What if you took something really tough you went through and turned it into a way to help others going through the same thing? That’s exactly what Jason did. He went from dreaming of a baseball career to working in business, and then made a huge shift to becoming a men's divorce therapist.
What if you took something really tough you went through and turned it into a way to help others going through the same thing? That’s exactly what Jason did. He went from dreaming of a baseball career to working as director of sales in the SaaS world, and then made a huge shift to becoming a men's divorce therapist. After facing his own difficult divorce, Jason realized he wanted to support others navigating similar challenges. He talks about how important it is to seek help during hard times and stay true to yourself in your work. If you're thinking about a career flip, Jason’s advice is to start small and pursue your passions on the side. He even shares a cool story about a golf caddy who turned his love for the game into a successful podcast and book, all while keeping his day job.
Episode Takeaways
Connect with Jason
Jenny Dempsey (00:00.302)
So we said, don't wait, but then the other thing is you can do it off the side of your desk. You don't have to quit your job to start a business. You can start posting, blogging, post a podcast. It's all very accessible around stuff that you're passionate about, and you never know what that passion is going to lead. Welcome to The Career Flipper, a weekly podcast featuring career change stories from people around the world in all sorts of industries.
about how they get from point A to point B and C and D and E and all the twists and turns in between. I'm your host Jenny Dempsey. After more than a decade working in customer service and experience leadership at tech startups, as well as teaching two Udemy training courses, speaking at business conferences and a bunch of other cool stuff, I got laid off. Despite all my experience, I now have almost 400 job rejections under my belt.
I just couldn't land a new job and I really started to question my worth. What am I supposed to do now? Then a friend gave me an old junkie table. I saw potential, which sounds wacky because what the heck? I had never done this before. I binged YouTube, TikTok and Instagram videos to learn how to fix it up and found joy in giving something unwanted a brand new chance at life.
which really resonated with me after getting laid off and feeling pretty unwanted myself. This led me to start my furniture makeover and restoration business, San Diego Furniture Flipper, where I rescue and restore good furniture to keep it out of the landfill. You can follow along with the makeovers over on Instagram. Alongside furniture flips, I host the show, speak at events, and yes, still do some small scale customer service consulting on the side.
But despite all this wonderful stuff that I developed over the last couple of years, I was feeling alone and honestly kind of delusional about my new path. mean, who goes from the corporate tech world to covered in paint and sawdust in their garage? So I reached out to a few people that I knew who've also flipped their careers. Hearing their stories motivated me and made me realize it's okay to change direction at any point in life. I realized there are way more people out there who've flipped their careers.
Jenny Dempsey (02:21.826)
more than once and more than I'd ever imagined. And that's why I started this podcast. It came to me in a dream to share these incredible stories and offer support to anyone considering having already been through or currently going through a career flip of their own. So wherever you are in life, I hope this podcast inspires you to dream bigger, learn from those who've changed their careers and embrace the changes and risks that can help you grow beyond what you ever thought possible.
Okay, let's talk about today's episode. What if you took something really tough that you went through and turned it into a way to help others going through the same thing? In this episode, you'll meet Jason Sriban from Victoria, Canada. And that's exactly what he did. He went from playing college baseball in San Diego to working as a director of sales in the SaaS world, and then made a huge shift to becoming a men's divorce therapist. After facing his own difficult divorce,
Jason realized he wanted to support others navigating similar challenges. He talks about how important it is to seek help during hard times and stay true to yourself in your work and life. But enough of me talking, let's get into his career flip now. Hi Jason. Jenny, hello. Hello, thank you so much for taking time to be on the career flipper with me. How's your day going? You know, it's been a great day so far. I've gotten lots done in my two new careers.
And so that always makes for a good way to start your day. Yes, absolutely. And you're up in, remind me where you're located. I'm on the west coast of Canada on an island off the mainland in the city of Victoria, the Garden City. Nice, nice. I love it. Well, we had a chance meeting. There was a LinkedIn post and there was a comment from you on the post and I just happened to be...
randomly scrolling and read it and was like, ooh, I need to talk to this guy. This is a very, very interesting and unique career flip. And I am so excited to have you on to talk about it. So let's just, I'm going let you take it from here, Jason. Tell me, tell me your career flip story. Well, you know, as I was thinking about my career flip, Jenny, you know, there's really been a couple of career flips for me. So let's talk about the first one, which is me leaving Canada to go to Southern California to play baseball on scholarship.
Jenny Dempsey (04:47.95)
and thinking that baseball and something related to baseball was going to be my career. you know, discovering that in junior college that a Canadian kid who spent most of the winter not playing baseball wasn't going to be really as competitive as most of the people that he was playing with. I ended my playing career at that point and forced me to go into something a little more traditional and that was business. And then and so, you know, 30 years later, you know, eight or nine different companies
four or five different kind of roles, senior management and executives, it was time for a career flip again. And, you we're recording this in June of 2024. So in October of 2023, after I was released from my last company, I got down to thinking about what I really wanted to do for the rest of my life. And did I really want to lose my job again? Because I'd grown a company too big and they got acquired by somebody else and they didn't have room for me.
And so that led to a little bit of soul searching, Jenny, in terms of the kind of work that I wanted to do and the kind of work that I was good at. Thankfully, for most of my career, I was in a position of leadership and people management and really got a thrill out of helping people find their best selves, discover their strengths, manage their careers, become leaders themselves. And it was almost like I was in sales and marketing most of that time.
the actual people management was more exciting to me than the actual sale. God forbid that, you know, a salesperson likes managing people more than he likes actually closing them. Right, right. And, you know, another friend of mine who I've been talking to about this had said, you know, you've been helping other people build their own companies and making them rich for your whole entire career. How about doing something for yourself and doing something with a little bit more meaning?
And that really hit me hard. And so I thought, started thinking about what, would I like to do? And obviously I'd been coaching for a decade on top of, you know, my executive work and the thrill that I got working with people on a one -to -one basis to help them get better was right at the top of my list, you know, and, you know, life experience too had changed for me too in the past three years. I've gone through a divorce, had seen how traumatic that was on
Jenny Dempsey (07:12.746)
on my own mental health. And the combination of those two things really led me down a path where now instead of one career switch, I switched into two careers. And so starting in January of this year, I pivoted my coaching business from executive coaching, divorce coaching, and I went back to school full -time, mostly full -time, in a master's program for counseling. And so, you know, what I've done in a year or so, year and a half,
I'll have a master's degree in counseling and oncology and be a registered clinical counselor is what they call it here in Canada. That's right. And be working with people who are, you know, again, going through the same kind of trauma that I went through, hopefully being able to help them, but then also being able to help people logistically through the ups and downs of divorce. And that was really the flip for me that happened at the beginning of this year. And, you know, it's early in my journey, but I got to say that I've really found my people. That's yeah.
It sounds like you have found your people and found your path to help those people. And that's such an emotional roller coaster. And, you know, as a child of divorce, the emotions that happen to you and the people around you are, I mean, it's a lot. And so how did you find the energy and, you know, to be able to kind of continue to pursue this as you were going through that?
Because I think a lot of our listeners might be in the thick of these very challenging, highly emotional, personal situations. And sometimes factor in layoffs, factor in divorce. Losing, there's grief. There's so much entangled in this. How did you find that energy and motivation to keep going? Well, I didn't do it alone. And that's lesson number one, which is when it comes to something traumatic, especially if something that's very personal like divorce.
And if you're like a lot of guys, your personal identity is sewn up in where you work, the job you do and who you're married to and your family life and the image you present to the world. And to have that taken away, Jenny, is quite traumatic. And for me, in addition to separating from my wife, Ian, I think we separated the first of April in the year we separated in July that year, I lost my job. And so in a matter of six months, I've gone from, you know, a fairly successful
Jenny Dempsey (09:36.21)
position to losing my house, living with my parents, losing my job, and talk about the low of lows. And the things that save me and the things that I recommend to people who are going through similar traumatic incidents is, first of all, don't do it by yourself. Tell people what you're going through. Don't put the burden on them, but tell them so they know and get professional help.
You know, I was lucky that I had a strong family core that I could lean on. I lived with my parents. If there's nothing more humbling than, you you've got two grown children who are outgoing to college and you're living with your parents, but lean on people who you can count on and get professional help. And for me, that was group therapy, individual therapy, and friends who had been through divorce themselves and could really understand what they were going through.
The key to me was then was to put aside the anger and the regrets and frustration and confusion. It wouldn't go. It was never going to go away, but at least I could understand it and manage it and then get to the point where I could start looking forward instead of backwards. And, know, when you start to look forwards after incident, traumatic incidents, especially around something like divorce, you start thinking about, well, what can I do that I couldn't do before? You know, the
you know, in therapy, they call it the miracle question was if a miracle happened in your life changed for the better, what would you do? Well, you hate to think about divorce or job loss as a miracle, but really it can be if you, if you pivot that way. And for me, that was, that was the turning point where, okay, here's who I am and here's the, here's the kind of work that I want to do. And here's the future I see for myself, not only for me, but the relationship I have with my kids.
relationship I have in the world and any kind of future relationship I want to have with, with romantic partners. Yeah. That pivotal moment where you're making that decision. Did you ever have anyone kind of share like maybe this wasn't a good idea or kind of was just like throwing things at you? Like that's a weird idea or kind of like judge you for any of the, you know, pivot from business and making other companies lots and lots of money and having that stable paycheck.
Jenny Dempsey (11:52.142)
to something on your own and also going back to school. Was there ever anything that kind of came up like that? I'm sure that my father was not pleased. Bless him. As a guy who worked in a national company for many years and then ran his own small business for 27 years, I think the concept of the risk
And the concept of uncertainty is not something he's comfortable with. Of course, he's a child of the depression. So grew up in a time when, you you only spent what you had and bless him because he gave it, he created a great environment for myself and for my sister to grow up feeling very safe and very, you know, there was no drama there. And except for a few friends who knew about, you know, the depth of the coaching that I'd done and some of the work that I'd done.
I think for my family, especially took some of them as a surprise. However, I will say that my sister said, fuck yeah. I'm so glad somebody's doing that. And I'm so glad that because men, there's an opportunity there for men. And I think you're the perfect person to do it, which is a real boost to me. But by and large, most of the people that I told about it, reactions were really positive. It encouraged me that it wasn't just a good step for me, but that was a good step for my community and a good step in general.
Yeah. Where do you find the people that usually that you work with? Or do they find you? Like, how does that part happen? A little bit of both. I try to be active on social media, you know, talking about my own personal experiences and trying to show people that it's OK that you failed, especially for men to fail at marriage after being successful in business their entire lives, perhaps. But really, my people come to work with me on the divorce coaching side.
through other divorce professionals, family lawyers, CDFAs, which are certified divorce financial analysts who tend to work with people figuring out their finances after they've gone through divorces. You'd be surprised about how many referrals I get from real estate agents. Really? Interesting. the first people to know about a divorce are usually people who have to make change to help people with their changes. So it's the financial advisors, the family lawyers, and the mortgage brokers. Yeah.
Jenny Dempsey (14:16.408)
Wow, interesting. And other therapists. think that, thankfully, you know, I hope that one day when I'm done my training, that I'll be the kind of therapist that'll look at a client and go, you know what, I'd love to help you, but you're not a good fit. Go to see so -and -so instead. And I've been blessed to meet a couple of therapists and a couple of divorce coaches who are, who like, you know what, I do good work, but I think you need talk to a guy.
And Jason's your guy, you're man going through divorce and you want a male perspective. Yeah. Yeah. And I'm sure that like opens up the doors of trust, like for men to express feelings, because that's not always accepted for many men as they're growing up and in society. And you being that person, I'm sure unlocks a lot. It's difficult for men because for most of us, we have a small social circle, Jenny.
And if we do, we rarely will talk about our personal feelings. And it's funny when men get together and they talk, it's often side to side. It's on a buddy's road trip. It's sitting at the bar watching sports. It's sitting on the bench at practice. It's rarely the way women communicate, which is face to face. And men also almost always rely on their wives as their primary emotional out.
And so you put all that into the mix and getting a guy to actually talk to somebody about their divorce and work with somebody to help them through the emotions so that they can get onto the big part of divorce, which is finances and logistics, can be a challenge. But it's very rewarding to see guys trust you with their feelings and their vulnerabilities because that's when you know you're doing well.
Yeah, wow. That's incredibly powerful. It's a very important role to be in. So I want to circle back to something to make sure that I'm understanding correctly. So, you you started the coaching, was that before you were in school? You just kind of started that and then went into the program and now you're working on finishing that up. Is that, am I understanding that right? Pretty close. You know, I've been doing executive coaching, working with first time people managers primarily for about 10 years before I made this flip.
Jenny Dempsey (16:40.214)
So I knew that I had the skills to coach. And the more I researched, you know, what people went through a divorce, the more it looked like, you know, stuff I've done in executive coaching, can apply to divorce coaching. Fair enough. But in reality, Jenny, I started my divorce coaching journey and my school at exactly the same time, like within two days of each other. Wow. All right. Yeah. One thing that I hear from
people that are considering a flip by choice is that they are like, well, I need to get this certification first before I need to do this first. Or I'm not, you know, I'm not, who am I to do this because I don't have this, this and this. And I think, you know, hearing you within two days of each other, you're just like, I have this background. It's not specifically in this topic, but I've experienced it. And I have, I can now combine the things that I know from past experience with my present experience.
help people moving forward and kind of putting those things together and making it so like you don't have to have all the certifications immediately to still be able to help and pivot. How does that kind of land with you? A hundred percent. There is a person that I follow, name is Justin Welsh, who's pretty well known on LinkedIn at least in terms of what he calls the solopreneur journey.
And he always talks about the expertise you have as the stuff you've learned in the last two years that somebody else hasn't learned yet. And I look at that and I go, well, Jesus, and what have I learned through my divorce process that I can share with somebody who's just starting in the divorce process now? And you're right, Jenny, you don't have to have a degree, a certification, a training. Although in divorce coaching, you can get something like that. The CDC Divorce Academy is a great place to get something like that.
But really, people are looking for somebody authentic that they can talk to, and you've got to be able to walk the talk. You know, it's pretty clear when somebody just wants to take your money and not help you out. Yeah. And I've been fortunate to be connected with a number of people who are in the divorce coach space, and all of them have the same story. Went through terrible divorce themselves, want to help others, clearly interested in the welfare of the client. And what illustrates that the most to me, Jenny, is the fact that most of them
Jenny Dempsey (19:02.018)
work on a retainer basis, not on an hourly basis. So they'll charge you a flat fee per month for unlimited access. Send me as many emails as you want. Let's talk on the phone when it works. Send me a couple of texts because really what they want to do is they want to be that person in the foxhole next to you because they were there and they knew they were alone and didn't have somebody to go with, which really differentiates a divorce coach from a lawyer.
picks up the phone and spends two minutes on the phone with you and dames you for 15 minutes at $400 an hour. Right. Right. Right. Yeah. That support. mean, that's priceless. That's your, you know, and it's confidential and they can trust you and whether it's email or phone or however they reach you, like that's an incredible resource to offer. And so I'm, yeah, sorry, go ahead. I was about to say it is, and it's really a privilege.
You know, as somebody who struggled themselves for many years through his divorce and somebody who also kind of loves the opportunity to hear people and help them be their best and see their best selves. Every time my phone rings, it makes me happy. Yeah. And it sounds like you're creating, like you're the person that maybe you wish you would have had when you were going through it. Does that sound right? Jenny, that's a hundred percent. And I hope that I would have been, I wouldn't have been
stubborn enough or too stubborn to take my own advice and go see somebody for help. I was lucky that I saw mental health professionals to help with that. My finances were pretty much locked in. I had good legal advice, including somebody who was in my family who's a lawyer, but also the family attorneys that I worked with. But yeah, I think that having somebody in your corner
who's really a thinking partner is a key part of all of that. Yeah. Ooh, yeah. I mean, I think of that for so many circumstances as well. Like, you you're part of a layoff as well and the experience with that, like having someone to go to even for things like that. And I mean, this podcast is a great example of, I started this because it was something that I wish that I had when I first got laid off and was considering, you know, what do I do next? And like, what options are there for me? And I needed something that was a really
Jenny Dempsey (21:25.376)
authentic, relatable, you know, thing of everyday people to kind of consider my options without feeling so delusional. Like I was on this path of like, what am I doing? This is I'm flipping furniture in my garage. Like this is nuts. Like I've been in leadership my whole career. Like, what is this? And so I hear that theme quite a bit with people that, you know, like you are just, creating.
it, whether the service or the resource that we wish we had when we were navigating something really challenging. And there's like, I just, I don't know, it gives me chills. Like the thing of making the world a better place based off of these really hard things that we went through. And you know, Jenny, one of the things that attracted me to appearing on this podcast with you was your clear energy around career flipping and how you wanted to help people with that.
And listen, you can see it in people when they're in a position, a job, a career, or a calling that really spins their crank. Because you know what office drones look like. They're going to work to collect the paycheck and then living their life somewhere else. And what an honor it is for both you and I to be able to flip into something that stirs the juices. And it doesn't feel like work most of the time.
Yeah, so true. That is so true to the point where sometimes I'm like, wow, I've been sitting here for a few hours. I'm like, but this is so fun. Well, I often feel that way after the end of a session with the divorce client. We'll have spent 45 minutes to an hour walking through what they're going through, talking about logistics. And like most coaching, it's a lot of them talking and me prompting, but then feeling really good at the end.
If I could do that the rest of my life, think I'd be a pretty happy guy. I love that. If you had any other pieces of advice to give to someone who might be, whether by choice or circumstance, considering a career flip that is drastically different from what they've always done, what kind of what advice would you give to them? Don't wait. You know, I have often been asked if I have any regrets,
Jenny Dempsey (23:41.676)
And I really don't. I believe that I'm in the place that I am because of what I've experienced. OK, all the layoffs, the moves, the multiple countries, the divorces, all of that. But where I am right now, I'm really happy. So I really have little regrets, except I was a baseball guy, lived in San Diego when I was first married and didn't get a job with the Padres. If I have a regret, it's that I didn't move sooner into an industry that I loved. So there's my one regret.
So the other thing that I will say is that, so we said don't wait, but then the other thing is you can do it off the side of your desk. You don't have to quit your job to start a business. You can start posting, blogging, post a podcast. It's all very accessible around stuff that you're passionate about, and you never know what that passion is gonna lead. I follow a guy on Twitter who's a golf caddy.
Not even a professional golf caddy, but he golfs, but he works at a private club that that hires out caddies to people who guess who come to play. And a couple of years ago, he just started posting stuff about his rounds. I think it's called caddy tales. He's since done a podcast, written a book, right? And his primary job is still carrying golf clubs around the course for members who are visiting this club. And so he clearly took that path where he didn't quit his day job.
He just started doing something he loved that was related to his day job. And it's turned out that it's put money in his pocket. Love that. That's wild. got to, I got to look that guy up. my goodness. Well, Jason, you know, the things that you are talking about are so personal and can help so many people. And I'm wondering how can people find you? How can they connect with you and, and talk? Jenny, that's lovely. So, my website is Scrivenprogram .com.
They can also find me on Twitter at TheJasonScriven. And my Instagram feed is Divorce101 for tips and tricks on how to deal with divorce and thrive instead of survive. Awesome. I hope people reach out to you and connect with you. Thank you so much for being on here. Also, not going to hold it against you that you're a Dodgers fan. We'll leave it at that. We'll see you in September. We will.
Jenny Dempsey (26:04.27)
Thanks for tuning in to this episode of The Career Flipper. Be sure to connect with Jason using the links in the show notes. If this episode gave you little boost, share it with a friend who could also use some inspiration. Rating and reviewing the show helps more than you know, and hitting that subscribe button means you'll get more amazing flipping stories like Jason's every Thursday. Your support helps me reach even more career flippers and those dreaming of making their own leap.
spreading all the good vibes and motivation we need on this journey. And if you're looking for a career flip and speaker for your event, want to sponsor the podcast or just want to drop a line and share your career flip, swing by thecareerflipper .com. I'd love to hear from you. Keep on your path, my friend. What's the best that could happen? Talk to you next week.