738: What Got You Here Won’t Make You Happy: How to Recognize When Success Is Taking You in the Wrong Direction

[00:00:00] Dan Ruley: The only times that I was truly happy in what I was doing was when I was teaching. And I realized that, you know, I had a career in, you know, 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.

[00:00:17] Scott Anthony Barlow: That's Dan, and he spent 27 years in sales. He was exceptional at the work, phenomenal even, so good he kept getting promoted, director-level titles, executive team, multiple six-figure salary, all of the external evidence that proved his success. But every promotion was also moving him further from the work that he actually loved doing, the mentoring, the teaching, the one-on-one development of people who were still learning their craft.

[00:00:43] That was the work that made him feel the most alive, and the higher he grew in his career, the less excited he was about the work. So what do you do if the thing that makes you miserable is not the job itself, but every time you get rewarded for doing it well? That's what we're going to uncover today.

[00:01:00] This is Happen To Your Career. Most people let their career happen to them, falling into jobs by accident, staying longer than they should, and wondering if this is really all there is. But a few people decide to stop settling and do something different. This podcast is for you to take control, get intentional, and design your work to fit the life that you want to build. Real stories and real research so that you can stop waiting and start making it happen. I'm Scott Anthony Barlow.

[00:01:25] If you read the Happen To Your Career book or listened to the audiobook, then you probably heard about the five hidden obstacles that stop people from getting to meaningful work, and we're gonna talk about one additional hidden obstacle that wasn't in the book. One that catches high performers more than almost any other, and that's being rewarded in a role that takes you further from what you actually want and what you actually need.

[00:01:51] We're gonna explore why Dan traded what he loved for what paid more, and why it only worked for a while before falling apart, and the exact framework that led him to fulfilling work so that you can use the same one if you suspect success has been taking you in the wrong direction. And this is still going to work for you even if you've just outgrown your roles.

[00:02:13] Let's start with the concept that's at the core of much of what we do here at Happen To Your Career, and we call that signature strengths. Now, these are the character strengths that are most essential to who you are, not the things that you've been trained to do well or the skills that you've picked up over your career.

[00:02:31] But the things that come naturally to you, that allow you to feel like you're being yourself instead of performing. Now, the most important thing about signature strengths is they don't change with your job title. What changes is whether or not your role, and what you're doing, and how you're spending your time, gives you access to those strengths, and that's where this hidden obstacle catches high performers. For example, here's something that happens all the time.

[00:02:56] You know, even if you've gone into a new role and you're naturally gravitating towards your strengths or towards tasks that utilize your strengths, then somewhere down the road, we get asked to do something or many somethings that we're capable of doing, and we might even do them very well, and then we're rewarded for that.

[00:03:15] We're promoted, we're given another project, and then we do well on that project. That promotion leads to more tasks that, again, that we're capable of doing well, and somewhere in that process, the thing that makes us exceptional in the first place, the actual work that used our signature strengths, gets smaller and smaller and eventually disappears from our calendar entirely. And this is what happened to Dan.

[00:03:36] Dan Ruley: When you're running a sales team that includes multiple levels of salespeople, everything from SDRs to account executives to client success, you're managing this team of people, but yet you're still trying to carry your own quota, too. That's next to impossible to do all of the things effectively.

[00:03:52] Scott Anthony Barlow: Managing teams and carrying quotas is quite a step away from mentoring and professional development, and this is a perfect example of the hidden obstacle in action because from the outside, everything looks fine. The salary is good, title's impressive, the trajectory is upward. But on the inside, when you look at your day-to-day experience, the work stops feeling like you.

[00:04:13] It stops feeling as rewarding as it once did. And if you've been feeling like something is off, but you can't quite name what it is, the best place to start is to identify the connection between strengths you have and the degree to which your work leverages those strengths. But let's cover another important distinction.

[00:04:30] Being good at something is not the same as it being a signature strength. Two completely different, potentially disparate things. You know, Dan was... he was actually really good at managing a sales team. He was capable, effective; he got results, but that capability is a set of skills. Now, think about signature strengths as what you are when nobody is asking you to be anything.

[00:04:54] And for that, Dan was teaching. Dan was always teaching, and in fact, that's one of the reasons why he got results. However, he found himself more and more in those areas where he got to do less and less teaching and mentoring. Now, once Dan understood the disconnect between his current workload and his signature strengths, he worked with our team to create his Ideal Career Profile, or what we call the ICP, for short.

[00:05:17] And just think about this as a really simple tool. We developed it to help answer the question, what does work actually need to look like for me to be at my best? And also, what am I not willing to compromise on? Where do I draw the line?

[00:05:29] So Dan built his profile around his desire to have autonomy and creative ownership at work, in addition to those areas of mentoring and teaching. And because Dan did such a great job defining this through the ICP, he ended up in a pretty enviable position with multiple job offers to choose from.

[00:05:49] Dan Ruley: 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, you know, for a specific amount of money, and basically, all I would be in charge of was having to teach it.

[00:06:03] 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.

[00:06:13] And ultimately, what made me choose 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.

[00:06:30] Scott Anthony Barlow: That's the ideal career profile in action. Not just, "I want to teach," but, "I want to build what I teach from the ground up on my own terms. Here's what those terms are." The ability to apply his own knowledge in his own way is exactly what Dan needed to find continuous fulfillment in his work. But he also identified something else that had been missing the whole time.

[00:06:50] Dan Ruley: There's a lot of people that talk about company culture, and a lot of it is, you know, to be perfectly blunt, pretty BS. You throw a pool table in the office and, you know, give people some snacks, and they think that's culture. It's not the same as organizations like Salesforce that have a real company culture where they actually care and nurture their employees.

[00:07:08] And those aren't things that you know until you've actually been able to experience it. So I didn't really understand that company culture was important to me until I started working so closely with Salesforce.

[00:07:19] Scott Anthony Barlow: Now, I think what's really interesting is we all know we need some level of company culture, but Dan didn't initially consider company culture as a non-negotiable until he witnessed the disconnect between culture and care during his time at Salesforce.

[00:07:34] And that's what an ICP does. It reframes your thinking from "I wanna get away from a company that does not value me " to "I need a culture of coaching, of people who genuinely want to help others grow, and I now know exactly what that looks like and can define that when it's real." So here's the fun thing that Dan did.

[00:07:52] He built a spreadsheet. He then rated companies on Glassdoor, narrowed down four or five of them that genuinely matched what he was looking for, and interviewed at each. And when he had multiple offers, because he did, he had a decision filter to run them through.

[00:08:08] Dan Ruley: 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," you know? And then you have to weigh the good and the bad.

[00:08:20] The organization that I had it boiled down to they were gonna pay me more, but that wasn't the most important thing to me. And, you know, 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.

[00:08:36] Scott Anthony Barlow: So here's what actually happened when Dan made the move. He stepped down. His new title was Senior Program Manager, which is technically a step down from director of sales on paper, but Dan was finally doing the work that he loved.

[00:08:48] Dan Ruley: 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, you know, and the title doesn't matter because I'm doing something that I really like doing.

[00:09:06] Scott Anthony Barlow: Here's the fun thing about Dan's story that I find most instructive. It was not this dramatic reinvention that everybody imagine has to happen, and honestly doesn't usually happen. He did not leave sales. He did not change industries. He went back to the version of sales work that had always fit him in a completely different context, in a context that now fit his current life and his current situation and what he wanted at this point in time, and what he was anticipating would fit him in the future.

[00:09:38] I think the other really interesting thing is that the version that he left years ago was he left it because it did not pay enough. Now he found a way to do it because he had defined specifically what he wanted, that led him to finding a way that allowed him to do those same types of activities and same types of work in a way that paid more than anything he'd ever made before, and the hard part wasn't finding a role that fit.

[00:10:01] Dan Ruley: Honestly, the hardest thing was probably getting out of my own way. In the back of your mind, when you have spent the majority of your career, you know, 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, you know, still a leadership role, but not quite at the same executive level.

[00:10:21] And I think the question is, 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 wanna keep doing?

[00:10:34] Scott Anthony Barlow: For Dan, the answer was no, and once he was honest with himself and got out of his own way, he was able to step into a role that both fulfills him and utilizes his strengths.

[00:10:44] Most people who feel stuck in the wrong role are not stuck because they made bad decisions. They're stuck because they made good ones. They worked hard, they got results, they got promoted. Each time, the organization did exactly what it was supposed to do. It moved them up, it rewarded them, and nobody told them up was also away. Away from the work that used everything that they were naturally the best at, away from the days that felt like them, away from the version of the career that, if they're being really honest, they would go back to in a heartbeat if the money were the same.

[00:11:13] And so Dan went back. The money was not the same. It was better, and the title was smaller, and none of it actually mattered because he was finally doing the things that he had been promoted away from for years. He was spending his time in the way that he wanted to.

[00:11:27] Dan Ruley: 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.

[00:11:34] Scott Anthony Barlow: If Dan's story resonates with you or you've spent months or years in a role that looks successful from the outside but feels off on the inside, or maybe you've outgrown a role that was really great at one point for you, and you're not sure what to do about it, send me an email, scott@happentoyourcareer.com. Put 'Conversation' in the subject line, and I'll connect you with the right member of our team, and we'll figure out the very best way that we can support you and help you build a plan to get where you want to go for your goals and the life that you're trying to build. I'll look out for your email. And until next time, I'm Scott Anthony Barlow, and this is Happen To Your Career. Adios. I'm out.