521: How to Overcome Overthinking and Finally Change Careers

Briana Riley 00:01

With overthinking, you are waiting often for some external sign, right? The universe is going to tell you what to do, gonna point you in the right direction. It's going to give you the answer. But oftentimes the answers aren't just laying around, we have to go seek them.

Introduction 00:26

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

Scott Anthony Barlow 00:52

Look if you're listening to this, it is highly possible you're an overthinker. We have many, many people that listen to this podcast that are very, very smart and very, very talented and very, very good at overanalyzing. I definitely fall into that category too. I've been an overthinker in so many different ways for many, many years more than I care to share. Now, we know that because we talk to folks like you, if you fall into that overthinker category, sometimes it's hard for us to see when we've waited too long, and we're getting stuck in limbo. Because we haven't made a decision to move forward. One day you wake up and realize that your job is sucking the life out of you, in one way or another. And maybe it's been great in the past. But now because you've been waiting and waiting for some huge flashing sign that screams, "now is the time to make a change!", you find yourself stuck in a whirlwind of indecision and inaction. How can you give yourself the push to take action and begin to change?

Briana Riley 02:01

You can't possibly know everything there is to know about everything. You have to just start with the information you have in front of you and move forward in some way with the pieces that you have.

Scott Anthony Barlow 02:15

That's Briana Riley. She's a career coach here at HTYC. She's a phenomenal coach. If you want to hear Bri's entire story, you can go back to Episode 505 called Gaining Career Clarity Through Reflection. She's also a self proclaimed overthinker. Many of our clients also consider themselves over thinkers. And Bri is extremely skilled at helping people escape the cycle and take a step forward. Bri and I discussed some specific strategies that she uses to help our clients overcome overthinking, and step out of their comfort zone and take action toward finding more meaningful work. But this applies to everything in life. It's not just about meaningful work. You're going to hear some really great advice on how to find the first thread that you can follow to start moving forward. So listen to that. But here's Bri kicking us off by explaining her definition of overthinking.

Briana Riley 03:14

For me, overthinking is, it's almost like a never ending thought cycle where you can just sit with one topic and allow yourself to kind of stay in that trap, allow yourself to kind of just keep going into different tangents and come back to it and flip it on its head and look at it a different way. And in that process, you feel like you're making progress, because you're thinking of all the different ways and then ultimately landing with not very much to do with it. The visual I get is like that hamster wheel where you are moving, like, wheel.

Scott Anthony Barlow 03:55

Moving so fast on that wheel.

Briana Riley 03:58

Exactly. Just like bucking it. And by the end of it, you get off and you're like, "Wow, I am in the exact same place."

Scott Anthony Barlow 04:06

So let me ask you this, then. And I think it's probably a pretty fair to say that what we've learned in the last 10 years is that when people fall into the overthinker category, there is this danger or tendency that if you fall into that category, and that is your tendency, then that also can pretty easily correlate with finding yourself in a current role that isn't making you happier, isn't providing fulfillment. So is that a fair assessment, first of all?

Briana Riley 04:40

Yeah, absolutely. It keeps you where you are, right?

Scott Anthony Barlow 04:44

I think that that is safe to say. But why do you think that is? Tell me a little bit about why you think that is.

Briana Riley 04:50

With overthinking, for folks that do overthink, because it starts off as a good thing where you're going to be encouraged to think about things in a different way and consider a new perspective, and what assumptions are you making. Those are great questions to be constantly asking yourself, and especially when you want to be a person who is self aware, and who is challenging themselves. So it starts off in such a good place. And so when you continue to do so, it's almost validating of, well, at least I'm being the self aware person, at least I'm sticking in this place of reflection and analysis. And it feels like with that I can be really intentional, I can be really purposeful, and all of those because it's such a good thing to start with, it's hard to then figure out like, at what point does it stop just being self awareness? And does it start being counterproductive?

Scott Anthony Barlow 05:57

Yeah, you know, the part I think you make me think of when I hear you talk about the point where it is no longer progression and actually becomes counterproductive, is we see this really interesting phenomenon with overthinkers when we're helping people create what we call their ideal career profile. So arguably, that's hard work for many people in terms of defining what it is that they want, and what extraordinary looks like in every area of their life and career. And then at some point, it needs to move from internal, where we're creating this definition, and then move from there to external, where we're actually taking that idea or set of ideas or checklist of what extraordinary looks like and then putting that into the real world. And what I find is that it's incredibly difficult for the overthinkers of the world, overthinkers unite, to go from that internal where it feels very comfortable, to the external where it is moving forward. Because I think the tendency is exactly what you described, like you want to keep assessing, and you want to keep analyzing, and you want to keep iterating, or whatever the appropriate word would be for that. And then that feels validating, which then feels comfortable, which then keeps you in that cycle. And it feels difficult to move from that internal and external reality. So my question for you is, how do we even think about moving past that type of problem whether it is in the form of career change, or anyplace else that we might find out? What are some of your thoughts on how people that identify as overthinkers, or overthinkers that may not realize that they're overthinkers yet, how do we move past that?

Briana Riley 07:48

That is the question.

Scott Anthony Barlow 07:51

That is the question.

Briana Riley 07:54

Yeah, I'm just gonna solve it. All right.

Scott Anthony Barlow 07:56

Good. All right. This is a podcast for the ages for sure. What have you found works though? Because I know just even working with you, I've seen you move through that yourself. And I've seen you put into practice. So as an overthinker. I've seen you work through that in real time. So I know that you got some tricks.

Briana Riley 08:16

Yeah, for sure. And this is one of those things that you don't just learn once, it's one of those things you have to practice and keep building a practice of it. Because overthinkers will always default to the overthinking because it is comfortable. And so to really work past it, there's a couple of different things that come to mind. The first, that really is the greatest starting point is when you're overthinking there's this idea that you need more information, you're missing something, you're not quite there yet, there's this goal in front of you, and you're just before it. And when you take a second to realize, okay, I maybe don't have all of the information, but I have something, I'm not starting from a completely blank slate. That is a really powerful starting point. Because you can't possibly know everything there is to know about everything, you have to just start with the information you have in front of you and move forward in some way with the pieces that you have. Otherwise, you'll be constantly chasing this ever moving goal. So it's really just picking that starting point, realizing that you're not empty, you're not completely having no experiences to rely on. You're starting from all of the experiences and perspectives and values that you have already.

Scott Anthony Barlow 09:55

So you're saying that in some ways, many times it feels like we're starting from the beginning. But in actuality, we're starting from the middle with all the collection of experiences and perspectives and everything that we have up to that point. So just acknowledging that, and realizing that that is reality, not the feeling of starting from the beginning. That's the starting point.

Briana Riley 10:19

Right. Just because we don't have all of the information, doesn't mean we don't have anything. And I think the question we have to ask ourselves there is, "how can we value where we are? And how can we appreciate the things that were already coming to that situation with?" So that's really like the first piece of how to start moving past this overthinking.

Scott Anthony Barlow 10:47

What else? Once we begin to realize that, "Okay, I'm not actually where I thought I was, in terms of starting from the beginning, I actually am bringing more to the table. I have more information than I thought I did." What's next? What works from there for you?

Briana Riley 11:03

Yeah. So you get to this place, you're like turns out, I know a thing or two, right? Just something, there's something that I know. Then you have to take action from that place. With overthinking, you are waiting often for some external sign, right? The universe is going to tell you what to do, gonna point you in the right direction, it's gonna give you the answer. But oftentimes, the answers aren't just laying around, we have to go seek them, we have to put something out into the universe to be guided in the way that we need. And so you have to be able to step up to the plate and start somewhere and take that first step. Even if it might be wrong, even if it might mean that you ultimately go in a completely different direction that you didn't think you could go before.

Scott Anthony Barlow 12:03

I love that. Here's a thing that I'm going through and experiencing right this very moment. So I can't say I always love getting into areas that are brand new for me and highly uncomfortable and kind of kick me back into that overthinking tendency, but I'm trying to love it more. And I'm trying to do it and trying to practice getting into those situations far more frequently than what I might have done 20 years ago. And so the latest version of that, for me is my wife and I have been... we've had this idea, as of about two years ago, that we may want to do short term rentals. And there's a variety of reasons that we want to get in there. She would love to own homes in a variety of different places, as our kids are getting older, so that it's easy for us to go and visit them. She loves visiting tropical places. So there's things like that. And then for me, I love the business challenge side of it and suspect that I might really enjoy that. However, in reality to go from where we're at, like currently, where we own no short term rental homes, to owning many in a variety of different places, it requires a huge amount of moving through areas where I think that I need to be thinking more and then ultimately overthinking. So the latest version of that is just four weeks ago, we had identified that there's this great property that we might want to purchase and build upon and everything like that. And the way that it's set up, would not work well for let's say, traditional mortgages and everything like that. So already, we're off the beaten path, which scares the crap out of me, just because I haven't done it before. So right now, like, literally right before we got on this conversation, the homeowner of the property is calling me so I'm getting to the point where like, we might decide to buy this thing or not buy this thing and everything in me that for the last four weeks has been telling me that I need to go and find out everything I need to find out. Like, I need to call all of the people that work at the county to ask them every single possible question, what's the list of 47 questions that I should be asking in order to make sure that this is not going to be a massive risk someplace else. And what I'll tell you is that the thing that has helped keep me out of the overthinking tendency and moving forward like you're talking about has been surrounding myself with other people that either have already done this or are encouraging me to go forward without all of the information. So I have a group of friends that like they've bought many properties and they're like, "No, Scott. It's not actually this big deal. Just send them a proposal and include three options on the proposal. Make sure all those options are good for you." And of course, like when they say it that way, I'm like, "Oh yeah, well, I can do that. I can do that." And then I can move to the next step. So real time, this really is the overthinker's lab. Where is that showing up for you? What's a recent thing for you where that has shown up? And then what helped you move through that?

Briana Riley 15:23

This is top of mind for me today. So as you might know, I do salsa dancing classes.

Scott Anthony Barlow 15:31

Yes, I love that.

Briana Riley 15:33

Yes, it's my highlight of the week, Monday nights, I go salsa dancing. And it's a very small group of us that are there in class. So maybe, on a good night, it's 10 people total that are there. And since we started talking about going into the wild, into the real world, and trying to salsa dance with other people who have way more experience, do social dancing just regularly, so they're more comfortable in the space, they know where to go, they know how to move and share the space, and we don't have very much of that. We've been doing this for a few months, at most, consistently for a few months. And so I was always on the end, anytime anyone would recommend it, I was the one sharing all the reasons why it doesn't make sense. I found myself, well, but we don't really know the best place to go for beginners. And what happens if we go and only some of us have partners with us and others are showing up without partners? How do we handle that? And we don't have a plan together. And we're never going to find the time that it all works and just kind of trying to figure out, like, how can we possibly do this because there's things that are getting in the way and we don't know what we're fully walking into. And I wanted to know all of the things. I wanted to know everything. I wanted to understand, before we went somehow, how much space I was realistically going to have because I don't know how to stay in my box just yet. And so I kept being that person for several months. And then one day, I woke up. And I was like, "We should go salsa dancing today." But then I immediately was like, "Oh no, that's too overwhelming." I started to walk back, I started to say "I don't know about this." I was just moonwalking out of that decision. I was really hoping no one would notice. But I had texted a group of my friends. And so that was a written down note with a, obviously, binding legal document and a text message to go salsa dancing. And they didn't let me back out. All the reasons: "Oh, it's getting late.", "We're kind of tired." all of these things, and they didn't let me back out. They really encouraged me just to, even if we don't go, even if it sucks, even if we're terrible, even if they blew us off the dance floor, let's just go and see it. And that perspective of "Oh, all I have to do is walk inside." That's it. My goal is to walk inside the building that helps me to be able to get there. And then I was just, I had so much fun that day. I was out there, we were dancing. We had so much fun. It didn't matter that we messed up. I went back, I had things that I could learn from it and apply to the next lesson and asked my instructor. And so I don't regret going and having all these mistakes. I don't regret, like, not knowing how much space to take up and bumping into people and probably causing a scene. But I would have regretted not having that experience because it was so amazing.

Scott Anthony Barlow 18:53

That's really cool. That's really cool. I didn't know that that's how it happened. This is fun. So here's what I'm hearing out of that too. A couple of really useful things led you to be able to move down that road, even though you tried to moonwalk your way out of it. Well, number one, that public declaration in one way or another, like, the texts to the friends where it's "Okay, now I have to go."

Briana Riley 19:20

Right.

Scott Anthony Barlow 19:21

And then another piece is setting the intention or goals on that leading activity, "I'm just gonna walk in the door. I'm not gonna worry about anything else, like I can leave or whatever. I'm just gonna walk in the door." Focusing on those leading activities, that is super cool. Both of those have been pretty helpful for me too. And even in that situation that I was talking about with short term rentals, I have a friend who's the owner of the coffee shop that I worked at all the time too and she access, like, the equivalent to the text that you sent off because she and I one day, for whatever reason, we're having a conversation. And she's like, "I've been putting off this thing that I want to do." And she wants to bring in a different type of business to her coffee shop. Actually, she has three coffee shops. But I'm like, "Well, I'll tell you what, there's this thing that I've been putting off, too. So can we ask each other every time we see each other?" So we see each other about once a week now. And every single time I see her, I end up moving forward on something that probably had, I felt resistance on or been overthinking about, or whatever else it is. So I love those two tools, or I don't even know what to call them– techniques? Actions?

Briana Riley 20:40

All of the words. I think, for me, it's like different doors that you can open to like, give yourself more space, different windows that you can open to let some air in. I think that's the visual that's coming to mind. It's like how can we create a little bit more space in here, right? With necessarily blowing out the entire wall, and now I'm going to do this entire home renovation. Instead, we just need a little bit of room. And within that space, you can take one little step.

Scott Anthony Barlow 21:13

That makes a lot of sense. Let's talk about this then in relation to career change. How can, when somebody's getting to that area of overthinking and that type of resistance in the process of making a career change, how can they open the window or open the door and let more space or let air in? What have you found or what have you seen work?

Briana Riley 21:39

That's a great question. I think that a lot of the people that we get to work with here at HTYC, they come in as overthinkers, and most likely that has been a part of the reas

on why they have been so successful in their career. So there is something to it.

Scott Anthony Barlow 22:03

There's something great about it, right?

Briana Riley 22:05

Something amazing. I mean, yeah, it's not "not" working. But it only gets you up to a certain point and thinking of someone in particular who, a client I'm working with, who she has all of these different ideas of ways she'd like to be expressing herself, and how she'd like to show up at work and what she'd like to get back from coworkers. And then she'll come up with all these different ideas, and we'll brainstorm them together. And then she would do this thing where she would finish a session, she do her work on her own, and come back and present to me all the reasons why it wasn't going to work, and all of the concerns that she had about.

Scott Anthony Barlow 22:53

All the reason why she can't go salsa dancing.

Briana Riley 22:55

She can't go salsa dancing, she can't possibly go salsa dancing. It's just not going to work. Because the career path is not as mapped out as she wants it to be, or people in this work aren't actually moving forward with the work. They're just cogs in a wheel. And what I was hearing in our conversations is, there's actually just a lot of assumptions that we make, where we think that we're turning things over and getting a better understanding, we're actually just falling back on the assumptions that we are holding anyway. And we're using whatever we can to reinforce those assumptions. And so what really works in that situation, what really worked with this client is telling, instead of in the session, instead of telling me why it wouldn't work, changing those assumptions into questions, right. So they're not like, "these are my concerns. These are the issues that I have with these potential career areas." It's, "these are the questions that I have about these career areas that I'd love to explore more", which is just giving you enough room to see that it could just be a question that you ask. It doesn't have to be the answer.

Scott Anthony Barlow 24:10

Yeah. That's great. So what would be an example of that?

Briana Riley 24:13

So she has this assumption that, so she's interested in understanding how people use products, which is a big area to explore. A lot of people are interested, and how people use products, and why people use different products. And she has this assumption that everyone in that position, everyone who does that kind of work, either gets trapped on the research side of it and stays in research and that's all there is, which in her head wasn't a valuable area of contribution from a company's perspective that it would be an expendable area, they would easily cut it if layoffs were to arise. Or the alternative was, if it wasn't trapped in the research side, it was just trapped in choosing the font colors that exist on the website. And is it just the visual, the aesthetics of a website or something. And so it was just that design part. And it wouldn't at all, in any case, include that more strategic thinking that she wanted to be doing. And so the question, instead, that we've got to is, what opportunities are there to take information that we can learn from a client or a customer base, and create a strategy, create a project that helps to deliver that product to them, that helps to improve the service that they're getting? And who might be doing that kind of work? Where does that work exist in companies I haven't heard about? And so in creating these more open ended questions, she was able to then realize, I don't have all the answers, and I have to move forward somewhere to get them. I can't just stay in my own head, I have to be going outside of myself.

Scott Anthony Barlow 26:27

Yeah, that's really interesting. And so I think the part that's really cool is that as an overthinker, like, as soon as you can get to the point where you can have that realization, that, for me, it feels like an epiphany, every time that "Oh, I don't have all the answers here." Again, for the 9,000th time to do something outside of my head in order to get to those actual answers and question the assumptions, then that's always a much more healthy place to get to, because then you can actually do something about it. So I guess once you have that realization, then what else helps you from there?

Briana Riley 27:10

I would say that curiosity is not the enemy. Curiosity is actually what powers that ability to change those assumptions into the questions that you need to ask. And even though it's also curiosity that drives that overthinking cycle, there is the balance of curiosity that is really important to lean back on as you keep moving through the process. So you ask those initial questions. And what helps is not, I guess, not expecting to solve all of your problems with those questions that you come up with. It's not that you're coming up with a fail proof plan. It's that you're coming up with a next step that leads you to your next step. And that's all you need to know. Oftentimes, we feel like, okay, well, we start here, we ask the questions, and then we'll know what to do. And then we'll get to where we're trying to go. And it's still that avoidance of well, what if I fail? What if it doesn't do what I need it to do? But the outcome doesn't solve all the issues. The outcome that we're looking for is, do I have more information that I can use to figure out my next step?

Scott Anthony Barlow 28:31

So it's about pivoting what is the goal or the target, and instead centering that goal from, well, changing that goal, rather, from figuring out everything, to instead getting enough information to move to the next step. And then from there, being able to get more information to then move to the next step beyond that.

Briana Riley 28:57

Exactly. It's not a, we're not trying to get ourselves on, people often say, find the direction I need to move forward. But the image that brings up is, you're just getting on the race track and you're running, right, you're just going towards your goal. But you're really just creating these building blocks, or kind of just stacking things on one another, until you've gotten to a point where you realize you're exactly where you need to be, and exactly where you want to be. And that shift from you just want to go linearly, you just want to move forward to you want to build on what you have, that's kind of where it helps clients to get.

Scott Anthony Barlow 29:43

I love that. I also know that it doesn't make it feel easier every time. In all honesty, part of the reason why I am continuing to, I don't know, take on things like short term real estate and other things that are very new for me, is because I don't want to ever forget what it's like. There's a psychological bias that as soon as you're out of a situation, or very quickly, when you're out of a situation, you forget, in actuality, what it's like to be in that situation, in many cases. And so I'm aware of that. I'm aware of the psychological biases and the impacts. And I feel like a good portion of what we do is help people maneuver through those situations that are off the beaten path, which then means that we have to move through so many stages of thinking, so many stages of resistance. And so for me, I think that what you're saying has really resonated over the years, where if I think about reappropriating what the goal is like, I just need to get in just enough to take the next action, and then just enough to take the next action, that has been super successful for me as a strategy. Although still to this day, I can't say that it feels wonderful, every single time. In fact, most of the time it probably does not. What does that feel like for you? And if you found a way to make that feel much, much better, I am all ears. Because I do it, I practice it. And also, it does not always feel wonderful.

Briana Riley 31:29

I would love to hear from anyone who has found a way to feel comfortable with it. But I actually don't think that's possible. I think if we were to feel comfortable with it, that would be working against the whole thing that would be working against where we're trying to go. And so I think that it's almost just learning to embrace that there's this discomfort. And from that discomfort, there's so much potential, there's so much that we can experience so much that we can learn. And on the other side, what are we losing, right? What are we losing if we move forward? Versus what do we lose if we don't. And usually when we compare those things, there's so much more that we can gain than we have to lose.

Scott Anthony Barlow 32:22

Tell me how you think about taking action? And when is the appropriate time to take action? And just any general thoughts for, what advice would you give to someone who's in that place that feels like or recognizes that their tendency is to overthink? And also wants to make big changes in their life and work?

Briana Riley 32:45

You know, it's interesting, because even if you ask that question of, at what point do you take action? That brings up for me, I'm already like, there's a nervousness there about my heart kind of dropping of, well, when do I take action? When does that happen? And yet again, my default reaction is to feel like "Oh, I don't know. How could I possibly know that, right?" And to overthink, of course, on the idea of overthinking and when to take action. So I think that when you're initially faced with a question, and you start down the process of deep reflection and deep analysis, and you're sitting with it, usually that feels good, because you know, for a fact like you don't even know where to start, right? So that initial question of, what do you want to do, or where do you want to be, or who are you and what do you value? There's a time that you do need to think about it. At some point, though, you run into this wall of fear, or frustration, and that's how it comes up for me a lot of the times of, I feel really nervous. I get kind of nauseous, some like, not sure. But that is the key like when I feel that feeling when I'm afraid, when I'm frustrated because I just can't understand something, that's the moment that I take action because I spent enough time thinking and reflecting and gathering that important information I needed. But when it scares me, when I know that there's something there that's not sitting right, that's when I know it's time to take action. It's not because I now have all the answers. It's because I know that there's something in front of me that I'll only get to if I move forward with it. And so I'm not waiting for that feeling of "Okay, it feels okay, I know what I'm supposed to be doing." There isn't that relief that you expect to feel of, "I've got everything I need. And now it's just a simple answer." If it feels too simple, it's probably not right. And so it's that part of moving before you feel secure, moving before it makes all of the sense in the world.

Scott Anthony Barlow 35:07

I'm just taking that in our conversation. I'm now analyzing that, and probably overthinking about it . I'm going to go listen to the message that this property owner has called me back with and then I'm going to call them back. And then I think that I know that I'm going to feel what you just described, real time. I know that what you say is true from past experience that I will feel like, I need to find out more information, and then analyze it and do all these other things that are really just stopping me from doing the thing, and moving to the next step, whatever that is. So I totally agree with what you're saying that, in many ways, like that is the indication that you need to move forward. And we only have the confidence from that after it's done, not beforehand. And I think for some reason, we all think that the confidence becomes beforehand, and then you go through all the things. And in this case, as you pointed out, no, you have just an indicator that you're uncomfortable with it. And that's when you need to move forward, and then that will lead to confidence down the road.

Briana Riley 36:26

Exactly.

Scott Anthony Barlow 36:33

Hey, if you've been thinking about making a change for a while now, and you don't really know how to best take the first step, or get started, here's what I would suggest. Just open your email app on your phone right now. And I'm gonna give you my personal email address, scott@happentoyourcareer.com. Just email me and put "Conversation" in the subject line. Tell me a little bit about your situation. And I'll connect you with the right person on our team, where we can figure out the very best way that we can help you, scott@happentoyourcareer.com drop me an email.

Scott Anthony Barlow 37:04

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

Speaker 3 37:09

How do you know how to get from where I am in this kind of stuck mode to taking these bold steps forward and doing the thing?

Scott Anthony Barlow 37:22

Lack of clarity around what you want out of your career can leave you feeling directionless and unsure about what next steps to take. It's like wandering in a fog, not knowing which way to go and often results in being stuck in a job you dislike for way too long. So how do you figure out what you want for a career when you have no idea where to start? Well, an overnight miracle would be nice, maybe a genie in a lamp. Heck, yeah. But we all know it doesn't work that way. Real progress takes intentional action after action. Well, the tangible changes you're looking for may not happen overnight, there are small internal steps that you can begin taking right now to start clearing that fog.

Scott Anthony Barlow 38:08

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.