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What To Do When You Don’t Love Your Work – Kyle Elliott

Shana James 

Hello, and welcome to this episode of man alive. I am excited to be here today. I’m your host, Shana James. And I’m excited to talk about what to do when you don’t love your career. Right? I believe you deserve a career you love. And while life isn’t all rainbows and butterflies, and you know, you can’t be perfect, necessarily, there’s also a way or when you think about it, you’re spending the majority of your time in your work. And so how can you actually, you know, either step into a career you love or make changes in a career you’re in. These are really important questions. So we have Kyle Elliot here to guide us to answer these questions. Kyle, thank you so much for being here.

 

Kyle Elliot 

Yes, thank you so much for having me. I’m excited to be speaking to you today. Yeah, so

 

Shana James 

as a career coach, I imagine you see the whole range of issues and struggles and you know, someone needing to make huge changes. Am I needing to make small changes? I imagine you see it all?

 

Kyle Elliot 

Yeah, I have some people who just feel stuck in their current role. And they say, Kyle, I don’t do anything I don’t want to do. I want to figure out what’s next for me. Other people who say, you know what, Kyle, I like my job. I just don’t love it. How can I make small changes to figure out what’s next for me at this current company, and then everywhere in between? So it really depends on the person and their situation. And sometimes those changes can be massive. And sometimes it just takes a little rethinking and reimagining.

 

Shana James 

Yeah, great. And, and what was some of your journey? How did you get into this career coaching role?

 

Kyle Elliot 

So this journey happened 100% by accident, so I never planned on doing that side, that’s helpful to share. Because a lot of people think you have to have a five year or a 10 year plan where you want to be is sometimes 100% by accident, now is the case for me. I originally started on fiber, literally charging $5 for resume reviews. $5. I’ll summarize literally $5 once Fiverr took their cut, it was like 375. So I must buy a box with one review added to two of them to afford a Starbucks or a $5 footlong. Oh my god. And then over time, I just kept raising my prices. My dad gave me that advice. Hey, once you have a waitlist, just double your prices, and I just kept doubling them. Yeah, over time. And then about four years ago, I had a great full time job in Silicon Valley that I loved. But I said, You know why? What if I ran this business full time, my staff kept asking and saying, hey, when are you going to leave us, Kyle? And I had never thought of that I didn’t at all. Besides university career counselors, I didn’t know people did this. I didn’t know there was career coaches who ran their own businesses. I did research made the leap of faith. And now I’ve been doing this for almost four years now running my business full time.

 

Shana James 

Wow. So you were doing fiber, then you also had another full time job using Fiverr. On the side?

 

Kyle Elliot 

Yeah. So as long as I just 510 hours a week, on top of college just to make extra money. And then it just blew up and kept growing. And I left Fiverr went to craigslist found people there, surprisingly. And it just kept growing and growing from five hours a week to about 30 hours a week.

 

Shana James 

Well, interesting. Also. Yeah, it also seems like you went from right. $5 resumes to now coaching some of Silicon Valley’s, you know, executives. Yeah, like, how did that happen?

 

Kyle Elliot 

Yeah, people just see, okay, Kyle, you’re coaching these Silicon Valley executives. That’s not where it started, and a lot of compliance or through word of mouth to someone who would find me on Fiverr than later left Fiverr refer me to someone and so much of my business came by word of mouth and referrals. Yeah, but people just kept. And I never even set out to coach people in Silicon Valley. And in high tech, it just happened by accident. Because a lot of the people who were referring each other or friends and classmates and colleagues in the Bay Area, were trying to get into Facebook and LinkedIn and Google and then one person would get into Facebook, and then their friends would say, Oh, my gosh, how did you get into Facebook? And then they would tell other people, and then it just blew up after that. Because when you think of hiring a coach, rarely do people say, Oh, I need a coach. It takes a lot of introspection to say that. But instead, someone else says, oh, have you considered a coach? And then they shared my name. And then it just happened over and over and over? Especially if they say, you know, have

 

Shana James 

you considered a coach, I used this coach who helped me actually get clear and get organized and do what it took to get into Facebook or to get into one of these companies.

 

Kyle Elliot 

Precisely and there’s nothing more powerful than someone else telling you. Here’s what worked for me, for you as well.

 

Shana James 

Yeah, yeah. So how, how do you know or how do you help someone know whether the career change needs to be major or Whether it’s something that could actually happen within the career or the company that they’re working for,

 

Kyle Elliot 

one of my favorite questions to ask is, what is the real problem here? What is the true problem? And going beyond just the surface to see, what’s the issue here that brought you to this point of questioning your career? in the first place? Was it a conversation at work? Was it finances? Was it something else, figuring out what it was actually led to this conversation, these feelings can be really powerful on pulling the onion back. And sometimes when you pull that onion back, you realize really it is the organization or it could be this role. And other times, it’s something completely different. It could be that you just don’t have enough spontaneity in your day. And that’s something that can be added in your role, without switching careers. And other times, it’s the repaired union and moved to another function or another organization. And I think even they are, the changes can be small it can be maybe you don’t have to leave this organization, you can just move to another team, if the real issue is a toxic supervisor. Or you can move to a different role. If I was just talking to someone before this call, if you really want to lead people in your current role doesn’t allow you that I could just be moving to another team, or asking for a promotion. So these changes aren’t always massive. I have a lot of clients who come to me and say, Kyle, I need to get a new job. And sometimes it’s maybe you just need a promotion, or a salary increase or change of how you’re looking at the situation.

 

Shana James 

Yeah, okay. And then how do you help people have the courage right to ask for a promotion or a change? Because that’s not necessarily just the easiest thing to do?

 

Kyle Elliot 

No, it’s scary. One of my favorite questions to ask, and it’s two part. So what’s actually two questions is, what’s the worst case scenario? What’s the worst thing that’s going to happen? And I’ve yet to have a client get fired? for asking for a raise nice, or for a promotion? And then what’s the best case scenario? what’s likely to happen? And I find just asking those two questions. And actually, what iffing all this out? What, what can happen if I don’t ask for a raise? What can happen if I do ask for a raise and looking at those worst case scenarios, and best case scenarios, can be really powerful to figure out what’s actually possible if you don’t take action on what’s possible, if you do take action, and help people really get out of their own way when it comes to taking action.

 

Shana James 

Yeah, clarity is so important. And that watching our minds, run away with these stories, right? Like, oh, I could get fired, or that person’s not gonna respect me anymore. If I asked for this, and, and, you know, oftentimes, just the opposite could be true, right? Someone might respect you more, or they might want to actually promote you because they’re seeing your drive or whatever it may be. But our minds are so tricky.

 

Kyle Elliot 

Exactly, exactly. And it can be helpful to have someone else, talk through it with you, rather than just yourself and being in your mind and having someone challenge your thoughts say, Okay, well, what, how likely is it that you’ll actually get a fire? And then people realize, okay, this is silly. But those thoughts can keep you up at 2am saying, Oh, my gosh, what if asked for a reason they fire me? Or what if I asked to switch to another team, and my boss hates me, I stay on the team, it can be really quick to go down that hole, but someone else reflecting with you and ask him those powerful questions can make all the difference in your career?

 

Shana James 

Yeah. Yeah. And as you talk about that, I think about a lot of the men I work with who are in their 40s 50s, who might want to make a career change, but it really shakes the boat, you know, they’ve got family to take care of and financial responsibilities. And I’m curious if you have any advice for those men.

 

Kyle Elliot 

Something I always ask my clients to think about because most of my clients are also in their 40s 50s 60s, senior managers, executives is to have a conversation with your family. So not just your partner, but with your family, about what you’re thinking and what you’re going through, bring it up at the dinner table and say, Hey, here’s what I’m thinking,

 

Shana James 

like family meeting your kids? Yes,

 

Kyle Elliot 

yes, I think it can be powerful. And depending on their age, if they’re four or five, you’re not gonna be about it.

 

 

You might get some interesting inspirations.

 

Kyle Elliot 

I just assigned a client of this because they were thinking it was a man he was thinking about his next role. And I said, Ask your kids ask them if I wasn’t ex executive, what can you see me doing instead? And they brought some amazing ideas. Wow, we’re about to talk through. So I think you’re gonna have to adjust it depending on the age of your children, but it can be powerful than involve this. involve them in this conversation because you spend so much time at work like you said, you really want to enjoy Are your families invested as well?

 

 

Mm hmm.

 

Shana James 

I can see, you know, having a nine year old. I mean, there are moments of just brilliance and clarity that come through kids. And then there are crazy silly things. But even the crazy silly things can lead to something that we would never would have thought of.

 

Kyle Elliot 

Yeah, I remember talking to another client, and she brought to me, she’s, my, my daughter said she doesn’t like but I email so much at my job. And I was like, that’s something for us to work on. Right? Sure. Just these little bits that children give us can be so powerful when navigating our careers.

 

Shana James 

So true. So true. I’m wondering I saw that you talk about caffeine eating your career process and in your your headline, what is it is like caffeinated with Kyle, is that right?

 

Kyle Elliot 

caffeinated. Kyle. Yeah,

 

Shana James 

caffeinated. Kyle, what do you mean by that? How do you caffeinate your career?

 

Kyle Elliot 

Yeah, so it’s twofold. One, I just love coffee. Like middle school, I would stop at Starbucks, literally, I’d walk to school and stop at the Starbucks and then carry my coffee to school. Oh, my God, Canada. And the second piece is I find when people are job searching, they tend to just blind down I that’s one of the biggest mistakes I see. Well describe them. Thinking

 

Shana James 

we’d say that again, they tend to wet.

 

Kyle Elliot 

Just then they describe themselves as forward thinking or dynamic, or innovative and bland. Their LinkedIn profile is bland or bland. interview is really bland. There’s not a story or examples. And when I think about calculating your career, I think about how can we add some caffeine to this, make it more exciting, make it more fun, give it more energy, and really find a way for you to stand out from other people. And that’s something I always ask my clients is okay, there’s going to be 250 or 500, or 1000. people applying for this role. Yeah, what sets you apart from every other person? And if you don’t know the answer, the recruiters and hiring managers really aren’t going to know the answer to that question. So let’s caffeinate everything and make sure you stand out from everyone else.

 

Shana James 

That’s so interesting. I love that I love coffee too. And caffeine eating your self. So that right the idea more creative, you’re standing out. I would think that a fear of many people, I don’t know, maybe it’s just my own fear is like, Oh, wait, if I’m too out there, I’ve actually had this around my career, because, you know, I talk a lot about sex. And I talk a lot about well, all the other things, it’s sex that actually like, well, people are gonna look at me and think things, right, because I’m talking about sex. So, you know, how do you help people realize it’s okay, or you know, it’s safer, you’re even gonna get more of what you want, when you put yourself out there as fully you uniquely you?

 

Kyle Elliot 

Yeah, I think that is you are going to turn off when you’re too out there. That’s just part of it. But you’re also going to make room for those people by pushing other people away, you’re going to make room for those people who align with you. And what I like doing with my clients is having them think about some of the best moments in their life when they propose to their partner, or when they moved across country, or when they have their child and think about what it all those great best moments have in common. And what they all had in common was risk eye class. If they take more risk, they’re going to her growth. Fabulous. Oh, wait, can we pause to encourage them to look at all these great, fabulous moments and see what they have in common, and it’s a risk. And I find it’s a risk to own your fabulous mess to figure out what sets you apart from everyone else and share it with the world. But if you do that and take risks, to have more great moments, because as we know, the more risk you take the mark, great moments you’re going to have.

 

Shana James 

God that’s a that’s a hard one to swallow sometimes.

 

Kyle Elliot 

It is. It’s scary. But I encourage my clients to look back at those best moments. And they all involved risk, and it’s scary, but it’s true.

 

Shana James 

Yeah. Okay. So we have to actually risk if we’re going to have something that feels enlivening aligned, you know that we don’t that we’re not actually feeling bland and Dahlan. Like Groundhog Day.

 

Kyle Elliot 

Yeah. Or I asked my clients, what’s your other option to just accept the status quo? And is that okay with you? Usually, the answer is no, I don’t want to accept the status quo.

 

Shana James 

But that’s a powerful question, because I think it can help people actually realize, Oh, that’s what I’m doing already. Right? I’m accepting or, you know, a lot of my clients, I’m like, you’re kind of settling for mediocre or you’re settling for something that isn’t letting you up. And a lot of times, I’m noticing with the guys who identify more as nice guys, right? It’s like if someone says No, or someone says, I don’t really like that, then they kind of just go along and they’re like, Okay, I guess I guess this is all I get right? Or I guess this is what it is, as opposed to that risk that you’re saying of. All right, I’m going to say who I am, I’m going to ask for what I want. I’m going to, I’m going to take that risk.

 

Kyle Elliot 

Exactly. And I like asking, when you marry your wife, or husband or partner, is this the partner you wanted to be? Or when you took this executive role? Is this the leader you want it to be? And people to stop and think, is this who I set out to be? And often the answer’s no, when it gets them to think, Okay, this isn’t who I want to be, who do I want to be? When I first entered this relationship with my partner, or with my employer? Who did I really want to be and how am I in alignment? Or not in alignment? With those initial intentions?

 

Shana James 

Wow, that’s powerful. Who did I want to be a candidate? Right? What Who? What was my vision for myself? Who did I see myself as What? What type of leadership or role did I envision? And have I given up on my dreams? Exactly. And

 

Kyle Elliot 

it’s okay for your dreams to shift but can be helpful? If you’re feeling out of balance at your career to say, Okay, what did I originally want? And am I still working toward it? Or did it change? And if it’s changed, how have I communicated that with other person in the relationship, my employer, or if we’re talking about a personal relationship, your partner and making sure there’s that communication of vision changed from when we originally entered this relationship about that? Oh, my

 

Shana James 

God, that’s so important, right? I mean, that’s ultimately I think the heart of everything I do is that communication and being able to first recognize, oh, my vision has changed, or I have these desires, and then to actually be able to communicate them in a way that inspires people and helps with collaboration, as opposed to shuts people down.

 

Kyle Elliot 

Precisely. And I think a lot of people have the tools to do it, but sometimes forget, they have the tools to practice that assertive, confident, authentic, honest communication with other people. And it can be scary. And again, it’s a risk to be vulnerable and honest with someone else.

 

Shana James 

Yeah. And I love that you just said the word assertive, too, right? It’s not aggressive. There’s, there’s a balanced way to be strong and also strong and clear, you know, without being an asshole about it.

 

Kyle Elliot 

Exactly. And I think there’s kind of this really spectrum, you have passive communication with other person wins, and you lose, you have aggressive communication, where you when other person lose is, and then you have a sort of communication where you both win. And that’s the role in any relationship. Oh,

 

Shana James 

I love that. So good. Okay, I just want to ask another question that’s on a slightly different topic, because I know you speak around the country on not only professional development, but mental health and social justice. And just wondering if you can give us a taste of that or how those overlap for you?

 

Kyle Elliot 

Yes, so mental health is one of the most pressing issues when we think of the workplace and people’s careers. And it impacts them so much when I talk with clients. And they think about their careers. So often their mental health comes up whether they’re formally diagnosed with a mental health challenge, or we’re just talking about mental health more broadly, like stress and anxiety. And it’s something I talk about a lot, both from the job seeker side, how can we reduce your stress and anxiety during the job search? And then both on the employer side? How can we I’m sure employers are creating environments that are safe for people living with mental health challenges to come out if they wish to, without also pressuring them to come out with mental health challenges. If they haven’t created an environment that’s safe for people to come out and say, Hey, I live with anxiety, I live with depression, I live with bipolar, or whatever mental health challenge they may have.

 

Shana James 

Yeah, I could see how, in a way the workplace or like your overlap between the workplace and mental health is a really powerful place to talk about it, because I could see it would be a place where people would actually want to hide that. But also, you know, again, we’re spending most of our time at work, it has a huge impact on our mental health.

 

Kyle Elliot 

Yeah, and our mental health impacts our work, and then our work impacts our mental health. So they go both ways. And again, we spent so much time there. And part of what I do with clients is to help them identify and on what sets them apart from everyone else. And part of that is showing up to work authentically. And if you live with the mental health challenge, but can’t go to work and share that or talk about it and feel uncomfortable, you’re going to be wearing that mask and not feel a sense of belonging.

 

Shana James 

Wow. So you actually encourage people to talk about these challenges.

 

Kyle Elliot 

It depends on the person so if they feel comfortable coming out if it makes sense for them and their employer is creating an environment where it’s safe. Then I’ll explore that with my clients. But other times employers have created environments where there’s shame. And yeah, despite the fact that we have seen with research that when employers encourage people to get help for their mental health that actually decreases absenteeism, it decreases workman’s comp, there’s so many benefits to by employers just haven’t invested enough resources in mental health.

 

Shana James 

Yeah. So powerful, I’m just kind of taking a moment right to recognize how how impactful it can be right? If you don’t feel safe to share that, then like you said, you’re walking around with this mask. But at the same time, if it isn’t a safe environment to actually talk about your mental health challenges, then you’re you’re in a bind.

 

Kyle Elliot 

Yeah. And it’s so challenging, and it’s my job. And my role I speak about this is to really work with employers to create places where people feel comfortable, if they wish to, to disclose their challenges and create environments where there’s a sense of belonging, where people are included, regardless of their mental health challenge, and are able to show up authentically and share their full selves. So my goal is to hopefully have a day where people can share their full selves, out one mask we work, and then go home and take it off. I just want people to go through love without this mask.

 

Shana James 

I love that we are aligned in that way, right? And talk about when you’re wearing a mask, you actually don’t get to first of all, it’s exhausting, right? Second of all, you don’t, you don’t actually get to be loved or seen or understood for who you are.

 

Kyle Elliot 

Exactly, exactly. It’s so tiring. And I think it goes back to risk. It’s scary to show yourself at work. Yep. Even in an interview, if you’re job searching, it’s scary to show up and be authentic and be you from the get go. And there’s two questions that come up a lot with my clients. The first is what if they don’t like me? What if they reject me? And then on the flip side, the question that comes up less often, but is even more scary is what they actually do like me, what if they like, everything I have to offer. And then I have to keep showing up as my authentic self every single day at work. And I think that’s just a scary if not scarier, Interesting. Interesting, that actually is scary for people to really fully show up, I

 

Shana James 

guess you know, that that maps over into my work as well. Well, thank you so much, this has been really interesting and clarifying and powerful, and what something that you would want to leave men with that we haven’t talked about yet.

 

Kyle Elliot 

Something I would think about is asking yourself, what legacy you want to leave on the world. And that can be both big or small. But a lot of my clients when we’re job searching, one of the questions I ask is, what do you want people to say about you at your funeral? And I realized that can be a little bit of a morbid question. Powerful job search, because you’re not going to have pictures of you at your desk, or presenting at a conference on a zoom webinar. at your funeral. It’s probably pictures of your family and friends, doing sporting events, whatever it may be that you love. And I think that can be powerful when navigating your job searches. How is this job going to support the life on a live and the legacy? I leave and I encourage people to think about that as they navigate their job, search their careers in their lives.

 

Shana James 

So powerful. I love that looking back from the ends right from the funeral or from what you want to be remembered for. It really helps people frame what is actually important to me. Why? Why am I doing all of this? Thank you so much, Kyle, where can people find more of you?

 

Kyle Elliot 

Yes, my website caffeinated Kyle calm or I spent tons of time on LinkedIn. Kyle Elliott with two L’s and two T’s

 

Shana James 

Awesome. Thank you so much for being here today.

 

Kyle Elliot 

Thank you for having me.

 

Even men at the top of their game find themselves wanting more from life. Whether it’s more meaning, a bigger impact, unshakable confidence, a hotter sex life, more money, deeper love, solid friendships or a powerful legacy: how can a man actually reach the end of his life and look back without regret?
Man Alive is a series of bold, raw and gritty conversations with experts on success, power, sex, love and legacy. For the past 15 years, host Shana James, a love and leadership coach, has worked with thousands of men and women around the world and collaborated with hundreds of teachers and coaches. Shana doesn’t buy into the need for rules, games or limitations. She works with men individually to find their unique power and keep them from settling for less than amazing.

 

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