246: Designing A Sabbatical To Live Your Happiest Life

Just that uncertainty, I mean, I definitely left my job some of the biggest challenges and questions in my head were, who am I without this job? This job has been my identity for more than a decade. So who am I without it?

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Scott: What happens when you decide that you no longer want the same life?

Robbie: I had a cool job that changed a lot over time. There was a lot of diversity. I have a lot of autonomy, so that kept me in my job for a long time because I was leader in the company. I made my own schedule. I made a lot of key decisions. And I worked with great people, but over time I was one a little tired. You could just, you know, getting tired and thinking about maybe something different would come along. I'm also thinking about what could I make happen and my wife and I started to travel more. It was kind of that pivot situation as the company was changing. My personal life was also changing.

Scott: Robbie Kaplan was living in Washington DC. She is working in a role that was honestly pretty great for her.

Robbie: At the end of February I left my job, which I had been at for almost 15 years and that was a job that grew over time, but at the end I was the merchandise mixmaster was my cool title. Basically man, I was the merchandise manager for a group of 12 ace hardware stores in the DC, Maryland and Virginia area and it was a really cool job. I was with the company since they started. When they have one store, helped it grow to the 12. I helped create the operations, branding, obviously the product on the shelf over time. So I had a very interesting job there.

Scott: But then she got a taste of travel and that short term getting away from everything made, her and her partner realized that they were living their happiest life. Now here's the interesting thing. She was originally a listener of the Happen To Your Career Podcast, who later on we got the opportunity to help make a change and she's made some pretty astounding changes over the last year and that led her to touring around the entire country in an RV, being able to explore. And I got the opportunity to catch her right in this new chapter of life as she toured through Moses Lake Washington. And for the first time ever we have one of our clients in studio in Moses Lake to take a listen to Robbie story.

Robbie: And at first we gotta take a couple trips and I would work remotely stole, you know, be in touch with everything that was going on and also have vacation time. But after doing that for a year or two, a couple of extended trips, I was like, this isn't working quite right. There's too much going on in the business and there's too much that I want to be doing personally for these things to mash up. I think an original goal had been maybe I could travel for say a month and work remotely and still do my job well, and I realized that wasn't really going to be the case, nor was I really going to be happy for my personal work ethic. I work a lot, my partner works a lot and I found myself working a long time, an extra hours and times I was supposed to be on vacation, I was checking my email. I'm not good at turning off. So working in a what was a retail business that was open seven days a week, you know, 7:00 or 8:00 AM till 8:00 or 9:00. I felt like I was on all the time, even if that wasn't required of me, which I do think is an important note. It was my personality type, not what was being imposed upon me. Yeah.

Scott: So you had that realization about it didn't feel like you're going to be able to turn it off in some ways.

Robbie: Correct.

Scott: So what happened in between there, you know, at some point you, well, first of all, you started traveling and that caused the realization, it sounds like for you and Sandy that you want to do more of that. Right?

Robbie: Right. It was something we love to do together and to do it together and we wanted more of that.

Scott: So you're like, hey, how do I get more of this? It sounds like there was a progression that happened in some ways where you realized, look, I'm not going to be able to do this in the way that I want to. Is that fair to say?

Robbie: That is fair to say.

Scott: So is there anything else that happened along that way that caused you to cause you to do it in the way that you're doing it now? What was the, what was the

Robbie: I had a weird quirky thing that happened, I guess I'll call it quirky and I would love to. I would love to be other people out there if this happens to them as well. So around last October of 2017, I was chosen for grand jury duty and that meant that for the next five weeks I was to report to jury duty every single day and I could not go to my job and I did not have access to my phone or email during the day. I was cut off from what my life was literally changed in a day.

Scott: No phone for you?

Robbie: No phone for me, which, you know, in this day and age is really hard. And a couple things happened. One is I realized within a few days I was not going to be able to focus on work at all. It just wasn't possible. I couldn't keep up dirty, busy time and thankfully I had to staff around that that could pick up the slack and we're so thankful to them. And then also because I would have, I was now going to be taking the bus versus driving and do any different. My whole schedule is different. My life was different. I decided to focus all my available time, free time on self care and using that I consciously made the choice that I was going to use any of that free time that I could spare on myself and to decide what I wanted to do next, whether that was doing something else in my company, changing up my job, or finding something completely new. And that was when I found your podcast and they listen to it on the bus every morning on the way to jury duty.

Scott: How long ago was that? Just curious.

Robbie: So that was last October, so 8, 10 months ago.

Scott: Just under a year ago. So that's crazy. First of all because now just slightly less than a year later, you're sitting here in the studio on the podcast.

Robbie: It is crazy, but it found the podcast and immediately was just drawn into it and thought the messages were really positive. It was a lot of cheerleading I really needed to hear. And also would... And also another thing that came through was that compassion and understanding for the place I was in, which was really drained, tired, needing a break. I knew I needed a break and now is having a forced break. It may not have been the most pleasant break, but it was a break enough where I could kind of regain my personal footing of what am I doing for myself. So that really was useful to me. And then right around the end of that time, I think you had a Webinar, a free webinar about was about bootcamp. But I came on with an ulterior motive of like, what can I get out of this for myself? So that's when you and I connected.

Scott: Yeah, I remember that. I remember that conversation too. So let me ask you this then. You know, with that, do you think you would have gone the same route had you not had that interrupt that break? Which can mean that I've seen that happen for a variety of different people and that can be a life changing event. Not always grand jury duty necessarily. But...

Robbie: Any? Any of them?

Scott: Yeah. Do you think that one, do you think that could have happened in a different way for you and two do you feel like some of these things would have happened without a break and I have no idea, but I'm curious what you feel.

Robbie: Well, what I think would have happened, I think I still would have left my job. I think I probably still would have found the podcast have found Lisa, but I think from a different context of just being completely worn out and I was afraid I was going to crash. Right? So even though I was tired, I wasn't at that point yet and the podcast and interacting with you guys really helped me reframe what was going on in a positive light and allowed me to exit gracefully for my job, come up with a plan, which is what I really needed. I have a resource and the resource team which I really needed and a frame what I was going to do next. Like I, any other job I had left previously was sort of either under a negative circumstance or not by my choosing and so I had a negative context to it and I wanted this to be positive and I think it was and also I was afraid I would quit my job, I need a break and not have any idea what was next and I specifically remember having a conversation with you where you said, oh, we can help you frame a sabbatical in a way that will not only let you take the break that you need, but what you really enjoy it and know what the work will be for you either later or during the sabbatical. And that really, that was the thing that got me Scott, that was because I didn't feel like I was quitting or giving up or failing. I felt like I was really moving in a positive direction towards what was next for me.

Scott: Yeah. That's so interesting. For a few different reasons. One, I, you know, I remember her saying that I remember having that conversation with you, but I realize now and recognize that out that most of us probably are not thinking about it in that way, or we don't have the breaks that happen either, like, so that break that you had with drudgery, I think what a lot of people do too is they keep on going and then they get to the point where they just literally can't take it anymore and then often that's when many people are looking for alternatives. So I guess the thing that I'm taking away from that is there, whether it's by your choosing or somebody else's choice, there are other ways to be able to get to that point, but almost all of them require you to be able to get above the situation a little bit in one way or another. It seems like and get whether get some kind of mental bandwidth.

Robbie: Yeah, exactly. And that has come up on several of your podcasts and with other conversations with Lisa, like just knowing, being aware and conscious that you're, you need to have that bandwidth to even make a change or take an action and it's very hard to find that for yourself, especially for a high achiever or somewhere he's caught up in the rat race and you know, just whatever the situation is, it can be difficult to do.

Scott: Yeah, totally agree. So first of all, like very public Kudos because that is awesome and I think that other people could have gone through that situation and not how to turn out the same way. So that's, that's awesome. And I recognized just since we've been doing this a lot, that that is not a small amount of effort even if it's forced upon you, it's still not a small amount of effort. So very nicely done. And I'm curious, what do you feel like was the hardest part of deciding that this is what you were going to do? Because essentially what you've done is you have, you've now created another kind of break and a new section of life for yourself in a totally different way than what you were living before. And you know, some people are gonna, some people are only gonna see the trap like the three months and everything like that, but recognizing that it's much bigger than that and it is, it really is a new, entirely new section of your life and a lot of different ways. And to even make the decision to move that direction, requires a bit of work too. So what was the hardest part of getting to here?

Robbie: The hardest part of getting to here, were definitely the hard conversations and planning for them was crucial. And talking through how it's going to have each of those conversations, both with my bosses, with my partner, with my family. You know, how is going to approach this was really important to me. I process internally. I'm mostly an introvert, so it, so I had to work harder at that. Like how did I want to present myself, how, what's it like, what were my goals and how did I want to have these conversations? And I think I was talking, I was talking to someone and I was like, it's gonna be really hard. It's going to, you know, it's terrible. I think it was my sister and she said it'll be fine, it'll be fine and then it's going to be really fun. I wrote it down, it will be fine and then it will be fun. And that was actually really true and I think somewhere along the way as someone on the podcast has also said, you know, like your life grows proportionally in relation to these hard conversations you have and it's true. And I knew, I knew that when I spoke to my bosses about what I wanted to do, that they would be supportive. I had no doubt about it. But having that conversation to make something real is not easy.

Scott: Thinking about it as one thing versus actually having the audacity and the courage to do that as a completely different thing. And so what helped you the most other than the very quotable? Tweetable. It'll be fine. Then it'll be fun because I love that. That's awesome. Well, what else helped you to be able to do that?

Robbie: Definitely the preparation. So talking to you, talking to Lisa before I even actually hired her as a coach. Having preliminary conversations and understanding that help that I could get and listening to the podcast. Also just hearing all kinds of great advice and then Lisa have really helped me hone in on what was important to me, what my priorities are for myself and how to really focus on that and how to understand that anyone else's reaction to what was going on with me was more about them than about me. So that was really important for me and helped and helped and helped me also plan out how did I want to approach work. Say I wanted to leave and also already have like an idea of when I want it to go, what my exit strategy was and how I wanted to deal with different situations because I had my hand in a lot of pots there. So it was no small feat that was leaving. I was also the most senior employee at that point. So it was a lot and I think it helped me exit well. My whole thing was I wanted to exit well, I want to leave people in a good position. I hope I did that. And leave having people thinking well of me and I hope I did that as well.

Scott: What do you feel like in building those next steps or building that plan? What do you feel like would work for you? Or what are some of the elements that you put into that? When you say, I built my exit plan, what does that actually mean?

Robbie: I made checklists of actually worse case scenarios. Like what if I go in and say I want to leave? And they're like, all right, well just go to that.

Scott: We'll see you later.

Robbie: Besides to that and all i think what happened, but what if. So I was just prepared, did I have my contacts, did I have important documents that I thought I needed, you know, were the most important things in my office, like, could I get them quickly if needed? I know in my situation I was very fortunate, I never once thought that would really be the case. And then thinking about the next projects and the calendar, like really writing out like here's what's going to be happening and so and so needs to be on top of it or so and so needs this to happen. And I left all my, pretty much all my emails there and accessible all the documents accessible. I had a wonderful assistant buyer at the time who's now a senior buyer and I really feel, felt like I could, you know, teach her a lot before I left and I gave two months notice. So it was a fully. We were working weeks of spending time with people and training them.

Scott: What were some of the parts, you mentioned several times along the way, like identifying what was most important to you in terms of your life, your career, what were some of those parts help people understand what for you and it's gonna be different for everybody. I think it's really important to acknowledge that, you know, what is, what's important to you is not going to be necessarily the same things that are important to me and important to the next person. But what are those things look like for you?

Robbie: For me at the time the priorities were definitely that I wanted to travel with Sandy and for an extended period of time and feel like I could do that without feeling guilty or without feeling resented. And that might've been a perception I had, but that was just what I had internalized. So I wanted that we have a house that's a fixer upper that we hadn't spent a lot of time on and I would like to live in a house I love, so I want it to be able to spend time on that. And those were two big things I would say. I'm sure there were others I can't think of right now, but it required more balanced in our family. Sandy and I are both high achievers. We work, we work till the job is done. We're not just going to stop at 5:00 or 8:00 or whatever. So it was not unusual for us to both be working at 10, 11:00 at night. Well, no one's caring for our family at that point. No one's caring for our home. So it's not that I'm going to suddenly be betty homemaker. That's not who I am either, but we needed more flexibility and ability to live the lives we want to live and have a great time. And we found we love traveling and really wanting to make that work. And so we were able to plan a three month trip that's now at three and a half months and get on the road where Sandy is working remotely full time. And I'm vacationing and also helping be Julie the cruise director basically for our trip.

Scott: A lot of times we'll have people on the podcast and we're talking about the new role they're moving into or whatever it might be, but in this case, for you as you identified what the next stage of life looked like, really involved this travel and having that flexibility and some of those other pieces that we just mentioned, but also if for those people that haven't traveled extensively, you and I were talking about this over lunch, but there is a massive amount of decision making that has to happen. It's not like it's a woe is me type situation because you're doing what you want to, but it is. It is hard in a way that you wouldn't anticipate because if like I'm on vacation. Vacations or you know, people don't associate that with hard a lot of the time, but it realistically as like it takes a lot of effort and planning and thinking and all of these other things too. So for you, help somebody that might be interested in doing this sort of thing where they go and they spend a period of time traveling and they're looking to put this into their lives for one reason or another, and in one way or another, help them understand a little bit about what that's actually like on a day to day basis for you.

Robbie: Well, I definitely think, like you said before, what's important to everyone is different. It's subjective and we actually, Sandy and I actually traveled very spontaneously. We may not know where we're sleeping until 6:00, 7:00, 8:00 at night and we might get there and it's too hot or the plugs don't work or you know, we can run into a variety of issues. There's a lot of decisions. Where are we going to sleep? There's several apps I consult to figure out where we're going to be parking that night. Home is where you park it in our RV. We, you know, we do have everything we need, we're self contained, but do we have enough food? Is the dog happy? Which is, you know, takes up a lot of energy. What will I be doing the next day of Sandy's working. Is they're reliable internet and wifi and cell reception, which is hugely important and became a bigger factor on this trip. Then we realized it was harder to find. And then if someone's working, what are our available travel hours? Where can we go have fun with the dog? There's, you know, there's just a ton of things which yes, it's fun. I can't complain about those things. But it is work and I will say kind of leads a little bit into something else I was thinking about a minute ago, which is that I do have a mental capacity at this time to think about what's next, what I want to be doing, but I'm still using a lot of mental capacity everyday. I'm not bored. And it was making me think about when I was leaving my job, everyone of course as well, what are you going to do next? And I would say, I don't know, what do you mean you don't know? Do you want to work in retail? Do you still want to be a buyer? I don't know. I'm really happy about that. As I said, I wanted to go figure out who I am now, shed the skin that I've had and see what's still interests me. And this trip has also allowed me to do that. I like to go somewhere new, walk into a store and be like, Huh, that's cool. That's not cool. Look, I'm still interested in, you know, merchandise mix in with the cool new product is, so I'm really okay at the moment with not knowing what's next but I'm nearing the end of the trip and so this podcast comes at like a serendipitous time or I'm like, Huh, you guys start thinking about, you know, what's gonna happen when we get back?

Scott: We will have the part 2 podcast later.

Robbie: Yeah. Hopefully, hopefully it won't be a cardboard box.

Scott: What you're talking about though is it's really interesting to me that like how far we have to get in some ways like how excited our normal routines and our normal things and also how okay or not okay. I guess I should say most of our society is with not knowing, and I was going to ask you, you were very much a planner type of personality. Is that the best way to say it?

Robbie: Yes. I think that's fair.

Scott: Okay. So now you've gotten to this completely spontaneous and also not knowing what is next. So what are the, for you and your personality, what are the hard parts about that? What are the parts where you found that liberating, if any.

Robbie: What is the question? What's hard? What's hard about not knowing what's next? Part of the question? Just that uncertainty. I mean, I definitely left my job. Some of the biggest challenges and questions in my head were, who am I without this job? This job has been my identity for more than a decade. So who am I without it? Will I have the same recognition or response or was the success I was having based on who I was and who was working with and all that? Or is it really self earned? Just regular self doubt I guess. And I still have that. Like, who am I saying one care? We'll see. Now I lost track.

Scott: Well, it's frustrating that that I find it frustrating that that never goes away.

Robbie: Sure.

Scott: It would be nice if it did, but it really comes down to a case of choosing what you want to do or how you want to be spending your time, even though that that self doubt is there.

Robbie: It's there. And I would say one of the things I've learned along this path the last several months is just like going for it and doing it. Like I'm sitting here with you doing a podcast. I remember listening to your podcasts and being like, that would be fun to be on there. Well, I didn't wait around for you release it. It'd be like, Huh, Robbie, you might be a good guest. I just said, hey, I want to come talk to you.

Scott: I'm coming to Moses Lake, get a spot ready for me.

Robbie: So I don't know what that says about you. You know, I, when I had the actual, I had a great opportunity to meet Lisa earlier in the trip and person. I've worked with her on skype and on the phone and...

Scott: For context, Lisa was her coach throughout the beginning part of this journey.

Robbie: Right and we actually met up at a small business type conference in Boulder and I earned a shirt. That's someone who's giving away that has a curse word on it, but say f fear and I was like, that shirt is for me. I really had to say that to myself like over and over again. I'm just doing. I'm going to ask for what I want. We're gonna decide what it is and just go for it. Why am I, why wouldn't I go for all the things that I want in this world and I don't want to be wasting any more time. Basically we don't know how much time we have. Right? I mean, I'm 45 right now. My father passed away when he was 48. I would hate to get to that point in my life and feel like, oh, I wish I had taken that road trip. You know, I wish I had taken a couple of months off of work or whatever it is. So I just really felt like I was in a place where I was ready to do something really different.

Scott: You know, what we, I don't think I've ever told this story before, but one as we were, I say we, it was my myself giving feedback from Alyssa, my wife at the time, but when I was choosing the name of the blog and the later the business, debated calling it Happen To Your Life and ended up not doing that because really wanted to do it through the lens of focusing on people's careers. But they're so intertwined and whether we like it or not, they are incredibly intertwined. And I think that what you're talking about, we don't, we don't know how much time we have left. My grandma just passed away. I just spoke at her funeral just a couple of weeks ago and is a reminder for me, you know, just like your dad is for you, that we just don't know how much time and I don't want to have regrets quite frankly afterwards. And I'd have to say that you've done a phenomenal job of having courage to pave that way for yourself. And it is, it is not easy. It is not easy. Absolutely.

Robbie: And I should also say, of course, that I am very fortunate that I have a partner who has been incredibly supportive of me, that we were able to plan enough to take this break and, you know, have this time in our lives together. I recognize not everyone has that ability to do that. And I think it is important that I was very scared to have that conversation with her about wanting to quit my job and wanting to take a break because of course everyone wants a break. Everyone would like to have a vacation. Everyone would like to have a sabbatical possible. But I knew it was crucial to my mental health and when we had the conversation, when I had that courage to say, this is what I really want, I was very pleasantly surprised that immediately she said, absolutely yes, like one, you need that break and we'll make it happen. And also in regards to traveling and like being able to do this, she actually was like, it works since my plans perfectly because I was, I have to go to Denver this summer and I was hoping we could take a long road trip and so it all kinda came together and of course that doesn't happen for everyone and of course there's lots of steps and hurdles for people to get to do what they really want. But having the conversations is really important, right? And the longer I was. I mean maybe I could have done it a year ago, right? But who knows?

Scott: Well, I think that inevitably some people are going to see the post that goes with this or they're going to listen to this and they're going to look at just the trip element and some people are going to say that is, that's not possible for my situation, but here's what I found though, that when you're willing to have the courage to declare what it is that you want more frequently than not, you find a way to be able to make that happen. And I think that's the part that people miss because so many people never have those conversations or so many people never take the steps toward because I feel like it's not going to be possible rather than spending their time on figuring out how it's going to be possible. So, just I can't say it enough how great of a job you've done with that. And I really, really appreciate you coming all the way to Moses Lake Washington. We've been, yeah. Everybody should make your way out to Moses Lake question. Actually. We've had, we've never had anybody come visit us before. We had two people that we worked with this week, but it's, yeah, this is the week to come apparently. Who knew? Yeah, yeah, absolutely.

Robbie: It's still worth it.

Scott: Still worth it. So appreciate you making the trip out here and thank you so much for sharing your story with all the HTYCers out there. This is amazing.

Robbie: I am so happy too because without everyone else's stories, I wouldn't be here either. So I'm happy to give back in any way I can.

Scott: It's come full circle. So I've got just one question left for you after going through all of this and for where you're at now and there's still plenty to come for you, but right in the middle, everybody's right in the middle. It's just what the middle looks like quite frankly, but what advice would you give to people that are kind of on the edge, on the precipice there? They know that they want something, but they haven't necessarily taken those steps yet or they're a little bit worried about whether it could be possible for them, whether it's a three and a half month long or longer road trip or whether it is making that change or leaving a job really well or whatever happens to be for them. What advice would you give them?

Robbie: Well, I mean I would definitely say figure out what your priorities are for yourself so you can follow them. Like tying into something else you just said. A piece of advice my dad always gave was like, go for the thing you absolutely want. That's the best case scenario and figure out how to make that happen. Don't start with the bottom or the, you know, case D, like start with case A and work toward that and it takes a lot of courage, but I think maybe making that mental head space where you can be more creative where you can gain a little bit of your own energy back and decide what's right for you. That would be my biggest advice and you know, listen to the podcast, and don't hesitate to like jump in or call or ask you questions. Now I'm like, you know, here's Scott's personal phone number, but I think that was just key feeling like your team was really accessible and willing to throw out some, you know, like tidbits of advice that helped me just even get started. Whether I came to you full time or not was really helpful.

Scott: I hoped you loved that story with Robbie. She's phenomenal and her first introduction to us was the podcast just like this one. And then later on she went over to our site and signed up for our 8-day mini course, the figure it out mini course to begin to get some clarity on what she wanted in her career. And if you want to do that exact same thing, it can help you get started in figuring out what really creates a compelling and filling career for you. Just text happen, H A P P E N to 42422. Or you can visit, figureitout.co, figureitout.co. And if you're feeling a little lost, then next week you're going to absolutely love of what we have instore for you. We have a return guest to the Happen To Your Career Podcast, who is coming on to talk about something that she knows very well, partially from experience and partially from interactions with so many different people over the years.

Maxie: I used confidence and self belief interchangeably and it's how much you believe that your abilities and whatever it is that you try your hand up. We'll have a positive outcome.

Scott: That's Maxie Mccoy. She's coming next week to Happen To Your Career for the second time. She's become a good friend over the last couple of years and this time she's back to talk about how to no longer be lost and even share a bit of an action plan on how to find your own way. So next week it's all right here on Happen To Your Career. We've got so much more in store for you and we'll be back with Maxie Mccoy. We'll see you then. Adios. I'm out.

Robbie: So nice to be here and why not come to Moses Lake.

Scott: And why not come to Moses Lake. It is a fantastic place.

Robbie: I see where the magic happens people. I'm right here in the center of it.

Scott: This is where the magic happens.