that I really went for throughout the applications. And then I got offers from a lot of them. And then I had to make the decision as to which one I wanted. And that's a good feeling. It's good to have that feeling.

Scott Anthony Barlow 21:37

What caused you to choose this one? What caused you, I mean, obviously, I know that it ended up being a pay increase for you, however, it was also more than just that.

Dan Ruley 21:50

Yeah, it was actually a really hard decision. Because it ended up coming down to two different organizations that I wanted to choose from. And it was based on employee reviews, it was based on what I read about their company culture, and then a lot of it was based around the position itself. So I basically had the option of choosing between one organization that they had a team of people that would write the sales training curriculum, and they would do all that grunt work for a specific amount of money. And basically, all I would be in charge of was having to teach it. And then you have the other organization that it all falls on your shoulders. And you develop the curriculum, you teach the curriculum, you do the gap analysis to figure out what else needs to be done. And ultimately, what made me choose Sage Intact over the other is that I had the freedom to be able to develop my own curriculum. I didn't have to rely on some other person that doesn't have what's in my head in their head. And to me, it's more rewarding to build something from the ground up. I mean, I love the idea that they have people that will, you know, curriculum development team, that's great. But I want to develop my own because I think that my way of teaching things fit better with my teaching style. They're both amazing organizations. And when I turned down the offer at the other organization, I truly felt bad, because I would have fit in right there as well. Their team was phenomenal. The people that I met with, I mean, I went through five different interviews, and every single person was wonderful. And it was the same thing with Sage Intact. So it came down to being a very difficult decision. But ultimately, it was because I wanted more control over what I was doing, it's why I chose Sage Intact.

Scott Anthony Barlow 23:31

When I think part of your ability to do that... just because you have multiple offers in front of you like we've worked with lots of people over the years where they have two or three or four, sometimes more offers, however, that being the case doesn't mean it automatically makes it easy, or any stretch of the word, just because you have multiple offers. One of the nice things that does do, sometimes, is help people be able to measure what's important to them. But I find that unless you've done enough work to know what truly is important to you or what you might need, then even that isn't necessarily fully effective. So here's the question that I have for you when you are in that situation, and you realize that, hey, this lines up more with what you actually wanted. Well, I heard you say, "I really wanted to be able to develop my own curriculum. And it's great that there would be all these people doing that in another no another organization, but it wasn't right for me necessarily." How were you thinking about that at the time as you were going through it? Because sometimes it can be a little bit emotionally taxing when you're trying to make this what feels like a massive decision and is a massive decision about how it's going to impact probably the next few years of your life at a minimum.

Dan Ruley 24:55

Yeah, I mean, it was definitely not a decision that I took lightly. I think that it was definitely it was a tough one. I just kind of evaluated what I'm going to take greater joy out of in the future. I mean, I absolutely could have gone and worked for this other company and probably have been able to develop my own curriculum at some point anyway, but it also meant that there was an additional level of red tape that I had to jump through in order to deliver a training session to the people that I need to train. And then with this organization with Sage Intact, you know, I mean, the way that I kind of meshed with my director, it was a better initial impression and a better initial relationship than I think I've ever had with any other company. And from the very beginning, she told me that, because of my skill sets, because of what my experience is, I get carte blanche to do whatever it is that I need to do in order to make their sales team successful. And that meant a lot. Because I do have a lot of experience. And I do know what I'm doing. And I think for somebody to recognize that and to be able to say, you do what you need to do to make us successful, I think that was huge, because it really makes you feel like you are valuable. And that's an important thing to feel as an employee. I mean, in all the years that I spent as the director at my previous organization, I never felt like I was valued. Even though that I was doubling and tripling their revenue numbers on a yearly basis, I didn't feel like I was valued. I went to all the executive retreats, and all that kind of stuff, but there was no real value there. It was very fake. But where I'm at now, I truly feel like I'm a valued person on the team and somebody that they all lean on and not in a bad way, not like we need them to do all the work for us. But give us advice, tell us how to do these certain things, pull him in on different conversations about other teams that he has experience working with. And I think that's important when you're interviewing with organizations, really pay attention to the people that you're interviewing with, because those are potentially the people that you're going to be working with for an extended period of time. And if you get a little hairs on the back of your neck started standing up, because you get a bad vibe or something, make a note of that, because you don't want to work with somebody like that, because ultimately, it's not going to work out very well. If I had known this 10 years ago, because I would have saved myself a lot of problems with a lot of different positions, because I had a gut feeling in the beginning, but it was like, "Something feels a little off. But I'm like, but they're gonna pay me a lot of money. So I'm just not gonna worry about it."

Scott Anthony Barlow 27:32

I'll smooth out with money. Right?

Dan Ruley 27:33

Yeah, well, and that's the thing, like a lot of people use that as the great equalizer. They have multiple offers, you know, they go directly to whoever is going to pay them the most. That's not the best.

Scott Anthony Barlow 27:44

What if that's not your highest priority, though?

Dan Ruley 27:46

Exactly. And that's kind of where I was like, the other organization that I was, had it boiled down to, they were gonna pay me more. But that wasn't the most important thing to me. And I think that while that it's okay for that to be the most important thing for some people, I think that they need to also think about the overall happiness of what their experience is going to be.

Scott Anthony Barlow 28:08

Dan, I think that is wonderful advice, thinking about what is the overall happiness. And I'm curious for someone who is in the same place that you were, where not that long ago, I mean, just months ago, you were thrust into a transition that you hadn't really planned in making that particular way, and you knew that at the same time, you didn't want to just accept anything moving forward. If you take yourself back to that place, and think about that person who's there, because we have many people that are listening right now, in that place, what advice would you give to that person?

Dan Ruley 28:47

I mean, first and foremost, stay calm. Don't freak out. If you are thrust into this situation, like I was, do your damnedest not to have a meltdown. Because you know, that is already going to set you back a couple of steps. Look at things objectively. Think about what it is that you want in life, what you want to be able to accomplish. Think about it in terms of, "If I have to wake up tomorrow morning, and do this specific thing, and then turn around and do this specific thing every day for the next 10 years, is this something that I really want to keep doing?" And if you can answer that, yes, then that's the direction you should go in. But if you can answer that with a, "I don't really know", then think about the other things that you might want to do. I mean, because it's not a small decision to make the pivot and change your career trajectory and pivot in a different direction. It's a big decision. So think about it objectively. Try to keep emotion out of it as much as possible, and figure out what you want out of life and out of your career, and then do everything in your power to go forward in that direction.

Scott Anthony Barlow 29:57

Most of the episodes you've heard on Happen To Your Career showcase stories of people that have taken the steps to identify and land careers that they are absolutely enamored with, that match their strengths, and are really what they want in their lives. If that's something that you're ready to begin taking steps towards, that's awesome. And we want to figure out how we can help. So here's what I would suggest. Take the next five seconds to open up your email app and email me directly. I'm gonna give you my personal email address, scott@happentoyourcareer.com just email me and put 'Conversation' in the subject line. And when you do that, I'll introduce you to someone on our team who can have a super informal conversation with and we'll figure out the very best type of help for you, whatever that looks like, and the very best way that we can support you to make it happen. So send me an email right now with 'Conversation' in the subject line.

Scott Anthony Barlow 30:50

Here's a sneak peek into what we have coming up in store for you next week..

Thomas Williams 30:55

I was extremely scared. I was extremely vulnerable. I'd never been excited about doing anything else. But for some reason, there was that little feeling inside of my stomach that says, "The time is now. Time is now to transition."

Scott Anthony Barlow 31:09

When you work in a field you're passionate about, it's really easy to get your identity wrapped up in what you do for a living. This type of work can be very fulfilling. However, when it comes time to make a change, it can be extremely hard to untangle yourself from your career and make the necessary changes to find true career fulfillment.

Scott Anthony Barlow 31:32

All that and plenty more next week right here on Happen To Your Career. Make sure that you don't miss it. And if you haven't already, click Subscribe on your podcast player so that you can download this podcast in your sleep, and you get it automatically, even the bonus episodes every single week, sometimes multiple times a week. Until next week. Adios. I'm out.